Vague. If at this point you’re like, “Girl, where is this going?” then welcome to the club. Me too, reader. Me too.

I recently had a romantic experience that started as an email, then a phone call (#34. “Forget discretion every once in a while and call him up.”), then a fairytale, and then, when the dust settled, we could see it for what it was: not going to work out. As much as I’d love to share the juicy details, including what was undoubtedly both the best ask-out and subsequent first date of my life, out of respect for the suitor, I’m going to keep that quiet. Which is a real bummer, because it is one hell of a story.

But therein lies the problem, and that’s what I do feel comfortable writing about: It was one hell of a story.

After ending things, I had what the kids these days (I am the kids) call a “crash out.” Rearranged my bedroom, ran like I was being chased on the treadmill, stared forlornly out to the sea like a sailor waiting for a ship to return home. But this crisis wasn’t over the boy (no offense). He was great—kind, thoughtful, fun, exciting. We can leave it at that. Though this Substack is essentially what brought us together, and #34. “Forget discretion every once in a while and call him up” did actually inspire the phone call; this essay isn’t about him.

It’s about the trouble with fairytales.

Those who have been following along for some time know that I’m no stranger to a saga. You’ve heard about Boat Enquirer, Wedding Boyfriend, and a certain someone from Hat Box Night. And those are just the characters who made the Substack; I’ve mostly held back from sharing details about those I’ve actually dated over the course of this adventure.

But presently I find myself at a bit of a loss because in both scenarios—the fun stories with no legs or the real romances with too much weight—I expected, at some point, a fairytale ending. I’ve long considered myself to be Goldilocks-in-dating, trying on different feelings until one fits.

Funny thing, about Goldilocks. When I make this reference, I assume we all see the same image of a precocious blonde girl wandering into a harmless bear family’s house, tasting porridge, breaking chairs, and testing beds. It’s a delightful cautionary tale about a home invasion designed to help children understand the idea of “just right.” Not just children, actually. This principle—known as the Goldilocks effect—has been applied across disciplines including psychology, economics, biology, astronomy, and love.

There’s not much heavy lifting needed to apply the Goldilocks theory to dating. It’s a dance of too hot, too cold, too big, too small, too much, not enough. The idea is that eventually you find one that is just right and you’re happy (until a group of bears chases you through the woods).

That said, Goldilocks doesn’t live in the “happily ever after” family of fairy tales. Valuable lesson and applicable principle aside, it’s a pretty twisted story, especially when you take into account the original telling of Goldilocks and the Three Bears.

The golden-haired girl romping through the home of a sweet bear family is the second, more palatable edition of Goldilocks. The original version, as written by 19th-century poet Robert Southey, centers on three good-natured, hospitable, fun-time bachelor bears who live in harmony in the woods until one day an evil, selfish, impudent old woman breaks into their house and eats their oatmeal. When they find her, she jumps out of a window and is never seen again. I’m paraphrasing, but you get the idea.

The point is that the fairytale is not always what it seems.

Fairy tales date back 4,000 years, maintained through oral tradition until writers like Southey and the Brothers Grimm (responsible for Cinderella, Rapunzel, Snow White, the Frog Prince, and more) put them on paper. Because they were passed down verbally, it’s difficult to pinpoint when or why these folk tales were first told, but even Wilhelm and Jacob Grimm recognized their history when they set out to preserve this prose in 1812.

Just like the original Goldilocks, the initial versions of the other fairy tales were not cute. They were horrifying—closer to a nightmare than a fantasy. If you want to do a deep dive, I suggest reading Grimms’ Fairy Tales. It’s free on Project Gutenberg. Some bangers in there.

Though the originals are gruesome, they obviously served as fantastic fodder for less intense editions, and the material was molded over time for the masses. Fantasy was spun from fear, and a new dream was sketched with colorful characters and softer smiles. These were the tales that raised us: the ones that taught invaluable life lessons. Follow your heart, talk to mice, kiss amphibians, never trust old women, listen to mirrors, and if a monster locks you in his castle, it’s fine because he’s likely just a hot man waiting to be set free by love.

The other thing in these stories: love conquers all. But what do they teach us about love, really? In Cinderella, we are made to believe the chase is worth the catch, yet we have no idea if the prince and she were compatible beyond basic attraction. Who is he voting for in the mayoral election? What’s his stance on social issues? How many kids does he want? Does he snore?

Fairy tales were never meant to be real. They’ve been warped into the idea that from a big adventure or grand gesture or trial and tribulation, things work out. But I don’t think that’s right, and I’m starting to worry that the mere idea of magic is more hurt than help.

So how does this connect to 129?

As I struggle to put into words why I feel what I feel, all I can come up with is the conclusion that my fascination with fantasy has prevented me from finding anything honest. It seems I’ve gotten caught up in the idea of a good story.

Which is why it’s time to close the book—at least temporarily.

For a long time, this Substack brought, hopefully, a lot of people joy. It certainly did for me. It was so much fun going on these adventures, and this project genuinely changed my life for the better. I’m not walking away forever (DON’T unsubscribe), but I do think that for the time being, I need to step aside and live in the real world for a change.

Instead of doing everything for the story—instead of BEING the story—I just want to figure out what it all means. The great mysteries of life: love and everything in between. Who knows, maybe I’ll keep working through the list and publish the entries for an eventual tell-all.

I’m certainly not going to stop writing, but I am going to stop giving it away. You know that great Nora Ephron quote, “Everything is copy?” That shit is my guiding principle. I live by it. But I’ve come to realize that while everything is copy, sometimes copy needs time to cook.

I didn’t know when I started #34 that this would be my conclusion. The realization came when I was looking through the list and past posts, trying to figure out what was off. For starters, it made me realize that I’m not really DOING the list items for myself, and I haven’t in some time.

In my journey through the 129 archive, I was struck by a conversation I had early on with the owner of Craftsman Ave, a workshop in Brooklyn. I’d just explained the project while trying to finagle a free knife-making class for #3. “Take classes men like.” He laughed and wished me luck. “You’re going to kiss a lot of frogs.”

Was he a witch?! I’m kidding, but also….

This is not to imply the men I’ve kissed have been slimy or green, but it fits with the idea that, from the start, this project was poised to be a pipe dream. It was always larger than life. It was magical; it made me feel magical.

I miss that feeling. I don’t like that I no longer believe in happy endings. The thing is, ironically, I still love fairy tales. The Princess and the Frog is one of my favorite movies. Tangled slaps. Don’t even get me started on Frozen. But those occupy a different place in my heart and mind. They’re not real, and I want to find the magic in my own world.

I could have just gone radio silent on Substack until I was ready to resume. Still, I wanted to write this because 1) I love niche history, 2) I can’t have my few loyal fans worrying, and 3) it’s okay if things change. It’s okay if who we are now is different from who we were when we started. It’s okay to wave a white flag. And it’s okay to keep trying.

While I look for the spirit of 129, I hope everyone who enjoyed this does too. Do weird things, meet unexpected people, live outside the box. See what you learn.

But don’t do it for the fairytale. Just do it for yourself.

I promise I’ll be back. I don’t know what the story will be yet, but I’ll have something to say when I’m ready. It could be sooner than we think—it might be different from before. Honestly, I’m excited to see what writing feels like, and what comes out, when it’s not just for the plot.

So, thank you for everything, and goodbye—for now.

Emily

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It’s been a minute (again). Life—or this time, love—keeps getting in the way. But we’re back, jumping in with #33. “On the first date, tell him you aren’t thinking of getting married.” Seems like a fair enough tip. It’s sensible to wait until date three or four to drop the bomb… well, unless you’re me, because on the first date, marriage definitely comes up. Why? Read on.

October 2024.

It was a crisp fall evening in Williamsburg, Brooklyn. We were eating outside at some Italian place — the food was nice, far nicer than our usual haunts, which consist mostly of boxed mac and pints of Van Leeuwen. We’d just about made our way through a bottle of wine when she started acting weird. A little nervous, a little cagey, like she had something significant to say but didn’t quite know how to get it out.

My palms clammed up as she stumbled through a speech about how long we’d known each other and how much we meant to each other. I looked at her across the table, heart racing against the unknown. I half expected her to get down on one knee when I realized where this was going.

“Emily, will you…”

My breath hitched. Was this really happening? Was she popping the question?

“Marry us?”

And just like that, I was officially the officiant for my best friend’s wedding.

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October 2025.

I write this after just having wrapped what can only be considered a rather relentless marathon of a wedding season: 27 Dresses for the modern age. Four bachelorettes, five weddings, three times a bridesmaid, one time an officiant, eight times a passenger at Chicago O’Hare, and three visits to Park City, Utah.

It was a summer of overwhelming love: of dancing in satin gowns and scarfing down hors d’oeuvres, of crying in black tie and laughing in matching pajamas. Of reconnecting with old friends and making new ones. Of bow ties and bottles. Of chicken or fish.

I struggle to describe these past few months exactly. To start, I’ve never been so exhausted in my entire life. I haven’t spent more than two full weeks in my apartment since July. My bank account is hanging on by a thread, strung up with the help of one full-time job and two side hustles. My body is in shambles, my brain is a puddle, and my heart has never been so full.

Out of sheer necessity, writing took a backseat these past few months. It’s hard to spin something out of nothing when your head is already spinning with flights and fittings, to-dos and too-lates. And now, sitting down for the first time in months with a blank page and a hell of a lot to say, I feel rusty. As Clair de Lune wafts through my headphones (an absolute banger for writing and otherwise) and my phone rests on Do Not Disturb, I realize how long it’s been since I’ve done this. Not just sit and think, but write and feel.

I can finally breathe again.

For months, my life hasn’t really been my own. To my newlywed friends: please know this isn’t a complaint. It’s a choice I made, and I have loved every moment. It’s an unbelievable honor to not only be invited to someone’s big day but also to be asked to play a part in it; to be wanted as a witness to someone’s (hopeful) forever. And, in my case, to be the one to legally make it so.

There’s so much to say about weddings — what they’ve taught me about love, about friendship, about myself. I want to talk about etiquette, the politics of bridesmaidhood, the pressure to be everything for everyone, and the importance of comfortable shoes and espresso martinis. I have feelings about wedding flings (if you’re single) and the meaning of bringing a plus-one (if you’re not).

While I didn’t walk down the aisle in a white dress, I did learn something every time I stepped down the flower-laden path. Thus, though I am not yet married, I have thoughts on marriage. Probably unsurprising coming from the girl working her way through a list called 129 Ways to Get a Husband.

I think I’ll start with officiating.

May 2025.

Right before wedding-palooza officially began, and months after I’d been asked to officiate… it was time to start preparing. The wedding was in late August, so a four-month lead time seemed reasonable.

Because I am me, I didn’t take the role lightly. First order of business: getting ordained. I had to become a minister to marry my best friends. Me, a proud Reform Jew, suddenly turning into a card-carrying member of the church?

I assumed the process would be rigorous — that I’d need a 40-hour course on, well, something. Maybe lessons on the sanctity of marriage, or a test on compatibility and faith. I figured there’d at least be a fee. Whatever the requirements, I was ready to undertake them.

Turns out it’s more work to get a bowhunting license than it is to get the power to marry.

Getting ordained took all of five minutes through a website called the Universal Life Church. I entered my information, clicked a few boxes, and boom! Ordained. The site asked if I wanted to purchase proof of ordination, but my friends assured me that it was a scam.

Still, I didn’t quite believe it. So I went to a different website. No harm in being double-ordained, right? Five minutes later, the American Marriage Ministries had also welcomed me into its holy ranks. With that, I saved my confirmation emails and turned my focus back to bridesmaid dress shopping (a saga that involved tears at three tailors and a last-minute apology to a saintly seamstress, but that’s a story for another Substack).

While being a newly minted member of the clergy was funny in theory, in reality, it threw me for a loop. Religion has been on my mind a lot this year. What it means to a person, how we practice, and the ways it continues to shape even the most secular of rituals. It’s something I didn’t think too much about until this summer; then all at once, the question was everywhere.

Every wedding is its own experiment in belief. Some are deeply religious, others completely agnostic. As I began building a ceremony for Mel and Donny (the bride and groom), I realized that a modern, nonreligious wedding is basically a choose-your-own-adventure game.

For most of my life, I thought marriage and religion were inseparable: the white dress, the three-tier cake, the chuppah, the chapel. Even in the movies, no matter the plot — My Big Fat Greek Wedding, Father of the Bride, Fiddler on the Roof, The Wedding Planner — love and God always seem to share top billing.

But here’s the thing: marriage actually predates religion. The first recorded weddings took place in ancient Mesopotamia over 4,000 years ago. At that time, these unions were treated as contracts, often to secure alliances, property, inheritance, and social stability. In the early days, the emphasis was on security and control. Security for the financial and literal longevity of a lineage, and control for the man to legally exert over the woman.

Of course, one could argue Adam and Eve were the first married couple, but that’s a theological rabbit hole I’m not diving into. The point is that marriage is very old, and until recently (relative to the timeline of humanity), it was a practice of pragmatism and power.

By the 19th century, as women gained independence, marriage started shifting from logic to love. The post-war economic boom of the 1950s helped cement weddings as a status symbol. And in the late 20th and 21st centuries, more and more weddings broke tradition, whether by secularity, size, or style.

Marriage began as a contract, not a sacrament. Yet somewhere between property agreements and Pinterest boards, it evolved from transaction to declaration.

So these days, why do people want to get married?

For some, it’s religion. For others, it’s the thing to do; for a few, it’s to get their grandmother to stop nagging. It’s for health insurance, or a green card, or because you got too drunk in Vegas and won a plastic ring in a game of craps. It’s companionship, a better mortgage rate, a family, a KitchenAid. It’s to not be alone.

As I spent the summer celebrating someone else’s love story over and over, I started asking myself the same question. Why do I want to get married?

For me, a wedding is not about the food, the venue, or the music. Those are important, but they’re not the point. I went to some outrageously incredible weddings this summer, but what stuck had nothing to do with the cost or the glam. At each celebration, it was clear that had the couple done the same thing at a courthouse in Brooklyn and celebrated with pizza in the park, it would have been just as powerful. Time and time again, what stood out was how people showed up for their people and the emotion in each room.

Why do I want to get married? To stand before my closest family and friends and declare my love. To make a promise. To find a partner.

And, to get a KitchenAid.

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August 2025.

After months of agonizing over the meaning of love and the proper structure for the ceremony, I was ready to officiate. Speech finished, dress tailored, bags packed.

Only one thing was missing: government approval to solemnize a marriage in Massachusetts. Womp womp.

I was an hour from leaving for the Cape when I learned my original suspicion about getting ordained too easily was correct. In most states, the online ordination is all you need. Massachusetts, however, has its own set of officiant rules — cue a full-on panic. All this time stressing about getting my words right, I never once considered I could get the actual marrying part wrong.

Within minutes of my horrifying realization, I was on a first-name basis with an online minister from the Universal Life Church who convinced me to overnight the clergy party pack, which not only included my necessary proof of ordination but also a parking pass, a press pass, a bumper sticker, and a personal lanyard. I regret nothing about this purchase.

Soon after, I was on the phone discussing logistics with Elizabeth in the MA Secretary of the Commonwealth’s office. Then Sue and Liney from Sandwich Town Hall, and finally Cheryl, my ride-or-die Falmouth town clerk. These were my Avengers, and boy did they assemble.

You know what they say: It’s not about who you marry, it’s the clerks you meet along the way.

Twenty-four hours later, the necessary forms arrived in Sandwich, MA. And the wedding? Perfect. The ceremony sang (as did the bride and groom). We drunkenly and incorrectly signed the marriage license at midnight (Whoops! This later warranted a phone call from Cheryl in the Falmouth Town Hall).

But before I could even digest the experience, it was time for another wedding, another bridesmaid. Yet somewhere between New York and Northern Michigan, or maybe it was Lake Geneva and Park City, I found time for reflection. The consensus? I am lucky to live through this. Wedding season meant 6 am flights, too much wine, swollen feet, crying in the bathroom, crying down the aisle, crying at the table, crying on the dance floor. It was every emotion all at once, and it was worth it.

October 2025.

I’m on break now. Well, one bachelorette to go in Miami, and then break: at least six months before Season 2 kicks off.

As I lie in bed writing (horizontal mode for the foreseeable future) and slowly begin to reconnect with myself, I feel bone tired, but so grateful. This era won’t last forever, so I want to try to appreciate every moment while it lasts.

That said, I leave you all with this.

The next time someone asks me to marry them, I sure as hell hope it’s for our wedding.

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Hello and happy August! I thought I’d get more editions of 129 out the past few months but summer was summering and…you know how it goes. Hope everyone managed to spend some time outside with loved ones and possibly dolphins, if you went to the sea. Honestly, I did all of us a favor by not publishing so that you could focus on whatever trashy summer read you brought to the beach instead. So, you’re welcome, and now without further ado…we’re back.

List item #32. “Get a hunting license,” presented an interesting challenge.

Since the onset of civilization, women and men have largely been sorted into two respective categories: gatherer and hunter. The anthropological data—presented in such high-brow forms like The Flintstones, The Croods, or the 1981 Ringo Starr star vehicle The Caveman—reinforces this, one fact clear no matter the story: women do not hunt. 

Is that actually true? 

A cursory Google says not. According to a University of Washington and Seattle Pacific University 2023 study, in 79% of the societies for which data exists, women were hunting. The evidence includes a re-examination of the 11,000-year-old remains of a female with a tool found buried under her head. Initially identified as a kitchen tool, upon recent investigation, researchers determined it was a hunting tool. The findings go further. It turns out 30%-50% of prehistoric individuals buried with hunting tools were female, but because of the assumption that such tools are just for men, the bodies had been misclassified as male. 

I could go on. But since this is not a scientific Substack, I will stop. My point is, contrary to what big caveman wants you to believe, women be hunting. 

In the prehistoric era, hunting was survival. In modern history, that’s not the case, so there’s less information on the gender divide of hunters. The most compelling statistics I could find were on the NRA website and I refuse to click on it <3. 

There have been famous contemporary female hunters—Annie Oakley, Karen Blixen, Gertrude Bell, Agnes & Cecily Herbert—but in the context of 1950s women, when the original 129 was published, there’s just not a lot of info.

While it was legal for women in 1958 to attain a hunting license, I struggle to understand how traipsing through the forest with a big gun could possibly land you a date. Unless looking for a bear in a literal sense rather than metaphorical, the great outdoors seems like an unwise place to husband hunt. 

What’s more, as it is no longer a matter of survival (for most), I can’t imagine myself getting on with a sport hunter out there just to shoot a prize. I understand others feel differently (see: The Hunting Wives on Netflix), but this is not their project, and it’s a line I prefer not to cross. 

So, #32. “Get a hunting license" put me in a real pickle. How could I accomplish this task in a way that felt organic, interesting, and ethical? 

It was clear there are two categories of hunting—survival vs. sport. The phrase “husband hunt” also rattled repeatedly through my head. Considering the above, I wondered if I could engage with the material without exchanging my morals. 

According to the Cambridge Dictionary (I liked their version more than Merriam-Webster), to hunt means “to search for something or someone.” No matter the objective—manhunt (criminal), man hunt (romantic), job hunt, house hunt, Easter Egg hunt, game hunt—the implication is the same. It’s the act of pursuit.   

So, I had this epiphany: maybe “everything is hunting,” or… “everything is dating.” Either way, once the dots were connected, it was impossible to unsee. 

It was through this lens that I went about my literal task: #32. “Get a hunting license.” What, you thought I wasn’t going to do it? Come on. 

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Guns are not for me, nor could I get behind killing animals. But what I could stomach was one of the oldest weapons in the book: a bow and arrow. 

Archery was an exciting option. Having grown up on The Hunger Games, The Princess Diaries 2, and Brave, an adeptness at archery screams power and confidence and cool. Plus, in the case of an apocalypse, it’s a genuinely useful skill.

Thus, one night months ago, I grabbed my perpetual partner-in-crime and frequent 129 guest star Annamarie, and we headed to Gotham Archery in Gowanus for an Introductory Class. We marveled at the facility. Bowling alley length lanes lined the cavernous hall. Archers of all shapes, sizes, and skills held the back line as their arrows zinged toward the target. Music blared. Regulars lounged in the seating area, while others perused merch by the front desk. 

As for Anna and me, we were relegated to the back room for training. Our strapping and sarcastic instructor, whom I shall call Arrow Andy, walked us through the basics: the merits of a compound bow vs. a crossbow; how to shoot and how to aim; the right way to stand and the wrong way to retrieve. 

By the end of the clinic, our arms were covered in welts, our target sheets tattered with holes, but we had passed the class. We strutted down the empty streets of Brooklyn with bright smiles, thrilled we could come back and shoot whenever.  

(Have we been back since? No, but it’s nice to know the option exists.)

Here’s the thing: hitting a paper target in Gowanus is not the same as being licensed to hunt in New York. The original #32 wasn’t “Try archery one time”; it was “Get a hunting license.” And a hunting license requires proof you’ve taken a state-approved certification course…which is how weeks later, I found myself at my laptop, staring down a 20-hour, $30 online Bowhunter Safety Education class.

If you’d asked me 10 hours in, I would have said it was a fruitless, futile activity; a complete waste of energy and money for someone with no intention of hunting an animal. But around hour 11, after I’d spent an absurd amount of time learning bowhunting history, the benefits, the challenges, and forcing my eyes to focus on very low-fi video tutorials courtesy of the New York State Parks department, something interesting happened. 

I reached the Ethics section. Lessons on how to be a respectful hunter and protect from harm. With every slide, the parallels become more and more evident. It hit me like an arrow, square in the chest (that is the kill shot, FYI). 

The Bowhunter’s Guide to Ethics could—and should—be applied to dating.

In fact, as I finished the course, passed the 80-question test, and marveled at my certification card, I couldn’t help but wonder if perhaps every new dater should also have to go through a training. Learn the rules of the game before you can play. Understand the risk, the reward, the cost, the benefit. Force everyone to be a card carrying Dater to show they’ve put a little thought into the task. 

This is by no means an online course complete with animations and interactive tests, but it’s a start. Without further ado, I present my field notes from the Official New York Bowhunter Safety Course…modified. 

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The DATER’S GUIDE TO ETHICAL HUNTING

Annotated with notes from the field 

Your ethical code doesn’t just happen all by itself. Consider how you’d feel after acting on a decision—would you feel proud or ashamed? And how would it affect other people? 

DATER’S GUIDE: If you’d feel ashamed for something you’re doing romantically either to yourself or someone else, probably don’t do it. 

To make ethics work for you, there are three steps to follow:

STEP #1: Realize that there are moral decisions to make, such as: “Should I shoot now and risk merely wounding the game, or should I wait for a better shot?”

DATER’S GUIDE: Know when to shoot your shot—don’t just blindly throw arrows. Make it intentional, and make it matter. 

STEP #2: Think of consequences of decisions and how they might affect you and others.

DATER’S GUIDE: Consequences, my friends! They’re real! 

STEP #3: Do the right thing. 

DATER’S GUIDE: Spike Lee said it, the Bowhunter Education Course said it, a poster in your high school homeroom said it. Do the right thing. 

That sounds simple; in real life, however, few answers are black and white. Laws are everything you must and must not do; ethics are the things you should and should not do…

The DATER’S RULES FOR ETHICAL HUNTING

Once again, annotated with notes from the field

RULE #1: Know and respect your personal limitations. Some limitations can be improved with a little effort.  

DATER’S GUIDE: Everyone has flaws. Embrace them, accept them, and don’t overcompensate. We can tell. No amount of Omakase can cover it up :)

RULE #2: Respect your equipment.

DATER’S GUIDE: YOU are your equipment! Self-respect is endlessly important when it comes to dating. We teach people how to treat us. It’s easy to lose a bit of respect in the name of a good hunt, but at the end of the game, if you give it up, you’ll be left worse for wear, scuffed and sad. Take care of yourself.   

RULE #3: Respect the property of the landowner and treat it as if it were your own. 

DATER’S GUIDE: If you’re at a bar on a date, don’t smash bottles. And if you go to someone’s apartment, maybe don’t steal their shit? 

RULE #4: Respect game animals and resources. Observing and learning about all wildlife can be an enjoyable educational experience, as well as a way to build confidence needed for the hunt.

DATER’S GUIDE: It’s never a bad idea to learn about the person you’re seeing. If they say they love a book, read it. If they have a favorite food, try it. If they’re from a culture different from your own, embrace it.

Or if they say where they work, follow them and stand outside their office with a magazine in front of your face Joe-from-You style, observing their every move so you know their coffee order, their coworkers, their train stop. 

But don’t stalk them, or anything. 

RULE #5: Respect your companions. Four key ways to maintain friendships on a hunt:

Shared values.

DATER’S GUIDE: Can’t align on key issues, can’t build a life together. 

Dependability.

DATER’S GUIDE: Can they plan? Do they show up when they say they’re going to? Do you feel anxious and confused, or safe and secure? 

Courtesy.

DATER’S GUIDE: How do they treat the server? Are they kind to strangers? Do they open doors for you, or let them hit you on the way out?

Communication.

DATER’S GUIDE: If you got caught in a zombie attack, could you effectively discuss and carry out an attack strategy? Food for thought.

RULE #6: The rule of first blood. The “rule of first blood” establishes a fair way to determine who can claim an animal that has been shot by two hunters.

DATER’S GUIDE: There’s a reason there have been countless rom-coms written about this very scenario. Well not THIS scenario, but two people falling for the same person. Honor who was there first.

Yes, of course there are exceptions to this—it’s circumstantial, situational, you can’t fight a feeling. But if someone calls dibs, just give it to them. Your hunting partner is more important than a random shot. 

RULE #7: Know how arrows kill. Shoot in the vital area—the heart or the lungs. A shot in the spine or from the back can lead to a slow, painful death.

DATER’S GUIDE: What if the arrow strikes and it’s a match? There’s a reason Cupid uses a quiver. If you get things right, a single shot in the heart is all it takes. One way or another, it’s quick. You know.

As the blade pierces into the soul, some version of you dies—the single one, the hungry one, the infatuated one—in place of something new. Even if the shot is a kill: you don’t get the boy, the job, the buck, it’s still an ending. 

A shot in the lungs is different, but powerful. It takes your breath away. 

And then there’s the miss. The gut punch, the blind side, the spine shot. It’s a cut you didn’t see coming, it’s an unexpected attack, and it’s slow and it’s painful. No one tries to hit where it hurts, but it happens.

RULE #8: Bowhunting (and dating) involves in a considerable amount of risk. To prepare for this, you should: 

Be in good health.

DATER’S GUIDE: Mental health matters! Call your therapist!

Prepare a hunting plan and make sure others know where you are.

DATER’S GUIDE: Share that location and have your friends check-in.

Use protection.

DATER’S GUIDE: Duh.

Know first aid.

DATER’S GUIDE: Be ready patch yourself up. Apply pressure to the wound to stop the bleed.

There’s risk in everything. That’s the beauty of life—you’ll gain nothing if you’re unwilling to lose something. You could fall out of a tree (who hasn’t fallen hard, once or twice). You could get hypothermia (nothing like a slow freeze out, eh?). You could choose rotten meat. But it’s part of the process. You can’t bag a big game—or a big love—from the safety of a camp. 

RULE #9: Know what to do when you think you are lost. When you find yourself in a survival situation, the most important tool is your brain. And be sure to just S.T.O.P. 

Stop when you realize you've got a problem.

DATER’S GUIDE: The hardest thing to admit is when you’re in trouble; it’s even harder to accept that it’s not working. 

Think about what you need to do to survive.

DATER’S GUIDE: Can you make it through? 

Observe the area; and look for shelter, fuel, etc.

DATER’S GUIDE: Stock up on snacks, Kleenex, movies, friends, and wine. Lots of wine. So much wine.  

Plan how you are going to use your survival kits. Don’t wait until dark to plan!

DATER’S GUIDE: It might end. Prepare for the worst, and hope for the best. 

Remain calm. Think clearly. Use the tools you have available to you.

DATER’S GUIDE: When your brain won’t stop buzzing, your heart hurts, you’re exhausted, you don’t want to keep searching—the only option is to move forward. You have to keep pushing and trust that you will be okay.

It might be a long journey. That’s fine. It can take a while to get out of the woods. 

If you’ve gotten this far, congratulations! You’ve completed the Dater’s Guide to Ethical Hunting. If you want a certification, feel free to doctor my official Bowhunting one. That’s all I’ve got for this one.

And remember: women be hunting!

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As I thought about #31. “If you’re at a resort, have the bellboy page you,” a specific hotel popped into my head. It doesn't have a bellboy, and calling it a resort requires a healthy dose of irony. But it is a place I have a connection to, an establishment tied to love, and an institution that recently paged me. So we’re going to go with it.

Three-ish years ago, I stumbled on an article from The New York Times. The headline read: “For Sale: The ‘Sexiest’ Hourly Rate Hotel in Manhattan.” The hero image featured a bed with one set of giant, cherry-red, LED-lit lips serving as a headboard. The copy was enough to grab my attention, but the photo was what kept me reading. What kind of place had lips as part of the key decor?

The answer is, of course, somewhat obvious: a quickie motel.

Located at 51 Tenth Avenue, The Liberty Inn occupied a three-story building in the Meatpacking District. The structure had been in operation as a hotel since 1908, although in the early days it was known as “The Strand,” primarily used for sailors (and, in 1912, journalists from The New York Times covering the arrival of Titanic survivors at Pier 54). In the early 1970s, it became known as the “Hide-a-way,” and then in 1977, it was renamed the “Liberty Inn,” a moniker that would stick around for some 50 years. That same decade, the first floor was leased to entrepreneurs who opened “The Anvil,” a gay nightclub that featured clientele such as Warhol and Capote.

In 1985, The Anvil shut down, and the first floor was converted into hotel suites.

At some point, the guests went from sailors, truckers, meatpackers, and salesmen to folks with a significantly different modus operandi. By the 1990s, the Liberty Inn was frequented by everyone from college students to retirees, couples, and businessmen taking an off-the-books lunch. No matter who they were, most came to the Liberty with a specific activity in mind.

It was, as this piece in the New York Review of Architecture aptly put it, a “cheater’s paradise.”

And then, in July 2023, the Liberty Inn was sold for a whopping $22.5 million. Which brings us to the present day and, unless they plan on making a radical business pivot, it’s doubtful the new owners — Hyundai Motor America — will be using the building for its previous purpose.

It was also in July 2023, around the same time the Liberty was sold, that I was sitting in a circle on a plastic chair in an art gallery in Bushwick discussing a new play with a group of actors and a director. The play in question was my own, titled At The Liberty Inn.

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October 2022: I had just wrapped the World Premiere production of before the flood, a play that had taken over my heart and head for the better part of a year. I was working as a “Wordsmith” at a fintech startup, making more money than I knew my little writer brain could earn. I’d moved to a Greenpoint apartment with new roommates and endless possibilities. And I was dating someone nice, who I maybe hated, but who wanted to sweep me off my feet in all the right ways, so I went with it. I also happened to read the NYT article about the Liberty.

Things were good. And, eager to start my follow-up to before the flood, I noodled on the idea of a play set inside a quickie motel. before the flood had a large cast, and the script called for a literal Noah’s Ark-style flood on stage. It was a challenging production to stage and produce (though my brilliant director and producer, Nina Goodheart, managed to create a spectacular show regardless). Putting on that play was the greatest career achievement I’d ever had, and it was what gave me the (perhaps unearned) confidence to pursue being a playwright.

