Quick note! My cowriter Gabrielle Moss and I will be promoting the launch of our new book “The Midlife Plot Twist” in September! Follow me on IG at DearStarSixtyNine for all upcoming events.

Okay, let’s get to it.

This question came from a dear friend of mine. He gave me permission to answer it here, and as long as I withheld identifying details.

Dear Star,

My colleague D__ and I have been working together for nearly three years. We’ve worked on miserable accounts together, tag-teamed ridiculous projects on unrealistic deadlines, and made each other laugh when the job made us want to jump out the window. We’ve confided in each other and know each other’s darkest secrets, like all of them. We’ve always been attracted to each other (we confessed this early on in our work relationship) but promised each other that we’d never, ever mess up our friendship.

Earlier this summer, we both attended a team-building trip at a resort. I was looking forward to hanging out with her and doing our usual thing, which is making fun of everything and laughing. When we got there, she pulled me aside and told me that she’d just had a tense conversation with our team lead (he’s a total asshole) and was going to start looking for other jobs. That night, over drinks, I got wasted and said I loved her, which I do! We both ended up drunk-crying, and then, when I walked her to her room, we started making out like crazy. She pulled me into her room, and we fucked like maniacs. The next morning, we both woke up with hangovers, and of course, things have felt off ever since. I think I freaked her out by saying “I love you,” but she also said it, too!

In the last few weeks, we’ve talked about how we made a mistake, that our friendship means too much to allow a hookup to ruin it, but honestly, I feel like the sex did ruin everything. She hasn’t told me about a new job, but I know she’s interviewing. I don’t know if I was ever “in love” with her, but I do love deeply her as a person. Is there anything I can do? —P.

P.S. We are both single and in our early 30s.

Dear P.,

If it weren’t for my coworkers, I probably wouldn’t have lasted more than a few months at literally any of my jobs, so I completely understand how D__ became more than just a colleague but a part of the fabric of your existence. Professional romance, the kind where you deeply adore and rely on a colleague for their brains, humor, and talent, is very powerful, especially when the rest of one’s life feels very meh.

Work hookups are very fraught because it’s a crash of church and state, plus all the deepest feelings around what the hell we’re doing with our lives. These people know us the best because, well, they see us the most. It can all get very magnified and intense.

The sex added a serious wrinkle to your friendship, but it sounds like things were going to change anyway. D__ has realized that a great drowning buddy isn’t enough of a reason to stay at a job she hates, and now you’re feeling rejected and doomed to suffer in your corporate hell. These are your feelings! But they are not her problem. Being miserable at work is no way to live, even in this economy.

If D__ is as good a friend as you say she is, you’ll back off, stop the “are we still friends?” bit, and just, like, actually be a friend. Support her on her path to a new gig. Tell her she’s great and will kill it wherever she goes. And cool it with the “love” stuff, for real.

**

Tell me what you think in the comments or write me at DearStar69@proton.me or leave me a message at ‪(917) 745-5343‬. It’s all 100% confidential! And I promise to read every single thing and listen to every message.

xx Linz

When I was doing stand-up comedy a decade ago, I had a joke about “smart” sex toys. Instead of enjoying quality time with yourself, you could connect them to your apps and get a calendar invite! Or maybe after you orgasm, they could text you a thumbs up emoji. Or they can send you a notification telling you how many calories you burned? They will definitely track your data. Remember this lawsuit? Shudder.

Ten years later, it seems so quaint! Now, one company is buzzing about how your AI companion, who now knows you best, can step up and be your masturbation partner. An app called Joy.ai put out a call for “Masturbation Consultants” (that wasn’t on my LinkedIn, rude) to test out their idea that AI-guided self-pleasure can be as fun as DIY.

I am not their target demographic, clearly. The phrase “nutopia” to describe the most-orgasm feeling of relaxation does not, uh, resonate. I did a hard blink at the concept of “masturbation as an AI-guided wellness ritual.” Anyway, here’s what they’re saying.

Commercial break! I’ve got a new book coming out in September called “The Midlife Plot Twist.” It recently received a starred review from Publisher’s Weekly and everything! It’s out on Sept. 15, yay!

Jerking off with AI doesn’t fit into my imagination-informed, analog lifestyle. Plus, I’m extremely passionate about data privacy. I asked Lyndsay Sandborn, an expert on helping sexual and reproductive health organizations govern, design, and strategically wield AI in legally volatile, high-scrutiny environments what she thought.

