In mid August, I thought my little Peepers was going to die. She’d been peeing around the house and crying at night when the vet told me to bring her in immediately. Tests showed a badly infected uterus that could rupture and kill her, and she needed emergency surgery. We made it to surgery day, but afterward Dr. Val had more bad news: her uterus was filled with tumors.

“I’m going to be straight with you,” he said in his deep, stoic Russian voice. “The statistical probability that this is benign is probably less than 1%.” I heard cancer and held back a rush of panic. Is my little peanut that I bathed in the palm of my hand when my life was falling apart in 2014 going to die soon, or live a life of pain?

I feel like I lose everything and everyone I love long before it’s time to lose them. I know this is selfish in a way, we all lose things we love. But to me it feels constant. Like my heart is shattered through hundreds of people, places, and memories all over the world, all gone forever. Two dozen of my friends have died since I turned 18. My father died while I was fighting with him. My best friends who I considered brothers are dead. My favorite cat of all of them died prematurely. Death is a strong part of my day-to-day existence, and though not unique to me, I feel it in a way sometimes that makes me wonder why I love people or animals in the first place.

So I spent the next two weeks preparing to lose Peepers. I hugged her so long my arms fell asleep. I wrapped her in blankets and cleaned her pink bodysuit obsessively. I scrolled my mind through thousands of memories with this little girl and the other cats I rescued in Panama. They’ve moved with me seven times across two countries. They’ve seen my heartbreak. They’ve seen me mature and grow up. They’ve met my closest friends and the cat sitters who love them like family. I remembered losing Cairo in 2019 and prepared for that hit again. What happens when a cat gets cancer? Will she be in pain? Will she die within a year? Will she lose her sight or mobility?

Then Dr. Val called four days before her stitches were coming out. This wasn’t the stoic Russian voice I had heard before. I could hear the smile on his face. “Great news Andy! I cannot believe it, and I’ve never seen it, but Peepers’s tests all came back negative! She’s gonna be ok. The tumors were all benign.” I dropped the phone and laid down in bed, too happy to fight the tears coming from my eyes. The world that felt like it keeps taking things I love from me gave me a break. She’ll die eventually like we all do, but NOT NOW, not like this. I don’t need to mourn again, and grieve again, and sit with those thoughts again. NOT TODAY, and not now, and not like this.

Peepers is no ordinary cat. She’s an unusually petite street cat from the skyscraper towers of Punta Paitilla, Panama. And in Dr. Val’s words, “the toughest little cat I’ve seen.”

“Pulgarcita” and the endless construction of Punta Paitilla

Cinthia and I had barely left the house on a walk to the store when we noticed her emerge from under the dark metal walls of a construction site. She let out a peep, high pitched and frightened, and Cinthia ran to pick her up and out of the way of the sharp metal and rocky path. “We have to save her,” she said. By the time I’d found the words to tell her to put the tiny black and white kitten down, she was already wrapped in her shirt and we were on our way home. We already had two cats, Mikey and Auri. I never really wanted cats, but I wanted our relationship to work and knew this was important to her. We’d been in Panama for about six months and the fights had become daily, not weekly.

She wouldn’t leave my arms, so I never made her

Once home, we bathed this little black and white cat and separated her from the other two. She was smaller than any kitten I’d ever seen, and we were shocked when the vet told us she was already about four months old. I told Cinthia we’d have to make a listing to get her adopted once she was healthy, and we did. Within a week, I pulled it down. The cat was staying.

I have a problem saying “no” to women, and when you compound that with a wide-eyed kitten who fits in one hand and sleeps at your neck, I lose all control. Cinthia named her “Pulgarcita,” which means “Thumbelina” in Spanish, and though I hated the name I obliged. Arguments were daily back then, so I picked my battles to save time.

We called her “Pulgis” for short. She spent every waking minute with me, following me to every room, sleeping in the curve of my arm, and resting her head on the edge of my laptop as I worked. This continued throughout her life, and after her “brother” Cairo died in 2019 she became even more attached. She didn’t get the name “Peepers” until 2014, which I chose because her meows sounded more like loud peeps from a bird.