For my next trick, I wanted to do something simpler. So I thought a two-person play set in a motel room — the Liberty Inn — might be a manageable follow-up.

But before I could get past a one-sentence idea in a notes app, life fell apart. I’ve written about this moment before; when everything changed, when shit hit the fan, when the good got bad. In a matter of months, I was dumped by the boy, eliminated from the tech job, and spiraling. At one point, things got so rough that I tried to adopt a cat, and was subsequently forced to give it away a week later.

I was lost.

Yet through all the chaos, through all the uncertainty, through all the pain, there was one thing that stuck around: writing.

I’ve always thought the most beautiful thing about being a writer is that no one can take it away from you. Regardless of how one defines success, the actual act of creating — of sitting down and putting pen to paper (let’s be realistic, fingers to keys) — is entirely in control of the creator. Writing can’t ghost you; it can’t let you down; it can’t terminate your employment or hurt your feelings. Even in the darkest moments, writing will always be there to light the way.

In those difficult months following the end of 2022, writing was all I had.

When I wrote the first draft of At The Liberty Inn, I was angry and looking for villains to blame. I found one in the character of Raf, a lazily-drawn caricature of the boy who I was certain had ripped out my heart. Working on the play became my therapy (which was good, because with no insurance at the time, I couldn’t afford an actual provider). The piece came to fruition as a story about a couple in a toxic situationship who break up at a quickie motel. As the couple — Raf and Katie (a lazily-drawn caricature of myself) — avoid the end, they jump into different role-play scenarios of who they could be in this room, only to discover they don’t work no matter who, what, or when they are.

I was sure that completing this would be my escape route. I talked myself into believing that if I could get the play right, everything would fall back into place.

Now, imagine my surprise when the piece was read in plastic chairs in a circle in an art gallery in Bushwick, and it didn’t solve all of my problems. In fact, it only made them worse. The play wasn’t ready… it wasn’t close. It was, like me, a mess. That’s disappointing in and of itself, but worse, I felt betrayed by the very thing I thought could never hurt me: writing. I had let myself down.

After the 2023 reading, I not only shelved At The Liberty Inn, but also my larger playwriting dreams. It was too hard and I was scared to keep trying. So I pivoted to other mediums: this Substack, copywriting, freelance articles, all of which I love doing. I put my life back together and myself in the process.

At some point in the two years between the Bushwick reading and now, I grew up. I learned more about dating, love, and actual heartbreak. I found my voice. I honed my skills.

When I wasn’t looking, in a way I didn’t expect, I changed. And I didn’t realize just how much until I was forced to confront the girl I’d been two years prior.

I had all but erased Liberty Inn from my mind until February 2025, when Cameron King, the fantastic director who’d hosted the Bushwick reading in 2023, asked if I’d revive the piece for a new play festival in June. It would be presented as a staged reading: not a full performance, but with an audience, a stage, and tickets. A bit stunned, I said yes and fished out the old draft, knowing I’d have to do rewrites and eager to procrastinate them as long as possible.

I pretended it wasn’t real until I saw the announcement in BroadwayWorld in late May. Whoops! In hindsight, I’d been avoiding it. The play was written during a painful time, filled with painful memories, and I was scared of what might happen if we reconnected.

It felt like an ex, and I had to check back in.

Rereading the piece was jarring, to put it mildly. It was like revisiting a version of me I no longer knew and certainly no longer was. This would become a theme of the revised play — the sensation of looking at your body of work and feeling like a stranger. The 2023 draft was written by someone who lacked confidence and had a limited perspective on love and relationships. I didn’t realize how naive I was until I read it and found myself wondering… What was I thinking then? I still had so much left to learn.

In the rewrite, I was able to appreciate the chaotic journey of the last few years and everything it had taught me: about love, professionalism, writing, adulthood, basic grammar (SAT tutoring paid off in more ways than expected). Finally, I understood what it had all been for. I was glad I had stepped away, and I was happy to return.

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The week before the 2025 Liberty Inn reading, I took a walk down memory lane: picking up binders for scripts at the Broadway Green Alliance (BGA has a binder recycling program that all theatre makers should take advantage of); pouring over lines of dialogue and scribbling notes like a madwoman in an eclectic downtown rehearsal space; being genuinely floored by the price of printing at a FedEx at 7:00 AM; doing rewrite after rewrite after rewrite. All of it was familiar, reminiscent of the before the flood days… but I was different.

And then it was showtime. And then I was petrified.

Heading to the theater kind of felt like going on a first date. The stakes are low because you haven’t put too much into it yet. But there’s still an investment. There’s significant risk and potential reward.

In the case of the reading, people paid for tickets. Our actors — the incredibly talented Jesse Aaronson and Annamarie Kasper — gave up their time. Cameron worked her butt off. And I spent countless late nights and weekends with this text, massaging it into something honest and fresh.

In the frenetic days leading up to the “show,” I actually left parties early because I was “excited to go home to my play.” And god, that felt great. Writing was for me again. Warm, safe, joyful, and loyal. I knew that, no matter what happened with the reading, revisiting Liberty Inn reminded me why I love what I have the honor of doing. There’s a magic to creating something from nothing, to letting your brain run free and seeing what comes out. It’s a thrill to map real life over fictional characters and ask big questions.

In At The Liberty Inn, the thesis asks if it’s possible to love something or someone even when you know it’s not right for you. It investigates why we stay and when we run. The power that the past can hold over us, and the intricacies of intimacy.

It’s a play about play, but it’s also just a play about people.

What gripped me about the Liberty Inn, the place, when I first read about it in the New York Times, was the idea that these kitschy little motel rooms, with no bellboys in sight, could hold more history and heart than we might ever know.

I was struck by the idea that just as a hotel can be sold and still retain its meaning, while people move on, grow up, and change, we never forget the moments and memories that have shaped us. I often wonder if exes see certain city spots the same way we do; if they remember the bench where you had your first kiss, the stoop where you had your first fight, or the subway station where you saw each other last. I have to imagine they do, if it matters at all.

It’s certainly the case for me.

So to the boys who broke my heart, I say: thanks for the material!

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The reading went well. Really well. Truthfully, I had no idea if people would like the play. I wasn’t sure if it was any good; I wasn’t sure if I was any good. After the lights went down, I hid at the back of the house and watched through slats in the risers, chest racing and palms sweating, heart leaping at every laugh, gasp, and guffaw.

Afterwards, I went around the corner to a bar in Midtown with the team and friends who had come to the show. As the dust settled and the nerves wore off, I reveled in the result. It turned out people liked it. It moved them. It made them think. It made them question. And there’s still work to do, but that feeling… that felt great.

And so, playwriting and I are going to give it another shot. Who would’ve thunk, huh? #31. “If you’re at a resort, have the bellboy page you,” made me get back together with my ex. Hope we don’t break up again.

It’s a Sunday in summer 2024. I’m sitting hand-in-hand on the airport bus with a boy I met at a weekend wedding, and we’re counting down the seconds to goodbye as the distance closes between Terminal 2 and Terminal 3.

We’d met at the welcome party that Friday, danced at the Saturday celebration, and spent Sunday morning together on a road trip down the Southern California coast, complete with sugary pancakes, breathtaking views, and panic-inducing traffic. Now, off to separate cities, our time together was ending. We both knew what it was: a wedding whirlwind. With an ocean between us, it was pre-determined that there was no future, yet still…there was a connection, a feeling, a spark strong enough to think we may want to keep the conversation going.

A fleeting kiss as the bus pulls up to my terminal, an awkward salute through the window as it drives to the next, and then he’s gone, leaving me with nothing but delusion and the excitement of possibility.

I knew he wasn’t looking for long distance. And, even though I knew it was crazy to think this would be anything other than a fling, I also knew I’d see him again. A wiser woman would have just left it, let the story end at LAX Terminal 3. But I’m not very wise. I’m hopeful to a fault, rom-com-addled brain always looking for a reason to believe in the unbelievable.

And so as my plane shot off into the sky and I watched the world shrink through a window, a singular question ran through my head: What if it works out?

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In some ways, this story satisfies the list item “Ride the airport bus back and forth,” but that’s merely a happy coincidence for #29. “On a plane, train, or bus, don’t sit next to a woman—sit next to a man.” I didn’t plan to write about my Wedding Boyfriend when I set out to tell tales of meeting in transit. But I’ll admit, driving along the Pacific Coast Highway months ago, somewhere between Carpinteria and Oxnard, the thought crossed my mind. I was pleased with the spontaneity of the situation and wondered what, if anything, would come of it.

Still, I wasn’t thinking about that weekend when I began this essay. The only thing on my mind was Rosalie Porter, a spitfire with a transit-related love story worthy of a thousand words. I was marveling over her great romance: one that spanned distance and decades, took place over telegrams and on transatlantic ocean liners, persevered through the wrong partners and the right risks. I was thinking about how hers was a story that worked out… and I couldn’t bring myself to write it.

I didn’t know why, but I was blocked. So I stalled and requested as many motion-induced meet-cutes as I could source. It wasn’t until I talked to my friend Mia about missing her shot with Milo Ventimiglia after a run-in on the subway that a central theme crystallized.

Almost everyone has a story about connecting with someone in transit, but what unifies them all—and what was missing from my essay—was not the method of meeting. It was the nature of the event itself: random, spontaneous, surprising. The sense of adventure, excitement, the very feeling that made my heart flutter on the airport shuttle. Despite the odds, one wonders if the relationship will continue after the bus stops, the plane lands, the boat docks.

It’s less about what happens when you meet in transit and more a question of what comes next.

Enter Rosalie.

Rosalie Pedalino was 22 when she got on the Europe-bound ship that would change her life. It was 1953, and the young woman from Orange, New Jersey, had not been abroad since immigrating to the States from Italy at age six. Given the era, this is hardly surprising. Her teenage years were defined by WWII and its aftermath as countries rebuilt and recovered. A jaunt around the world wasn’t exactly plausible.

But then came the boom. The 1950s brought prosperity, hope, babies, more war, and some peace. It was an era full of contradictions: economic growth (rampant capitalism driving a wealth gap), the expansion of suburbia (redlining and the onset of Levittowns), and, of course, the iconic American family (sexism and the confining of American women that ultimately led to second-wave feminism). For many American women, the world simultaneously got much larger and far smaller than before. The traditional trajectory was simple. Find a husband by whatever means necessary (see 129 Ways), get married, and have children.

Rosalie was on that path. She’d planned a European adventure with her best friend Blanche and was all set to go when her long-time sweetheart—local banker Frank Ward—proposed marriage. She accepted and went on the trip.

The two young women set out for Europe. Blanche by sky, a newly engaged Rosalie by sea.

Rosalie met David Porter on her first day of the voyage. It was 4:00 p.m.—tea time. She was alone and eager for a companion. “I go up to the big lounge, and I look over the room, and I see a very handsome young man sitting with a newspaper.” She wistfully recollected. “And so I stroll over there, sit down, and say, ‘When you're finished with your newspaper, may I have the crossword puzzle?’ Well, he looks up at me, and he says, ‘Of course.’”

They started chatting.

David was bound for Istanbul, where he would teach at Robert College. Rosalie was engaged to Frank back in New Jersey. There was no way it would work out.

So in the beginning, they were merely adventurous friends with a motley crew of travelers. “We're on the ship nine days, and young people from all over the country are sailing to Europe,” Rosalie continued. “And it was nine days of partying. There were Smith College students. There were young business people. And all we did was have a lot of fun.”

“Orchestras played, and there was dancing every night. There were wonderful dinners, cocktail parties, tea parties. There were three swimming pools on the ship. And when we've been drinking and carrying on until two in the morning, we would go out on deck, and we would jump in the pool with all our clothes on.”

At the end of nine days, the boat docked, Rosalie met Blanche in Italy, and David headed off to Turkey. Logically, that was the end of David Porter, but even so…

She thought they might keep in touch.

What if it works out? It's 2019. Liz is on a flight from Berlin to London for a work trip. She’s seated next to a strapping young gentleman. They hit it off. She’s heard this story before—her ex’s parents met on a plane—and is hopeful as the aircraft takes off. The first hour goes great, a perfect date at 10,000 feet… and then he gets political. In a bad way. The descent turns into a debate as Liz curses herself for ever engaging with a man while locked into a seat in the sky. The next time she flies, she keeps her headphones in.

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Rosalie and Blanche had been racing around Europe when a telegram arrived from David Porter. “Come to Istanbul.”

It’s easy to imagine: Rosalie holding the telegram, staring at Blanche. What if? Blanche looking at Rosalie. Why not? They made the impulse decision to cut Switzerland out of their tour and instead fly to Turkey, a place entirely foreign for a young American woman to visit. Eager for experience, they weren’t phased by the exotic location. Perhaps it was even what made the trip enticing. A week-long tour of the country ensued as David and friends hosted the women.

By now, Rosalie had decided to call off her engagement to Frank Ward. Not because of David, but because she had decided it wasn't a good match. She had seen the world and realized she wanted a bigger life than he could offer.

As for David Porter, “At that time, I saw David as a terrific guy who was fun, handsome, very bright, a friend for a fling—no serious ideas.”

It’s a tale as old as time. There was a connection, they both felt it, and knew there was no future. The best they could hope for was friendship, right?

So, they said their goodbyes. David told Rosalie, "When I get back to the U.S. in a few years, I'll want to see you—even if you're married and have half a dozen kids."

They promised to keep in touch.

What if it works out? It’s 2014. Francesca is 19 and commuting into the city from New Jersey for class at NYU. She’s on a bus at Port Authority waiting to go home when he boards. Bus Man. She notices him the second he steps on; he does the same. What if he sits next to me? She nervously frets, her heart racing as he moves down the aisle and plops in the empty seat to her right. Exactly where she wants him.

Neither puts headphones in; both are trying to figure out what to say. She spends minutes searching for gum, working up the guts to start a conversation, when he takes the plunge and asks her a question. They talk the entire ride home.

At their final destination, names—not numbers—are exchanged. But it’s 2014 and Facebook is still cool, so Francesca sends a friend request. Almost immediately, he messages her.

They date for four years. It didn’t last forever, but it lasted for long enough. “Love can happen on New Jersey transit,” Francesca commented. “I remember having this feeling of like, ‘I could be sitting next to my husband and if I don’t do anything about it then I could miss out.’ Good general life advice [is] to just do the thing. You never know.”

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With David and Turkey behind her, Rosalie boards a Boeing Stratocruiser from Rome to Paris, the last leg of her six-week trip abroad. In search of a cocktail, she heads to the first-class cabin bar and strikes up a conversation with Colin Cagnacci, a charming young Australian on an extended business trip. One thing leads to another, and soon they’re dating around the world, dancing in Paris, London, and New York.

Back in New Jersey, Rosalie officially ends things with Frank and begins dating Colin—an engineer living and working in Pakistan—long-distance. Soon, he proposes, and she accepts.

They plan to marry in the States the following year, after which Rosalie will move to Pakistan. “I think that's half the reason I fell in love with him,” she said. “‘We will live in that country, and I will start writing.’ Well, it went on for about a year, and little by little, I became disenchanted.”

Once again, something in Rosalie had shifted—she knew she was searching for more than the man she met on an airplane somewhere over France. Rosalie mails Colin’s ring back and ends the engagement.

And then she takes the world into her hands. Literally. Rosalie becomes a Pan Am stewardess and continues to travel, adventuring on her own terms. She feels free.

Rosalie and David Porter still keep in touch.

What if it works out? It’s February 2023, and Malia is on a NW train bound for Penn Station. She’s going home to watch the Superbowl with her mom and running late. An early morning at work caused her to drag her feet and miss the afternoon bus. But she’s finally on her way.

The night before, Malia had received an Instagram follow request from her crush Zack, whom she’d been trading likes with on TikTok for months. She’d raced in to tell her roommate, Macy, about the development. Sure, it was an internet infatuation, but it meant something, right?

As the NW stops at 5th Avenue, Malia looks up at the closing doors. Her heart misses a beat. Walking on is no one other than Zack.

In disbelief, she looks away, nervous. No way. “Out of all of the subways, out of all the stations, out of all the subway cars, he’s on mine the next day?” The train starts moving as he cautiously raises a hand to wave at her. “Are you Malia?” He asks. “Yeah! …Are you Zack?” They beam at each other. He joins her on the bench as they dive into earnest conversation.

The train ride only lasted four stops, but it didn’t matter. They knew this was the beginning of something much bigger than a single subway ride.

Two weeks later, Malia and Zack meet for coffee. The rest is history.

Interestingly, as their relationship unfolded, they realized they’d spent years just missing each other: in neighborhoods, with mutual friends, on trains. “Our paths were parallel for so long, and then all of a sudden, one day, both of our paths just crossed, and that’s the way that we are now. We’re together.” She remarked fondly. “The right person could always be the right person, but if you don’t meet them at the right time, it might not work out the way it was meant to.”

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It’s September 1956. David Porter is home from teaching in Turkey, now in the army, and is on leave. He gives Rosalie a call. It doesn’t take long for each to realize how deeply they care for one another. An engagement is planned. After years of passing ships, they have finally docked: they’re both single and in the right place at the right time.

But then… it falls apart as quickly as it came together. “On talking with my local priest about a marriage ceremony, we discover serious religious differences—so difficult to resolve that we break up.” David returns to his army base, and Rosalie goes back to Pan Am.

The engagement is off.

What if it doesn’t work out? I’m an ocean away from New York, at dinner with the man I met at a wedding several moons before. I’m nervous. What felt like months of talking had led to this meal. What would happen now? I babbled away, sharing flight details and playing with the remnants of my Sunday roast. Where do we go after this? Had it all been in my head, was I delusional, or was there possibly—

“I’m so glad we were on the same page,” he reached across the table and looked at me earnestly. “About what this was.” I cleared my throat and finished the last of my wine.

We didn’t keep in touch.

A single Rosalie is en route to Washington, D.C., to visit Blanche and her husband. It’s 1957. Rosalie is an older and wiser woman than the 22-year-old who got on a boat to Europe in 1953. She’s well-traveled and sure of herself.

She knows what she wants.

Unwilling to let a good thing go, Rosalie reaches out to David, who is now in D.C. for the summer and preparing to return to Istanbul to teach.

They meet again; this time, it’s end game. Now or never. David proposes. Rosalie accepts. Ten days later, the newlyweds leave for Istanbul.

They adventure together for 56 years, until David’s death in 2013.

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Malia and Zack are still together, and they still ride the NW. “Any time we’re taking the train, we always give each other a kiss and tell each other we love each other when we get to 5th Ave. When we aren’t together, we’ll text each other every once in a while and just say, “5th Ave ❤️.”

Rosalie and David had three sons. Eventually, they moved back from Istanbul to the States. Rosalie went on to get her degree, then her doctorate. She traveled the world consulting and was able to achieve all she had dreamed of: finding a life partner, becoming a parent, and pursuing a career as a writer and activist. Rosalie has lived a life full of stories, but I’ll let her tell the rest. Her book American Immigrant: My Life in Three Languages is linked.

Francesca graduated from NYU, got off of Facebook, onto Hinge, and found someone new. She’s still in New Jersey, but moving to San Francisco next year.

Liz is talking to people on planes again, but she keeps her headphones close by in case the conversation takes a turn for the uncomfortable.

And as for me, I am still waiting, wishing, wondering when—not if—it’ll work out. I’m trying to sit next to more handsome strangers while in transit and hoping if a conversation inspires, it’ll be more Before Sunrise and less Strangers on a Train.

The tales I’ve heard are inspiring, regardless of their outcome. I’m endlessly grateful to all who shared their little love stories, but especially Rosalie, who reminded me of the merit and power in pursuing a big, bold life. To trust your gut, not settle for anything less than magic, and know that things will be okay.

Time changes how we keep in touch; a telegram in 1953 might be a TikTok DM in 2025, but the sentiment is the same. All it takes is a chance meeting to spark something special. It’s the right place, the right time, and the right person. The rest will figure itself out.

When Rosalie first saw David in 1953, she thought, “Let me go see. It was an instant of impulse, never thinking that anything would come of it, of course.”

What if it works out? It doesn’t until one day, it does.

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The economy. It’s all anyone talks about these days. The reason? It’s bad. Eggs are expensive, stocks are in free fall, Forever 21 is bankrupt (again). It seems like we’re staying afloat—the canary in the 21st-century economic coal mine will sing when the Costco hot dog costs more than $1.50—but still, holes are springing up all over the boat, and water is starting to pour in.

I know what you’re thinking. “Emily, you are no economist, back in your lane.” Or, “This Substack is about dating and adventures! If I wanted a panic attack I’d turn on MSNBC.” Or maybe even, “Didn’t you get an E in accounting?”

These are valid points. My rebuttal (to the imaginary mob coming for my financial credibility) is that dating and the economy are inherently intertwined. One might argue they go hand in hand.

According to MassMutual.com, “The average American spends roughly $168 per month—or $121,000 during the course of their lifetime dating.” This was from 2022, so we can imagine that just like the cost of living, this number has increased. In that same article, a poll by MassMutual (they didn’t pay me for this, I promise) revealed that nearly one-third (29%) of singles said their financial situation had deterred them from dating or getting in a relationship. Young adults (41% of millennials) were most likely to indicate that their finances kept them from dating seriously.

The financials of dating are astounding. Think about drinks alone: in New York, a cocktail goes for $24, and if it's a good night, you’re not just having one. To be actively going on first, second, and third dates—which may or may not turn into anything—and continuously pulling out all the stops, giving the old razzle dazzle at every bar and restaurant in town, can be financially and literally exhausting.

So how can you make romance feel special in a city (and an economy) that gets more and more costly by the day?

Behold, #28. “Show him you can have fun on a cheap date—but don’t overdo it!”

Think of this as a Choose-Your-Own-Adventure to a perfect inexpensive date. If you’re not in New York, you can use this template and sub in options for your own city. Feel free to start at any given time, but this is technically intended to be done from 11:00 am to 11:00 pm, Broad City style. Just because you’re on a budget doesn’t mean you can’t ball out for a 12-hour day! So ignore the part about not overdoing it. This definitely does, and it’s worth it. Without further ado…

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A CHEAP DATE

11:00 am

Coffee in the park (winter alt: a hotel lobby, ideally with a fireplace). If you’re really trying to achieve zero spend, suggest a location within walking distance of your apartment, otherwise MTA will hit you with a fat $2.90.

As for the drinks, send your date a gushing text about your new coffee maker and beg them to let you bring a freshly brewed espresso. They’ll jump at the offer and see you as someone who is not only budget-savvy but also a responsible adult. That’s hot!

A quick financial heads up: you’ll need to get reusable cups, espresso beans, specialty milk, a flavored syrup if you’re classy, and if you don’t own an espresso machine, they start around $30 (Bialetti Moka Express) and run up to around $5,900 (La Marzocco Linea Mini).

After coffee, take a walk in the park (or around the hotel lobby).

1:00 pm

Omg… that went so well! Time flew and now you’re hungry—or is that just butterflies? Either way, a bite seems like the next reasonable activity. But it’s certainly not the cheapest.

Unless you’re RICH, here’s what you do next:

Quickly develop a street act (two-person show, close-up magic, singing either very well or so badly people pay you to stop, or finding Billy Eichner mid-episode of Billy on the Street and get a “for a dollar!” question right.) Spend no more than thirty minutes rehearsing, then parlay your talent into somewhere between $15 and $20. Quit after that—not because you’re not good enough, you’ve got a real future, but because you have a date to dine with! Eyes on the prize!

Eating out is unquestionably expensive in New York, but there are ways to do it inexpensively. Often some of the best food costs the least. Many of The New York Times Best 100 Restaurants feature menus where two could reasonably get a meal for under $20. Take, for example, #10: La Piraña Lechonera, a Puerto Rican restaurant run out of a trailer in the Bronx, offering pork and rice for $14. If you’re not a purveyor of the Times, hop down to Chinatown and wander into a Dim Sum spot with dumplings for a few dollars. And then, of course, there’s the classic dollar slice—actually somewhere between $1.50 and $2.00—but still a steal.

If all else fails, head to the two-story Burger King in FiDi. On the right day you could stumble into a writing workshop hosted by Dream Baby Press. A few kids meals should be on budget. Plus, you get a toy!

Another financial heads up: At some point, you may need to use transit to get around. That’s life. Factor that into your funds.

3:00 pm

The food was fast; the meal was not. You picked over scraps while staring into each other’s eyes, getting deeper and deeper into the date. Now at hour four, you could call it and make plans to see each other again soon. That would be perfectly acceptable. Normal, even.

Not everyone is normal. Onward.

By now, you know each other well enough to engage in some gameplay. Hey! Get your head out of the gutter! You’re going to a vintage and/or thrift store for a movie montage dress-up. Nothing more.

In any given neighborhood, you could throw a penny and hit a thrift shop. And if it landed inside, they’d probably resell that penny as a “vintage street coin” for $5. And I’d probably buy it!

New York City thrift shops are a true treasure trove. I’ve heard that the Goodwill on Upper East carries designer bags, and the Housing Works Park Slope is a coverall lover’s dream. Urban Jungle in Bushwick offers everything from cowboy cosplay to Margaritaville chic. And Screaming Mimis in the Village sells more sequins than even ABBA could bear.

Here’s where the fun comes in. Give each other scenarios to dress for. “You’re going on vacation with your new stepkids, and they hate you.” “You’re about to commit a major heist at the Medieval Times in New Jersey.” “You’re a 19th-century vampire just trying to make it work in 1977.”

These are a few ideas to get you started, but please be creative. Carry on for as long as is fun or until someone from the store politely asks you to leave. (Alternatively, they may ask to join in. The last time I played, we stayed for an hour and became close personal friends with the staff).

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5:00 pm

Admin time. You’ve been on this date since 11 am, take a minute to check in with your family, friends, and pets. Just because you’re having the time of your life doesn’t mean you can ghost your people! Tell them what’s up and send a video of you marching around Beacon's Closet dressed as a 1990s power banker who wants to give it all up and go to clown school.

5:30 pm

You’re hungry, you’re thirsty, the staff at the store let you keep the outfits because you “made it weird” and “ripped them beyond repair after that cartwheel.” Time to make like Marnie and Charlie in Season 5, Episode 9 of Girls—masterpiece “The Panic in Central Park” —and use this fancy dress for all it’s worth.

Head uptown to Met. Hopefully it’s a Friday or a Saturday, because that’s date night. Really. The Met offers live music, drinks, and special programming from 5 to 9 pm on weekends. In the warmer months, the roof is also open. There’s a bar and a band and a packed house of art-loving aficionados basking in the sunset. This event is free with museum admission, which is Pay What You Wish for NY state residents and NY, NJ, and CT students with valid IDs. So if you have extra cash from the street act, put a few dollars in. But also, do what you must.

If you want to drink, you and your date must embark on a challenge: charm your way into a free cocktail from a smitten stranger! Of course, there is the possibility that either you or your date hit it off with the drink purchaser and they fall in love and leave you in the dust. But if that happens, it’s a sweet story for them and a risk you have to be willing to take.

7:30 pm

Provided your date hasn’t left you for the soda savior on the roof, you can exit the Met. You’ve spent nearly eight hours together; it has not broken the bank. Cool!

You wander down the museum’s marble steps and into Central Park. Your hands knock against each other as a nervous energy fills the air. You interlace a finger. Then another. Then another, until you’re walking hand in hand by the Great Lawn. The park is filled with sounds of evening delight: a popped bottle of champagne, peals of laughter from friends on the grass, a barking dog chasing a squirrel, elderly men practicing Tai Chi under a tree.

Then… music? A jazz musician wailing on his saxophone in the arches of the Bethesda Terrace. Or if it’s summer, it might be a Summerstage concert at Rumsey Playfield, offering free (and ticketed) shows. If it’s August 2025, it’s possibly decorated actors performing Twelfth Night for Shakespeare in the Park at the newly reopened Delacorte Theater. And if it’s a nightmare, it could be James Corden reviving the Late Late Show with a fully staged crosswalk musical at the intersection of West 79th and West Drive.

Let’s pretend it’s a jazz musician. You sit by the fountain as the sky turns from dusk to dark.

You buy an ice cream from the cart. Yeah, we’re having dessert before dinner. Yeah, we’re spending money now. (If you’re strapped, do the street act again, then pick this up.) The music scores your moment as you finish the cone and wipe a bit of drizzled chocolate off your date’s face.

You look up at the stars. You can’t see many, but you’re surprised to see a few. You lean into each other and gasp as a comet flies by. Oh, wait, never mind. That was the asteroid headed for—

Kidding. But what a way to go, right?

9:00 pm

Hands held tightly, you amble out of Frederick Law Olmstead’s wooded oasis. You and your date feel worlds away until suddenly, you hear cars whizzing by and see pedestrians scurrying across 59th and 5th. You slip back into reality.

Or maybe you don’t. Maybe you say fuck it and sweep each other up into a big romantic New York City kiss. A New York City kiss is a perfect smooch that is inevitably ruined by being splashed by a puddle, a leering man shouting “me next,” a too-friendly dog, or getting in the way of Richard Kind (happens more often than you’d think).

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9:05 pm

The grumbling stomachs are too much to bear. It’s time to eat.

You could do it together—go to a diner that may or may not actually have diner prices (Cobble Hill Coffee Shop, Tom’s, Square, Kellogg’s, Pearl). Or you could go back to your apartment and serve up a steaming plate of spaghetti aglio e olio, the three-ingredient dish cooked by Jon Favreau for Scarlett Johansson in the movie Chef (arguably one of the most sensual cooking scenes ever filmed).

You could also call it a night, shake hands like adults, and go back to your respective homes for leftovers or whatever waits in your fridge.

As for me? Once we’ve gotten through the first ten hours and are sufficiently hooked, there’s only one reasonable next step: demand the nine-course tasting menu at Per Se.

11:00 pm

Go to bed! Whatever that means… ;)

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This is a tale of two Yales. First, a tame visit to the New Haven campus, and then an evening at the Yale Club of New York City that was anything but.

Last summer, while in Connecticut for a weekend trip with friends, I cajoled them into taking a detour to wander the storied streets of New Haven and the Yale campus. It was a quintessential East Coast afternoon: muggy, sweaty, sticky, miserable, and magic.

I struggled to keep my gaping mouth shut to flies as we took it all in. Ivy-covered walls, lush green quads laden with lounging students, foreboding stone buildings named after America’s most esteemed Robber Barons. Parts felt reminiscent of my own college campus—University of Michigan, majestic and ionic, historic and hopeful… like anyone can be anything on these grounds.

Anyone can be anything, but at Yale you need a student ID to get inside. My tour was mostly limited to building exteriors. We knocked on the door of the Skull and Bones tomb (no one answered); went to a bookstore and bought a mystery novel (Some Luck by Jane Smiley; I have yet to read); and enjoyed a blissfully cold, mint chocolate chip-flavored ice cream cone at a cute little parlor.

And then it was over. There was nothing else to do.

As we loaded back into our car and relished the air conditioned air, disappointment set in. That couldn’t be it. Where was the Logan Huntzberger type (Gilmore Girls boyfriend, the playboy son of a publishing magnate, and my first crush) to sweep me off my feet and debate the merits of Hunter S. Thompson? Where were the big adventures? What would I write about? I hadn’t met anyone. The list said “Go to Yale,” so maybe I should have taken that more literally: posted up in a coffee shop, snuck into a class, auditioned for the Whiffenpoofs. That’s what I’d missed. The original list probably actually meant for women to be students at Yale. Right?