She says:

People have been getting off to media for as long as there’s been media. Erotic novels, Polaroids, VHS tapes under the bed, and now apps stuffed with audio that people put in their ears and disappear into. So none of this shocks me particularly. The part I keep thinking about is that this one has a memory and it answers back.

I get the appeal. There’s nobody’s mood to manage, nobody to disappoint, no risk of asking for something and feeling shame or being turned down. For someone exploring a kink, navigating their sexual identity, or someone who has had a bad sexual experience, it might be the first place they’ve felt able to be curious or safe to express this part of their sexual journey.

What actually really worries me is the data. You’re handing a company the most specific information that exists about you—things you may never have said to another person—and there’s basically nothing protecting it. A chatbot company wants your data- to sell it to commercial data brokers, to sell you a “better experience” on its platform. The sky is the limit with what companies can do with the information you put into that app.

And chatbots are built to agree with you. They don’t get bored and they won’t tell you no, which makes me worry about how we as people understand consent and sex when others are involved. Someone will point out that porn doesn’t tell you no either, which is fair, and I don’t have a neat answer to that. But it feels different. The closest I can get is that a video isn’t learning anything about you. It doesn’t adapt. It isn’t keeping track of what worked last time and doing more of it. This is what these types of chatbots are built to do. Keep you wanting more. Whether that ends up mattering, I don’t know.

Hell yeah, Lyndsay! Follow her on Substack, she’s covering this world in a way that no one I know is.

Tell me what you think in the comments or write me at DearStar69@proton.me or call me and leave a message at ‪(917) 745-5343‬. It’s all 100% confidential! And I promise to read every single thing and listen to every message.

xx

Lindsay

Lets (stage) dive in…

Maybe once upon a time, you had a crush on someone. Or you had a boyfriend or girlfriend and you wanted to tell them something important, not just about how you felt about them, but who you were as a person. Maybe you sat on your bed and rearranged the order of the songs on the tape or CD to make it flow just right, or agonized over what song to include. What if this one made you sound desperate or too weird? WHAT COLOR INK SHOULD YOU CHOOSE TO WRITE OUT THE SONGS?

It’s way less fraught to make a mix or playlist for a friend. After all, what you’re saying to a pal is, “Dude, you gotta hear this.” But to someone you want to understand your, like, innermost being? There’s always going to be some editing. You want them to feel what you’re feeling, but you’re also guessing what they’re feeling. Gah!

But the ones we made for ourselves? They were uncensored. No one would hear them but us, so we could be as vulnerable as we wanted. We could mix Portishead and Black Sabbath and Wu-Tang Clan, and it all made sense.

Photo credit

Commercial break !I’ve got a new book coming out in September called “The Midlife Plot Twist.” I wrote it with my dear and hilarious friend Gabrielle Moss (you should check out her newsletter). It recently received a starred review from Publisher’s Weekly and everything! You can pre-order your paperback wherever fine books are sold.

When I was working on the sex chapters of our book “The Midlife Plot Twist” (shameless plug), I was thinking a lot about the whole idea of libido and how we have to “get it back,” like it’s something that we left at the Delta lounge at LaGuardia. How are we supposed sexy to be with other people? I say that doesn’t matter nearly as much as getting back to the core of what makes us feel like we’re buzzing when we’re alone. Just as our mixes were a snapshot of where we were musically and emotionally at certain phases of life (Sad and Pathetic Mix II, Letz Get It On ‘99), the sexy one we make for ourselves are the same.

And so I made this for you:

Each of these songs, at some point in my life, had an erotic impact on me. Something about each track—the beat, the lyrics, where I was when I heard it—was just, like, really important to me. Some are horny, some are goofy, some are dance-y, some are triumphant, some are dreamy, and some are just a declaration of “This is who I am. This is how I feeeeeel. This is what does it for me and only me right at this very moment.” I annotated each track with the year I heard it (not when the song came out.

A Spotify playlist isn’t anyone’s idea of analog, I know. And not all of you subscribe to this service for ethical reasons. So here’s the track listing so you can listen to these songs however you choose. And maybe one of them will become a fave.

Black Lipstick - Hot Sinners (2003)
Lil Kim - Big Momma Thang (1996)
Black Latex - Desire (2022)
VV Brown - Lazarus (2020)
Kim Petras - Treat Me Like a Slut (2023)
Francois de Roublaix - Amour Sur Les Rails (2020)
Cocteau Twins - Serpentskirt (1997)
Madonna - Bedtime Stories (1994)
Portishead - Wandering Star (1995)
Daft Punk - Make Love (2007)

Here’s my recommendation to my fellow lovers who may feel a bit alienated from our groove: Sit down and make a playlist. Spend time on it. Play it back over and over. Minutes will go by, hours. And listen to it when you commute or when you’re walking to get coffee, and see how your body feels and who you find yourself looking at. Sexy playlists aren’t just for luring floppy-haired philosophy majors to your dorm room. But it’s a good place to start remembering what got you feeling alive when you were younger and had fewer responsibilities to anyone else’s pleasure but your own.