Cinthia also left in 2014 with an ultimatum that I’d either take all five cats or she would abandon them in a park. I told her the ultimatum was soulless and gave her an hour to leave before I had security remove her. It wasn’t the best way to end a relationship, but I had no fight left in me. The cats were now mine exclusively, and we made it work no matter where we were or who we were with.

The Jackson Five

Having five cats is a life-altering situation but it’s still easier than one kid, and astronomically cheaper. My cats moved as I moved, from a dump apartment to a glass-towered three-bedroom palace in Paitilla, then to the beach in Chame and back to the 100-year-old loft in Panama’s old city. Cairo died of Feline HIV five months before I left the country. I was in Boston on the way home from Spain when he was hospitalized, and he was dead the next morning. I had no idea he was sick and no chance to “say goodbye,” or whatever version of that you’d do with a cat. I flew home to a bed with one less cat in it, and it hurt.

They were and are like family to me. They’re the one emotional constant I’ve had in over two and a half decades of living on my own, far from family and far from anything else stable. I bribed a Panamanian vet $1,000 to rubber stamp the US requirements for entry and shipped them to Miami one month after my move. My job didn’t afford me the same luxuries here as it did in Panama, so the apartments got smaller, but the cats stayed close. They always stayed close.

I don’t have children, so maybe this is the closest I’ll ever come to understanding that strange responsibility of keeping another living thing alive while watching your own life pass through theirs. Pets become markers of time that way. They were there for the apartments, the relationships, the jobs, the countries, the people who came and went, and versions of me that don’t exist anymore. They don’t know any of that, of course.

They just know that I’m their person and they’re supposed to sleep beside me at night. Maybe that’s why I panicked so much when Dr. Val told me Peepers probably had cancer. I wasn’t just preparing to lose my cat. I was preparing to lose another living piece of a life that has already disappeared in so many other ways. Someday I’ll have to do that, and someday that little peep beside me will be gone too. But like I said before: NOT TODAY, not now, and not like this.

As of this afternoon, I have been sober from alcohol for 607 days. I started drinking heavily at age 20 and barely stopped for more than a week for the next 23 years. Drinking gave me some of my best stories, biggest adventures, successes, and failures, but eventually I hated what it was doing to me more than I loved what it gave me. I quit cold turkey on New Year’s Day 2025, and 607 days later, I’m healthier physically and mentally and learning who I am without it.

Since getting sober, I’ve lost my Dad, gone through some mild heartbreak, traveled internationally, and faced major changes in my career and life. I went through all of it without the mask alcohol gave me, which meant confronting things I’d spent years avoiding. Learning how to live, grieve, hurt, celebrate, and change after two decades of alcohol-fueled hedonism has been the biggest transformative experience of my life.

Here are five things sobriety has taught me so far:

1. There is plenty to do without drugs or alcohol.

Contrary to what you tell yourself in your addict-driven mind, it turns out you can do a lot of fun shit sober. I learned how to socialize at night without booze at kava bars, coffee shops, and even alcohol bars by simply abstaining and starting conversations with patrons over Coke Zeros. I rarely go out now, but it’s still an option when I feel like being social. I go to the beach, walk, swim at the pool, and I’m in the process of joining a tennis club nearby.

Anything I used to do drunk that was worth my time I can now do sober. Concert? Down. Watch the Red Sox play the Marlins on a Wednesday? Bout it. Cook dinner with friends and stay up late talking shit and laughing? On my way. Get dressed up for classical music and a dinner date? Sign me up. Everything I actually enjoyed about drinking, except the drinking itself, is still there.

2. You can’t run from your emotions.

This is a hard one, but it’s a necessary lesson sobriety eventually forces you to learn. I never admitted how much I ran from my emotions until I got sober. When you’re a highly social international drunk, you can drink almost any uncomfortable feeling into submission. For me, running from those feelings became a talent.