Well…

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The great irony of #27, “Go to Yale,” is that undergraduate women were not allowed to enroll at the college until 1969, eleven years after 129 Ways to Get a Husband was published in 1958. My best guess is the authors of the original list meant one of the following:

• Go to Smith or Vassar or another college and bus to Yale. Before (and in the early days of co-ed), women from other colleges were imported for mixers. They were known as the “weekend women.”

• Enroll in one of the graduate schools. In 1958, all Yale graduate schools except the Yale School of Forestry were open to women. That program was the last tree to fall—it went co-ed in 1966. Yale’s professional graduate schools had been co-ed since as early as 1869, when the Yale School Fine Arts first opened the door to women. Other programs took longer; in 1885, Yale Law School accidentally enrolled Alice Rufie Blake Jordan after she applied using only her initials. She graduated, but another woman did not walk through the doors of Yale Law until 1919.

• Stand in the quad and look lost? No, really. From my research, seeing a woman on Yale’s campus who was not a professor’s wife was something of a marvel. In a 1968 article from the Harvard Crimson describing her three days at Yale during the now-infamous “Coeducation Week” (don’t worry, I’ll get there), author Jody Adams wrote:

One ecstatic sophomore stopped me in front of Sterling Library and told me that seeing a girl at Yale on a Monday was almost more than he could bear. After four years of prep school and two years of Yale he had been led to think that "girls folded and disappeared from Sunday evening to Friday morning."

Standing outside of Yale’s Sterling Library this past summer, I remember feeling dismayed I couldn’t go in and sniff a book. No ID card, no entrance. It never dawned on me that in 1958, a woman at Yale would have experienced the same closed door, except for an entirely different reason. In 2025, if I really wanted to take this list seriously, I could technically apply to Yale, register as a student, move to New Haven, and do the damn thing. The option exists. A little over 50 years ago, that was not the case.

I’m ashamed to admit that until my Yale adventure, I’d never really considered the work it took to get women on campus. Bad feminist, I suppose. Or maybe it’s the privilege of growing up in an era when women’s educational equality was never something I had to think about: Michigan had been coeducational since 1870 (Go Blue, am I right?).

Yale, on the other hand, was behind the times.

According to The Atlantic, in 1968 Yale had “only ever accepted men as undergrads, while some 75 percent of other American colleges and universities were coeducational. Yale was also one of only three Ivy League schools where women could not enroll at all in undergraduate classes: While Brown, Columbia, and Harvard, for example, were still technically male-only, students from their institutions’ adjacent women’s colleges—Pembroke, Barnard, and Radcliffe, respectively—could also take classes.”

Coeducation was a hotly debated issue that came to a head during a student-sponsored Co-ed Week from November 4th - 8th, 1968. The idea was to invite women to campus for the week, open a dialogue, and host a debate. To quote Aviam Soifer ’69, one of the event’s organizers, “To make a valid decision about what women want in a coeducational school, it seems logical to talk to women about it.”

750 women from 22 colleges came down for the event. A little over a week later, Yale’s then President Kingman Brewster proposed a formal coeducation plan to faculty, who voted in favor 200 to 1 (you have to wonder who was the lone holdout?). When presenting his plan, he cited the coeducation week as “providing Yale with "uncommon excitement.""

The event was largely a success, a pressure point where everything shifted. But not all were friendly to the idea of women studying at Yale. The best account I found was the Harvard Crimson article by Jody Adams, who, at the time, was a Radcliffe student. The entire article is worth a read—entertaining and honest, Jody did not hold back. She attended a rally, chatted with visiting female students, lunched at Skull and Bones. In her three days on campus, she also wrangled a freelance piece for The Yale Daily News (okay hustler!). Her experience in the newsroom, not unlike her experience on campus, struck me:

There I was at Yale, for no reason except that a group of boys just couldn't stand it anymore, sitting in a strange newsroom, writing some story about some lady masturbating with a cross. It was bizarre and slightly absurd. All at once I was feeling isolated and quite lonely.

This was a theme.

In the fall of 1969, 250 freshmen and 250 upper-class women were welcomed to Yale. The New York Times reported “Yale Besieged by Female Applicants,” a headline that implies an enemy heading for the homefront. With coeducation, the first battle was won, but the war was far from over. Everything in the early days for women at Yale was a fight. Getting into classes, financial aid, basic safety.

The doors had been cracked, not swung wide, open.

Of course, I also didn’t think about this as I waltzed through the welcoming entry of the Yale Club of New York City on a snowy evening in February 2025. All I thought was, “Wow! Check out that crown molding!”

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In the shadows of Grand Central Station, the Yale Club, located at 50 Vanderbilt Ave, is the largest college clubhouse ever built. Restricted almost entirely to Yale students and alumni, the 22-story club boasts everything from hotel rooms to a swimming pool to a rooftop bar. It’s an architectural marvel, ripped right from the Gilded Age.

As I took a step inside and shrugged off my coat, I gaped at the great foyer and the large staircase leading to the club upstairs. I was there for a drink with my old roommate Marina, her boyfriend Sam, and their friend Theodore. A graduate of the Yale School of Architecture, Sam had a membership and graciously offered to bring me. “For research.”

“Research” involved drinking one of the best martinis in Manhattan (bested, in my opinion, only by Bemelmans) in the Yale Club’s Main Lounge. This room not only felt but apparently is frozen in time (based on a photo I found from the archives, it has changed little).

Servers in suits wandered with silver trays, dispensing drinks and Cheez-its. A guest played hauntingly beautiful music on the grand piano in the corner. Folks chatted in respective groups, flitting between the nearby bar and whatever couch occupied their fancy. The walls were adorned with portraits of U.S. presidents who had gone to Yale. Quite the feeling, to be watched by Bill Clinton while sipping on Hendricks and olive juice.

This was #27. “Go to Yale,” Part Two, and I was eager for action. I scoped the room, practically swimming with khaki clad investment bankers. I’m not actually sure if they were all investment bankers. That’s an assumption—sue me. You can probably find a good lawyer at the Yale Club.

We went on a tour of the club. There was a section to watch the hockey game, a room for billiards, and a library. Oh, the library. I traced my fingers along shelf after shelf of books as we wandered the floor. Gorgeous wood desks, screaming for occupancy. A piano tucked in a corner. Utter silence. It was a place for learning. I could have stayed there all night.

But we made our way back to the Main Lounge.

“Who’s your favorite president?” Halfway to our couch, we were stopped by a man in a sport coat with a thick accent: The Irishman. He grinned at us, jerking his head toward the portraits. “You know, on the walls?” Marina slinked away as the Irishman and I locked in. My heart fluttered. The list had done it! A fun and flirty meet-cute within the confines of the Yale Club! Huzzah! The magic was almost too exciting to believe. He and I laughed, enjoying the moment, exchanged names, and shook hands.

And that’s when I saw it: a ring.

Back with the group, my head was spinning. He couldn’t be married. No way. Why so brazenly approach, flirt in the middle of the social club, friends watching left and right? It didn’t add up.

“Can I join you?” The Irishman returned, this time taking a seat on our couch. He joined our conversation with a purpose I couldn’t place. He mentioned a wife. He mentioned kids. He made intense eye contact. He left to watch the hockey game. What was happening?

And then once more, The Irishman returned as my friends and I prepared to leave. They peeled off, but I held my ground—I wanted answers. He sat across from me, settling into the plush armchair, and smiled. Cheez-it crumbs littered the floor, and a woman lazily plucked the piano in the corner.

“Are you married?” He balked as I looked at him expectantly. Here it was, that big twist, the explanation, it’s New York, there are all kinds of reasons why—

“Yes.” My heart sank. I was mad, or sad, or… I had so badly wanted to be wrong.

“Then what are you doing?”

He hung his head in shame, though whether it was from being called out or caught is anyone’s guess. “Honestly… I saw you from across the room, and I just wanted to talk to you.”

“And what did you think was going to happen?”

“I don’t know.” He plied me with effusive compliments, which though nice, felt tainted. “I don’t know.”

I could have told him that I was working my way through a list called “129 Ways to GET a Husband,” not “129 Ways to Meet Someone Else’s,” but instead I just stood up. Bill Clinton watched me as I left.

As my cab home sped over the Brooklyn Bridge, I ran the experience over and over in my head, waffling between what felt like a fun encounter and a deeper disappointment. I was bothered by it for obvious reasons, but there was something else I couldn’t place. I think it had to do with how the whole thing went down. The Irishman didn’t do anything technically wrong. He could have thought it was harmless flirting. But I didn’t, and I couldn’t shake that disturbing gut feeling.

I thought back to the first female Yalies and realized that the story—my feelings—rested on something bigger than being hit on by a married man at the Yale Club.

In 1969, the Yale women did not have it easy, but they must have had guts. Dubbed the female versions of Nietzsche’s “Ubermensch”—supermen— by a male student in an essay for The New York Times Magazine, the first female Yalies earned the moniker “superwomen.”

In many ways, they were. They fought tooth and nail for their education. The office of financial aid refused to offer resources to women, citing a commitment to the men first. There wasn’t even a gynecologist on campus until 1969. As far as all-male classes go, one professor was quoted in The Yale Daily News saying, “Until society makes its role assignments equal, I can’t help feeling a deeper satisfaction and sense of accomplishment teaching all-male classes. As a professor, I feel a greater sense of accomplishment when I direct my efforts toward those who will one day have a greater role in society—men.”

Sexism ran rampant: a common quote after coeducation was that Yale would now be producing “1000 male leaders and 250 wives.” In 1969, an informal survey of Yale women showed difficulty in establishing friendships with other women because there are so few of them, overcrowding and lack of privacy, and lack of dating. They resoundingly rejected the notion that they were there for an MRS. Degree, despite what many of their male peers implied.

The school was inhospitable to the women it worked so hard to admit. This is not surprising. For many, the motive behind coeducation had nothing to do with women. It “was based not on Yale’s seeing her mission as the education of both sexes, but on fears that Yale cannot continue to attract the nation’s top males to a non-coeducated campus,” according to Paul Taylor, a reporter for the Yale Daily News.

The women were brought on campus to appease the men. A revolution occurred instead.

Of course, the revolution that came in the 1970s was more than just Second Wave Feminism. It was the civil rights movement, Roe v. Wade, Vietnam, the Black Panther trial, all coming to a head while Yale attempted to create a coeducated campus coexistence.

In my research, I was struck by rhetoric from both supporters and opponents of the movement. The 50-some-year-old quotes sound eerily similar to conversations happening today both in favor of and against civil liberties, gender equity, and basic human rights. Reading archived articles advocating for diversity, equity, and inclusion at Yale in 1968, I’m struck by what’s going on in the present, as we watch institutions and corporations shirk and shutter programs designed to provide access.

It is a fascinating exploration, but this is a Substack post, not a senior thesis, so I have to wrap things up. I recommend the book Yale Needs Women, which goes into depth over this history and more. If you read it, let me know. We can start a book club.

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When I started #27, “Go to Yale,” I thought I’d end up with a quippy anecdote about my love of Gilmore Girls or a semi-salacious story about an evening at the Yale Club. And the thing is, if I’d taken the list item at face value, I’d actually say it’s a pretty solid idea. College campuses, alumni clubs, and—if you went to Michigan—football bars are amazing places to meet someone with common interests, mutual friends, and similar experiences. Just make sure they’re not married if you hit it off.

But this is about more than just a good place to pick up a partner; the history of Yale’s coeducation is a reminder of why I started this project in the first place. Yes, to meet people. But also to look at what the world was like for women in 1958 and compare it to how we operate now. I shudder as I witness history repeating itself and those hard-earned rights being lost. I am moved and motivated, however, by the fight and the tenacity of these trailblazers—not just the Yalies, but every single woman who rejected the status quo and dared to question a different, more equitable reality. It feels very Socratic to end this with the question: How do we honor that? And what happens next?

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I’m back just in time for Valentine’s Day! If for some reason the audio is giving you any issues, you can also listen on Spotify :)

My mom is in a Facebook group called “MOT Jewish Matchmaking Moms” aka Mothers of the Tribe. (I wish I were kidding). It is, as the title suggests, for mothers of single Jewish young adult children. Seemingly a cross between a support system and a matchmaking market, I’m not quite sure how it works. All I know is occasionally my mom will text me a version of, “Josh S. may reach out!” Josh S. is presumably someone whose mom met my mom in the Facebook group, and the parents thought their kids would get along.

It’s sweet, if a little overbearing. Yet, something about it brings me comfort. To know there are scores of worried parents taking their children’s love lives into their own hands and learning up close and personal just how abysmal dating can be these days? At least they get it now.

And, while I’m skeptical of the group, I understand the logic behind it. It falls in line with list item #26. “Be nice to everybody—they may have an eligible brother or son.” I think this is actually pretty sound advice from our lovely antiquated listicle: people love to set people they love up. Romantic or platonic, there is a sense of pride to be had in connecting a couple or fostering a friendship. Set ups are awesome! It feels safer, like the odds are better. Like choosing a doctor, we’re usually more inclined to pick someone who comes recommended and in-network; vetting can save a lot of grief, cost, and potential headaches down the road.

“I have someone I want to set you up with!” Still, no one is prepared for when their mother or grandmother or long-lost aunt excitedly calls with this news. I figured my mom meant someone’s son whom she’d met in the group, or a stranger she encountered at Trader Joe’s, or a friend’s daughter’s husband’s brother’s co-worker. But instead, she gave me a woman’s name and number. A matchmaker.

Welp.

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I’d be lying if I said I wasn’t a little amused. Matchmaking fascinates me—and evidently, I’m not alone. Shows like Indian Matchmaking, Jewish Making, and Million Dollar Matchmaker are smash hits both on Netflix and in real life. The actual services of these professionals can cost tens of thousands of dollars for a few matches… and people pay.

It’s not like this is a new concept. It’s the opposite. The name “Yenta” is so embedded in our culture that the character has transcended the Fiddler on the Roof debut to become a societal eponym. But while Yenta may be the poster child, as long as there has been media, there have been matchmakers on screen.

We see it in Mulan during the iconic “Honor to Us All,” where our heroine’s set-up ceremony goes disastrously wrong, and she does not bring honor to anyone. (Fear not, she will later.) There’s Dolly Levi in Hello Dolly!, wherein our widowed lead searches for a miserly “half-a-millionaire’s” match and ends up marrying him herself. (Matchmakers need love too.) And Hello Dolly! is based on the 1954 Thornton Wilder play The Matchmaker, which is based on Wilder’s 1938 play The Merchant of Yonkers, inspired by John Oxenford’s 1835 farce A Day Well Spent. (There are no original ideas.)

Matchmakers go way back. The first record of such an individual appears in Genesis 24 when Abraham sent his servant Eliezer to find a suitable wife for his son Issac. Eliezer devised the now infamous “Camel Test,” in which he waited by a well until eligible maidens appeared. Eliezer, appearing a weak and weary traveler, asked for a drink of water. Whoever not only obliged but also quenched his many camels' thirst would be Issac's bride. The test was to show devotion, lovingkindness, and responsibility. And it worked. Eliezer found Issac a wife in Rebekah, one of the most famous women in biblical history.

Ironically, this does satisfy the prompt #26. “Be nice to everybody—they may have an eligible brother or son.”

The idea of a “Matchmaker” is evident in nearly every cultural history. The Japanese practice of Omiai can be traced to 16th-century Japan among the Samurai class. The arranged marriages, brokered by a Nakōdo, were viewed as a way to consolidate power and protect wealth. In ancient Greece, where marriage was considered a public interest, the task was often left to the Promnestria, women thought of as professional gossips. And in frontier-era America, farm families would send their children to “social dances,” where chaperones could observe burgeoning romances.

In modern times, the matchmaker is still very much employed—in Japan, many use a Nakōdo, for example, but the stakes and standards are different now. We have evolved. No one gets paid via dowry. Women (allegedly) have autonomy over their bodies and decisions. The internet and travel have rendered the world far wider than a small village or an isolated farm.

The need to marry for a strategic partnership or to preserve familial power is largely gone. In its place is a different driving factor: love.

Despite what Austenian fantasies and Shakespeareian sagas would have us believe, marrying for love and dating is a relatively new concept. Or maybe Austen and Shakespeare meant to poke holes in the system and show stories outside the norm to prove that love can usurp logic. Maybe that’s part of why their work is so endemic and everlasting. The point is that dating didn’t really enter the conversation until the 1920s when women started to gain independence.

But we don’t have time to go into the transformation of courtship that ultimately led us here to 2025. I wish we could make a pit stop in 1958 and examine the cultural forces and historical context that inspired and made plausible a list like “129 Ways to Get a Husband,” but I am trying to be concise here. We haven’t even gotten to my matchmaker or the blind date it led to.

What’s important is that matchmaking is nearly as old as Eden, whereas the Statue of Liberty has had a longer tenure than the concept of dating. Taking that into account, it makes sense that modern romance is such a shit show. In the timeline of human history, it’s pretty new. Maybe we’re still figuring it out.

I certainly am, so I humored my mother and decided to meet my (match)maker.

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Modern matchmaking can often sound like a real racket—I implore you to go to the sites of the professionals who claim to charge men $1 million for their services and make it make sense—but my matchmaker seemed in it for the right reasons. In fact, she wasn’t even a matchmaker; she emphatically stressed that she just wanted to facilitate introductions. She was not in it to make money but to help others make sensible connections and find love.

So I gave it a shot. She had helpful, though somewhat harsh, insights. She seemed genuinely invested. But unfortunately, I wasn’t. After a few weeks, it all felt like more work than it was worth. Perhaps five hundred years ago, or even a hundred years ago, when there were fewer options and getting water from a well was the deciding factor in a partnership, it would’ve been easy. But these days, a simple match doesn’t seem possible. Why settle when you have a planet of people to pick from? Dating feels like trying to order off the menu at The Cheesecake Factory—overwhelming, endless, and you’re never quite sure you made the right choice.

In my case, I knew I wasn’t in the headspace to walk down the road she paved for me and that, at least at this moment, the whole endeavor was doing me more harm than good. So, I made the difficult decision to break it off. I hope we can still be friends.

The night after I ended things, I was sitting at home when something peculiar happened. A text message: “hey emily this is X! I’m your Bookbear match.”

Bookbear match? I ignored it. Twenty minutes later, another message from another number. “Emily! This is Y. We were set up via Bookbear Express.”

With a jolt, I remembered. Two weeks before, while in the throes of what I am calling my matchmaking month, I got an email from the Substack Bookbear Express. It read: “Last day to fill out the matchmaking survey!” What the hell, I thought as I completed the 67-question form. It required value ranking, favorite books, partner preferences, and a few photos. Without a doubt, it was the most comprehensive and thoughtful questionnaire I’d ever filled out.

X and Y were my matches. I checked my email. I’d also been sent two different people and was given only their phone number, favorite book, and a blurb. It was up to me to reach out.

Evidently Match X and Match Y got my info and decided to roll the dice. I was delighted and set dates with both. The lack of information was invigorating. If my foray into matchmaking taught me anything, what more does a person need if you have shared values and a common connector?

Well, for Match Y, it was a picture. A few days before our date, he asked if we should exchange photos so we know who to expect. I immediately responded with a resounding but polite “No.” It was slightly off-putting that he asked and even more disappointing when he “got busy” soon after. In hindsight, I can’t blame him. Perhaps he was scared or worried about being catfished and wanted to prepare. But the fun of the experiment was not preparing. Why ruin it?

We live in an information era where you can FBI agent your way into anyone’s life with a few identifying details and a quick google. Ironically, Match Y’s first and last name was provided by iCloud intelligence or whatever. I could have looked. But it’s so rare to have an opportunity to walk into something truly blind and let the experience be whatever it will be, devoid of expectation or preconceived notions or extensive research. I didn’t want to know.

It was the chance to be in the moment, to take a risk (in a safe, public setting), and to challenge convention.

So Match Y and I rain checked, possibly indefinitely. But Match X was game.

On a chilly night in early February, I hopped on the subway and headed to the West Village for dinner. I was terrified but determined to see it through. This was happening. This was real. An actual Blind Date.

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What is a blind date anyway? On the train over, perhaps to calm my nerves or to convince myself I wasn’t being crazy, I researched it. This, I did want to know.

According to Wikipedia: “A blind date is arranged by a mutual acquaintance. The two people who take part in the blind date may have never met or seen each other, hence the phrase "blind date". Sometimes one person is more interested than the other, which may make it more difficult on the person arranging the date to judge whether the date will be successful.^[6] The date is usually two hours or less, as it is just a first date.^[7] The date is also very adventurous in the way that neither party knows what to expect and whether or not they will hit it off. The location is also affected by the spontaneity in that it is often a public place so that both parties feel comfortable.”

Look, we all know how a Wiki rabbit hole goes—especially when you’ve got time to kill on the train. Next thing I know, I stumbled upon a 1940’s radio show called Blind Date.

Blind Date was launched in 1943 as a means to entertain servicemen at the Army Radio Technical Training School in Sioux Falls, South Dakota. The premise was simple: two military men compete for a date with one woman. After an interview with the host, they get on the phone for a call with the lady in question. She then walks through the door to meet her match. Cute.

The show was so successful that it was sold to NBC Radio and moved to New York City. Hosted by Arlene Francis, the national program was a hit and the precursor to the television show The Dating Game. On Blind Date, winners were given a night out at The Stork Club (a piece of NYC history on par with Studio 54 and The Copa) and $5. Losers received $15, tickets to a Broadway show, and their mothers got lotion. Seems like a pretty sweet deal either way.

Sitting on the C, I queued up an episode—September 28th, 1945. The program was a blast from the past. A robust orchestra scored as Francis joked with painfully awkward sailors on furlough and military men finally home from war.

I was struck by two moments in particular: one, with John from Oakland, CA as he made his case to his potential date, an American Airlines stewardess.

JOHN: “This is John from Oakland CA. How would you like to go out with me at The Stork Club?”

STEWARDESS: “Heavens, yes. Do you think you can you carry on an interesting conversation?”

JOHN: “Uh huh.”

STEWARDESS: “Can you discuss the arts and sciences?”

JOHN: “Uh huh.”

STEWARDESS: “What do you think is the most vital question right now?”

JOHN: “Well it’s like this, since you picked me up, it’s up to you. And well you know how it is!”

Suffice it to say John did not win. It was nice to hear that in almost 100 years, not much has changed. An interesting and vibrant woman, eager for conversation, met only with “uh huh.”

But then came Corporal Martin S. Belefant, a recently released soldier and POW during the final years of WW2. He was competing for the affection of another American Airlines stewardess, Mona, who had just had her moment with Ed, a Navy man from New York. Ed’s big line was, “Hello, Mona, I’m scared.” So, the bar was high.

In the interview before his call, Arlene asked Martin about his time at war.

ARLENE: “Were you in the bulge, is that when you were taken?”

MARTIN: “I WAS the bulge!”

Audience endeared, the laughter carried the room as Martin phoned Mona.

MARTIN: “This is Marty Belafant, the Bronx cowboy. Bet you’re glad I’m from the Bronx.”

MONA: “Why should I be happy about that?”

MARTIN: “Well haven’t you heard, the Bronx is going to be the 49th state! In fact the Bronx is what makes greater New York greater.”

MONA: “Say, are you trying to make a date with me or the Bronx Chamber of Commerce?”

MARTIN: “You, of course. I’d look pretty foolish dancing with the Chamber of Commerce.”

The chemistry was palpable. It felt like the start of something big—the start of something weird—and I found myself transported from a rat-filled tunnel under Manhattan to a radio station in 1945, helplessly rooting for Marty and Mona. This is what love at first sound is like. This is magic!

Marty and Mona head off to The Stork Club, and the program ends as my night begins.

I take out my headphones and stand before a charming Italian spot on a side street in the West Village. I’m hoping my date is more like Marty than John. I’m hoping we get along, we like how the other person looks, we laugh, maybe we end up at a Stork Club of our own. I’m hoping the matchmaking survey did its job, and we’re here for love, not logic. I’m hoping.

I go inside.

Four hours later, I’m back on the C train. I lost my scarf at the jazz show we caught after dinner. I’m buzzing with excitement and eager to call my best friends as soon as I get home. I’m not sure if I’ll see Match X again, but the night was perfect regardless. The thrill of learning someone’s life, the dance of stolen glances and first impressions, the flutter of possibility. The night was nothing like I expected; he was nothing like I expected. But then again, I didn’t really have any preconceived notions. I had gone in blind. There was nothing to lose and everything to gain.

As I wondered if we’d go out again, I returned to Mona and Marty. Did they end up together? It seemed like they would. It seemed like they should. That chemistry, that charm, that click. It was undeniable. It should be that simple. Right? When you hit it off, it means something. We get to look for love instead of marry for logic, so when there’s a connection, that should be it.

I found an obituary. Martin S. Belefant, Purple Heart, died in 2011, leaving behind his wife Eva of 59 years.

He didn’t end up with Mona. By simple math, he married in 1952; nearly seven years after his appearance on Blind Date. What happened that night at The Stork Club? They could have had the time of their life; it could have been a dud. Like with any first date, we have no idea what baggage a person brings. There are so many reasons something good doesn’t last that it’s not worth it to wonder. Maybe Marty’s decision to go on a silly show inadvertently led him to his person. Or maybe it was fated. Or maybe it’s none of my business. I am making conjectures about a man I heard on a 1945 radio show for three minutes.

There’s a larger takeaway about dating and matchmaking and “being nice to everybody—they could have an eligible brother or son (or daughter or sister).” It’s what ties this all together. Anything can lead to anything, and this is supposed to be fun. We are mere players in a process that is as old as time but now with more power and choice and potential.

So take the risk. Meet the matchmaker. Fill out the survey. Go on the radio show (or I guess like, Love is Blind). Let your mom join the Facebook group. Be open to strangers. Be someone people want to set up—be someone people root for. And root for yourself while you’re at it.

Be kind to others. It’s the easiest trick in the book.

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It’s been a minute since I’ve posted a 129! I decided to take a break to reset and rebrand the Substack. (Thank you to Keepsake queen Julianna Salguero for the help). At the year's end, I felt proud of 129 but frankly burned out and like I’d lost the plot. I think I found it again. I’m going to try and return to the roots of this project—what made it fun in the beginning. What does that mean for you, dear reader? Hopefully nothing other than the promise of the premise coming to fruition. Doing weird shit and meeting cool people along the way. If you think I’m missing something else let me know, but if not…thanks for reading! xx

P.S. if you’ve ever been on a plane, train, or automobile and met someone, had an interesting encounter, or had a Before Sunrise-esque experience, will you shoot me a message? I’m searching for stories :)

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Believed to welcome good fortune and prosperity, “Las doce uvas de la suerte,” should be consumed in quick succession, one grape for each toll on the clock as it changes to a new year.

I first heard of this when I worked on Amazon’s With Love, a holiday rom-com with an entire episode dedicated to New Year's Eve. We filmed that episode during a hot, sticky week in July 2021 on a soundstage deep in the San Gabriel Valley. The set was festive, and the shoot was fun.

A year and a half and a lifetime later, grapes were back on my mind. The tradition had blown up on TikTok with a slightly narrower lens: eat twelve grapes at New Year's to find love. I’m unsure where the “must sit under the table” part of this came in or originated. In hindsight, it may have been deeply unnecessary, but in the moment… desperate times.

I was not taking any chances. I ate the grapes.

January 2024, good luck grapes on my side, I said I would give it a year. The operative word here is it, which means my career and relationship status. I’d write with abandon, try everything, date everyone, lean in, and trust the process. I set lofty goals: get a book deal, finish the list (all 129 items), and find my person. I vowed to hustle, work, push, and fight. After that, I would take a break and go to the beach with my special someone. After that, I would be done.

Well, it’s been a year. No book deal, no husband, no finished list.

Were the grapes a $25 waste? (The cost of Doordash grapes on NYE). Maybe.

Was the year a failure? Not even close.

New Year's Eve 2023, I was sitting so far underneath the table I couldn’t see anything beyond the floor. That’s what those three goals were: the floor. In hindsight, what had seemed like such big ideas were very, very small. A book, a boyfriend, and a behind-the-times list? That was the best I thought I could do?

Midnight grapes are said to bring luck, prosperity, and love. Oh my god, did they ever work.

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129: A Year in Review

Looking back, my mind is blown by the people I’ve met, places I’ve gone, and pieces I’ve written — all because of this silly little project.

It was a year of learning: to clean and scale a fish (#11), the ideal golf swing (#7), the history and controversy surrounding Matisse’s famed Serf sculpture (#3). Of lessons in vulnerability, defeat, the work it takes to get the life you want, and the strength to ask for what you deserve.

It was a year of emails…oh, the emails. Coinciding with my efforts to be more open and honest with romantic partners came a shocking amount of relationship situationship penpalships. I’m not saying there were 30, but there were more than two, which seems like a high number of people to share Austenian-level correspondence with. Some stories are not for the Substack, but one certainly was: Seeking Co-Owner of a Boat (#14) and Seeking Co-Owner of a Boat, Part 2 (#15).

What started as an innocent flyer advertising for a co-owner of a vessel spiraled into a real-life You’ve Got Mail with a British Boat Enquirer passing through town. What I thought would be a fun anecdote spiraled into a story spanning months: endless emails, one cautious coffee date —

The Boat Enquirer saga came to a fizzling finale one night in Brooklyn early this fall. The whole encounter felt like something out of a movie: epic, extraordinary, rare.

There were the hours on Zoom with Dorothy, a widow who’d lost her husband, Sy, in early 2022. I spoke with Dorothy for #6. “Read the Obituaries to Find Eligible Widowers.” Still, instead of doing the worst thing possible and actually following the prompt, I used it as an opportunity to tell a great love story. Dorothy and Sy were married for 60 years, together until the end.

Dorothy and Sy met on a Coney Island beach in the 1950s.

In 2024, folks are matching in slightly different manners. People like Sydney Watt and Zoe Black, whom I met after attending and interviewing them about their singles mixer, “Friend of a Friend.” Gathering 60 singles for a get-to-know-you in a Brooklyn backyard, the event was perfect for #18. “Tell Your Friends You’re Interested in Getting Married.” It presented an alternative to apps, something young folks seem increasingly dependent on.

I spoke with the men of Minneapolis, who I accidentally catfished when I wrote #5.“Look in the Census Report for Places with the Most Single Men.” It was through Hinge conversations about the necessity of dating apps that I came to a horrific conclusion:

But there’s also a massive rejection of this idea that seems to be gaining traction. People want to be with people. That’s what I learned this year. They want to be in the world, spending time together, rolling the dice. Strangers are often willing and eager to chat if you just extend a hand. Romantically and platonically, humans crave companionship. It’s that simple.

2024 was a year of community.

Driving a convertible through upstate New York (#21) with my good friend, the endlessly funny Ritam Mehta.

Discussing the loneliness epidemic (#16) with my college pal (and New York Times best-selling author!) Kyle Prue.

Turning Brooklyn upside down via #10. Hat Box Night (and then again in #25, the sequel) featuring a massive cast of recurring and new characters.