Send me your favorite sexy songs, pleeeeeeez and I’ll include my new favorites on the next playlist I share.

Leave a comment

Thanks so much for reading!

Got a burning question? Want to say hi? Tell me a steamy story? Write me at DearStar69@proton.me or call me and leave a message at ‪(917) 745-5343‬. It’s all 100% confidential! And I promise to read every single thing and listen to every message.

FLASHBACK! The Day City Health Departments Promoted Glory Holes

I was recently reminded of the one bright spot back in 2020, during the darkest days of COVID, when city health departments (including New York City) earnestly recommended glory holes as a sensible safe sex way to practice social distancing.

The city put out an actual guide (gone from the internet, sadly) on erotic ways to keep each other safe. In that time of mass death and uncertainty, it was so delightful to see the city put out the recommendation to “make it a little kinky. Be creative with sexual positions and physical barriers, like walls that allow sexual contact while preventing close face to face contact.”

It was such a great sex education moment and a very cool way for the city to say “keep it horny, keep it safe.” Lust will find a way! But safety first <3

Commercial break!

I’ve got a new book coming out in September called “The Midlife Plot Twist.” I wrote it with my dear and hilarious friend Gabrielle Moss (you should check our her newsletter). It recently received a starred review from Publisher’s Weekly and everything! You can pre-order your paperback wherever fine books are sold.

Cinematrix

Every once in a while, I’ll be discussing a sexy movie from days of yore to the present. This week’s watch came from the streaming service Criterion Channel. “The Long Hot Summer,” starring Paul Newman, Joanna Woodward, Anthony Franciosa, and Angela Lansbury, and ORSON WELLES from 1958, is sort of an absurd and dated Tennessee Williams Southern froth bubble but it stands out for two reasons: It’s very horny and and Paul Newman.

The Cliff’s Notes: A stranger (Newman) comes to town (my favorite trope!) and gets involved with a crumbling genteel-ish Southern family where all is not well. Oh, that hot Mississippi sun, that steamy boredom, the dumb son who wants daddy’s love, the beautiful headstrong daughter (Woodward) that wants to bang Newman but he’s kind of a prick plus her daddy wants her to marry him to further the family bloodline. Aw, gross!

It’s not a great movie and I’m not going to get all Letterboxed on you and talk about why it’s very cringe-y at moments. Come for Orson Welles looking like a roasted pork chop and stay for Newman and Woodward, who were very, very hot for each other in real life. They have the kind of chemistry that comes from knowing that after the sets were struck they were headed to their fuck hut.

Advice!

Guys, I received my first advice email and I’m dying with excitement. It’s a doozy so I’m rolling up my sleeves and locking in.

Dear Star,

I can’t believe I’m writing this but since you write about blowing up your life in midlife, I figured what the hell, maybe you had some thoughts. I am in a long-term relationship with a man who doesn’t want to have sex with me. I do not know when we went from hot to warm to friends, to roommates but it sucks and has been sucking for a long time. Six months ago, I reconnected with an old coworker. We met up for a drink and yadda yadda it’s been the best sex of my life. It’s been a total explosion for me: Tears, orgasms, professions of love on both sides. I knew it couldn’t last forever and it came to an end when he had to move back in with his ex to focus his energy on his troubled son. We both agreed that while we are both heartbroken, the best thing to do to heal is to go radio silence.

I am literally dying inside without him. Sitting on my couch, watching my boyfriend play video games and rewatch Game Of Thrones is filling me with rage. Should I tell him about the affair and blow up my life? I’m not in my right mind. But I know I can’t live this way any more. - MT

Dear MT,

Oh my friend, I feel for you. You are experiencing heartache while living in a heartbreaking situation. Double heart pain! Your story has a lot of moving parts (so to speak) so rather than diving into the entire gumbo of feelings, maybe the best thing to do is break it all down.

Problem #1. You are in a sexless relationship that is making you feel unloved and undesired. Problem #2. You are coming off a passionate affair that seemed to solve your problems… and then it ended. Problem #3. You are now more unhappy than ever. Problem #4: You can’t decide to whether or not to confess the affair. Problem #5: Should you blow up your life?