I can’t do that anymore. I feel EVERYTHING. I have to do the hard work, no cheating. I have to feel it when I’m stressed, angry, grieving, rejected, or insecure. But I also get to feel it when I’m happy. Happiness becomes more authentic with sobriety because you know you actually produced it. That’s a gift no amount of booze could ever give me.

3. More people are sad than I thought.

One of the most eye-opening and somewhat tragic things I’ve noticed since getting sober is how easily I can see sadness in other people. I look at some people who binge drink as tormented rather than happy, desperate rather than in control. I see weakness where I once saw confidence. When you’re drunk, you can’t see it because you’re participating in it.

Sober, you can almost feel the pain coming from the types of people you used to relate to and subsequently drink heavily with. It’s hard to explain. It’s like a sad cloud that feels incredibly familiar yet increasingly repulsive. The ramblings of wasted people become tedious, and the loss of emotional and physical control starts looking pathetic rather than fun. Sometimes I wonder how often I looked exactly the same way.

4. Your time is more precious than you think.

Addiction is a thief of time, which in one way is part of its appeal. For all the “boring” dead time you fill with alcohol-fueled entertainment, you’re also robbing yourself of time to be productive, mindful, present, and accountable. A drunk lives in a perpetual state of brain fog, bridged by moments of clarity that last until the next happy hour starts. This is how I spent more than two decades of my life.

When you quit drinking, one of the first things you notice is how much more time you have. It can take a while to figure out what to do with all of it, but the extra time and mental clarity have allowed me to read more, write more and better, exercise more, and spend more meaningful time with family and friends. I have no more nights I can’t remember and a lot more days I actually do.

5. I value accountability more than ever before.

Sobriety is rooted in accountability because the only way to quit when you’re an addict is to eventually hold yourself accountable. What surprised me is how contagious that became. Once I stopped making excuses for myself, I became much less interested in accepting excuses, dishonesty, and chaos from others as well.

I used to let almost anyone into my life as long as they were interesting. Not anymore. I now need trust before I let someone get close, and when that trust isn’t there, I don’t try to force it. I simply accept what I’m being shown and walk away. It’s not a perfect process, but I’m clearer about what I expect from myself and from the people around me sober. My life has become much more peaceful because of it.

607 days later

I don’t regret all those years of drinking, in fact, I actually greatly appreciate them. Not doing so would mean regretting too many people I loved, places I went, nights I’ll never forget, and stories I’ll probably tell for the rest of my life. Alcohol was part of my life for more than two decades, and for a long time, it was fun. Until it wasn’t.

What I regret is how long I believed I needed it. I needed it to socialize, celebrate, travel, grieve, fall in love, get over love, kill boredom, make friends, and sometimes just make it through an ordinary Tuesday night. It turns out I didn’t need alcohol to do any of those things. I just needed to learn how to experience my own life without trying to alter it first.

It took me 23 years of drinking and 607 days of sobriety to figure that out. I think I’ll stay for the rest of the experiment.

I met Carl at an outdoor bar near my apartment in Casco Viejo. My friend Kevin and I were power drinking vodka sodas after one of our walks and talks. Carl was fresh off a run, drenched in sweat, and sat down to power drink with us. Like most impromptu gringo summits in Panama, the conversation moved from women to booze prices to politics and, eventually, business.

After a few sweaty beers, Carl told me about the giant houseboat he owned on Lake Gatun, deep in the Panama Canal, where he hosted jungle tours and overnight guests. Kevin, who ran a well-known local tour company, raved about my social media skills and insisted we work together. There are many tour companies in Panama, but none like Kevin’s. If he vouches for a guy, or a tour, or an experience, it’s worth looking into.

By our sixth or seventh drink, after some naturally skeptical probing about whether I was “a man he could trust,” I pitched Carl on a social media hand shake deal for $1,000 a month, cash. “I could hire a local for half that,” he said. “But the locals will fuck it up, so you got a deal. Meet my driver Saturday at 6 a.m. at Hotel Central, and don’t bring a lot of shit.”

Just like that, I had a new client.