It was also an exhausting year. From the excitement of diving in and launching the project to the occasional feeling that maybe the effort was fruitless. It can be easy to look at metrics as meters for success — subscribers, likes, audience (and literal) engagement. But it’s not that cut and dry. What looks great on the outside might be hollow on the inside. Bots can inflate follower counts; a smiling photo on Instagram does not necessarily equate happiness.

All it takes is one gesture or a kind note to make a person feel seen. Time and time again, when I wanted to give up, there was a push to keep going — from you, dear reader.

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It was a year of good people. I am endlessly grateful to everyone who took a chance on this project in some way or another. To my Mom, who tirelessly edits every Substack. To my Dad, who reminds me to soldier on when things are hard. To my new creative partners helping to take this project in an exciting and unexpected direction (stay tuned!). To the first few paid Subscribers! To my wing people who show up for every activity.

It was a year of enlightenment, encapsulated nicely in this conversation with Good Hang’s Randa Sakallah and Harry Krinsky. We started by chatting about (#9) feeding pigeons in the park and ended with meditations on life and dating.

There aren’t any rules, and we should try to figure out how to have the most fulfilling and fun experience before you meet your person.

It was a defining year, full of meaning and magic. Pushed out of my comfort zone and confident in the chaos, I became someone I didn’t know was possible.

It is cathartic to look back at our years in review in terms of what we learned and loved as opposed to simply what was accomplished. A goal is just a line item on a list to check off — and if this project has taught me anything, it’s that the list item is simply a suggestion and a starting point.

New Year's Eve 2024: I’ll be eating grapes again, this time (hopefully) covid-free, standing up, and not alone. I’ll set new goals. I’ll dream new dreams.

I have no idea what next year has in store, but I am sure I’ll be continuing 129. We’re only 25 items in, so… much to do. Already lined up for January: a professional poker player who has promised to teach me to play my cards right, a war tanker in Red Hook ripe for a stowaway, and a street corner and lasso with my name on it.

The Modern 129, this Substack’s paid tier, will continue to come out monthly, featuring ideas for how to get a life now in 2025. I stand by this element and hope it helps others break out of their funk. If they’re in one. And if not, it’s just researched and curated tips for a good time.

This year, I was accused of real-life Sex and the City and How to Lose a Guy in 10 Days. Next year, I want to get hit with some other iconic characters. Godzilla, perhaps. Could be weird.

It’ll all be weird. Because that’s what this is. That’s what life is. Weird, wonderful, and worth it.

Happy holidays!! xx

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The short answer is Hat Box Night is an activity so epic it warranted not only a sequel, but also a threequel. (That's not a term but it should be, so consider it invented).

Hat Box Night is no ordinary evening—it’s a boundary-pushing, dare-filled social experiment that turns strangers into accomplices and bars into playgrounds.

Just like in the movies, a good sequel will find a way to bring the audience up-to-speed in-between installments, whether via on-the-nose dialogue, a quirky opening montage, or re-inserting the final five minutes of the first movie into the first five of the next. Real ones won’t need reminders; they’ve already held a marathon rewatch session featuring snacks and running commentary. But, I must humbly admit, not all my readers and listeners are so devoted that they have had the time or inclination to link-hop back to the story of the first Hat Box Night. And that is okay!

Here’s the deal: last March, my friends Erin, Annamarie, and I brought a 1950s-era hat box to Ray’s Bar in Greenpoint, Brooklyn. By the end of the night, we'd made new friends, broken down barriers, and created an unlikely posse that felt like peak NYC magic.

Afterward, I retired the box to a closet shelf, and the night lived in infamy as a Substack post. Life moved on: jobs changed, apartments swapped, marathons skated, relationships ebbed and flowed. The world turned, and the hat box gathered dust. I knew one day it would be pulled out of hiding, called into action like a superhero who absconded to Belize after a fateful battle with an enemy. When the time was right, the hat box would rise again.

It was early November when not one, but two friends went through break-ups of varying degrees of severity. This timing coincided with less-than-favorable election results and a drought in New York City, a place somewhat famous for its cinematic rain in the fall.

Vibes were off, morale was low, the world felt spooky, and the girls needed a night.

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Hat Box Night: The Sequel

Like any good franchise, we embarked on our adventure by following a formula carefully crafted during Hat Box Night one. The first step was simple:

1. Acquire a hat box.

I pulled the box out and reminisced through old dares. Sifting through the slips, I felt like that old woman from Titanic looking at relics of her ill-fated Atlantic voyage. The memories came flooding back. “Ask a stranger for advice on something real.” “Improvise a choreographed dance.” “Convince someone you know them and double down on it.”

Needle drop; cue a song chorusing with energy and nostalgia.

We’re back in action.

2. Contact your most down friends. Invite them out for a night of shenanigans. Insist they wear their fun pants.

There’s something inherently more exciting about texting, “Should we have a Hat Box Night?” instead of, “Do you want to go out?” It’s like “U up?” vs “Hey I know it’s late but do you want to do a puzzle, have a drink, talk about our deepest desires and greatest fears and maybe even kiss?” Same idea, different approach.

The invites went out, and the Avengers assembled, ready for an evening that would live up to the lore of Substack post number 10.

3. Cut up slips of paper and grab pens. Stick ‘em in your purse and pockets.

I will be finding rouge pieces of paper in my purses, pants, and apartment for the rest of my life.

4. Go to dinner and brainstorm a few dares. This step is optional, but the mental pump-up pregame is mandatory.

Dinner was day-old salmon as my friend Danielle and I sat on the floor of my new abode (I had just moved and therefore not yet acquired a table or chairs or a couch), glasses of wine in hand, and began writing. Danielle, who’d moved to New York earlier this fall, was game for her first HBN, eager to take the city — or rather, Brooklyn’s quaint Cobble Hill — by storm.

5. Pick your destination. Choose a bar that’s not so loud that you can’t hear, not so packed that you can’t move, not so pretentious that you can’t play. Grab a seat.

We began at Congress Bar, allegedly a buzzing neighborhood spot. It was buzzing, for sure, but not at the same frequency as Ray’s back in March. This crowd was a bit tamer, more adult. You know the type — people who actually invest in a 401k and have a pesky back ache and are on a first-name basis with their butcher. While Ray’s had been packed with patrons ready to party, Congress was a collection of cool kids calling it a night at 10:00 pm.

By the time we got settled, our group had expanded to include friends Annamarie (a recurring character from last HBN), Maureen, and Jess. I wasn’t sure where we’d be more successful having a night out — Ray’s or Congress. Only one way to find out.

6. Write out as many “bar dares” as you can think of. Be creative.

The way Hat Box Night works is you fill the box with dares populated initially by the first group of participants. But the start was slow — too slow. We were writing; no one was biting. I was nervous. Were we coming up with the right dares? Were we doing enough? Maybe we needed to stop talking and just focus so we could have some fun. In hindsight, I hear it. “Focus so we can have some fun?” Ew.

Clearly I needed to let go of my expectations. If I didn’t loosen my grip on the whole thing, I’d suffocate the night. So the old rules went out the window. This Hat Box Night was going to be different than the one in March. I made peace with the present: it would be what would be.

But still, it would be fun if like, someone took the bait.

That someone was No Shot Sal*, an older gentleman with a fancy scarf and a stuffy attitude.

*Similar to last Hat Box Night I will be using pseudonyms, because they’re fun.

We presented our hat box filled with papers. No Shot Sal pulled out, “Ask someone their thoughts on the Wicked movie.” His brow furrowed. “But it hasn’t come out yet.” We consoled him, explaining someone could have thoughts on a movie even before its release. No Shot Sal couldn’t wrap his brain around this concept. He grabbed another slip. “Buy everyone shots!”

“Okay!” Sal agreed, then left. We never got our shots.

We did, however, make two new friends: the gregarious Upper West Wendy* and Just Left LA Lily*. They’d witnessed the Sal saga with wide eyes, wondering what on Earth was going on. Upper West Wendy pulled a slip. It was a classic: “Pretend you know someone and double down on it.” She walked over to a loner at the bar and we watched as she really, truly, desperately tried to convince him they had met. It didn’t work, but at least she tried.

Two strikes and it was time to move on from Congress Bar. Not that I cared — I was being chill, remember — but the problem was the place. As we plotted a secondary location, our group expanded: we were joined by friends Lexi and Ayla, and another recurring character: Tall Guy, first found during Hat Box Night one. He brought his friend, who we shall call Button Down Ben*.

We had high hopes for Talea, a brightly lit brewery down the street; it was about as bumping as a sheet of glass. Gathered around a long table, box in the center, down-to-clown Tall Guy grabbed a slip: “Ask someone their favorite song and sing it to them.” He approached someone who we will call HOW IS YOUR FIANCÉ* (this man had a fiancé and the group he was with made sure we knew) and started to sing. It was funny and sweet, a flicker of the game's original premise.

But that was the only one. The box got lost at the other table (the home of HOW IS YOUR FIANCÉ) where it was forgotten and shuffled around. After rescuing the hat box, it was time to move on… again. Our group, though smaller, remained determined. We would find our place.

We wandered like Goldilocks through South Brooklyn — Brooklyn Inn was too quiet, Public Records too pricey, but the Hollow Nickel, with its pickleback shots and unpretentious vibe, was just right. Sweet relief sank in as I settled into a seat and set the box on the table. The item of the eve was, “Challenge someone to a thumb war.” One valiant battle with Tall Guy later (he won), we called it a night.

The next morning, I sat on the floor of my apartment with a cup of coffee and looked over the unused slips. I’d promised an adventure but when the dust settled, all we had to show for the night were 10,000 steps and a bunch of blank paper.

Despite my fun night, I worried — I let everyone down? Had I failed my friends?

With a start, I knew the solution: we’d have to do it again.

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Hat Box Night: The Threequel

One week later. Saturday in New York City and this time, I was going to get it right.

The issue was not the place, but rather the neighborhood. Cobble Hill, though lovely, is known for its booming population of babies and dogs. We needed to go where the young people were. We needed to go where the scene was. We needed to go to the Lower East Side.

I’d come prepared with a list of every potential bar in the area so we wouldn’t be a wandering crew carrying a hat box. We were going to have fun, dammit!

The night began again with Hat Box OG Annamarie. In the movie version of this story, she gets top billing and by the threequel, ideally a fat check. (For the record Annamarie is an amazing actress, so if anyone actually wants to make a movie adaptation of HBN, you need to cast her).

We convened at my apartment (which now had a table and chairs, but still no couch), before hopping on the train to Dimes Square, where we were met by friends Grayson and Anna.

For those thinking, “Do you mean Times Square? Copy edit your work, my God.” This is not a typo.

Dimes Square is a micro neighborhood between Chinatown and the Lower East Side that was established during covid as a hub for the internet’s coolest and grungiest writers, podcasters, artists, and scenesters. I think at one point Dimes was considered the 21st Century answer to the beat generation’s Tompkins Square Park / Greenwich Village. Allegedly the Kerouac and Ginsberg of the 2020s can be found smoking cigs and drinking natural wine on a car-free street between Delancey and Allen.

Dimes is also a hub for New York’s finest and frattiest. On any given night, the bars within the tiny geographic designation are packed and pushy and no one’s polite about their space. So obviously, it seemed like a good place for a good time.

We bopped. We hopped. We shopped. We could not get the bar right. Consider the following my guide for you: places to go (or perhaps to avoid) in Dimes Square.

Le Dive

In the summer, this restaurant spills out into the street, giving a certain Parisian quality. In the fall, or because outdoor dining has been shut down, Le Dive is confined to a tiny indoor space. It was packed by 9:00 pm. “Come back at 10,” the bouncer sternly announced, eyeing my hat box with genuine confusion and disdain.

Bar Belly

It came recommended by friends who excel at going out. Unfortunately, it seems to be recommended to a lot of people. “We can put you in the sister restaurant until there’s room at the bar,” the hostess told us. She too looked curiously at my hat box.

Metrograph

To some, this is an indie movie theater known for playing films on 35 mm (a big deal for cinephiles). To others, this is a bar full of people who are really excited about movies on 35 mm. We got out of there before someone could tell me that my hat box reminded them of their favorite Frank Capra film that they would soon describe in detail.

Clandestino

More like ClandestiNO! This was the only place the hat box got some action but, much like dating a man in finance, it was quick and disappointing. Wall Street surfer bros Zyn Zach* and Juul Jack* pulled slips out, frowning as they struggled to read in the dim light. “Challenge someone to a thumb war?” “Ask someone their favorite color?” To Juul Jack’s credit, he tried. but the jam packed bar made it nearly impossible for a thumb war. “This is dumb.” The boys shoved their way back into the throng and we exited.

It was time to leave.

Walking down Essex Street, the box suddenly felt heavy. What had on previous nights been a delightful prop and conversation starter suddenly seemed cumbersome and stupid.

But we soldiered on, moving out of Dimes and up to the Lower East Side proper. Our destination was The Back Room, a prohibition era speakeasy (no, really, look it up) known for serving drinks in teacups. Surely this would be the right home for a hat box!

Womp womp. The bar’s two-story set-up and reserved tables meant holding the hat box with one hand and a teacup in the other. Once again, I found myself wanting to throw the box into a corner, to ditch the dang thing and be free. I was embarrassed, maybe even a bit sad.

“What is that!” We were stopped by a gaggle of girls in the alley on the way out of The Back Room. They gaped at the hat box. My heart soared.

“Want to do a dare?”

“Hell yes.” The girls pulled their slips out the hat box and read them, giggling. FINALLY! The moment was here, people were catching on, it was happening —

“HEY!” A bouncer in a fedora bustled towards us. “No standing in the alley. Get out. Go!”

“Maybe next time we do this, we won't bring the hat box.” I remarked to Annamarie as we wandered through the East Village later that night. We’d parted ways with our friends. “Maybe we just go out with the mentality and a few of our favorite dares instead?”

The heart of the hat box, we concluded, has nothing to do with a bulky vintage blue contraption. Sure, it’s a conversation starter. It removes a barrier. It gets you off your couch (if you have a couch). But it’s not entirely necessary. The important factor, what matters most, are the people you are with. Night after night, friends who love and care for each other participated, leaning in and saying yes to an objectively weird activity.

People want to be with each other, to be pushed, to have an excuse to go out and be silly. People want to show up.

Our evening ended at Amor y Amargo, a biters bar in the East Village. Danielle met us with her friend Molly. We didn’t touch the hat box. We had a great time anyway.

As I think about bar hopping and dating, I realize how the two are similar: both are hard to get right when you’re searching for something so specific. Instead of wandering for hours, maybe we’d be better off giving places and people more of a chance, even if one or the other doesn’t fit everything you’re looking for. Perhaps there’s something to leaning into imperfection, and discovering the good in what’s right in front of you. (Of course this doesn’t always work. Sometimes a bar can be really boring and a person can be really wrong).

There’s also a note about removing expectation from reality, how the most fun was when caution was thrown to the wind, and we followed each night wherever it went. HBN1 was a raucous round of dares at Ray’s. HBN2 was a slow burn with a big finish. HBN3 was for the girls.

Finally, before this movie smashes to black, credits roll, and you leave my little theater, the last lines offered are these: Hat Box Night was started and resurrected in honor and pursuit of friends. Time and time again, I’ve walked away from these evenings with a full heart, reminded how fortunate I am to be this age in this place with these people. Kind, brave, smart, fun, strange people. The pressure to provide a perfect party was self-inflicted, brought about from a desire to ensure everyone felt seen and that the night was worthwhile. But nothing is perfect, and everything is worth it if you just appreciate the moment, let go, and follow the fun.

For now, the hat box is back in my closet, where I assume it will stay for some time. Eventually, it will be needed again. But for what, who, or why? We’ll have to wait and see.

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Close your eyes. Now, open them so you can read this. 

Imagine you are standing before a museum. It’s an architectural marvel in the middle of the woods, a stately-three story structure with red brick and ivy running up the walls. The building feels forgotten in time, ripped out of a storybook and dropped into reality. A babbling brook rushes along the side of the building and bluejays fly overhead. Unsure how both you and the museum got here, you decide to go with it, stepping over the moss-covered cobblestones and pulling open the heavy wrought-iron doors, eager to see what’s inside. 

The entry hall is cavernous and striking; a colorful mural of a pompous horse by the sea decorates the domed ceiling. Your every step is amplified as you head to the reception desk, ready to fork over a fee only to discover that admission is free. Capitalism does not exist here. Grasping your ticket, you make your way further inside and look around. It’s late in the day and most of, if not all, the other patrons have left. Rays of early evening sun flare through the lobby’s floor-to-ceiling windows as you grab a map (also free) and peruse the offerings. Kind of an odd collection, you think to yourself as you mosey on. 

If it was quiet in the lobby, it’s dead silent in the gallery hall. Your every step and breath echoes through the gorgeously adorned space as you curse yourself for wearing those heeled shoes today, trying to tiptoe to minimize the noise. At the end of the museum’s main hallway, a security guard dozes off in a chair positioned directly in front of an imposing eight-foot paper mache woman whose bedazzled breasts tower over the guard’s head like an awning. A beat-up and dog-eared copy of “He’s Just Not That Into You” rests on the guard’s lap, and you wonder if perhaps he’s working through some stuff. 

The guard lets out a loud snore as you pass through the first doorway and into an exhibit. 

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You’re startled by an old woman standing in the gallery, wrinkly hands folded behind her back and subtle smile stretched across her painted face as if she’d been waiting for you.

“I’ve been waiting for you,” she croaks out. “Oh!” You exclaim, a bit terrified, wondering if like the museum, she also appeared out of nowhere.

“I’m Doris. You’re the only person visiting the museum. You would like a guided tour?” It sounds more like a command than a question, so you nod yes. 

Doris lets out a wicked smile. “Yipee,” she proclaims and pads to the exhibit description sketched on the nearby wall, red orthotics soundless as she steps. “This is a weird museum, and this is a weird exhibit.” You do not feel like you needed Doris to point that out, but you’re glad she’s self aware. 

“Do you know Keith Haring?” She stops in front of the wall of text. “Of course,” you mutter, suddenly hopeful that you’ve stumbled into some private collection of the 80’s pop graffiti artist. “This exhibit is nothing like him and the art is worse.” Doris explains. 

“Do you know Monet?” Doris looks at you expectantly as you nod. A quick glance around the room confirms these are not the paintings of French impressionism founder Claude Monet, so you wonder where this is going. “I’m not a fan.” Doris states solemnly.

A beat, then she turns to the exhibit at hand. “Let’s get into it, shall we?” With long, languid sentences, Doris reads the writing on the wall. 

Doris stops and looks at you sternly. “This is not a real style of painting, do not try to look it up.” You weren’t planning on it. She continues reading.  

Doris finishes reading with a flourish, clears her throat, and hobbles over to the first painting. 

Doris pulls out a lemon from her chaotically crocheted bag and holds it up to fruits in the painting. “They look nothing alike! When life gives this artist lemons, she should not try to paint them.” Doris leaves the lemon on the floor and marches on. 

“I discussed this painting with my therapist, per the description’s suggestion,” Doris offers after loudly reading the text. “He suggested I start coming in three times a week.” 

Doris doesn’t offer any commentary. She instead stares at the purple monster, lost in some thought you’d rather not interrupt. After a few moments, she wipes tears from her eyes and turns to you. “I have nightmares about this painting.” She adjusts her thick wool cardigan and steps towards the final piece.  

“... Well?” Doris barks at you. “What do you think?”

You’ve reached the end of the small exhibit, deeply underwhelmed and overwhelmingly confused. Part of you wants to ask for your money back, even though you didn’t even pay. As you inch towards the exit, Doris stops you, her manicured claw pointing towards something dangling haphazardly from the far wall. “Wait! There’s one more!” 

A single sheet of paper, a note from the artist typed out in 12-point Times New Roman, hangs tacked up by scotch tape and a Hello Kitty band-aid. 

“You see? She knows she’s bad,” Doris blurts out after you finish reading. This one, she let you take in on your own. “It’s kind of funny, right? Plus it makes the other artists on display feel confident. If this girl can do it, anyone can.”

You sit with the words for a moment, then Doris aggressively sighs. “Okay. The tour is over now. Would you like a hard candy?” 

Doris reaches into her bag and pulls out a handful of lint-covered Werther’s Original Butterscotch, offering them with her outstretched palm. You politely decline. Doris shrugs, unwraps one, pops it into her mouth, and wanders back over to the purple monster. 

You take one final look around the room and exit the exhibit. 

The guard is still asleep, and a pool of his drool has formed next to the paper-mache woman’s toe. You consider calling it a day and going home. But entrance was free, so… what the hell. You walk across the hall. 

The next gallery is yours. What’s inside? 

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A special edition of 129 ran last Monday in Defector for List Item #23. “Blade Across Europe”; The View from the Way, Way Back of the Berlin Inline Skating Marathon. This story was the first bit of writing I’d sold on spec and I couldn’t be prouder. The experience of covering a sporting event while also participating in said sporting event was cool, then scary, then exhausting, then exhilarating, and then it was over. Being a paid writer, it turns out, is not so unlike rollerblading a marathon. 

For details on the saga (and it was a saga), I’d suggest you check out the piece and then come back. But since we exist in the context, here are the spark notes: I rollerbladed the Berlin Marathon, I was very slow, I was chased by a bus called the Broom Wagon, I ate shit, I got back up, my finish was broadcast to the masses as I ended the race in literal last place. It was epic and made for an excellent article which again, you can read here.  

That same Monday, hours after the story had been published and as my 15 minutes faded faster than a sunset, I went on a date. It was a fine date; fun, even. What better way to celebrate the accomplishments of the day than a night of easy conversation and Espresso Martinis in a dimly lit cocktail bar?

In the end I was glad I went. But in the beginning, it was the last place I wanted to be. Thirty minutes before I was set to leave, the internal Lizzie McGuire-fied version of Emily was kicking her feet and screaming, heels dragging as some unseen force shoved my animated alter ego towards the front door. I told myself the trepidation was because I wanted to stay in and have cozy time, to work on my opus, to watch paint dry, to finally get past page one of Intermezzo. 

In reality, the raison de résistance was something much simpler: I just wanted to avoid the possibility of getting hurt. 

As much as this project is about more than dating and was designed to transcend its derivative source material, (129 Ways to Get a Husband) at the end of the day, it was still inspired by a pretty basic desire: to find my person. I have spent a lot of time trying to pretend that this isn’t the case, that I’m better than an antiquated list, that I am happy on my own. That is largely true — I am happy and I am certainly better than a listicle which tells women to “Go on a diet if they need to.” But it’s also important to admit to myself and to you, dear reader, that I am perpetually in search of love. Maybe not a husband yet, let’s not get ahead of ourselves, but certainly a partner to share life’s big moments with. Big moments like getting your first piece of writing published. 

So I went on a date. Though the details of the evening are not relevant to this essay, the emotions surrounding the event hold much significance. I promise we will get back to rollerblading — there’s a reason this is #23. Blade Across Europe — you just have to stick with me. 

In the days after, I was continually stunned by how affecting and paralyzing the fear had been. How much power it held. That somehow the very idea of vulnerability had become almost too much to bear. Perhaps it’s because for much of the last year, I’ve found myself caught in the vicious cycle of hopes up/heart hurt, and lately I’ve thought it might be easier to give up entirely than continue going round and round and round. I’m not sure when things changed, but suddenly the scrapes feel more like scars. The mountains are taller; the cliffs vaster; the end increasingly far away. A setback is a step back. 

Reflecting on my post-rollerblade date resistance, I realized with horror: my resolve has faded. 

Literally (Berlin) and figuratively (life), it feels as though I’m chugging along in last place while my friends zip to the finish line. And yes, eventually there is a finish line, and my story of getting to the end is excellent. It’s the kind that only happens in movies, a tale that’s so outlandish it can’t be real. This year I find I’ve had a lot of those: really great stories. I’ve been swept off my feet only to be swiftly dropped on my head, caught up in act one of rom-com after rom-com. 

I’m grateful for the stories. I’m grateful to have spent this time doing so much living. I’ve met incredible people, both in romantic and platonic contexts. I have grown as a human, a partner, a writer, a friend. I’ve gotten better at asking for what I need — what I deserve — and walking away from those who can’t provide it. I’ve been an open book (blog!) and it’s paid off. 

Still I find myself faltering, ready to wave a white flag and surrender, to pack up the metaphorical rollerblades that are my heart and sell the damn thing on Facebook marketplace. Maybe buy a cool bag with the profit. Surely, that’s the better option. 

Yet I can’t do it. Maybe it’s masochistic, it’s definitely masochistic, but I just can’t seem to quit getting hurt. The promise of a happy ending is too enticing. 

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About three weeks before the marathon, I decided to give up. I’d just returned from yet another fall at the park and felt utterly hopeless. Frustrated and weary, I threw my blades in the corner of my apartment, cleaned my bloody knees, and curled up in bed. I was done. 

That night, sleep evaded me as I tossed and turned, only one thing on the mind: rollerblading. It was as haunting as a significant other who breaks up with you out of the blue — it doesn’t make sense and eats away at your every thought, dream, nightmare. But at least in this situation, I could find a rhyme and a reason; I could figure out where I was going wrong.

With dating, sometimes you never know why things didn’t work out. With rollerblading, there is the internet. And the internet offers information! Nothing hits quite like a 2:00 am Wikipedia deep-dive, am I right?  

Here’s what I learned: Rollerblading was popularized in part by a man named Scott Olson, a Minnesota ice hockey player who, in the 1980s, decided to improve upon an old pair of inline skates so he and his brother could play hockey in the summer. The resulting product became the Rollerblade™, Scott became a millionaire, and the country became enraptured by the sport. While it has since waxed and waned in popularity, it remains a staple for skiers, hockey players, figure skaters, and runners eager to cross-train or practice in the off season.  

Perhaps it was the reframe to approach blading like a skier: more of a glide and less of a spastic jerk. Or maybe it was the analogy that rollerblading is just ice skating on land. Possibly it was the vintage news clip of Scott Olson circa 1982 explaining the art of the rollerblade. Or it was nothing intellectual whatsoever, but rather the decision to call it quits that freed me from the shackles of my own dumb brain. Whatever it was, the morning after entering the depths of wheel-induced despair, I felt pulled back to the park for one more try. 

Boom! Just like that, the puzzle pieces fit together; the IKEA dresser instructions finally made sense. Something was different. Something had clicked. 

Skating around the path that day, I was struck by a sense of peace. I knew I would fall again at some point soon, but I didn’t care; I was on cloud nine. For the first time in my rollerblading journey, things felt right. Actually… it felt a lot like being in love. 

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Love is a powerful emotion. The act of loving, of giving yourself over to a process you cannot control, of trusting in something greater than yourself, is profound. It often pertains to another person — a partner, a friend, family — but it also extends to ourselves. It is not infallible. To choose to love is to willingly glide on rollerblades knowing at any moment you could hit a branch or lose your balance or do nothing at all and still fall flat on your face. It’s scary and deeply painful. It is dangerous. 

Even the possibility of the feeling — the first few months of a new relationship, the early stages of a friendship — is exhilarating. Love is fullness and freedom as it simultaneously constricts and explodes the heart. 

Of course, none of this is groundbreaking information. Any good romance novel or movie would convey the same sentiment, likely with stronger prose and hotter people. Still, I’d be remiss not to include it because it is the pursuit of this feeling — that click — which has propelled me forward for the last year, both on blades and on dates. 

But one has endless endurance, and the exhaustion has set in. I’m no longer certain that I’ll ever get to the end and this whole ordeal is starting to feel like a fool’s errand.

So why did I go on that date, and why am I writing this, and why should you care? 

Berlin. 

Finishing that race was genuinely the last thing I expected to do. Before the competition had even started, my notes were filled with contingency plans, half-drafted essays on the merits of giving up. I had accepted defeat, convinced that a win was not in the cards for me. 

That wasn’t entirely incorrect. By just about every measurement, I did not win at the Berlin Marathon. I didn’t complete the full 26.2; my split pace was abysmal; I cried publicly; I fell hard; I was the last person to finish the race. 

But I finished the race, proving my worst instincts wrong and surprising even myself. If skaters were given a scorecard, instead of the expected acronym DNF (Did Not Finish), three letters would be eternally emblazoned next to my name. 

DFL: Dead Fucking Last. 

My win looked different than everyone else’s. It wasn’t traditional, it wasn’t predictable, it took longer, and it involved a lot of emotion and spectacle. It was uniquely mine, something I had worked for and earned. It got me on Marathon TV. It was worth the wait. 

I write this because I imagine I’m not the only one who has thought about throwing in the towel at some point or another. I hope these words offer some solace or inspiration or just maybe a ten-minute distraction. 

If rollerblading has taught me anything, it’s to trust the process. It’s knowing that getting to a finish line doesn’t mean the course is over — there will be more challenges and crashes. I’ve learned to embrace the falls and accept them as par for the course, to understand that things won’t always hurt, and they won’t be this way forever. A marathon is long, and so is life. 

All we can do is keep the knee pads on, tighten the helmet, make sure the wrists are protected, strap on the skates, and keep going.

Head high, heart out, full speed, waiting for the click.

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Technically instead of biking, I bladed through Europe, but why worry about semantics? On Saturday, September 28th, I rollerbladed the Berlin inline skating marathon with my best friends. It was one of the wildest things I’ve ever done, and this is coming from the person who learned to clean and scale a fish. Training for the event consumed most of my leisure time this summer and all of my therapy sessions. For months it was the only thing I thought about, the bane of my very existence. My emotional distress blades accompanied me on journeys to Michigan, Brooklyn, London, Austria, Colorado, Connecticut, and Germany. They’ve been with me during break-ups, break-throughs, and broken nails.

I have so much to say about the marathon — including an insane story about crossing the finish line that I couldn’t fictionalize even if I tried. I will be sharing those thoughts in a few weeks (in a fun special edition!).

Before and after the marathon, I did some traveling, something I haven’t been able to do since college. In preparation, I spent hundreds of hours standing in front of a mirror practicing #22. “Use Your Eyes to Good Advantage.” The result had me looking like this.

Some people obsess about how to pack suitcases, I make myself cross-eyed straining to perfect seductive blinking techniques.

My friends and I actually did use our eyes to a healthy advantage on our European romp. In London, light staring earned the attention of a gloriously tattooed bartender at Kwānt, the only non-members club in Mayfair that would take us after midnight. One glance across a bar on a boat in Treptow brought us Nikolai, a chain-smoking artist eager to explain the continued divisions between West and East Berlin. Our pupils bore into the soul of a burly brown bear at the Innsbruck Alpenzoo, the highest-elevation Zoo in Europe. And in Munich, a batting of the eye invited the attention of just about anyone; hostels and Oktoberfest are hotbeds for cornea-induced camaraderie. We danced on tables with Fedora-clad Venetians and screamed on rollercoasters (there are RIDES at Oktoberfest!) with clean-cut engineers from Oklahoma.

Safe to say avoiding eye contact would have made the trip far less social. So I’d highly recommend using your eyes to good advantage a la European women.

Similar to the marathon, I have much to say about the past few weeks. But the top line here is that I’m grateful. As with many of the 129 list items, the best part was simply sharing these adventures with the people who matter most.

So here’s the part where I pivot and introduce something different: a new section of 129, inspired by my desire to help everyone experience the same kinds of joys this list has brought me.