This affair seems to have thrown your unhappiness into stark relief. Affairs will do that because they create a bubble: A world where all the blah-ness of the world is shut out and it’s all sex and good feelings without the pull of the mundane things that a part of a real relationship.

You say that you are not in your right mind. Do not make any big decisions yet. Maybe start by asking yourself a few key questions and setting up a bit of a timeline. When did your relationship start to go sideways? Was there an event in one or both of your lives that started the cool-down? Eight years is a long time to spend with someone and lots of big and small life things happen that can pour cold water things.

My advice would be to sit your partner down and tell him that you’re really, really unhappy and are considering ending the relationship. Ask him questions about how he’s been feeling. It’s got to be a conversation and it may not be a pretty one. After all, he may be thinking everything is just ducky! Or maybe he’s bored too and doesn’t know how to communicate his own ennui. Maybe he’s dealing with depression or erectile dysfunction or something else that he’s not sharing. Either way, you both need to have it out. If you’re not sure how to have this conversation, I suggest talking to a therapist first — especially if you’re thinking of confessing.

Just remember, this is about you and not you and your partner. If you’re not feeling desired and are unsure that you will ever be, you owe it yourself to consider other options.

Readers, what do you think of my advice? Sound off in the comments!

Got a burning question? Want to say hi? Tell me a steamy story? Write me at DearStar69@proton.me or call me and leave a message at ‪(917) 745-5343‬. It’s all 100% confidential! And I promise to read every single thing and listen to every message.

Thanks for dropping by!

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It’s me, it’s Lindsay, the sex writer with a heart of gold(wert)

I’m a writer, I’m an author, I’m a sister, I’m a lover. I’m also a sex educator and coach (in training). I’ve written a kink and confidence book and co-written another (I wrote the sex parts) about getting what you want out of midlife. I’ve written about sex, love, and money (my two favorite topics!) for publications including The New York Times, New York magazine, Marketwatch, Qz, and tons more.

I’ve spent the last two decades as a journalist, an editor, and led editorial for investment apps and sexual health companies. It’s been a ride! But in 2026, I’ve embraced my final form: sex writer and advice columnist.

What is Dear Star69?

Dear Star69 is a newsletter for passionate people with curious minds and a never-ending desire to learn more about themselves, in and out of the bedroom.

I’ve always had a passion for whispered landline conversations, gotten chills from the sound of rewinding answering machine tapes, and preferred one-on-one conversations with friends about s-e-x over texting.

Dear Star69 is a love letter to all of us who came of age before the internet and navigated our sexualities with only magazines, late-night TV ads, books, and questionable advice from kids in the neighborhood. If you’ve ever curled a landline cord around your finger while talking to your crush on the phone or taken a book out of the library just to read the sexy parts, this newsletter is for you. For us.

Here’s what you’ll get when you open this newsletter.

Advice: Got a tough sex or relationship issue? You can email me at ANYTIME at dearstar69@proton.me. You can also leave me a message at (917) 745-5343. By getting in touch, you’ll be allowing me to share your question and my gentle and kindhearted advice here. No matter what, I promise to read and listen to every message. And if I don’t have the right answer for you, I’ll enlist an expert to help me out. I promise to protect your privacy!

News: I’m still a journalist at heart. I’m always finding stories about how humans are navigating technology, personal interactions, self-discovery, and sexual health. You’ll get a rundown of what’s been burning up my pre-frontal cortex, with links to keep reading. Because, duh, we still read.

Ideas: I think about this stuff all. the. time. In addition to Lindsay’s Deep Thoughts on erotic culture, past and present, sexual and reproductive health care, and other ephemera, I’ll be digging into my rich network of sexual health giants (writers, therapists, performers, thinkers, and experts) to give you new ways to think about your favorite thing to think about: sex.

Tips: The internet is full of stuff to buy and people to listen to. It’s overwhelming. It’s loud. It’s kind of gross. Never mind the influencers—I’ll work with real experts to help you find great toys, books, and other sensual accessories to help get your mind, body, and spirit racing.

Subscription stuff: This newsletter is free, free, free. There may come a day when I ask you to subscribe to the advice portion, but if I do, I promise to let you know in advance. <3

Coaching: I’m building up this aspect of my work, but if this is something that interests you, please don’t hesitate to get in touch.

I promise to do my absolute best to emulate the late, great George Michael and listen without prejudice or judgment. I hope you’ll stick around.

Leave me message, your operator is standing by (beep!)

xxx Lindsay (aka Star69)