A barely legal houseboat harbor in the Panama Canal

Carl’s driver collected me and a small group of tourists at the hotel, then drove us to a tiny dock beyond Miraflores. From there, we boarded a panga and disappeared 30 minutes into Lake Gatun, a massive stretch of jungle-lined water in the middle of the Panama Canal. This part of the country was uninhabited, inhospitable to modern human development, and long devoid of native tribes or American Canal workers. The jungle was dense on the shores, and the lake was deep, dark, and unbothered by the passing ships a mile or so away.

Jungle Land Panama was not just a tour company. It was a heavily modified houseboat floating beside the dense jungle shore. There were no roads, electricity, police, permanent neighbors, or other tourists. Carl had claimed a quiet corner of the lake and transformed a small vessel into a three-story “eco lodge” for people who wanted an authentic Panamanian jungle experience, delivered by an American.

The first floor had a dock, kitchen, bar, and picnic tables. Upstairs were barracks-like guest rooms, plus a few “luxury” options with queen mattresses, mosquito nets, and electric lamps. The roof had plastic patio chairs and a plank guests could launch themselves from into the lake. Everything looked handmade because it was, but it was built well. Carl clearly knew what he was doing.

Spending a day with Carl was worth the price of admission

The Jungle Land tours were great. We started with fresh fruit, cold beer, and a panga ride along the jungle shore to visit howler monkeys and search for wildlife. Carl’s routine was closer to stand-up than nature guiding, full of sexual jokes, animal fear mongering, and stories that hovered somewhere between sarcasm and truth. My job was to capture the fun for social media without recording anything that might “get him canceled.” This was harder than it sounds, since nearly every Carl story involved raunchy jokes, booze, gambling, or casual criticisms toward Panamanians.

After lunch, guests jumped from the roof deck, took kayaks onto the lake, sunbathed, or drank at the bar. Carl’s staff consisted of three or four unpaid interns, all English-speaking Europeans under 25. At sunset, we gathered on the top deck as the jungle erupted around us. We were just a few hours from Panama City, but it felt like another planet. By dinner, the booze had turned strangers into old friends. Carl gave a speech about nocturnal animals and the local ecosystem, which somehow spiraled into a libertarian rant about taxation, government, and how “out here, the jungle makes the rules.”

Then came the night tour, which alone was worth the price of admission. A floodlight sliced through the absolute darkness as fish moved beneath us, crocodiles watched from the shore, and howler monkeys screamed from the trees. After 45 minutes of snaking through dense jungle, we reached Carl’s “secret beach,” where a Panamanian man waited beside a roaring fire. We drank the cooler dry, debated nature versus civilization, threw military-style hunting knives at trees, and smoked joints the Dutch guys had smuggled in. Whatever Jungle Land lacked in legality, it made up for in entertainment.

What Carl was really building in the jungle

Back in the city, I got to work scheduling posts, tagging guests, and spending enough on ads to justify my existence. Within a month, Carl became nervous about the money. He understood nothing about social media and suspected I might be exactly what I looked like to him: a slick-talking city gringo running a $1,000-a-month scam. He liked me though. I could tell he thought I was a good guy, but also that I confused him with my work, in a way that many older men would skeptically look at a social media manager as someone who lacks “a real job”.

We met for lunch and went back to his mostly empty luxury apartment on Avenida Balboa. Carl hated modern society, but still needed a place in the city to conduct business. His apartment sat inside one of those soulless 50-story glass towers that cut into the skyline in Panama City and looked more like a flop house than a home. Carl was built for the jungle. He was an Army veteran from St. Louis who had served in Asia during the 1970s, though he never told me what finally drove him south.

He did tell me why he stayed. Carl believed that living on a boat meant he could avoid government trying to dictate how he lived. And, of course, property taxes. What began as one man hiding from the government on Lake Gatun slowly became a business. He expanded the boat piece by piece, added rooms, hired interns, and started calling it an eco lodge. The police knew where he was but rarely visited. The government knew too and, according to Carl, was always searching for a way to shut him down.