Over the last year, I have spent a lot of time researching how we interact with each other in the 21st Century. Past versus present, ways to put ourselves out there, and activities to broaden our horizons. One of the questions I am flattered to be frequently asked is, “How the heck do you find this stuff?”

A good magician cannot reveal her secrets, but I certainly can share my results.

I’m rolling this additional segment of 129 out as a paid tier. The list item essays (#10. Carry a Hat Box.”) are still free to all, but the extra bits — “The Modern 129” — will be for paid subscribers. Once a month, I’ll drop a portion of this new list, which is full of curated and heavily researched ideas for how and where people are putting themselves out there in 2024.

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As I near one year (!) of 129, I have become keenly aware of how much this project changed my life. It’s opened up my world and made it more fulfilling than I could have ever imagined. It inadvertently funded a trip to Europe so I could rollerblade a marathon, for goodness sake! (Like I said, more on that soon).

I am overwhelmed by gratitude for this endeavor and genuinely surprised by everything it’s given me. Expect a hefty retrospective in November. Prepare to cry.

Everyone should get to have this much fun (if they want to). And while I do think anyone could do the original list (seriously, hit up your local fishmonger and ask for a cleaning lesson), the 1958 edition leaves a lot to be desired. That is, of course, the beauty of the main 129 Ways to Get a Life — seeing what holds up and what doesn’t. And that part of this Substack isn’t going anywhere.

I’ll continue to take one for the team and make my way through the source material (probably weeks away from “Stand on a Busy Street Corner With a Lasso”). But I’m also going to start sharing brand-new ideas: how to meet people now.

What would this list look like if it started from scratch in 2024? The Modern 129 is my best guess, and these are items 1-5.

I encourage you to do them, share some, and let me know how it goes.

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The Modern 129 (1-5)

1. Join an intramural sports league.

Picture this: on a Thursday night in May, you walk past McCarren Park in Williamsburg — or maybe Wash Park in Denver or Mission Dolores in San Diego. No matter the location, the scene is the same. Clustered under white-hot lights stands a pack of adults ranging from age 22 to 35, sneakers dirty from running around a field.

Their discussions on where to get a post-game beer are easily overheard, and it's fun to watch the flirting, laughing, and shouting between teammates. They're a diverse team, residents on the island of mismatched toys, brought together and bonded eternally by one thing: intramural social sports.

Adult athletic leagues are hardly a new concept. In fact, they're one of the oldest in the book (the rise of amateur leagues can be traced to the late 1800s after structural shifts in working-class America created time for leisure). So, why now? What's so special about a gaggle of 20-somethings roaming the streets in matching neon t-shirts? 

I know people who have entered a league alone and finished the season with a romantic partner, a best friend, or an entirely new community. My sister met her husband on a Denver kickball team. These leagues offer a way to get out into the world, be active, and connect with others.

Where can I find one?

Here are some of the leagues I’ve found. I’m personally a Volo girl. My softball team has lost every single game in their five-year history!

• Volo (Baltimore, Boston, Charleston, Denver, Los Angeles, Morristown, NY Metro, San Francisco, San Diego, San Jose, Seattle, Washington D.C.)

• ZogSports (New York, New Jersey, DC, Los Angeles, San Francisco, San Jose)

• Chicago Sport & Social Club 

• Come Play Detroit

Things to talk about while kicking around the ‘ol pigskin:

• How a Scottish Softball League Cured My American Loneliness (New York Times) 

• The Last Days of Summer by Steve Kluger — Look, this has nothing to do with intramural sports, but it’s one of the best books I’ve ever read and not enough people know about it. Bring it up at your softball game.

• In Social Sports It’s About Camaraderie, Not Competition (New York Times) 

  Most participants are looking for a social experience. “It is all about you creating a personal connection with other people,” he said. Like Ms. Keenan, most of the people signing up for social sports leagues today are urban professionals in their 20s and 30s. Jean Twenge, a psychology professor at San Diego State University, said people in their 20s today were less likely to be married or living with a partner than in previous generations, so they had fewer social connections and were looking for more ways to make friends.

2. Learn chess.

Chess is where the hots are, apparently. 

I first heard about a “social adult chess club” about a year ago from my friend Abby. It was described as a way to meet friends and hang out in an interesting setting — no prior chess experience necessary. After further exploration, it really seems to be a thing. What better way to get to know a stranger than sitting across from them, strategically moving little monarchical figurines around a checkered board?

For those who are a bit socially shy, chess provides a buffer. For those who live to yap, chess creates an easy in and an intimate opportunity. It’s a conversation starter; it’s simple yet complicated; it’s intellectual; it’s cool! It’s different and daring. Do it.

Where can I find the Queen to my King?

• Pawn Chess Club (NYC) — The aforementioned chess club that started it all. Have heard wonderful things. Their next meeting is October 5th!

• LA Chess Club (LA)— I read the LA Times article about this (see below) and thought, “wow, I am actually not even cool enough to play chess.”

• Any other social chess clubs in cities? Send them and I’ll update this!

Content! I need chess content!

• LA Chess Club Is How Gen-Z and Millenials Are Finding Community and Dates (LA Times)

• How Life Imitates Chess — A man named Garry Kasparov (considered the greatest player that ever lived) “distills the lessons he learned over a lifetime as a Grandmaster to offer a primer on successful decision-making: how to evaluate opportunities, anticipate the future, devise winning strategies.” Sounds like that Freakonomics book everyone’s so stoked about.

• The Eight by Katherine Neville — I found this on a reddit thread. It’s about a “computer whiz who must enter into a cryptic world of danger and conspiracy in order to recover the pieces of a legendary chess set once owned by Charlemagne and buried for one thousand years.” Book club, anyone?

• The Queen’s Gambit by Walter Tevis — Remember the 2020 Netflix Covid banger starring Anya Taylor Joy? You know how it did for Chess what Challengers did for Tennis? This is the book that started it all!

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3. Put your name and contact info on a sticker, stamp, or business card. Take to the bar and pass it out!

News flash: simply asking for someone’s phone number or Instagram is out. Just give them yours already! Hand it to them in print, ink, or adhesive! We don’t have time to waste with small talk and an awkward shuffle around requesting contact info.

It’s an election year, dang it — take action!

There’s no way people are actually doing this, right?

• Yes they are. In this video, a girl puts essentially a Hinge profile’s worth of information on a pink business card with the note, “I thought you were cute & liked your vibe so I’m making the first move.” It’s endearing and awesome.

• No really, they are. This girl is at the bar stamping the arms of anyone she finds attractive. She also went viral. Cool!

• Don’t believe me? They are. Remember that episode of The Office where Michael Scott gives his business card to the bar manager at happy hour? She calls him. They date. It doesn’t end well.

So what, I’m supposed to just make a sticker, stamp, or business card?

• Stamp — There’s a million places to make a stamp. And how fun! Imagine waking up after a night out with a number stamped on your body. Seems like the start of a zany Zach Galifianakis comedy.

• Sticker — Stickers are fun. They make people happy. They are multipurpose. They are everything. Just don’t order from Sticker Mule.

• Business card — They’re literally calling cards. What more is there to say?

4. Take an improv class.

If I had a penny for every person I know who’s met their partner or best friend in an improv class, I could pay for an improv class (they are not cheap).

I could wax poetic about how much I love improv. Taking an improv class teaches you to think on your feet, find the fun in uncomfortable situations, and listen to your partner. It pushes you out of your comfort zone. It helps with public speaking. It encourages a point of view and fosters the imagination. It can sometimes land you on SNL.

And then there’s the community. Whether you’re in a 101 class or on a team that performs weekly, improv opens the door to a world of wonderful, silly, and (mostly) welcoming people. The friendships don’t rest in whether or not you’re purusing comedy as your career; in fact, many of my favorite improv folks have nothing to do with the performing arts of writing. These are just people who love to laugh and want to surround themselves with like-minded individuals.

Where can I do improv? Better question is where can you NOT do improv? Improv Is Everywhere.

• NYC: Brooklyn Comedy Collective, Upright Citizens Brigade (UCB), The Second City, The Pit

• Chicago: The Second City, Improv Olympic (IO), The Annoyance

• LA: The Groundlings, UCB

• Detroit: Go! Comedy

• Toronto: The Second City

“I’m not funny.” “Improv is weird.” “There’s no way it’s worth it, right?” Wrong.

There are endless articles, books, and movies testifying about how great improv is. Here are a few :)

• How an Improv Comedy Class Revolutionized My Dating Life

  ​​It started by accident. There was a funny guy in my class. I said, “Let’s go see a show,” only to realize, when I showed up, that it was a date. Turns out that it’s pretty easy to ask guys out. Previously, asking a guy on a date fell into the same category as lighting my whole body on fire. Because I hadn’t had time to obsess over the date, I didn’t feel as strongly about this guy as I usually did. What a perfect time to try out my new party trick: being vulnerable. Everything is temporary. When you do an improv scene, you know your work is disposable. So to with dating. You might as well be honest and real. If it’s terrible, you never have to see that person again. If it’s good, you might get laid. If it’s great, you might get a boyfriend.

• Say Goodbye to Awkward Dates with These Improv Tips — I wanted to balk at this but honestly, there are some really helpful and insightful points here. This is probably why comedians are so successful at being in relationships.

• Truth in Comedy — This is sort of the Bible for improv kids. Perhaps tied with the Upright Citizens Brigade Comedy Manual. Both were required reading for my college improv troupe.

• Don’t Think Twice — Technically a movie, but it's canon. Have to include.

5. Read a book alone at a bar or restaurant.

This is a reclaiming of that silly romcom trope: “person reads alone at a bar, gets asked out, and finds love.” That doesn’t usually happen, but a lot of us (me) expect it to. And when we go into a situation with a specific expectation for something amazing to occur we are often disappointed (see: #1. Get a Dog and Walk It).

So why did it make the list? Because it’s something that should just be for you. Being comfortable alone is as important as being able to jump into new social or romantic situations. There is a sense of power that comes with knowing you can be your companion, even if only for a quick meal or a drink at a bar. If life is a balancing act, then we need to incorporate solitude into socialization to even the scales.

Good places to post up:

• This is really specific to your tastes and your city. But some places to start…

  • Any fancy hotel lobby, really.

    • NYC: The Hoxton, The Ludlow, The Marlton

  • A classic diner. You know the kind.

    • NYC: Three Decker Diner

  • Somewhere with red wine and fancy fries.

    • NYC: Balthazar, Long Island Bar

What my literary friends are reading and you may want to as well:

• The Overstory by Richard Powers

• The Idiot by Elif Bautman

• Pachinko by Min Jin Lee

• I Feel Bad About My Neck by Norah Ephron

• The Dud Avocado by Elaine Dundy

• Demon Copperhead by Barbara Kingsolver

• A Court of Thorns and Roses by Sarah J Mass (sorry not sorry)

• Destiny of the Republic by Candice Millard

• F*ckface and Other Stories by Leah Hampton

That’s it! How’d we do? Do you like this new segment? Try some of this out and let me know how it works! I’d love to hear.

Either way, get stoked for #23. Blade Across Europe. Coming soon!

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This idea came about a few months ago when my good friend Ritam Mehta (comedian and one-half of the funniest Substack around, Low Lift Ask) offered to join for a list item. If you ever want a partner in crime, he said, count me in. I told Ritam the same thing I told national treasure Conan O’Brian when he asked to be included – look through the original list, let me know what you’re excited about, and we’ll dive in. Conan was intimidated and never followed through. But Ritam? Ritam was game. 

#21. “Buy a Convertible. Men Like to Ride in Them.” That sounds fun, he texted. So I marched to the nearest auto dealership, slapped down my AmEx, and bought the shiniest drop-top on the showroom floor. Drove away tens of thousands of dollars in credit card debt, scooped up Ritam, and we sped down the Brooklyn-Queens Expressway into the sunset. 

I’ve said it once, I’ll say it again. There is nothing I won’t do for this project. 

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Yo, that would be crazy! Sorry to disappoint, but I did not actually buy a convertible. Millennials and Gen-Zers don’t buy anything, remember? We rent. 

Ritam and I decided to rent a convertible for a day and take it on a delightful jaunt through upstate New York. Some may have been made aware of the magic of upstate New York in late summer/early fall via Taylor Swift’s All Too Well (10 Minute Version) (Taylor’s Version) (The Short Film), a cinematic masterpiece featuring a young Sadie Sink (playing Swift) zipping down tree-lined roads with Dylan O’Brien (playing local villain Jake Gyllenhaal). Others may just know the area because it’s pretty well known.

We booked our whip through Turo, a peer-to-peer car rental app that is like Airbnb for automobiles. It’s cool and I’d highly recommend it, but Turo ignored my email asking for a discount if I included them in this Substack, so I won’t be saying anything more on that. 

The site offered a variety of convertibles scattered across the greater New York metro area. A Porsche in Pelham Bay, a Mustang in deep Jersey City, a Volvo in the Village. All were exciting, but none were right. None felt worthy of a road trip. (And the Porsche was $500 for the day). The thing is, convertibles are cinematic. They’re exciting. Thinking of riding in one conjures images from Thelma and Louise, The Notebook, Scarface, Ferris Bueller’s Day Off, The Hangover. All chill movies with chill people where nothing bad happens to anyone. 

The car had to be special. It would set the scene, which is why there was ultimately only one choice: a red Jaguar F-Type, courtesy of Miguel from Turo. 

How to Have the Ultimate Upstate Road Trip In 200 Miles Or Less Because After That Turo Starts Charging You 0.70 Cents Per Mile

YONKERS, NEW YORK

The third most populous city in New York state, Yonkers is located at the northernmost tip of Manhattan, just above the Bronx. It is also known as The City of Seven Hills.  

Ritam and I stepped off of the Metro North and headed to the car pick-up point. We had no idea that what Google Maps called a “10-minute walk” was more like a steep hike up a never-ending hill. There are a lot of hills in Yonkers – seven, as we would quickly discover. On the upside, the climb provided a scenic tour of the area, which before I’d only been vaguely familiar with due to Neil Simon’s Pulitzer Prize winner, Lost in Yonkers, a play following two grieving, newly motherless boys who spend a summer in Yonkers with their Grandma and Aunt.

We finally reached our destination, out of breath and sweaty. But then we saw the car and just like that, it was all okay. Keys in the ignition, Google Maps set to our destination, the Ultimate Road Trip Playlist cued up, we hit the road.

SEVEN LAKES DRIVE, HARRIMAN STATE PARK 

The Seven Lakes Drive is a parkway stretching for 18 miles across both Harriman and Bear Mountain State Park. From south to north, the lakes are Lake Sebago and Lake Kanawauke in the towns of Haverstraw and Tuxedo; Lake Skannatati and Lake Askoti in Tuxedo; Lake Tiorati in Tuxedo and Woodbury; Silver Mine Lake in Woodbury; and Queensboro Lake in Highlands.

The Seven Lakes Drive drive was Ritam’s suggestion and scenic as hell. He’d been looking for something to see on the way to our first destination in Monroe, New York. Isn’t it funny how some of the best discoveries are out of necessity? 

BLOOMING HILL FARM 

A small family-owned farm and restaurant in Monroe, NY, Blooming Hill is a hidden gem in the Hudson Valley. 

I mean… wow. Again, a suggestion of Ritam’s.

We ordered enough food for a small family. It was farm-to-table, so everything was fresh and local, and much of the produce was grown on-site. One summer hash, Pomodoro pizza, sourdough waffle, and hash browns later, we wobbled out of the restaurant and over to the farm shop.

The stand was laden with homemade hot sauce, sourdough pizza dough, and a cornucopia of vegetables. I’m embarrassed to admit the only thing I considered buying was merch. (They’ve got great baseball caps!) As Ritam paid for his hot sauce and plums, we asked the cashier her favorite things to do in the area.

LEGOLAND NEW YORK 

RUMMAGE SALE, LOCAL CHURCH

The theater space at a local church in Newburgh, New York. Every inch of the wall is decorated with hand-painted theater posters from shows dating back to the 90’s. 

Here, we spent some time chatting with a member of the Church whose name I wish I could remember. She’d been in many of the congregation’s plays and introduced herself after watching me gape at the show posters. 

“Oh! Were you also in The Wizard of Oz?” She asked. “I was in that cast, but I don’t remember seeing you.”

I responded that I was, indeed, in The Wizard of Oz (the coveted role of Tree #2), but back in Michigan. She looked disappointed. I didn’t bother to point out that the Church’s (and her) production of The Wizard of Oz ran in 1997, and it would have been difficult for me to perform as I was not even yet able to walk. We talked a bit more about the joys of local theater and then Ritam and I left.

We did not buy anything.  

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MOTORCYCLEPEDIA MUSEUM 

An 85,000-square-foot space displaying the collection of over 650 motorcycles that father-son duo Gerald and Ted Doering have amassed over a combined 80 years.

This museum is one of those places – those special spots you’d never get to unless you stumbled upon it or sought it out. Not only was Motorcyclepedia incredibly curated and cared for, but it was staffed by wonderful, kind folks. Ritam and I were guided by Denny, a former interstate repair man and car enthusiast who started working at the museum to help out his friend, owner and motorcycle aficionado Ted Doering.

Denny taught us about Rat Fink, the anti-hero to Mickey Mouse created by Ed “Big Daddy” Roth. He showed us every pop culture bike in stock, ranging from the original Adam West Batmobile to the one the Fonz used in Happy Days. He introduced us to his friend Peter, a fellow employee with the essence of a middle-aged Billy Crystal if Billy Crystal were Italian and also had a thick upstate New York accent.

When we asked Peter a question about the bikes, he replied, “If I’m wrong I have to tell you a bad joke.” He was right, but told us the joke anyway. 

I’m not saying go visit Motorcyclepedia just for the jokes, but it’s a value add. Peter’s stand-up and Denny’s tours come with the cost of admission, along with a full set of Indian Motorcycle trading cards, a bandana, and a pin. Well worth $15. 

GAS STATION

An establishment beside a road selling fuel for motor vehicles. Did you know you can buy phone chargers at gas stations? News to me. 

STONY KILL FARM ENVIRONMENTAL EDUCATION CENTER

A 750-acre farm in Fishkill, New York. The historical property offers everything from a community garden to ample hiking trails to a thriving livestock population. 

I had put this destination on the list in the hopes of attending the “Open Barn” hours, which occur every Saturday and Sunday from 11 am - 1 pm (February - November). Unfortunately, we had too much fun at Motorcyclepedia and arrived too late. The barn was closed, but the animals still roamed freely. Ritam and I parked the car in front of a rusty red barn and found ourselves walking down a dirt road in search of… what, exactly, I don’t think we knew.

Perhaps we were just drawn to the cadre of fly-ridden cows watching us from the nearby pasture. Separated only by a thick fence of barbed wire, we observed the cows playing an exciting game of tag as bored sheep grazed nearby. 

We headed towards an old farmhouse that was the Environmental Education Center. During the week, it’s home to the Summer Explorers Camp, but on this Saturday, it just seemed haunted and empty. It was there we met a woman and her baby, who casually mentioned that we should, “Go look at the beehive.” 

We immediately zoned in on the beehive. It was all that mattered. It was everything to us.

But there was no beehive to be found. We looked for about three minutes before giving up hope and deeming the mysterious stranger a villain sending us on a fruitless (more like honeyless) quest.

“BEEHIVE!!!” We screamed in agony, our echoed cries rivaling that of Marlon Brando’s “Stella!!!” in A Streetcar Named Desire. The elusive hive would haunt us for the rest of the day, and potentially the rest of our lives.

Attempting to move on, we returned to the car, passing through a garden teeming with butterflies and smelling like clean air. I was struck by the silence. We were all talked out, at least for the time being. So we just walked, only the sound of grunting cows and distant cars punctuating the peace.  

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BEACON, NEW YORK 

HUDSON VALLEY FOOD HALL 

An international food hall in the heart of Beacon, New York. 

Ritam and I went here to recharge our bodies and cell phones. We got iced coffees from Dhaka Coffee, which Ritam says to note, “Might be the best iced coffee I’ve had in my life.”

Ritam has good taste, so this praise should not be taken lightly.

HAPPY VALLEY ARCADE BAR 

An old-school arcade ripped right from the 90s. 

Games are 25 cents a pop, UFO paraphernalia peppers the walls, half the machines are out of order, the bar is ripe with beer. Here, we discovered just how much fun you can have with $3. After several games of Pac-Man and some two-player situation involving asteroids, we found our favorite machines. For Ritam, it was a car game where you turn a knob to keep the vehicle on the screen. For me, it was Gauntlet Legends, an epic dungeon brawl between a wizard and her enemies.

The only way the place could have been better was if it had Penga, A.K.A Canadian Pac-Man. I grew up playing this game in my family’s bowling alley in Windsor, Ontario (lore for another list item). My siblings and I would sit in the arcade for hours on end, feeding the machine Loonies and Toonies (actual Canadian currency) until our Mom was done working for the day and it was time to get in the car and drive through the Windsor tunnel back home to Detroit. 

At Happy Valley, I was flooded with nostalgia. But I suppose that’s the point of a retro arcade. It takes you back in time.

WONDERBAR 

A small bites and big cocktails restaurant connected to The Beacon, a 3-screen movie theater featuring blockbusters and independent films in an old building from the 1930s.

Over wine, tater tots, and broccoli, I scribbled down notes on receipt paper, eager to remember everything we’d seen and everyone we’d met. My phone was dead, again, now charging in the back of the restaurant. There was something lovely about being detached. Makes you take it all in a bit more when you can’t snap a picture or jot down a thought. I believe this is called “living in the present.”

HYPEBEAST STORE WITH SMALL DOG

I don’t remember what this store was called, but the owner seemed kind of stoned and had a small dog. They sold cool hats that did not look cool on me. 

SIBLING

A children’s boutique with an emphasis on timeless design and quality materials. 

Under the guidance of Robin, a painter originally from New Mexico, I purchased a baby gift for my new niece, Marley. It is very easy to spend a lot of money in a children’s store, I have learned. Everything is all too cute. 

YONKERS, NEW YORK  

And then… we were back in Yonkers. The sun set and the day was winding down. It had been a long, good day, and we were both tired.

On the train back to Grand Central, surrounded by city folk—many perhaps returning from their own Metro North day trips up to Beacon or another Hudson Valley town—I started to worry. Had it been silly to rent a convertible just to visit places we could’ve reached by public transit? Had I wasted our time, our money?

But then I remembered: it was never just about the destinations. Convertible or hardtop, a road trip isn’t about Point A and Point B. It’s everything in between. The weird pit stops, the unexpected views, the unforgettable characters. It’s the kindness of strangers and stepping into a world outside your own.

We could’ve taken a train, but then we wouldn’t have met the woman at the rummage sale, or Peter and Denny at Motorcyclepedia, or experienced the magic of Seven Lakes Drive. More than that, we wouldn’t have spent almost twelve uninterrupted hours together. In a world full of distractions—endless obligations, online pull—it’s rare to spend that kind of focused time with a friend.

But in the convertible, it was just us. No distractions. Just two friends, hair blowing in the wind, as a red 2017 Jaguar F-Type (pronounced jag-wire) tore down an open road.

GREENPOINT, BROOKLYN

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Hi! Quick housekeeping: I’m exploring a potential bonus item that would justify introducing a paid tier to 129. I love this project but it adds up! Literally! To be clear, the list items (ex: what you’re reading now) will always be free, but if people are interested, there may be an extra something special for paid subscribers. I’d love your input — please fill out the Google form here!

Now back to our regularly scheduled programming. Thank you! xx

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#20. “Change Apartments from Time to Time.”

At the beginning of August, I received a very disturbing email. The subject line read: LEASE RENEWAL OFFER. ​​​​For months, I’d been waiting for this moment with a sense of impending doom, certain whatever was inside would not be good. And I was right.

I am going to have to move. 

Moving sucks no matter when, why, or how you do it. It’s exhausting and stressful and destabilizing and expensive. But for me, staring down the barrel of my sixth apartment in three years, moving now feels like a cruel twist in a Greek epic—a never-ending Odyssey in which the ship never seems to reach land.

As I wallowed in StreetEasy-induced self-pity, it dawned on me that for years, I’ve inadvertently and unwittingly been carrying out #20 on my list: “Change Apartments from Time to Time.” I’ve become a revolving door of addresses, a transient nester desperate for a place to put down roots. How very Frances Ha of me. 

Since moving to New York in September 2021, I’ve resided in a questionable living room on the Upper West Side, a glamorous walk-up on the Lower East, and a boho-bougie bedroom in Alphabet City. Each sublet came with different roommates, roaches, and ramifications. It was the good, the bad, and the ugly of Manhattan renting, and by the end of my first year in the city, I knew I’d experienced enough to know the following: I was meant to be in Brooklyn. 

In October 2022, I relocated to Greenpoint, a tiny slice of Brooklyn tucked into the borough’s northernmost corner along the East River. 

Originally inhabited by the Keskachauge tribe and then stolen and settled on by the Dutch West India Company, for centuries, Greenpoint — like most of New York — consisted of lush green farmland, slowly stripped down to build a city. By the late 1800s, the neighborhood was established as a manufacturing haven, home to shipyards, brass and iron foundries, glasswork factories, sugar refineries, and breweries. In the mid-20th century, Greenpoint was recognized as having the largest pencil producer in the country (Eberhard Faber Pencil Company) and what was, at the time, the most significant oil spill in United States history (1950 Greenpoint oil spill). Throughout most of the 1900s and early 2000s, it remained a working-class, immigrant neighborhood with vibrant Polish and Italian communities.

In the mid-2010s, the area became synonymous with HBO’s Girls. The show’s protagonist, Hannah Horvath (played by Lena Dunham), housed a revolving door of roommates at her now famous India Street apartment. They congregated (and worked) at the Cafe Grumpy around the corner, biked down McGuinness to Bushwick, and experienced the full range of human emotions from Hannah’s iconic front stoop. 

Girls may not have been what put Greenpoint on the map as a desirable place to live, but its rise coincided with a radical transformation of the neighborhood. In 2005, a rezoning of the East River waterfront paved the way for luxury residential buildings and ample green space. Over the next decade, decaying industrial warehouses became swanky hotels and restaurants, and junkyards were cleared for high-rise housing. The old pencil factory — shut down in 1956 — now sits across from a bar aptly named The Pencil Factory; in place of glasswork factories are expensive glassware stores; and, well, the oil from the spill stuck around, allegedly still seeping into the area’s groundwater today. 

By the time I arrived to the party in 2022, Greenpoint was no longer a niche neighborhood but rather an address that elicited an “Oh, I wish I could live there” from almost anyone you talked to. Even in the two years since I have called it home, the area’s history and identity seem to be in constant evolution. Every month, more local institutions shutter under the pressure of increasingly high rent. In their place pops up trendy ice cream shops, Michelin-star restaurants, satire-worthy natural wine bars, and, in late July… a Sweetgreen. This one was especially disheartening; until recently, I prided myself on living in a neighborhood where the only basic lunch bowl-type restaurant was Eden’s, a salad pop-up operating out of a dive bar on Franklin Street. 

Something about the Sweetgreen felt like a nail in a slowly closing coffin; commercial and sterile, it represents everything the neighborhood is not. Greenpoint is weird and quaint. It boasts more pierogies than people, it’s only accessible by a train that seldom runs on time, it’s got townies, it has a “cat gang,” for crying out loud! The Oak Street Cat Gang consists of three semi-feral cats living outside a duplex on Oak Street, a few houses down from the 1887-era Greenpoint Home for the Aged, a charity ward built for single and widowed women of the time. 

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Greenpoint has a soul. Of course I suppose this is true for most of New York City and its surrounding boroughs — perhaps that’s why we love it here so much, the literal and figurative character baked into these storied streets. But there’s something about my specific neighborhood that feels magical, like I’ve stumbled into the Hogwarts Room of Requirement. It’s fleeting and arcane and all too good to last. 

Since moving to Greenpoint, I’ve lived in two apartments: one on Guernsey Street and my current place on Meserole Avenue. The Guernsey Street apartment is a story for another essay (or my therapist) (or both). It was a difficult home during a difficult time, and the only thing that made living in it easier was a love of the neighborhood. 

On the other hand, Meserole Ave is a pinch-me-palace, a massive three-bedroom gem that I lucked into last fall via the Instagram story of a theater camp friend. 

It was love at first sight. The roommates—two girls my age—are normal, kind, and cool. My bedroom is larger than any space I’ve ever lived in, boasting natural light and a breathtaking view of an old lady’s backyard. It has a dishwasher, air conditioning, roof access, a big comfy couch, and, best of all… a sense of hope. From the moment I walked through the door last September, I had a feeling that things would be different here, that I would be different here. For the first time since moving to New York, after four apartments, seven roommates, hundreds of boxes, and thousands of tears, I finally felt at home. 

Naturally, I’ve spent the last eleven months waiting for the other shoe to drop. It was all too good to be true. Things couldn’t be this easy; something had to go wrong. And so when the changes started coming — the Caffe Panna, the million-dollar listings featured on Netflix’s real estate hit Owning Manhattan, the Sweetgreen — I plugged my ears, desperate to silence the canary screeching from the coal mine. But then July 31st became August 1st, and a renewal offer arrived in my inbox. Our rent was raised, and the quarry collapsed in on itself. 

Faced with the prospect of yet another move, I experienced something of an identity crisis. Things had just gotten good, the story stable; what if another shake-up made me fall apart again? I felt sickened at the thought of apartment tours and moving boxes and spackling and packing up the person I had finally gotten so comfortable becoming. It was like a break-up, and I was devastated by the dissolution… I really thought this relationship would last. 

I felt afraid of the unknown. Who would I be without Meserole Avenue? 

So much of life — most of life, maybe — is centered in and around where we live. And if reality is not, television certainly is. Mary Tyler Moore, Friends, New Girl, The Odd Couple, Seinfeld… the apartments are so significant to these stories that they should get series regular rates and producer credit by season two. And so, while pondering my near-constant real estate reinvention, I wondered how much would have changed if these iconic characters had lived in another space.

What would have happened if Jerry Seinfeld had moved to a different Upper West Side block halfway through Season One or if the gang from New Girl had downsized to a slightly less cavernous loft in Silver Lake instead of DTLA? Would Girls still be Girls without Hannah’s India Street apartment? Would Carrie be having as much sex in the city if she’d been priced out of that iconic Upper East Side walkup?

This is not to suggest that the trajectory of our television heroines would have wholly changed had they signed a different lease. Carrie would still be a writer, Jerry a comedian, Hannah a narcissist, Ross a dinosaur lover, and Schmidt, Schmidt. 

An apartment doesn’t define who a person is, but it does affect who they become. The neighbors, the neighborhood, the roommates, the rats, the coffee shop on the corner, the subway stop a few blocks away. It’s all color, painting a story between the black-and-white lines of an airtight lease. 

It is the place where we cry and eat and work and sleep and fuck and dream and break down and rebuild. It’s four walls and a bunch of furniture, and it somehow manages to hold the weight of an entire existence. 

Or… does it? Am I being dramatic, imbuing meaning into the inanimate, letting sentimentality and nostalgia make a book represent far more than just the words on the page? Can’t an object just be an object, and a room just a room? I’m not sure. The more I think about it, the more I am struck by uncertainty about what is more important: people or place. 

Are we defined by where we live, or is it a matter of who we are when we live there?

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The same interrogation accompanies the adage: “Home is where the heart is.” What is that heart, and where is that home? Is it a physical space or a feeling? Could you live in 15 different places in one year so long as you had the peace to feel happy doing so? Or would the endless moves create a whiplash of person and personality, a mess of reinventing the wheel so many times it becomes unrecognizable and could never be used to operate a motor vehicle? 

In Friends, Seinfeld, Mary Tyler Moore, Girls, Sex and the City, New Girl, characters change while protected by a sense of permanence: their apartment. Except for an episode or two for a good story arc, we follow folks who become different while their homes stay the same. 

So what happens when neither is static—the person or the place? Does it inspire evolution, or does the constant lack of stability inhibit positive progression? 

I am, of course, thinking about myself (okay, narcissist). About my ever-changing, never-constant landing pad. I wonder what it’s done, is doing, and will do to me. 

Who have I left behind in the moves? And who have I become in the rebuilding? 

I don’t know the answer. But as I sorted through my shit, working to come to terms with reality, I began to see the benefit of embarking on something akin to a series of short-term situationships. Of course each experience has changed me. How could it not? There has been pure joy and fresh hell in these spaces. I’ve walked away from each stronger, smarter, a little bruised, full of stories, unsure of the unknown but ready to face whatever is ahead.  

Like dating, finding a new apartment is overwhelming and fraught with possibilities. 

Maybe the new place will have a seat on a bay window overlooking a tree-lined street; maybe the new partner will be an amazing cook. Maybe there will be cockroaches; maybe he’ll snore. Maybe the neighbors will be loud and rude; maybe her family will hate you. Maybe you’ll form a close bond with the bodega man; maybe his friends will adopt you as their own. Maybe the neighborhood will suck, maybe he’ll break your heart, maybe the place will be haunted, maybe she’s haunted by her ex, maybe the windows will rattle incessantly from the nearby train and the AC won’t work and it’s not as big and doesn’t feel like home and you don’t laugh like you did and you’re lonely and it’s all foreign and weird and you miss your old nail place and coffee shop and running route. Maybe it will just feel like more relentless change, another disappointment of putting your heart into yet another thing that will not last. 

Maybe it’ll be a disaster. 

But maybe the move was necessary, the shake-up essential. Maybe once the boxes are broken down, the paintings are mounted, the mugs organized, the books shelved, the clothing hung snugly on the velvet hangers in the closet, maybe then you’ll realize you quite like where you’ve ended up. Maybe once you give something — or someone — new a chance, you’ll find it’s better than you could have ever imagined. 

Or maybe it sucks, and in twelve months, you pack up and do it all over again. 

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If any part of you thinks I am being serious, then dear reader, I fear you don’t know me very well. Or, if you’re new here, and really actually don’t know me yet, let me be clear: while it may have been a harsh and awful truth in 1958, in 2024, that is what the kids call a joke.

When one thinks of a woman in the workplace, their mind may jump to The Devil Wears Prada's Miranda Priestly, a notoriously kind and fair boss. Of course that is also a joke (I’m being silly today), but this part is real: despite her many, many flaws, Miranda Priestly stands tall as an example of a trailblazing, badass, no-nonsense leader who defied expectations to achieve something extraordinary.

I’m not sure anyone should aspire to work for, or become, a Miranda Priestly type, but in thinking about #19. “Don’t Work at a Company Run by Women,” I found myself itching to talk to real female leaders. The non-fiction, non-nightmare kind. I wanted to know how they got where they are, what obstacles they’re up against, what’s their life like, what do they hope for, are they hiring?

So I did just that. My first conversation was with Julia Dixon, the founder and CEO of ESAI, the original AI platform leveling the playing field for college applicants and young professionals. But, I’ll let her tell you more about it.

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Julia: I’m Julia. I'm 28. I live in New York City. I am a marketing professional-turned-founder, who is trying to transition to full-time founder.

Emily: Are you still working as a marketing professional?

Julia: Technically, yes. I am now able — and we can get into this — but I have now raised an entire round [of funding] that we're closing for ESAI, which means I'm able to now do this full time. So we're in transition mode. I guess technically I’m not really a marketing professional anymore, but I do play a large marketing role in my own company, which I actually think was a huge superpower.

Emily: I want to go into where you've worked before. I think that's going to be a large part of this. You've just raised a massive amount of funding for ESAI, so why don't you tell the world what ESAI is, and can you give me like a brief overview of how you got here?

Julia: ESAI is an AI platform primarily for college applicants and young professionals as a whole.

The origin story is that I used to be a college advisor. It was more of a side gig for me. I wanted to pay my rent while I was interning and started formalizing what I was already doing informally in undergrad: helping all my law school-bound and med school-bound friends edit their admissions essays. I've always been more of the writer and creative type and all my brilliant science friends were like, “help me write an essay.” And then I had people's siblings asking me and random friends of my parents asking me and I was like, I gotta start charging for this and I started working with some high schools as their go-to advisor. I was able to build my own little side business, but it was just a human-based service.

And the kind of obvious problem was I was only really working with well resourced families. I charged on the lowest end of what these kinds of advisors charge, but most of them, especially here in Manhattan, charge $300 an hour. And some of these more elite services that work with you year round, or even for all of high school, charge well over six figures, sometimes $750,000. This is a service for very wealthy families, and that's cool. If you can afford that, it's proven to be very helpful.

But I wanted to create a way that all kinds of students could get this support. Very individualized coaching in terms of… what should you write your essays about? What school should you even apply to? How do we match your story to those schools? All those things that are a lot for a 17-year-old to grasp when it comes to creating a personal brand and summarizing everything about yourself.

I realized AI is really good at those kinds of things. It's great at making unlikely connections. It's great at taking a large amount of data and distilling it into something simpler.

That was the origin, and we've been scaling from there. We've reached over 10 million kids on TikTok, helped over 100,000 in the admissions process last year, and now we're doing this thing for real.

Emily: It's the best kind of writer origin story. You started using the skill you have, which is writing, to make money for yourself and survive. And then you were like, wait, I can help other people. And now you're making a whole ass company.

Julia: It was certainly not the game plan. I never was like, “I'm going to start my own company,” but it's just one of those things where I genuinely had a light bulb moment. It was so early in the generative AI boom. I was like, no one's doing this.

And so it just happened.

Emily: So it wasn't in the plan. Can you walk me through what the plan was? What was your resume before you started this? Where were you working?

Julia: I've worked at Weber Shandwick for the last six years, and shout out to them. Best place to launch my career. It's a pretty full service communications and marketing firm. I started there in a traditional PR, earned comms role and then transitioned into their more future facing tech team, which is where I got a lot of the knowledge that informed ESAI.

That was also accidental. My former boss and mentor, Chris Perry, exposed me to emerging tech before I knew I cared about that, and taught me how to think five years in the future, specifically from a marketing lens, but also just in general.

It wasn't meant to inform me starting a business. It just gave me this understanding that I think helped me see opportunities where I wouldn't have before. Otherwise I've mostly done traditional marketing for consumer brands, everything from Coca Cola to big cruise lines and consumer electronics. I thought I was going to have a successful marketing career for a long time. 

 But then I just saw another path and became obsessed with it. And here we are.

Emily: The obsession is great. Part of the reason I asked where you worked before, is this is a prompt called “Don't Work at a Company Run by Women.” And marketing and comms firms, would you agree it’s more heavily a female field?

Julia: So I can at least speak to Weber, but I know this is the general vibe across these big agencies and even marketing departments in house. Yes, it's very much predominantly women. And most of the men are gay men. We would always talk about this in my agency and at other agencies, so this is not just a critique of Weber, but it's so many women and gay men and it's empowering and awesome because we're running this… until you get to the highest up folks and then suddenly there's all these straight men. It's this very female industry until you get to the tippity top and then it's not.

That said, Weber Shandwick has a female CEO who is actually retiring and transitioning power to another female CEO. So it's not like there's not women in leadership, but there's suddenly a lot more straight men towards the top.

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Emily: I don't think it's an accident that working at a place where you're surrounded by empowered women made it so that you could think, okay, like maybe I could start my own company.

Do you think that the men at the top is part of a delayed trickle down effect? In 10 years, are there going to be more women? Or is that just emblematic of a larger system that we haven't yet cracked?

Julia: I don't know if I know the answer to that. I think of a lot of the people that worked at my junior and mid level marketing roles: all these women will end up in leadership. And I hope that means that we'll keep seeing more women at the top. I just think somehow these men get pulled back up in these top roles even though it’s not as much of a pursuit among young straight men to go into a comms agency.

Maybe this isn't inherently bad. It's just interesting. There's this willingness among women to take — agencies are known to be pretty low paying — so there's a lot of opportunity, you can definitely do well. But at the beginning I just feel like women are willing to sacrifice money for something that they really want to do, or that feels creatively empowering.

I don't have the data for all this.

Emily: I have some data, which is that as of 2024, only 10 percent of Fortune 500 companies are women-led. And the number has increased in the last ten years, but it's now a little stagnant. It's the same number that it was from 2023, which I think what you said is really on point about men just taking whatever… I'm hopefully going to talk to someone that works in finance because those are famously male led industries.

It's obviously much harder for a woman to make her way up in something that is not only cutthroat, but also systemically designed to uplift the man. I'm wondering how these men find their way, for example, at a place like Weber Shandwick, back to the top.

Julia: You're getting at this whole idea, which is, why wouldn't men take an agency job in the first place? Because it’s not like men aren’t creative.

They just don't pursue creative things as much in general. But in defense of men, something I don't say super often, they are faced with more pressure to have big earnings and be providers. I felt this myself, which is so crazy because now I do not feel this way, but I felt like I had a little more flexibility in my career cause I wasn't necessarily expected to make a lot of money. I wanted to be successful, but success to me meant pursuing the most interesting and creative thing, getting recognition and good results from my job, it didn't really mean money.

It meant being able to afford to live in the city I live in. Now, that’s changed for me a lot. For a lot of reasons. But I just think that men feel like they have to pursue these high earning jobs because they have to be earners. And it's so ingrained in us that, even though I didn't actively think that way when I was picking a career, it was a factor subconsciously.

Emily: It's fascinating because this whole thing is adapted from a 1958 list when in 1958, they were like, don't take a job at a company largely run by women. Also, there weren't companies largely run by women for the most part.

Julia: Yeah, that's definitely true because there still aren’t.

Emily: I tried to do some research before and find out what are these companies that this magazine is warning women against?

There aren't a ton. And in the fifties, women only represented roughly 30 percent of the workforce and 70 percent of them were in clerical positions. Secretary roles. And I wonder if that's where this idea of… and this is a tiny tangent, but I promise it makes sense.

A couple months ago I was with some friends and we were grilling. And the boys immediately were like, “Oh, we'll handle the grill.” And the girls were like, “Don't worry we'll make the fruit.” (We're not making fruit, but we'll cut up the fruit.) And we got into this whole thing of, where did the idea that only men can grill come from?

And it's the same thing: in the fifties, it was a marketing ploy to sell grills. And it ingrained this idea that grilling is very masculine.

Especially because until — if you'd like the exact number: 1974 — women couldn't have credit cards. I just wonder if this idea that a man has to enter a career that is financially lucrative comes from these stagnant fifties ideals and the whole history of humanity.

Julia: I 100% think so. In the way it was ingrained in me. In some ways it’s nice, I felt like I had this freedom to really follow my passions because money didn't matter as much, which is great, but it's also rooted in this very sexist idea that I would probably marry someone who would make more money than me or be the primary earner. I never said that out loud or even specifically thought it, but I know that was somewhere in my mind and probably my parents’ mind. My parents encouraged me to do whatever I wanted, and I think they did my brothers too. But I just, I think it is very true, and it's rooted in very old ideas.

I see it in the way that whenever we have a family gathering, all the men immediately sit on the couch and all the women immediately go ask how they can help in the kitchen. It took me so long to even notice that pattern and be like, “Why can't I walk into my aunt's house and sit on the couch?” I'm expected to go help her. And my brothers aren't, and no one ever said that, but that's just the assumption.

Emily: The problem here is I actually like being in the kitchen. I'd love to help, but if I'm there and that disparity happens, I'll sit on the couch just to prove that the system can't win.

Julia: It's a hard one to protest because I do believe in being helpful, but also my brothers should go and be helpful.

Emily: Yeah. I'm like, you got to help.

Okay. So you used to think, all right, I'm going to marry someone who make more money than me, but now, to quote Cher, you're a rich man.

You've been pitching ESAI and apologies because I'm not as well versed in pitching a tech company as you are.

Julia: I was not until pretty recently, but I can tell you I've learned a lot.

Emily: Yeah. So before you even talk me through, I want to put one more thing out that I read about women-owned startups. It's a little dated. I would love to know what the updated stat is. But in the same way that the wage gap exists in payment, BCG (Boston Consulting Group) put out an article that the wage gap exists in women when they're pitching to investors for early stage capital.

And as someone that just pitched for early stage, can you talk me through how did that go? Did you run into this at all?

Julia: The stat that gets thrown around a lot on LinkedIn, I don't know what the latest figure is, but it's always around this, is only 2 percent of venture capital goes to women. So of all the money that gets fundraised every year, 2 percent of it goes to women. So that gap is way bigger than just the pay gap in salaries.

It's insane. Women do not raise money like men do. And part of it is that women don't start companies at the same rate, which means there's just a bigger pool of men trying to raise money, but also because it's harder for women to raise money. Both things are true.

This is such an intense topic to talk about because first of all, it's really hard to raise money for anyone, especially right now. It's like the worst fundraising environment it's been in over a decade. There was a really big spike in 2021 where people were raising money with relative ease and now it's in the toilet. That actually gets even worse for EdTech, which is technically our category. So I'll just say it was hard for a lot of reasons. And I think being a woman is one of them.

Similar to how people will rip on DEI in the workplace, people will sometimes say, “There's all these special funding programs and impact funds that only fund women and people of color.” There are some, but there's, first of all, really not that many. And they'll pick one. It's not like these big VC funds that fund hundreds of companies every year. No, they'd all try to be more inclusive, but none of them ever share their data or very few do about how many women they funded each year, what percent of their portfolio companies were created by women or people of color.

The first success I really had in funding was out of LGBT funds and LGBT communities. I do think women and minorities have to lean into them cause there aren't as many and in my case, that's not where I raised most of my money, but it is where I got my foot in the door and the confidence to keep going.

So I’m glad these things exist. I don't know if I already said this, but we just raised over $1 million in our pre-seed round. It was very hard. I have a lot of tips on how people and especially women should approach raising money for a startup.

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Emily: What was the most unexpected, challenging thing about raising that money? 

Julia: It's so hard because there's a knowledge gap. There's so much information online and you can basically take a masterclass in raising startup funds, but you'd have to watch hours and hours of programming. And when you're trying to build a business at the same time, that's really hard. At the beginning, people would ask me these very specific questions about our terms and our runway and our burn rate and all these things that now I get asked every day and are easy to answer. But at the beginning I was just like… “I just have this idea.”

And it was more than an idea. By the time I was pitching it, we had legitimate traction in terms of users and virality and all this stuff, but at the same time the bar keeps getting higher. Like it used to be in a pre-seed round, you're basically pitching an idea with maybe some credible founders who came from that space.

But now it's you have to have actual revenue. You have to have a ton of users. You have to have some serious not just vision, but go-to-market strategy. So the bar keeps raising. And I do just think that people are more doubtful.

A lot of people will take my calls and then they go, “I like that idea, I would love to stay in touch with you.” And I'm not aggressive enough to get them to close. Especially in the beginning would get a lot of people on the phone and get like a lot of nice feedback. And it'd be really hard for me to be like, “So are you interested or not?”

And I feel like men always take the opportunity a little more seriously. I actually pitched one fund in particular. They loved my idea and it was one of the best meetings I had early on in my fundraising journey and they were so, “You might be a little early for our fund, but we'd love to angel invest before the fund would come in, and this idea is so awesome, we've been looking for something like this.”

I got so excited. And then they ghosted me after that, which is not rare, but that one surprised me. And then I found out a couple of months later, they funded a very similar idea founded by two guys still in college.

Emily: No!

Julia: They had started later than me, had no traction. They're younger, with no professional experience.

Emily: I hate that. So that's an interesting segue, because you're working in a nascent field. You're in EdTech, you're in AI, where there's less of a history, obviously, because it's new. Are you finding that you're being treated differently?

Are these emerging markets offering new ways for women to make headway? Or are these patterns repeating itself? Like these two college kids are getting more funding than you do?

Julia: In some ways, like the VC and startup world, regardless of the exact hype of the year, remains consistent. People only take warm intros, which means you already have to be connected to get on calls in the first place. And that's a huge barrier that I could talk about forever, but I will say it is not impossible to crawl your way in. After just going to two of the main conferences, I feel like my network has really expanded and people love intro-ing each other to people because it's free and so it's not impossible, but it takes a while to spiral up and build some credibility among a certain community. But EdTech is pretty small and once you get a few under your belt, you get warm intros pretty easily.

All of that stuff stays consistent regardless of if we're talking about Crypto or AI or just SaaS platforms or whatever has been the focus of the last decade. What I do think is different is because it's so new and there's so much excitement about it, we're seeing people carve really unique spaces in it, like you can basically build an AI with AI. There's so much equalizing with this technology. Almost anyone can do it. That doesn't make it easy, but I truly use AI to help me figure out code and help me figure out everything.

I just don't think I could have built my AI company without the help of AI.

So I do see women doing really cool stuff that's creative and different and impactful. There's also specific communities. There's a Women in AI Education Slack group that has a thousand people in it now. It's all about celebrating women in the AI space. There's definitely stuff popping up, but I don't know if it's radically different than it has been for the last, who knows how long.

Emily: History of the world.

Julia: Yeah.

Emily: The other AI thing that's interesting, especially with the Women in AI Slack group, is what I was reading about the AI gender bias. I think it said 20 percent of AI workers are women right now, and because it's machine learning, the people feeding the machines are more often than re-feeding these biases

Julia: This is the problem with everything. All of the medicines we have were tested on men, and all of the safety features in cares, and now we have AI. And I, can speak to our own system in particular, our two main people behind the actual training and proprietary method in our AI are myself and my chief academic officer, Dr. Carol. If anything, ours might lean the other way. So I think we have a nice balance, but it's a huge consideration and it's maybe not as life threatening as, medical biases, but it's a real problem, and just another case for why women need to be in tech and in AI.

Emily: Women in STEM. So at ESAI, you have you — your title is CEO — you have Dr. Carol, who's your chief academic officer. How big is the team right now? And what was building it like?

Julia: Garrett is our CTO, Chief Technology Officer, and that's the core team. We have a really awesome BizDev intern, Jillian from Northwestern. And then we've got about five or six additional Product and Dev folks. So our Product Officer is Yohan Demont, and he was one of the first people to come on to ESAI and be, like, a real C-level person. He brought in our UX designer and our AI engineer, Ao, and our additional developers. We have a couple of new developers, so we've got a lot of people circling the organization. Not everyone is full time employee and some people work under the dev house we work with.

And some people work more under me. But yeah, we've got about 10 people working on this thing every day, which is pretty cool.

We started doing these daily stand ups to get everyone on the same page and it has been a little surreal to be like, wow, a year ago, I used to say the word we, so we sounded more legit when talking to people. And now there is a real we, like we are ESAI. And so it's been cool to see it grow.

Emily: Do you ever wake up and just pinch yourself? This is real.

Julia: Sometimes I'm like, why did I do this to myself? I am nine days behind on my inbox, and it's just nuts. But yeah, it is definitely surreal. 

Emily: I want to talk about the term girl boss. And we can go as deep into the female focused women leader language as you want. But I'm thinking about like girl boss, She-E-O, the future is female.

A) do you hear this stuff, and B) what do you think about it?

Julia: The one I hear the most is girlboss. First of all, I’ll say a lot of it is from my own friends in a funny way, and it's not that deep. They’ll just be like, oh, Julia's girlbossing again, and it's funny, it's fine.

But in general, when some more random people say that to me, the obvious critique that we don't call it boyboss and it's just a little condescending in a way, like, “Aw, you're really trying to do that, huh?”

It feels a little gross, but I think on a deeper level it feels like this weird tendency to almost justify that, I'm starting a business, but I'm still really feminine, and I'm doing it in a feminine way. Don't worry.

There's something deeper there that feels almost like it's a defense mechanism to be like, yeah, this is the girly way to do business. So I’m still desirable. People love to say that to me and it's usually a joke, but I am like, “Why was that your first reaction?”

Emily: In some ways I feel like it undercuts an achievement because they'll be like, she's founder and she's a woman instead of just, or when people add that descriptor, and this goes for women, people of color, blah, blah, blah. It's like, why can't you just be that one thing?

Julia: Yeah, that Fleabag scene where she's I just want to be a person in business and not a woman in business.

But there's the other argument, which is we need to celebrate women in AI and women founders, because there aren't any, we need to lift them up as examples.

And it's a qualifier that's accurate. I get that. It's just, when it's the automatic descriptor in a setting that isn't really necessary. And you're like, “Why was that something you felt you needed to do?”

But I will say in the EdTech industry, compared to some other tech industries, there is always a note that there's so many women teachers, but a lot less women EdTech founders, which is interesting because you think it should be more similar, but I do think there's as a whole still more female EdTech founders than there are in other fields because education tends to touch on a women's focus.

I haven't faced a ton of this in investor calls or interviews I've done, but it's just even random people that I'll meet socially. They're always like, “Oh, she's a girl boss.” I'm just like…

Emily: If you insist.

The last big question I have for you is as you look at the next year, the next five years, to the point of girlboss and there being this disparity of women leaders, it's just generally harder for a woman to move her way up the ladder. Often, we find there's that stereotype of “Women don't always support women in the workplace,” or they can be harder on each other because they view each other as competition. As a leader and someone that is growing a company, what do you look out for and how do you center yourself and make sure that you're being the boss you want to be for other people?

Julia: To the point where women don’t look out for each other in the workforce, I've never felt that. And maybe that's a testament to how great of a place Weber Shandwick was, but it was, like I said, almost all women. And so if it felt like that, then no one would have any career growth.

So I've never felt that, some of the people who have advocated for me the most in my career have been women. Obviously I want to pay that forward. To me, one the biggest problems is that it's not that usually, of course, there's some blatant sexism going on, but it's not usually that the companies or decision makers are sexist themselves, but they're forced to make decisions based off the fact that the man came into the room with this very much ultimatum, deals defined, whatever, asked for more, and women don't.

It's not because the women are less smart or less deserving or even less good of argument makers or debaters, but we've just been taught to not do that and not cause a scene and not be too aggressive and not come off that way because it is received differently, even if you do the exact same thing.

So I think it's really hard. I've had conversations like this with my roommate who works in HR. If you're dealing with two candidates and one comes in and puts their foot down and says, “I'm only taking a salary above this.” And the other one doesn't, that the HR person can only respond to what the people tell them.

I hope that I can be someone who helps women just figure out how to advocate for themselves and be better arguers — not they have to be argumentative — but to make a strong argument for yourself.

The same goes for funding. You have to be ready to field so much pushback and so much questions and just have the confidence to do that. Sometimes when people ask me a question, I now have the confidence to say, “Can I disagree with the line of questioning a little?” and just be like, “I'm not sure I even agree with the question you're posing.” It's fine to push back as long as you're respectful. So that's something that, yes, I hope to obviously give fair shots to all my employees and women in my life, but also empower people to advocate for themselves the way that men just seem to be naturally empowered to do.

Emily: I do wonder, if the way Weber Shandwick was set up was a place where you felt empowered. And I agree. For the most part, all of my jobs have been in female led and female empowered organizations. And I think it is where you learn these behaviors that influences how we move through the workplace.

Julia: Totally. So would you prefer to work for a female run organization?

Emily: Absolutely not. No. If there's a female CEO, I'm like, remove my resume from the pile, please. I cannot be, yeah. Kidding! Yes. I want to work in places where I'm inspired and it's, often women inspire me cause they're badasses.

Okay. Final question, because this questions is influenced by a dating listicle.

Has this affected how you think about relationships and how you think about dating?

Julia: I feel like in a lot of ways, me coming out and dating women has empowered me, mostly in subconscious ways, to do things that are also outside of the cultural norm: do something crazy like start a company. I still think I bring a lot of reason and risk analysis to the decisions, but I'm just more comfortable doing other things that are unexpected because I've already faced the biggest backlash I'll ever face. (I hope.) It feeds off the other way too, now I suddenly see myself as maybe — even if I did have a husband who makes a lot of money — that's never something I want to rely on. Nor do I think that anyone should ever approach their career that way.

But I think all those subconscious assumptions have gone away. Even my own risk analysis, I have to make sure that if this thing goes to hell tomorrow, I have other options and I can provide for myself and ideally a partner that contributes.

My partner works a really non traditional job and I work a sort of non traditional job, so it's very complicated to schedule things. We just had to cancel a big trip that we were really excited for because actually both of us had career random bombs go off and we just we're now losing money on a trip we’re not going on.

It's hard, but for me, especially because my girlfriend's a dancer and I'm raising money, we are both constantly getting these rejections and good news. I felt like I was auditioning with investors and she's auditioning to casting agents and we had have these weird parallels, but it's good. We very much support each other and very much live in different universes also.

Emily: Which often makes for the healthiest kind of relationship because you can be like, here's the wild thing I did today. 

Removing the need for financial security from a partner can open it up because then you're looking like, who's the person I want instead of, are they going to take care of me? Because you can take care of yourself.

Okay. I could talk for hours, but people are running companies, no one has time to listen for hours. Do you have any parting thoughts?

Julia: I'm thinking about starting a TikTok where I talk about more of these things, about how to raise money for a company and how to do really hard stuff like this. So let me know if you would watch that.

Emily: Yeah, we will. And if you're in need of an essay, go to ESAI?

Julia: Any college admissions support, figuring out what schools to apply to figuring out your personal brand, we got you. First tool is free.

Emily: I would watch your TikToks.

Julia: Thank you so much.

Emily: Okay. That's it. Goodbye!

After talking to Julia, I spoke with Amelia Montooth — the founder of Mutuals Media — about her thoughts on female leaders in the workplace. I was intrigued by a similar theme which emerged from both conversations: historically women have been trained to wait for life to happen, while men are expected to just go for it. 

We are conditioned to wait. For permission, an opportunity, a text back, a first move, a lucrative offer, a husband to return from war.

In many ways, dating is not so different from fundraising for a start-up. There’s rejection, imbalances of power, and risk-taking. It’s an imperative yet impossible task: to steadfastly believe in your own self-worth and value as others question it; to get back up after a set-back; to believe in what could be, rather than what currently is.

Julia and Amelia both touched on how their rejections of the “standard” heteronormative stereotypes we’ve come to accept empowered them to take a gamble on themselves. I’ll be writing more in depth about this, and my conversation with Amelia, in a follow-up essay, but for now it’s just something worth considering.

“Don’t Take a Job at a Company Run by Women” is a small example of a larger issue which has permeated our society for, excuse my language, a long-ass time. What else are old norms and ideas are holding us back from? It reminds me of the horrible (sorry to those who love it) phrase, “If he wanted to, he would.” It’s true, but not because it’s right — maybe because it’s just what we’ve come to expect.

Julia and Amelia did something different. They challenged convention. In their cases… they didn’t wait, they didn’t ask permission, they didn’t doubt.

They wanted to, so they just did.

I’ve been intrigued by the influx of “singles meet-ups” seemingly taking the world by storm for a while now. In New York alone, there’s a run/dating club, a dinner party series, a party party series, and of course, a plethora of pickleball leagues. So, when I was sent an invite for “Friend-of-a-Friend: A singles mixer for monogamous, straight, or queer New Yorkers trying to get off the apps and meet people the old-fashioned way,” I obviously signed up.

Not only could it be fun, but the activity fit perfectly into #18. “Tell Your Friends You’re Interested in Getting Married.”

The night after the event, I hopped on Zoom with FOF's organizers: Zoe Black and Sydney Watt. Together, we took a deep dive into the event's intention, dissected the rise of singles mixers, and unpacked dirty details from the evening.

I began with a simple question: how did Friend-of-a-Friend come to be?

*This interview has been condensed for clarity. For full conversation, listen to the audio!*

Zoe: I feel like we've been complaining about dating as most people have, talking about the apps and how transient and not very full of connection they can be, and thinking about different ways of meeting people. And then I can't remember how we were talking about a mixer of some nature, like an in-person event.

Sydney: We were checking out this new bar in my neighborhood, Corto, and they just had their opening or their soft opening, so we were hanging out there and you said “I have some friends who have a backyard space and we've thought about doing a singles mixer there,” and then you asked me if I was interested in doing it and I was like yeah in fact I want to be on the committee.

Emily: It sounds like a cool Avengers assemble moment: everyone had a unique component that made this work, right? Maddie and Hannah had the backyard, Sydney the event planning experience, Zoe the advertising and organizational. Who did the graphic, by the way? 

Zoe: Rachel [Forcillo]. 

Sydney: She was our graphic designer for the event. And Zoe was our Comms Director. And I was Experiential Director. I've actually over the past year been obsessively reading about singles mixers, how they're organized, and problems a lot of them run into. So when we were putting this one together, we started off being like, who's the event for?

We decided that the event primarily is for women, even though there are people of all genders who are there. It's for women and for people whom women want to date. And something that I noticed just through my reading was that a lot of these events have issues where not enough guys sign up, a lot of the guys flake. It becomes a sort of competitive atmosphere, I already feel like the dating scene in New York can be competitive for a lot of women in that just the dating economics of it — it feels like there's an imbalance of numbers.

So that was a big thing we were thinking about when we were planning it: How do we want to curate the people? What are the sort of ratios we want? What are the built-in narratives of living and dating in New York? Namely, that there aren't enough single men to go around for all the women that we want to overturn. And that guided a lot of our decisions for how to ultimately structure the event.

Emily: One of the things that was so amazing about it was it didn't feel competitive, and it didn't even feel like there was pressure. Even if you go to a bar and suddenly you see someone across the bar, and you meet and talk for five minutes, there's this insane pressure of “I have to make this work, I have to get them to like me,” otherwise it's not a story.

And the way it was curated, it wasn't for one preference only… it was a choose your own adventure depending on what you're looking for and who you're looking for. And that made it feel really democratic and supportive.

Zoe: To your point about the pressure-filled scenarios that we find ourselves in with dating, so much of dating in New York is going on one to three dates and then making a call right then of just “this is my person or this isn't my person” and that's it and that's how I'm going to live my life.

Whereas I feel like this event had a lot of chances to meet everyone. You're not basing it on one conversation. You're saying yes or no. We gave everyone's contact information. We were like, go be friends, go hang out, whatever type of relationship you want to have with people like that.

Sydney: Zoe I feel like some of this also pulled from, whether intentionally or unintentionally, our conversations about dating. We come from somewhat different perspectives in that you're queer, I'm straight, and I feel like talking to you about dating, there's much more of a dynamic built into the queerness.

From what you've told me, there is some more fluidity in what a relationship is going to be that I have not experienced as much in my personal dating life. I think that was also some of the energy that you were speaking to of what we were trying to bring to this event.

Zoe: I also tend to talk about these things from my own very narrow perspective of dating. So let me know if also anything is like, oh, that's just your specific experience, but I think that is something that we tried to bring to this event.

Emily: One of the things I love and hate about dating is the universality. Obviously, there are different experiences based on who you're dating and what you're looking for, but at the core of it is you often feel like you have to make this decision of, is this person gonna be my person?