Carl could be kind and generous, but a palpable tension seemed to leak from him in some obviously painful ways. He spoke about women mostly as sex objects and resented anyone he considered progressive, feminist, or insufficiently submissive. He even messaged escorts through the Jungle Land Instagram account, leaving me to discover the conversations whenever I logged in for work. He said he was in debt and looking to sell partnership stakes in the business. He wanted to retreat even farther into the jungle and let somebody else run it.

The city got him in the end

After a month, Carl laid me off. He couldn’t connect my work to bookings and couldn’t justify another $1,000. We stayed in touch and drank together a few more times before I left Panama in 2019. Not long after, Carl died of a heart attack back in the city he had spent so much of his life trying to escape. I heard the news from Kevin, and then shortly after was reached out to by the holding company that bought Jungle Land and needed me to release the company’s social media passwords.

Maybe Jungle Land was never really a tour company. Maybe it was Carl’s rebellion, built plank by plank in the middle of a lake where taxes, feminism, government, and every other enemy in his head could not easily reach him. He was a kind man, a little crude, funny, wounded, and more generous than his demeanor may have suggested. For all his struggles with understanding people in the modern world, he understood the jungle. He introduced it without polish or pretense, handing guests a beer, pointing toward the monkeys, and letting the darkness speak for itself.

Carl was one of many gringo characters I met living and dying in Latin America, men who came south insisting they were chasing freedom when most were running from something they could never name. They fought society, the government, women, age, and sometimes themselves, building strange little kingdoms where the rules no longer applied. Most disappeared without leaving much behind. Carl left a handmade houseboat floating in the Panama Canal and a few thousand people who, for one night at least, saw the jungle as he did: wild, lawless, beautiful, and worth escaping into.

My relationship with Spain began like most of my relationships did back then, with a one-night bender. In 2017, I stopped in Las Palmas de Gran Canaria to meet Brendan and an Irishman before crossing the Atlantic to Panama on the Nomad Cruise. I had overlooked Spain entirely until then, and the country needed less than 24 hours to make me regret it. Las Palmas sits more than 1,000 miles from Madrid, floating off the coast of West Africa, but that small taste was enough. I shipped off to the Caribbean wanting more. I needed to get back to Spain and do it right.

A year later, I did what the British have been doing for generations. I booked a “proper Spanish holiday” on the Costa del Sol and brought my Mom with me. We chose Málaga, a city most Americans couldn’t locate on a map and most Europeans treated as somewhere to land before continuing to Marbella. It sat in the heart of Andalusia, close enough to Granada and Sevilla for a visit, but far too alive, beautiful, and seductive to use merely as a way to get somewhere else.

How to spend a day in Málaga

Picture a morning that starts in a small but well-appointed room in a century-old townhouse. You open the shutters and look down at a plaza filled with birds, older people resting on benches, young people smoking cigarettes before school, and cafe workers clocking in for the day. It’s 70 degrees and dry enough to leave the windows open, letting the cool air move through the apartment along with the faint, mood-altering smell of lemon-infused magdalenas baking two floors below. You head down to the bakery, get two of them and a coffee for under five euros, and start walking.

You can walk almost anywhere in the historic center without having to think about cars. The streets are lined with patio tables, art on display, books for sale, and bars that double as political boxing rings where old men air their grievances over cigarettes. You walk from Plaza Uncibay to Plaza de la Constitución, then to Plaza de la Merced to gawk at the Picasso statue and wonder what parts of this city followed him into every strange and beautiful thing he painted.

From there, you can pass the Roman Theatre, climb toward the Alcazaba, or wander without any plan at all until the narrow streets release you in front of the cathedral. You can pop into the Picasso Museum on your way to ice cream or pint near the park. Málaga always seems to reward indecision, which is what travel is made for, in my opinion. Walk long enough in almost any direction and you’ll find another plaza, another crooked alley, another table where someone has ordered a bottle of wine at an hour Americans would consider irresponsible.