And if not, what am I doing? And the difference often in queer relationships versus straight relationships, I think — I'm not going to make a large generalization — sometimes the lines are more blurred. You could go on a couple of dates with someone and be like, we're going to be friends, but I don't want to date you.

Whereas with straight relationships, more often than not, it's like you go on one or two dates, you're not feeling it. You never see that person again. 

Sydney: I think it's challenged for me, maybe how I should approach things with men, because it's not that I need a million new straight male friends, but I don't know. It's definitely our conversation, Zoe, that made me rethink how I'm participating in dating in the early stages.

Zoe: People I’ve gone on dates with, and it didn't really work, but they were like good enough terms for me to be like, “Hey, would you want to come to this event and potentially meet other people?”

And they were like, absolutely. You were really cool. And I trust your judgment.

Emily: It was funny when I came and was waiting outside, I ran into a friend who was with their ex, and they were like, we dated for a year.

Zoe: Wait, did they come individually? They were both individually invited?

Emily: Yep. 

Zoe: Shut up.

Emily: They are now friends, and they were a queer couple. It was very emblematic of that thing we just talked about, which is that they were both like, I don't love that my ex is here. But at the same time, they were fine with it because they were like, I think this person rocks and I'm still friends with them even though we did date for a significant amount of time. 

Zoe: Friend-of-a-friend gets messy.

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Emily: That's a tiny tangent, but then walking in, in the hallway, the barrier was broken almost immediately. We were in a group of five. I was with the two exes I knew, and then these two guys, and we were standing outside of the door at the end of the hallway where this apartment is, and everyone just looked at each other like, do we go in? Does it open for us? What happens?

And to the point of dating, I think something that people often get into is not a rhythm, but rather you sleepwalk through the first few stages. You're like, okay, I gotta get through dates one through three. I gotta see if I like this person. This [event] was completely unexpected, and there was an element of excitement and surprise that made it fun. 

Sydney: I love hearing all of this because this is the first of these we've put on and so much of it is trial and error.

You're not privy to what's going on inside, and we're not privy to what's going on outside, and we're inside like, oh my god, we gotta get people through this line faster. It's taking so long. It's a lovely reframe for my mind to be like, oh no; sometimes things are accidental and they actually aid the experience.

Zoe: Something that we didn't do in the beginning was once everyone was checked in was to make them form smaller groups and randomly move people around so that they talk to different people. But I think what happened with the outside and the small groups in the hallway kind of did what we were trying to do, which is break people up semi-randomly, give a reason to interact, and get them out of their shell.

Sydney: We thought the waiting outside was going to be such a con to the entire experience. 

Zoe: But it brought everyone together. 

Emily: I think the other reason this sort of event is lovely and fun and why there is this explosion of singles events right now is that we have an oversaturation of choice and too much control.

It's great that all the power is in your hand, if you really want to go on a date, you can download an app and swipe and find it, but it's so much choice and it's so much control. And I'm not saying that I want to be matchmade by the local Yenta, but it's nice to just give yourself over to a system for a night.

I think a lot of people went into this event wondering how planned out it was going to be and hoping that there would be that sense of structure so that we could talk to each other but we weren't wandering around blindly. 

Sydney: It felt like putting on a show on opening night, but because it's an event that only happens once, opening night is your dress rehearsal. And so there was a lot of improvisation. We thought that we were going to do intros with every person going around saying their name, pronouns, a fun fact about them, and who they were interested in dating. Then we realized that after it took so long to get people in, that would have been another hour and then the event would have been three-quarters of the way done. 

Emily: For those who weren't there, there were about 60 people, right?  

Zoe: 53 total people and seven volunteers.

Emily: It was packed in a good way, in this backyard in Brooklyn. A cocktail bar in one area with amazing cocktails. 60 Brooklynites and our hosts…

Zoe: There was a beautiful garden, tiki torches, and lights around. It was very sweet and romantic and not too hot.

It was actually the perfect day to do it. But what I wanted to mention on top of what Sydney was saying is that not only were we improvising the whole time, I think we had the perfect group of people to be able to do that because everyone was just like, all right. Sounds good. Okay, cool. We'll do this. Everyone was in a mindset of yeah, and we're going to get it done.

Emily: To use the theater metaphor: I'm sure it ran like the first and last night of a massive interactive show where you can't see the cast, the director, the stage manager is sweating and probably has cried eight times but it doesn’t matter because the show is running and the audience is stoked to be there.

This event was like seeing live theater, whereas going on a dating app is watching TV. There was so much that could go wrong.

Zoe: So much vulnerability.

Emily: There's an audience and you don't know, the mixing of people could have been the worst vibe ever. People might not have been down. They might not have played along. A TV show doesn't matter; they're watching it in their sweatpants, eating a pint of ice cream.

Something I loved were the wing women and the slips of paper, which were used as a conversation starter. But before we get to the wing women, we all had these ribbons. Let’s clarify what the ribbons were for, because that was a very smart way to signify what you're looking for and who you're looking for.

Sydney: We knew that we wanted to have a visual signifier for who was interested in who. We originally were thinking of corsages because of a garden party, but we're working on a shoestring budget here, so we pivoted to ribbons.

We had green ribbons for anyone who was interested exclusively in women and or nonbinary people. We had purple ribbons for women who were exclusively interested in men. Who am I missing? Oh, we had blue ribbons for people who are interested in everyone. 

Emily: And then white was for the hosts and the wing women.

So the wing women, they're walking around with slips of paper. And you're in the middle of a conversation with people of all different color ribbons, and then someone hands you a slip of paper, and they're like, can you please go to someone else you haven't talked to tonight and use this prompt?

My prompt was: do you consider yourself vanilla or kinky? Which started A LOT of conversations.

When you came up with the prompts, how did that work? And what was the thought behind it? 

Zoe: I'm trying to remember how the wing women came about. We had a list of things that could not go wrong, but things that we might have to address.

If someone is feeling particularly shy or if there's a friend group that won't get away from each other and we're like, okay, here are a couple of things that we might need to address throughout the night. How do we do that? That was a big reason: how do we make sure everyone's included and everyone's talking to everybody?

We thought that people would be in that mindset of, "I'm here to meet people and actually talk to them and not just talk about surface-level things.” So we gave them AN opportunity to do that. Also, shout out to our wingwomen Aubrey and Claire.

By the end of the night, everyone had a slip of paper. I'm like, oh my gosh, everyone's been moved around and strategically placed. They did such a good job. 

Sydney: When we were designing the event, we were trying to decide how formal or informal it was going to be. You think of a typical speed dating event, for example, and it's super formalized. You're probably talking to a new person every three minutes. It's one on one. I've only ever been to one singles event; it was right before COVID shutdowns and it was not structured at all. It was perfectly lovely, but it was difficult to have conversations with new people.

So we were trying to figure out a way to straddle that line of not making it feel, like nerdy, but also not like everyone had to fend for themselves. 

Zoe: As someone who has not done the amount of research that Sydney has done or been to as many events, I'm so curious about how this stacks up compared to other events and what the pros and cons of all of these different event types are.

Sydney: This thought is coming to my mind as we're discussing, is these two almost contradictory issues with dating on dating apps, and these aren't new ideas, but I haven't thought of them together before.

Often you find that you maybe only need a very little amount of time to know if you have any interest in someone. It's a little amount of time in person, that is, but at the same time, with apps, I think that we become so desensitized to what we might find attractive if we were to give it the chance that sometimes we're not even matching with someone to realize if we are or are not into them in the first three minutes of meeting them.

It's like contradictory tensions that I think are part of the reason why people get really burnt out on the apps. 

Emily: A hundred percent. I think it doesn't make sense. And I guess that's the point of dating. It's both sides where you want to give people a chance, You want to see past your first impression, but at the same time, sometimes your first impression is very right.

I think about this all the time; I guess this is just the crazy craziness that is life. When you think about it in the sense of a dating app, it's whittled down more. But how wild the person you end up with, it's a matter of in real life, you either talked to them in the vegetable aisle at the grocery store, or you didn't, or you either accidentally swiped one way and didn't even mean to. It's so much chance.

Sydney: I've probably read every article that has been written about dating. But there's been a huge flux of them recently and I know the Atlantic did an article about meet-cutes and traditionally meeting people as opposed to off the apps. A point that they made that I had not thought about previously was that you didn't as often just meet someone at a grocery store, you didn't as often just chat up a stranger at a coffee shop.

Of course, that's how some people met, but it was way more often via people in your network. There was more of a culture of setting people up than there is now. I think the apps have made it so convenient to have your dating life and your social life separate until you’re basically in a relationship with someone.

I've certainly met friends’ partners many times only after they've made it official. And that shift in culture over the last ten years or so since apps really got destigmatized has led to people being a lot antsier about introducing people we know… is it going to be awkward if I introduce this friend to this friend and then they break up? We just don't have that muscle anymore.

It's been outsourced almost entirely to technology. Which, I don't know, it's just anti-community as well, and it's depressing. Yeah. 

Emily: But also it's hopeful. The actual prompt I'm using for this 129 item is “Tell Your Friends You’re Interested In Getting Married.” And certainly, I don't think everyone at the event was interested in getting married, but taking a page from 1958, the idea was the active practice of making sure your friends knew that you are looking for something serious and long-term and you want them to be looking for you in their circle. And what you both [Zoe and Sydney] did was that. People's friends sent them to this event because they knew they were looking for something. And they were like, go to this. Create a community. 

Zoe: It was like a specific subset of people who, yeah, are very intentional.

And we got a lot of, honestly, when I would ask people, they would say, “Oh, I know someone. Oh wait no, they're a mess right now.”

Or, we got people who other people thought were not only interested in a relationship but also they approved of them being in a relationship. It was almost like therapist-approved people. I actually told my therapist about this, and she was like, huh, I've got a couple of people that might benefit from.

Sydney: So Emily, we, Zoe and I, were harassing people to sign up or to sign their friends up or to share it with their network.

I reached out to some people whom I haven't seen in a decade or people who didn't even live in New York, but I knew they had big networks in New York. We were putting in a lot of time and work to get people to actually sign up for the event and not just the same five, ten, fifteen people we see most regularly.

And I think having us as the middlemen, not even asking directly, “Is there someone you know who you think would be good with me,” but asking, “Is there someone you know who you think would be good with anyone?” It broadens the landscape of who could come, and I would guess took a lot of the pressure off of the people who are volunteering their friends because they knew it's out of their hands who this person at this party is going to really connect with.

Emily: I've been thinking about what made this whole event unique, too. Granted, I haven't been to anything else, but while you've been reading, I've been deep in TikTok watching, which isn't the same thing, but it's the live version of “I read an article.” What made this event so special was that it felt like there was a certain level of care that went into it. It was really intentional.

People put forward the people they care about. Thinking about the bigger events that we're seeing everywhere, I mentioned there's that Matchbox party that has a 30,000 person waiting list. And then there's Drinks First, which is similar. I think you go and it's a singles party.

What's the line between wanting to make something big that can serve a lot of people, and at what point do you lose the joy? At what point does it become just another machine and how do you tow that line?

Zoe: Something that Sydney and I have in common is that we really like making things happen. And so a lot of this didn't feel like work. It was just like, oh yeah. And then that goes there, and then that goes there. And ooh, what if we did this? It was exciting and fun and all the things that we like doing.

This was event number one, so we only have so much data to go on. Yeah, that was something I've been thinking about, too, because we've gotten a lot of really good feedback from it. All these people who couldn't go were like, when is the next one? And it's like, how much of this do we want to turn into a grind versus keeping with the intentions that we've had going into it?

So I don't know. Are we there yet, Sydney? 

Sydney: I've certainly been having these thoughts too. Someone at the party said, “This could be a startup,” and yeah, sure. Maybe it could. I don't know how to do that and still keep the curated feeling of it.

I really can't emphasize enough that we were not doing this event to spin a profit, and we certainly did not. To me, it felt much more aligned with a community service. I don't think anyone who is involved in this event was hoping that they'd go home richer after it was, and if they were that's a bit diluted. 

Zoe: And also like half of us were there to participate! Let's set up a thing for ourselves to get set up. We're bringing in all the cuties and then we also want to meet all the cuties!

Sydney: What was always at the top of my mind was because I didn't participate, but if I were going to one of these events and someone else was running it, what's going to make me feel the most comfortable? What do I wish was happening and out there? I felt like we succeeded in creating something that we hoped someone else would have created. When we didn't find it, we decided to do it ourselves.

Zoe: A lot of our conversation was putting ourselves in the shoes of the people there and we're brainstorming of okay, but would it feel weird if I was in this position and XYZ happened? Would I be worried that I don't know what the dress code is? What do you think people are doing with their schedules? How far in advance should we blah blah blah? It's like everything that we did from the stance of like, how would this feel as a participant?

Emily: The dress code was funny, and for me, the sweet irony of the fact that I came from an engagement party to a singles event… cannot make that up. Yeah, I was like, okay, I gotta leave this, hop over to the singles party.

I think it is the dichotomy of this age. There’s that joke everybody makes that you are either like — and I don't like the phrase “the most single you've ever been in your life” because I think most people maybe aren't, but I think it's just — you're either getting married or you're still looking.

What I took away from this and what I think was so incredibly special was that to the point of your later twenties, let's say past 26, you get into this weird place where not everyone's on the same page.

Everyone is doing these incredible things and hitting these life milestones. But it can feel really lonely. Even when you go out, it's the friends you're going out with; the vibe is just a little different. And I don't think alienated is the right word, but it's so easy to burrow yourself into that hole and be like, I'm the only one. What this event did was so beautiful and refreshing to see a backyard of 60 people who were like, not only am I in the same boat, but I'm going to show you what's joyful about this and what's cool about meeting people at a new stage of their life. They're showing up when they're not 23 and throwing up on the side of the road or something. Not everyone's doing that, basically… now you're meeting people at a very different moment when they're really interesting, fully formed people. And this event reminded me of that.

Sydney: That makes me feel good. Wow. Wow. 

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Emily: Sydney, you were asking for a little bit of tea and if there's a crush I'm walking away with?

Sydney: Yeah. Are you going to reach out to anyone?

Emily: Yeah. Offline I'll tell you who, but there were definitely a couple of people where I was like, wow, okay, vibe, good conversation and cute.

Sydney: I noticed you were over at the fire pit for a long time, right?

Emily: I got pulled!

Sydney: We realized afterwards that space was away from the rest of the group. It was a little more romantic.

Zoe: There were a couple of people over there towards the very end that I was like, oh, I don't want to bother them. They're so in it.

Emily: You could see towards the end of the night who was, like, gravitating towards who, which was cool as well. What about you two? 

Zoe: I've reached out to someone.

Emily: Oh my God!

Zoe: And then she was like, yeah, sounds great. And I was like, Oh no, now I need to like, think of a thing to do. So I'm in the process now. 

Emily: That's so exciting. Sydney?

Sydney: I was in a very different headspace and spent the entire event of making sure that everything was happening. Though I did chat with some people, I felt that all of my very brief interactions with people that were mostly me trying to pull them away and get them to have a conversation with someone else.

I thought there were definitely some cuties who I spotted from afar. But no, that was not my mental space going into it. Maybe for a future event. Or maybe someone else throws an event so that, they'll with their committee bear the brunt of responsibility and I'll show up as a carefree guest.

Zoe: Maybe how this lives on is we make a template, we make a how-to, and we sell that. I love that. 

Sydney: Profit first. 

Emily: Profit is obviously the most important thing.

Okay. So, the night is over, the postmortem is done, you've popped the bottles. What's the one personal or societal thing that you're walking away from this with? What surprised you about the whole process?

Zoe: The amount of interest and enthusiasm that people had. I went into it thinking oh, this is just another option among all of these dating mixer situations out there right now. But the fact that people were on the sidewalk before they even got to the door, and at the door when I was chatting with them and they were like, “I am thrilled to be here. You guys put so much effort into it.” People were complimenting it on the stoop. I was like, what do you mean? You're not even in it yet, but just the entire experience of it was something that people really appreciated and had a lot of enthusiasm for.

And then you felt that through the conversations, through the entire night, people were excited to be there. And didn't want to leave at the end. And we had to be like, the night's over. It's a Sunday night; please go home. 

Sydney: I second that. I'll also say that as much effort as we put into planning this, a party is really only as good as the people who show up for it. The feedback that I think I heard most consistently throughout the night was everyone here is so cool and I've liked everyone I've talked to tonight.

Whether that was a romantic interest or a platonic friend potential, I think that's what warms my heart the most. People really did get along and not only that, I think they brought their best selves to the event and were willing to be vulnerable throughout it and really make the effort.

Because we can't make people do that. We can design it as well as we want to. But we can't actually make that magic happen. That's up to the people who show up. 

Emily: And magic it was. Okay, that's all I had. Do either of you have anything you want to put out into the world any other thoughts, feelings before we wrap? 

Sydney: We're both still technically single. So I guess if this really speaks to anyone who wants to reach out, our DMs are always open. I'm speaking on you behalf too, Zoe.

Emily: They're single! They're ready to mingle! They're hot and they can organize! Thank you both so much. Bye!

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GreenFin24! 

I stumble to the kitchen, grateful for the leftover coffee I’d thrown in the fridge the night before. Mason jar of watery black goodness in hand, I head back to my room and get ready for the day. The event’s dress code is “business professional,” a phrase that my work-from-home-writerly ass hasn’t encountered since that brief stint in business school sophomore year of college. 

Today I am not a writer, but rather a part-time employee at the 2024 GreenFin conference, “The world’s premier sustainable investing and finance event.” Held at NYC’s Javits Center, it promises fruitful connections in finance and sustainability, insight on ESG investing, and access to products that accelerate a corporation’s climate strategy. Reader, I know what you’re thinking. What a perfect event for Emily! This makes complete sense. 

It, of course, does not. That’s what makes it fun. 

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Backtracking a bit… list item #17. “Get a Part-Time Job at a Convention Center,” was an exciting premise. I consistently lose money doing 129 Ways, so an activity that could increase my bank account was enticing. Plus, convention centers offer endless opportunities for unique interactions. I would know. 

During the summer of 2019, I spent a lot of time working in convention centers. Unemployed that June, I took a job as a “host” at the E3 Gaming Expo at the Los Angeles Convention Center, holding a giant cardboard arrow under the relentless California sun until I was medically evacuated for heat stroke. A few weeks later, I was back, this time blessedly indoors as a stand-in for Snapchat execs during their event’s tech rehearsal, cosplaying as founder Evan Spiegel. By July, I was gainfully employed as a Hollywood assistant, and once again found myself at a convention center for San Diego ComicCon. Not even a month into my dream job, the gig was a joyful weekend of costumes and a real taste of success. 

A lot has changed since that fateful summer: E3 shut down in 2023, Snapchat now has a weird AI chatbot, and I no longer have that dream job. There’s been a pandemic, the planet’s gotten way too hot, I moved cities, JLo and Ben finally got married. I felt as if it had been a lifetime since I’d been in a convention center (in actuality, it was five years). 

So stepping back into a vast hall of booths, banners, and businesspeople was a welcome, if not nostalgic, prospect. Plus, it’s rare that an item can actually be taken at face value. #17. “Get a Part-Time Job at a Convention Center” didn’t need updating or analysis. The reasoning was as straightforward now as it was in 1958: you meet people where you work, and conventions expose you to endless attendees.

The first step was identifying upcoming conferences in New York City. I started at the Javits Center website. The Javits Center, located at 655 W 34th St, is NYC’s major convention facility and the busiest in the United States. Like much of New York City’s architectural history, the center is marred by controversy, including a 1995 allegation that it was operated under Mafia control (@Tony Soprano). These days, however, Javits is more known as “The place I got my covid vaccine!,” which is what more than five New Yorkers exclaimed when I said I was going.  (The location set the national record for most vaccinations in a single day at 14,000). 

For June, my options were a fancy food conference, a wine convention, or the green finance event. Specialty Food Association didn’t respond to my email, Vinexposium didn’t match my availability, but GreenFin24 was promising.

GreenFin24 wasn’t hiring part-time staffers; they were offering volunteer positions. Applicants were asked to submit a brief essay on their ambitions and personal/professional information, with preference given to students. Luckily, a crisis of faith in early May led me to briefly quit writing in pursuit of a more pragmatic path: grad school. Mere weeks before applying to GreenFin, I had bought a GRE book, met with admissions at several major schools, and registered as a non-matriculated student in Graduate level statistics at SUNY Stony Brook. I was ready to toss everything out the window and get a Masters in Policy Administration. (For the record, this remains a possibility. Working in and writing about advocacy is a dream). 

But for now, all that matters is this spiral meant I was not lying when I said I was a student at SUNY Stony Brook. I sent in the application and forgot about it. And then in early June…

Hilariously, volunteering at GreenFin would cost $50, but it seemed worth it. I paid the fee and requested time off from work. Soon, the day arrived, which brings me back to where I left off.

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6:15 a.m. I am out the door, dressed in head-to-toe Zara. The irony of wearing fast-fashion to a sustainability conference is not lost on me. I pop into the bagel shop next to my apartment and order breakfast and a large coffee. With ten minutes to spare, I sit by the window, sipping my drink and eating my bagel, marveling at the rare quiet of the city waking up. 

I jot down a list of people who may also be awake this early: 

• Doctors 

  • Ex: my friend Lexi

• Subway conductors 

• Those workout people who do more in a morning than most of us do a year

  • Ex: my friend Erin 

• The not-yet-gone-to-bed intern whose “night was like a movie” 

• Everyone inside of Bagel Point

I stop there, realizing the list is silly because it’s New York and people have things to do. Everyone who’s anyone is awake right now. I finish my bagel and head to the train.

7:00 a.m. I arrive at the Javits Center, joining a group of fellow volunteers, all in suits and clearly accustomed to such attire. I gulp, hoping no one can tell I'm an imposter. I am quickly greeted by an Aussie who we’ll call Poppy. Perkier than Elle Woods after three coffees, she seamlessly brings together a group of strangers, creating what would become our morning posse. There was Poppy, our de facto leader on the hunt for a new job, her friend Ella, an HR consultant transitioning to corporate strategy, and Lauren, a college grad so fresh you could still see the hope in her eyes. 

Orientation was quick and painless, and then it was time to collect our badges, complete with our names and jobs. For me, that was… Student. Whoops. I contemplate creating an alter ego as a SUNY Stony Brook student. But at this point, the idea of grad school seemed far less enticing than it had a month ago, especially after realizing it might have just been a reaction to a break-up and not worth the massive debt and life disruption. 

Luckily I was able to change my title to the more accurate, “Podcast Producer, Non-Profit.” (Recyclable) lanyard around my neck, I got to work. 

8:00 a.m. to 9:00 a.m. My new crew and I man the check-in desk, greeting conference attendees as they grabbed their badges. In between interactions, we sipped coffee and got to know each other.  Poppy, a conference veteran, had been working the sustainability convention circuit for months. Ambitious and graceful, she was there to make connections and maneuver into her desired job. Poppy was a power player in a volunteer’s vest.

9:15 a.m. The volunteer organizer informed us we’d be helping at the workshops instead of the check-in desk. (Promotion alert!). Ella and I were assigned to a three-hour training on “transition finance.” As we got to know each other, I wondered when I’d need to reveal that I wasn't actually a member of the Green Finance community but rather a writer using the experience for content.

I started to tell her but was interrupted by attendees needing their badges scanned. We focused on our job for the next ten minutes, then stood in the back as the session began.

The conference room’s drab fluorescent lighting and rapt audience gave me a pang of collegiate nostalgia. It was a joy to be in a room of eager learners, even though the presentation on transition finance was absolute gibberish to me. So, also kind of like college. I took notes. 

Climate conference notes 

• Double materiality – a concept in sustainability reporting that considers both the impact a company has on the environment and society, and how those factors affect the company's financial performance 

• CSRD – The European Union's Corporate Sustainability Reporting Directive

• ISSB standards – International Sustainability Standards Board provides an opportunity for companies' disclosures to be globally consistent and comparable across capital markets.

• Cross jurisdictional quagmire (???)

• Cool to be in a room of experts even if I don’t understand any of this 

• CTAP – climate transition action plan

It was interesting, but a lot. Just as I felt myself zoning out, the first session stopped. The leader announced it was time for the interactive hour, and volunteers should join. Oh, shit. 

Our task was to create a climate transition plan (CTAP) for an energy company using the model we had just studied. My imposter syndrome was at threat level midnight as I sank into my seat at a nearby table, Ella by my side. We all introduced ourselves. It went something like this. 

“I’m Carl and I work at Goldman Sachs.” 

“I’m Megan with the Energy Department.” 

“I’m Lee from Citi.” 

“I’m Emily and don’t worry about it.” 

Record scratch. Everyone turned to me. 

“What?” Carl questioned. “What do you do?” 

“It doesn’t matter. I would say don’t worry about it. I do a lot of things that are hard to explain.” 

The perplexed group moved on, and I wiped my sweaty palms on my plaid pants. They couldn’t know I was a fraud! I needed them to believe I belonged.

As we got into the activity, I started to believe it too. Eventually, that is. For the first twenty minutes, I felt like Liz Lemon from that episode of 30 Rock where she goes to the GE Six Sigmas conference: out of my element, a weird writer among sharp corporate finance folks. But, like Liz, I managed to contribute actual ideas… and they were low-key good. We discussed the perks and pitfalls of transitioning a grid from coal to clean energy. How would it affect local communities? Who would educate them? What about lost jobs? How to get investor buy-in?

At the end of the hour, we presented our work. There weren’t grades but I feel like we got an A. 

I also fessed up to my table, sharing why I was actually here. They looked at me like I had three heads, so I slinked to the back of the room for the final hour of the workshop. 

Notes from the final hour 

• Just transition and environmental justice / human rights risks with climate transitions

• Regenerative agriculture and employee livelihoods 

• Food waste and hunger — related to just transition and thinking about how the transition to clean energy will affect people (human rights) 

• Every major company needs to have a transition plan to clean energy 

• Concerns for transition: affordability, environment, community engagement, loss of jobs 

• The importance of data and metrics in a transition

The morning ended, and I walked out feeling smarter and more confident; the imposter syndrome had faded. It was thrilling to use my brain in a way I rarely do.

I recently went on a date where the guy said women think they're bad at math because they're told so, not because they are. This sentiment was echoed at GreenFin. I assumed I was bad at corporate planning and big-picture thinking because I’ve been told I'm just creative and therefore not apt at business. But why can’t a person be both? Artistic and analytical? Even if I prefer the creative side, it was nice to know my strategic mind works just as well.

12:00 p.m. Ella and I filled heaping plates of what has to be some of the best food I’ve had in weeks. Like, it could be served for a hefty price at a restaurant quality. However, attendees did pay $4,000 for this event, so maybe the food matched the cost. We headed out to the roof, which boasts an epic view of the Hudson. 

Over lunch, Ella and I talked about relationships, career prospects, what we hope for our future, what we love about our present. I admitted feeling like a fish out of water. It was comforting to have a buddy for the day, someone to share the experience with.

12:45 p.m. Stomachs obscenely full, we wobbled over to the expo for the freebies. While chatting with people who asked what I did, I stuck with the vague, "Don't worry about it." They probably thought I was either a spy or just rude, but whatever. I got a free water bottle out of it. 

Moving from booth to booth, I was struck by a sense of hope. The expo was brimming with representatives from different companies, all of whom had some version of the same goal: make sustainability mainstream and profitable. I’m not one that is all like rah rah capitalism, but I recognize that it runs our world. It was comforting to meet the folks in finance working to make our earth better instead of simply shareholders richer. 

1:00 p.m. - 3:00 p.m. This feeling was further cemented at the two-hour keynote. I recorded it, hoping to hang on to nuggets of wisdom. But this essay is already long, so here are highlights: 

Keynote notes

• Business motto: “What’s gonna make the company rich, what’s going to make the company poor, all the rest is email” lmao

• Political moment is making sustainable investing harder 

• Volatility of each clean tech movement and the fundamentals are becoming stronger 

• NY state common retirement fund (sustainable investments and climate solutions) 

  • One of the best performing pension funds in the country

3:00 p.m. I bid adieu to Ella. We’d see each other again on Wednesday, for our second shift. 

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I never saw Ella again. 

By the time Wednesday, June 19th arrived, I had crammed an entire week into just 36 hours. Between wrapping my shift on Monday and gearing up for Wednesday, I juggled a painting class Monday night (for #18: “Learn to Paint”) with my paid gigs: early morning freelance copywriting on Tuesday, feeding a stranger’s cat, my regular 9-5, and SAT tutoring that evening.

Exhaustion set in, and I was nearing burnout. I questioned the wisdom of pushing myself beyond sustainable limits, especially after attending a conference focused on sustainability. While I thoroughly enjoyed my first day and felt I gained valuable insights, I needed a break far more than I needed to return. So thus concluded my time at GreenFin24. 

People don't always take the time to consider what it's like to actually work at a convention, or in any of the routine roles in the places we frequent. In the last few years, I've held a variety of part-time jobs: yoga studio receptionist, babysitter, assistant, greeter, production assistant, dog-sitter, tutor, and hostess. I've become adept at turning on the charm and ensuring the guests are blissfully unaware of what happens behind the scenes. They'll never know you hauled 30 sweaty yoga mats up a flight of stairs last night, crying in the steamy studio as you cleaned and hung each one. They'll never consider that you arrived two hours early to set up machines, unload chairs, and ensure the posters were placed and the name tags printed. 

And so while exhausted by the hustle – of constantly being on and working less-than-glamorous gigs to scrape by – I’m also grateful for it. It's a privilege to have one job, let alone too many. I’m lucky that people have taken chances on me and that I have been trusted in such unique settings and roles. 

It’s shaped my worldview. Someone once said that working in the service industry teaches you there are two kinds of people: those who understand the struggle and those who don't. Being in the trenches at a restaurant, catering to diners who are assholes about their chicken cobb or the creepy line cook who won’t stop asking you to “check a dish out in the kitchen,” gives a certain perspective that you wouldn’t otherwise have. Best of times, worst of times. 

These jobs have introduced me to some of the most resilient, badass, hard-working people I’ve ever known. People with big dreams and hearts who are often overlooked. Gritty, tenacious, determined hustlers unafraid to get their hands dirty to achieve what they want. 

At GreenFin, I was struck by a sense of comfort in familiar territory: the instant solidarity of the volunteers, the knowledge that we are in this together, on our feet for hours, smiling blankly, making small talk to pass the time. The lunch, the food that was so good it felt illegal, sitting outside on the roof deck talking about ambitions and dreams with a new friend. There was no pretense, just passion. 

Of course, my experience is also couched into an immense amount of privilege. To have the time and energy to reflect on this endeavor is a gift, and one that not everyone has. Taking time off to volunteer at a sustainability convention was only possible because I had jobs – albeit, too many – which provided the flexibility and autonomy to do so. Even writing requires a certain socioeconomic advantage. It’s time-consuming, emotionally draining, and the payoff is rare. 

I hope to get to the day when I can work one job instead of five, when writing is less of a pipe dream and more of a profitable endeavor. That said, I wouldn’t change anything about the present, and I’m not in a rush for the future to happen. It makes for a full life and a lot of stories. 

When push comes to shove, I love everything part-time jobs have given me… except maybe the heatstroke.

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More often than not, this project is an experiment in doing something. It has taken me to the fishmonger, to the dog park, to the golf course, to the side of the road with a flat tire. But even larger than doing, it is about learning. As I thought about list item #16, “Point Out That The Death Rate of Single Men is Twice That of Married Men,” I knew I had some options. I could go on a date and see what the reaction was. I could put this stat on a flier and paste it around town. I could shout it from the rooftops. I could send it to an ex. But what intrigued me the most was the actual statistic and what it said about marriage, mortality, and loneliness. And I was nervous to share this fact because it seems like something that, unprompted, might make someone angry.

In considering who to interview, I decided to consult an expert. An expert, specifically, in pissing off men. Without further ado… Kyle Prue. 

EMILY: Welcome!

KYLE: Thank you for having me. I am an author and a content creator. My metric used to be when I was dating is that I would tell people that I was a “multimedia artist,” and if they laughed at me, that was a really good sign. If someone was like that's really cool and took it seriously… you can't take me as seriously as I take me or this is never going to work.

EMILY: Yeah, you're like, I have to go through a tunnel and never come back. Kyle, among many other things, you are a writer, a smart person, you've existed in the world… you also are very good at pissing off men. Kind of famously so.

KYLE: I have an early copy of my manual, How to Piss Off Men.

EMILY: Oh my god!

KYLE: So yes, I am a little bit of a male anger anthropologist. I have gotten my ass kicked for the last three years weekly and now I know all about it.

EMILY: You literally have written the book on pissing off men. For the record, you've also written YA fiction.

KYLE: Every once in a while, I'll mention being an author from before this, and people are like, what? And I'm like, it doesn't matter.

EMILY: In college that was the most random and amazing fact about you. Oh, for everyone who doesn't know, Kyle and I were in the same improv troupe together.

KYLE: Yeah, there was a university-supported improv group that had really big shows, and we had tinier, cooler shows. The other group was like McDonald's, and we were like a hole-in-the-wall restaurant that gives you food poisoning one out of ten times, but you can't stop going.

EMILY: Because the other nine times, it's the best food you've had in your life. They probably have a C rating in terms of health code. But we did good improv, and now we're all here, and the funny thing about our improv troupe is they've done quite well for themselves in the real world.

KYLE: I also think that that group made everybody who was in it a lot cooler.

EMILY: To segue back to the book, everyone in our college troupe had weird niches. I don't know if I would have predicted that you’d go on to write a book on pissing off men, but it was a cool thing that you had in college.

KYLE: A little nugget of lore was that I had written this young adult fantasy trilogy, and the other lore that I had was that I was actively passing away from Lyme disease. Just like slowly 150 pounds and withering away, living too fast to die old. I was having seizures and stuff, and I was like, listen, I got two years, and I want to spend them on improv.

EMILY: Let's circle back to Lyme disease because we're here to talk about the death rate of men.

KYLE: Nobody knows more about it than I do. 

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EMILY: As I've explained, I'm doing my list — 129 Ways to Get a Life — and one of the ones was to “Point Out That The Death Rate of Single Men is Twice That of Married Men.” First of all, it’s true, but before I even ask any questions… gut reactions to that statement?

KYLE: Absolutely, I understand why it is. I've had multiple brushes with death, like this all ties in really nicely. As a person who takes like a hundred pills a day — half of them are medical, but most of them are vitamins. Once every couple of days, one gets caught in my throat, and I'm like, if I can't pass this shit, it's over, man. At the same time too, if you’re not taking vitamins, you’re going to die a lot sooner.

EMILY: I was telling someone this yesterday — I don't know if you know this — but for men between 25 and 55, there's some statistic that they only go to the doctor if they have an STI. I was researching it, and one doctor said, “As a primary care doctor, I think the number one reason men avoid the doctor is fear.” They don't want to be vulnerable, so they don't go unless they have an STI, and then they show up at age 55, and if no one's been pushing them… 

KYLE: I think there's a two-pronged way in which you could sort of fit into this, listener and/or Emily Bice. Number one is if you enter into a relationship with me, you are less likely to get STIs if you're good and don't cheat on me, and therefore, you won't have to go see the scary doctor. But level that up one degree — if you and I have intimate conversations about our shit and everything that's going on, you're going to go to the doctor, you're going to say this is no worries, actually. I feel very comfortable talking to you because I have to talk to my partner all the time about whether or not we believe this is going anywhere and should we get a dog?

EMILY: Yeah, and should we be around for it? Someone else pointed out to me where they were like, Emily, everyone dies, eventually —

KYLE: So true. 

EMILY: Yeah, I was, like, fair, but I think the reason this stat exists is because of the benefits you get, and it's someone pushing you to take better care of yourself. So it's those conversations where someone would be like, also, are you eating a vegetable?

KYLE: There's so many habits that I have picked up when my partner comes over, those things are in the shoebox in the closet, you know what I mean?

EMILY: Can we get an example? 

KYLE: Totally. So I'm filming a season of my show (Rabbit) in a couple of weeks, and because of that, I've quit everything — I've quit drinking, I've quit sugar, I really lock in because I need the necessary mental health and focus. But the one thing I do rock with is stimulants. So I mainline probably 400 milligrams of caffeine per day, either through Celsius or Yerba Mate (Celsius brand partner hashtag hashtag hashtag), but I would never do this in front of a human person who loved me.

EMILY: When you're not alone, someone else is watching out for you, and also someone else is watching you.

KYLE: Every once in a while, my partner will be like, “Hey did you eat today?” And I'm like, “I don't think so.” She's like, “It's 7 p.m. you gotta get on that.”

EMILY: And that's going to keep you alive for a decade longer than others.

KYLE: Here's what I will say: I am in the doctor. I got rid of Lyme disease, and then I was like, let's see what other shit we can get on. I go just for vibes sometimes.

EMILY: Who doesn't love the doctor? But I think you're the outlier — because one question I had was, do people go to the doctor? What's interesting about the 1950s version of this list versus now, is it's the same rate. So much of this list has changed; if you look at what they suggested in the 50s and then you translate it to 2024, it's completely dated — but the death rate continues to be twice as much. So I'm curious… as a generation, we care more about our health, right? We care about mental health, physical health —  

KYLE: There's something so masculine about destroying your body. You know what I mean? There is such a feeling of bombasity. It's very epic to whittle away at yourself and ruin your body. 

EMILY: So, do you think when you enter into a partnership, that need goes away?

KYLE: I think it changes the perspective. If you're a single person, you're like, I will destroy my body for what I want. But when you are with somebody, or you have a family, or you have a dog or a succulent or whatever you're like… it's actually loser-ish to destroy myself.

EMILY: Part of this whole scenario is that when I think about these, I go down a rabbit hole. It started with mortality and marriage and then led me to what we've seen all over: this epidemic of loneliness. It brings me back to the idea that if you're feeling lonely, you're not wondering, “Is there someone that’s watching out for me?”

KYLE: Part of the epidemic of loneliness and part of being a person affected by that is a lot of these people really wish to be witnessed in their pain. I think that also feeds into the idea of destroying the body when you're alone. You're in pain, and you have the need or desire for people to see how bad it is.

EMILY: But then I wonder… agree, I think some of it is you need to feel seen in your loneliness. Especially because so much of what our world is right now is separated by screens, and it's a fake representation of someone else's reality, so a lot of it could be digital and not real, but then you look at something like this actual statistic where someone that is on their own their whole life is statistically predestined to die earlier because they're alone essentially.

KYLE: I think when you're with a group of people, you just make better decisions. If no one's around to care about what happens to you, then I think you also stop caring about it as well. If you eat fast food five days in a week and you're alone, no one's gonna call you on that, no one's gonna care. But if you're in a relationship and you eat fast food five times in a week someone's probably gonna be like, “Yo, that's crazy.” There's so much behavior that feels completely rational and normal when you're alone, but if you're in the house with somebody, it's embarrassing.

EMILY: The other point of this project is to think about how we view love in modern times, but also life, and friendship, and companionship. So I think with friendship, I'd be so curious if someone studied what the life cycle of someone with a really robust social circle looks like even if they didn't find their partner.

KYLE: Totally. I once was trying to schedule a date with a girl. We had two bars in mind, one that we'd both been to and knew we liked and one we'd never been to. And I said, “We should go to the one that we've never been to” because your brain will compress information it's received before. So if you're in a place you've never been, the experience feels longer than if you're in a place you've been before. It's the same thing if you drive to work every day, the drive feels like 10 minutes even though it's 20. But if you drive somewhere you've never been before it feels like an hour even though it's 45 minutes. Your brain sees stuff it's seen before and it crushes it all. So I was like, if we go somewhere new, this will be a new experience. It'll make our lives feel longer, and she was like, “If you become a regular somewhere, it breeds community, and people in communities actually live longer.”

And I was like, I don't think there's a difference, but we were planning a date we're sixteen DMs in… is there any difference between your life feeling longer and your life actually being longer? I don't think so. I always thought about that from that day on. If you live in a community, your lifespan goes up because people check on you. 

It's interesting with lifespans especially with these kinds of statistics you're looking at. We've been really misled as a culture for so many years because there are so many things that they say are indicators of good health, but they're actually indicators of high net worth. So if you say, like this is the statistic forever, one glass of red wine a night is actually healthy. People who do that live longer. And it's like, no, people who drink red wine every night can probably afford to go to the doctor.

People who own horses live 15 years longer, and you say to yourself, man, riding horses must be great exercise, and the answer is no, if you can afford a horse, you can afford to go get your heart looked at. I'm wondering if community, in a certain sense means, do you mean being able to afford to live in a suburb? Is that how you're qualifying community? I'm always trying to sparse out whenever I hear years of life statistics. Where are we fitting economic status into this?

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EMILY: Absolutely. I think it's the outliers. We're not seeing a full story. Even the marriage thing —I think the better version of this is living within people that check on you probably expands your life because what if you're in the worst marriage? What if you're in an unhappy marriage your whole life or you're with a person who doesn't take care of you? That statistic doesn't encompass all of it, and it just has this one raw number.

KYLE: I also think that men are inherently competitive with each other, and some men are competitive with their partners, but that's a little less likely. It's possible that if your partner says to you, “Have you eaten today,” you're like oh, I haven't eaten today. If one of your guy friends says to you, “Have you eaten today?” you're like, “You're not my boss, don't critique me; I've been grinding, I've been locking in.” The issue with male friendships is I think they rarely extend to care. They rarely extend to what do you need, wherein I think partnerships always go there. That's an interesting tenet of male relationships that I think women do check on each other and try and determine what everybody needs at the end of the day.

EMILY: I tried to look up the woman statistic, and again, this is all broad strokes of me finding what I find. There is still a statistic that exists for an unmarried woman versus a married woman, but by and large, women live healthier lives whether or not they're with someone because they practice care in a different way.

The other thing about men and what you just said… I was at a coffee shop a couple of weeks ago, and I saw this guy sitting on his laptop reading a Medium article that says, “Men Are Suffering From Hug Starvation.” There was a part of me that was like, should I offer to hug this guy and then that felt even weirder… but it is another part of it? The way men are trained to display affection is not with physical touch.

KYLE: Guys do hugs, but it's the kind of thing where you clap each other's back hard almost to diffuse intimacy. There's a real big difference between, like, a soft hug where you feel the other person and you hear their breathing, and how I hug my guy friends, like dap up into a kind of hug or whatever. But that's been the standard for centuries. A lot of things that we have currently — handshakes and common courteous gestures — are from a time in which they're basically meant to show I don't have a weapon. The reason you used to shake hands above the wrist was because you were feeling inside their sleeve for a knife. I'm trying to remember the other gestures created basically just to be like, “I'm unarmed.”

EMILY: I wonder if the, is it a cowboy where you, um —  

KYLE: A salute?

EMILY: Is that to show you don't have a gun?

KYLE: I don't know. I just remember seeing something recently, people talking about how many different gestures and little tidbits of common courtesy we have that are basically like old holdovers… oh! Clinking glasses was to share liquid, to be like, I didn't poison you. Humans come from such a brutal and terrible history of murder and violence, and now we're all in this moment of ease, and we're all just in so much pain trying to figure out how to find kinship in each other.

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EMILY: The other thing I just want to say is that all of these statistics and this information is just for heterosexual partnerships. So, we've no idea what those rates are for any relationship that isn't a man and a woman. Again, thinking about community and this sense of looking for kinship, exactly, it's just this larger dearth of… we don't have a sense of togetherness right now, and I feel like people are scrambling trying to figure out how to get it. And partnership and living within communities, even if it is an economic thing, at whatever economic level you're in, we’ve been in a community since the beginning of time.

KYLE: Totally. I also think big tech exists primarily, like the primary function of it in a lot of ways, is to estrange you from communities because individual people are better buyers. Like they're better capitalists than people who live in communities. In communities, you cook for each other and don't buy as much stuff, but if you live alone, you order food, and you blank.

There's this Leonard Cohen poem called S.O.S. 1995. He has this line in it that stuck with me forever. “You are being bred for pain.” He's trying to reveal to, I think, the people of the world. Yeah, like these people, whoever they are, capitalist government, they're breeding you for pain.

He says, “You are clamped down. You are being bred for pain.” 

EMILY: It's even the thing about big tech and how it has completely gotten rid of community and is breeding us for this sense of loneliness. And I could talk about this for years: what dating apps have done to the way we view partnership. They have commodified it to a place where people just don't engage in the way they used to. And I think creates this gamification of how you view looking for a person and a partner in the world.

KYLE: If you talk to people in bars now, they're like, what are you doing? You just do not go out and meet people in bars anymore. Big tech, like seeks in a lot of ways to make everything sleeker and more convenient and faster. And I think that's a horrible algorithm to apply to falling in love because it's horrible, and it's messy, and it's really strange. It's not supposed to be easy or clean. If an algorithm matched me up with someone, I don't want them. It's supposed to be complicated. So often, so many things feel empty because if I didn't have my phone and I didn't have the Internet, I'd be leaving my house for most of the day every day. Getting things and meeting people. Every time I ever talk to a stranger, it's never gone poorly. People are happy to talk to you out in the world, and I'm like, why am I terrified to do it? 

EMILY: Kyle, you are in L.A. I'm not. But when I left L.A., part of it was that I felt so alone. That's why I love New York: there's this constant sense of community here, and I meet strangers all the time. 

KYLE: New York, you're all bound together by New York in the sense where you are all fighting New York. The weather is always hotter or colder. You're walking up, it's smaller, it's cramped. You're fighting all the time. And so, it's all New Yorkers versus New York. That's the solidarity, and we don't have any of that here because we don't ride any public transport. We're all alone in our cars. The existential struggle of Los Angeles is like loneliness and do I matter? Where in New York, I feel like the struggle is mainly material. How am I going to make rent for this hallway that I live in?

EMILY: And it's an expensive hallway. We live in this society that has made it so you kind of have to have a person if you're going to have the same shot at life, it feels like sometimes, it is also economic.

KYLE: I do not believe monogamy is inherent to people. A lot of people are like, well, a lot of animals mate for life. And yeah, but when humans were animals, they did not. That's a good thing to remember. But I do not believe that any other system besides monogamy would really work as a core function in America because it is so heavily incentivized. I have the same feeling, I'm like, do I have to get married at some point to be able to afford things or buy a house? It's really strange.

EMILY: Have you heard of the friendship marriages in Japan? So, there's a trend in Japan since 2015. I think there's been 500 marriages. Some people are entering “friendship marriages,” which is a literal marriage where they agree they don't want anything romantic with each other. They just want to get married for the societal benefits and acceptance. Even think about an arranged marriage or a matchmaker. Sometimes people fall in love with that person, or they don't, but they're like, it's beneficial. 

KYLE: The reason people in arranged marriages, I think, are happier in a lot of ways… they are happier. Check the statistics; they report higher signs of happiness to people who get to choose their spouses because you don't really give them a chance to question it. Where, and I think you choose from a million people, you have so many options now because of the apps, because of technology, and you get married, and you spend your whole life being like, should I have picked one of the other 999,000 people? It's so hard to make a decision and stick with it when you have infinite decisions.

EMILY: The funny thing about apps right now is we're kind of in between the two where you're algorithmically being arranged, but it's not one option. And I do wonder if, with big AI in ten years, there will be that sci-fi version of you are just assigned a person that makes sense to you, and you go with it.

KYLE: The thing that I think is complicated about matching up and all that, in the whole dating app thing or whatever, is there is an aspect of dating and of relationships that is completely ignored by all of these algorithms and setups and everything. Like I'm looking for a person who's blank, because pheromones are real. That's like an actually studied phenomenon. You could meet someone who is, quote-unquote, perfect for you. They have everything that's on your checklist. They come from the right socioeconomic background. You have enough similar experiences to vibe, but you get together, and you are not genetically compatible. I think that's the thing that's always going to make it really complicated. No matter how good we get at this technology thing. We're always going to be attracted to people we shouldn't be.

EMILY: We're always going to be human. Even with all of these weird constraints that make situations like this seem like this is the only logical option. You're always going to want what you're going to want, even if you lie to yourself and think. Okay, we could talk forever, but the other thing I wanted to ask you about is pissing off men with this prompt.

So, my question: At what point would it be okay to say this to somebody on a date?

KYLE: At what point would it be okay to say, “Men in relationships live way longer than men who aren't.”

EMILY: Imagine you're on a first date with someone, and it's not going well. And then all of a sudden, this person turns to you, and they're like, “Just so you know, the death rate of single men is twice that of married men.”

KYLE: Yeah. I think you could say that to a guy who's being really dodgy about defining the relationship. Being really dodgy about the DTR. He's like, I'm still finding myself. I'm not sure if I'm in a good place to jump into a relationship. I think that's when you pull out, well, you know, the death rate for a single man is twice as high as married men. So just knock that around in the old noggin and get back to me. You leave, and he's sitting in his apartment like… did she just curse me? He starts choking on a pill. He spits it out. He’s like, I've got to call her and lock that down right now.

EMILY: You're trying to break up with someone, and they say that.

KYLE: This is the most baller thing is like, I've had this experience maybe once where I'm breaking up with someone, and they're like, “Oh, it's a shame. I'm moving on now.” And I'm like, wow, like it's baller. It's really cool. Even if you don't feel that way, you should endeavor to try it sometime, like getting broken up with and just being like, “I understand. You were, you've been great. I'm going to send for my things.” And then, as you're leaving, just drop, like, “Just for your sake, I do hope you understand that single men do die twice the rate of married men. Goodbye.” He'll never forget you for the rest of his goddamn life.

EMILY: And every time he goes on a bad date or something doesn't work out, that's going to come back to him. And it's just a ticking clock of, I'm going to die.

KYLE: It's going to give him the yips, and then he's never going to be able to date effectively ever again because it'll become this self-fulfilling prophecy because there's so much at stake.

EMILY: The other thing I was thinking about is to maybe try and manipulate someone into dating you by just putting this statistic in every vein that they can see it, like sending them an email that has it and it's on a billboard and, like all they can think about is their impending mortality.

KYLE: You make your own newspaper and start delivering it to their door. I actually have a billboard right outside my window, and I'm the only person in the world who can see it because it's blocked by my building from the street. So, everything that goes up on there, I'm like, this is just for me. So, if that popped up on there, I'd be like, somebody did this. 

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EMILY: All right. We're going to end this with a little activity. So, I've sent you the list, and I want you to look through it. If we wrap it back into why you're an expert in this, you're great at finding the things that are just out-of-pocket shit. Which of these list items are you like, this would be the thing that would work the most or be the absolute worst?

KYLE: Be friendly to ugly men is very funny. The funniest thing about it to me is the idea that it's like this guy finding out that you're being nice to him or friendly to him because you read on a list I should be nicer to ugly men. You've been dating a guy for like two years, and you're like, “It's funny. I just remembered I actually started being nice to you because I had read that if you're friendly to ugly men, it could lead to love. And look, it did. Isn't that beautiful?” He's like, what?

EMILY: Do I stay or do I go? I don't know. Because you pointed out that the death rate is higher.

KYLE: Yeah, exactly. This one says, don't take a job in a company run largely by women. That's like tips to get sexually harassed forever. Ask your mother to take in male boarders.

EMILY: There's a couple of them also that feel like ways to get potentially murdered or in quite dangerous situations. There's one where it says to tell him his money intrigues you. What if someone told you that?

KYLE: Your money intrigues me. I'd be like, what money? They're like, “Your one-bedroom apartment is very sexual to me.” I'm like, huh? Wow. Times are tough.

EMILY: In this modern world, they are. Kyle, this has been great. Do you have any parting thoughts before we go?

KYLE: Yes, I think. This is a little bit like what you're doing, but I think everybody should get in the habit of having experiences that they can't qualify or monetize, or explain to anyone. I think so much of social media is “make yourself into one page.” Instead, go and try and go out and have all the weirdest experiences you possibly can, because life is not supposed to be simple. Things are complicated, and don't lean out of that; lean into that.

EMILY: Beautiful. You should write a book. When does your book come out?

KYLE: My book (How to Piss Off Men) comes out September 17th. And I want everybody to read it and buy it. Buy it from an indie bookstore if you can. Barnes & Noble, wherever books are sold. And then take it on the go. Piss off a man, and maybe, maybe that'll spark something. Maybe that’s the way to get a husband.

Start pissing ‘em off.

EMILY: Thank you Kyle!

Before we wrap up: as we talk about loneliness and partnership and community and mortality, it feels important to note that all jokes aside, this is a real thing. Whether you’re single, partnered, or somewhere in between, maybe use this as a reminder to check in on somebody that you love. Make sure they’ve eaten today. Make sure they didn’t have ten Yerba Mates. Give them a hug (Or don’t, if they don’t like hugs, but see if they need a hug, and if they do, give it to them).

Do what you can to make someone feel less alone — you could be adding years to their life.

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In other words, one who is a “diplomat” is supposedly a foreign policy expert and a master in international relations, but the role’s reach and impact often stretches far further than a slugline on a CV could ever capture.  

The actress Shirley Temple (yes, of the delicious cranberry and soda drink) held such a position. After a successful career as the child darling of Hollywood’s Golden Age, she pivoted to politics, serving as the U.S. Ambassador to Ghana and later Czechoslovakia. She was the nation’s first female Chief of Protocol, an officer responsible for advising the President and Vice President on matters of international relations. 

Paul Cushing Child, the husband of culinary icon Julia Child, served as an exhibits officer with the United States Information Agency, a diplomatic position within the State Department. His posting in Paris is what led to Julia Child’s discovery and subsequent love of French cuisine, which led to her authorship of Mastering The Art of French Cooking, a seminal work that not only reshaped the role of gourmet dining in restaurants but also in American kitchens, including the home of one Julie Powell, a New York author who wrote her way through Child’s opus, blogging to an eventual movie adaptation – Julie & Julia – the very film that inspired this Substack. 

So what I’m saying is, without diplomacy, 129 Ways to Get a Life would not exist. And I think we can all agree the birth of this blog is the single most consequential result to ever emerge from an American working in the foreign service. 

Okay, okay, this item is not about the history of diplomats. It’s about straight-up employment. But in these modern times? In this job market? Ugh. Seems like a lot of work. And it is! Extensive research on https://www.usajobs.gov/ revealed that to apply for one of these abroad adventures, a test is required. It is the FSOT – Foreign Service Officer Test – an online exam for which I missed the June registration date by three days. The thing is, I would have taken the test. I’m dedicated to my craft. So dedicated, that had I been able to carry out the exam, there’s a high possibility I would have seen the entire process through, gotten a job in the Foreign Service, and ended this with the announcement that I am relocating to Bulgaria for a job in the U.S. Consulate. If only I hadn’t missed the deadline! Remember to check your calendars, folks. 

Alas, I moved on to Plan B: sourcing a story that is not my own. I sent out queries looking for anyone willing to share an experience working overseas. It could have been about anything: a tale of friendship, a piece of history, a harrowing saga, a boring anecdote. But I got lucky. 

This is a love story. 

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For the sake of privacy - and perhaps also national security - minor details, locations, and names have been altered. Maybe in 30 years we’ll pull an Argo and declassify the whole saga, but for now, this is the best I can offer. What’s more romantic than a bit of mystery? 

“Jenny” was 25 when she boarded a plane to a faraway land for a government job overseas. Unlike the Midwestern metropolis she was leaving behind, her new country had yet to catch up with the current century. It was a world of sweeping scenery and looming skyscrapers – vast orange sand deserts, home to ancient cities carved into stone, were eclipsed by neo-futuristic towers seemingly ripped from Architectural Digest. Beautiful and foreboding, the place was extreme in heat, wealth, and ideas (though these days, that could be anywhere). Jenny had been sent there to work as a diplomat, young for her role and high in her rank. She was an outlier, but the blonde-haired, blue-eyed, high-achieving woman was used to such a status. It’s what made her special.

The assignment catapulted Jenny into a whole new world in the blink of an eye (or rather, the span of a transpacific flight). In the place of carefree 20-somethings – young professionals concerned with spreadsheets and deliverables, circling back on Monday and the Bar of the Weekend or the beau of the week – were dignitaries and royalty, aging ambassadors and foreign service officers tasked with mediating the weight of the world. In her new environs, The Bar of the Weekend was an infamous watering hole located inside the compound and outside the country’s laws on libations. It had been there since the Embassy’s construction some 50 years earlier. 

The Bar, the Embassy, and its respective residential quarters were places stuck in time. A city-within-a-city, expats lived a life akin to a Luhrmann movie; flashy, fancy, glitzy, hot. There were torrid affairs and drunken nights skinny dipping in the pool and enough partying to give even a particularly overzealous college student pause. 

Of course, there were rules and regulations — precautions to keep safe, honor the traditions of the land where they lived, and uphold the hierarchical system within the Embassy employees. Some guidelines were official, but others were mere suggestions, not enforceable or justifiable but certainly the status quo. 

One in particular was communicated to Jenny upon arrival: do not date a Marine. 

Tasked with guarding the compound, the U.S. Marines stationed at the Embassy were Jenny's closest thing to her life back home. The cadre of fit, exuberant 20-somethings living together in barracks in a foreign country felt familiar to the young diplomat. They reminded her of the friends in the city she left behind, except instead of protecting the brand voice of an exciting new start-up, the Marines were guarding classified information and national security. Same vibe, different responsibilities. 

It made sense that Jenny would befriend the Marines; and, perhaps, it is no surprise that she would fall in love with one. 

She didn’t mean for it to happen. Jenny’s intentions were to keep her head down, put in her time, and impress her bosses. Hers was the opportunity of a lifetime, and she planned to make the most of it. She was also acutely aware of her age, gender, and rank – the combination of which made her something of an anomaly at the Embassy. For every achievement she held and feat she accomplished, there existed the potential for it to be washed away by confirming her co-workers’ base expectations of what a fun 25-year-old might be up to. A woman working in a sea of men, walking through doors that twenty years prior would never have been open, holding her own in foreign languages with foreign leaders who may still wish those entrances were closed… Jenny had a lot to lose.

(For the record, the ability to be taken seriously may have been threatened by any relationship she engaged in at the Embassy. The second a woman is deemed desirable, certain men and women get tunnel vision. Credibility is lost as the individual is whittled down to nothing more than an object. It's a tale as old as time… literally. In Beauty and the Beast, many women are actual objects: teapots, feather dusters, wardrobes. But then again, the men are candelabras and chairs. It’s actually less of a sexism thing and more of a curse issue. I digress.)

Although it was taboo to date a Marine, there were no rules against befriending them. So for the first six months, that’s what Jenny did. They were her brothers-in-crime. They all needed each other: the country could be lonely without camaraderie. So, to protect the sanctity of their new posse, the Marines made a pact: no one would pursue Jenny. 

Jenny and the Marines wined, dined, and partied, often ending the evenings at genuine speakeasies hidden within the city, clandestine clubs where drinks were poured well into the wee hours of the morning. Her status granted her and her compatriots a spot on any list, including parties on farms in the middle of the desert where they’d dance and drink in the company of expats and princes. 

At the end of the eve, they’d stumble back to Jenny’s house, a three-bedroom villa a stone’s throw from the Embassy. It was their routine. And then one night, everything changed. 

It was around 4:00 a.m. and Jenny and the Marines had just finished a rousing round of hide-and-seek in the park near her house. Out of breath after racing through the bougainvillea, they desperately needed a drink. They made their way up to Jenny’s roof, guzzling water as the city below glittered in the night sky.  

It was at this moment that Jenny and… “Jack”, let’s call him Jack… stole away and found themselves near the service quarters (yes, there were service quarters). Who knows exactly when, why, or how it happened, but one thing led to another, and… 

“You better not tell anyone!” Jenny whispered as they made out under the moonlight. 

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For the next five months, Jenny and Jack carried out a covert affair. Of course, the Marines caught on quickly and forgave Jack for breaking their pact (which he had, in fact, initiated). But no one else found them out. While Jenny sat in meetings strategizing with foreign intelligence leaders, Jack stood guard outside of the Embassy walls. During his night patrols, he’d hide love notes in various rooms for her to find the next day. She’d uncover his romantic dead drops under red tacks on maps, between the pages of heavy almanacs, behind portraits of world leaders. Each time, Jenny would fret, worried a co-worker may see and mistake her for a spy committing espionage, but the nerves weren’t enough to stop her: she was hooked. 

It didn’t fizzle. In fact, it heated up. 

Jenny and Jack were sneaky, but the Embassy has eyes, and people talk. After half a year of ignoring each other in public and only associating in group settings, a co-worker’s husband spilled the beans during one of the Embassy’s weekly steak nights (a social event not to be missed). As Jack walked past the diplomat’s table and Jenny averted her eyes —

“Can you just say hi to your boyfriend and stop pretending you’re not dating?” 

With that, the secret was out.

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A year later, Jenny and Jack got engaged, and a year after that, they returned to the States. 

Leaving was bittersweet, but it was time to go. When Jenny and Jack had arrived three years prior, it was at a specific moment when the world was stuck in time, removed from reality and rules. But the country was opening up; restrictions were easing, the Embassy was changing, and so too would the life Jenny and Jack led if they stayed. It was the end of an era. The days of skinny dipping on Tuesdays, sneaking through the gardens, and partying in the desert were likely over. The whole operation was becoming more buttoned up, more professional, less wild. In the words of the great Lester Bangs, “Rock 'n' Roll is over.”

Would it have happened if Jenny and Jack had arrived at the Embassy two years later? Would the compound still have been a pressure cooker for passion, a delinquent whirlwind of drugs, diplomacy, and drinking? Or would it have been merely an office, an overseas posting with cordial co-workers, lovely living quarters, and a decent steak once a week?

Would it still have been an adventure?

As her plane home climbed through the sky, Jenny watched the world that had once seemed foreign and now felt familiar fade into the distance. It was full of memories now, each landmark and location a reminder of the person she had grown into while overseas. Before her diplomatic duties, Jenny had been a rule follower back in the States, keeping to herself and playing it safe. It had even been a risk to accept the position, let alone live outside her comfort zone while there. Who knows if she would have met Jack had the timing been different or the Embassy less laissez-faire. Maybe it was fated, an alchemical mix of timing, luck, and chance. Either way, it happened. And that’s all that matters.

Jenny and Jack are getting married in the fall of 2025. They’ve invited some friends from their overseas posting and are building a life together in Washington, D.C.. Jack now hides his love notes in the National Portrait Gallery, behind the photo of President James Garfield.

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