By afternoon, the city spills toward the Mediterranean, and you do your best to oblige it by heading to La Malagueta Beach. You walked there, and within minutes you’re baking in the sun beside topless Spanish princesses gossiping in the sand, a Moroccan family wading into the water fully dressed, and hippies near the taxi stand juggling and playing flamenco while joints are passed around. You eat fried boquerones with lemon, drink something cold, and watch bodies darken beneath a sun that seems to never set.

It’s now 10 p.m. and it’s still just barely light out, but you’re hungry again. You walk back toward the plazas in wet shorts and flip-flops, your feet still covered in sand. You find a place where they carve legs of acorn-fed jamón into paper-thin slices of salty meat. You indulge, chasing it with cheap potatoes on a toothpick and three-euro glasses of red wine.

Everyone around you is stunning. Everyone is looking up, not down, being loud, taking pictures, snapshotting memories into their minds that will serve them in the future when they feel the grays of life return. Not here though. Here everyone seems to be glowing and genuinely enjoying themselves so much, no grays could survive it. You can feel the tension leaving the tourists and the confident calmness of the locals who know they live somewhere special and still cherish it.

By the time you’re done with dinner, it’s nearly midnight. The bars, cafes, and restaurants are all still open. Crowds spill into the streets to wander, then disappear back into darkened dens filled with music and sweet vermut poured from barrels. The streets smell like kebab oil, tobacco, and beer. Teenagers huddle around Baroque statues, sneaking vices from their parents. Men stand outside nightclubs trying to lure tourists inside. Your door is unlocked when you get home, and you don’t even notice before falling asleep with the windows open again.

A city that asks nothing of you

The strange thing about Málaga is that nothing monumental ever happened to me there. I didn’t fall in love, change careers, have a spiritual awakening, or make some reckless decision that became a better story years later. I spent a summer there with my Mom, then returned near Christmas with both her and my Dad. I ate well. I walked everywhere. I slept with the windows open. For a few weeks, I was completely satisfied with the life directly in front of me. The city felt calm without ever feeling dull. It was rich in art and culture without having turned either into another thing to package and sell to tourists.

I’ve been to cities with more to see, more to do, and far more reasons to brag about having visited. But Málaga is still my favorite. I think it’s because I liked how I saw myself there, even during a period when that version of me was drinking. I wasn’t rushing toward the next thing or worrying that I was wasting time or money. Maybe that’s all a favorite place can be. Somewhere you remember being happy without having to work so hard at it. I last visited Málaga years ago, but some part of me has been resonating with the magic of this city ever since.

Remember how they looked at you, with hope for a new life.
They saw the world as something new, the first time through their eyes.

Remember how they spoke, and how they said to not perform,
to speak straight from your heart, without pretending for the show.

Remember how they stayed, then stayed again,
each time you asked them not to go.

Remember how their face lit up
when they unwrapped that last gift.

Remember how they cried when life became too much,
when they felt they had nothing left to give.

Remember how they smiled so big when their favorite song was played,
on the ugly dive bar jukebox as you welcomed the next day.

Remember how they ran to you, from train to bus to train,
to make it to your birthday before they went insane.

Remember how the kitchen smelled when they made their mother’s food,
how flour clung to busy hands while pride lit up their mood.

Remember how they built a book
with pictures of your life.

Remember how they woke up early
so you wouldn’t miss your flight.

Remember all the beauty that you saw behind their eyes,
so deep and present and beautiful, words could never capture or disguise.

And when your mind returns to all the things you think you’ll never know,
Remember how they looked at you, and let all the rest go.

In a world that seems to be actively trying to isolate us more, going out to dinner feels like it’s become a lost art; a chore that many people reserve only for special occasions or keeping a relationship alive. Delivery apps dominate the food sales at restaurants that used to be full. Bars struggle to pull in young people looking to get laid and make friends like they have for centuries. Sharing a meal with family and friends is now an exception to the status quo and not the standard for most Americans.

We spend more money on food than ever before, yet less time eating with others. More broadly, we spend less time together in person across nearly every aspect of life, not just around the dinner table. The result is a society that feels more lonely, more detached, and more anxious. Our “third spaces” have become digital, like most of our life in the modern world. Escapism happens at dinnertime in front of a screen, often alone, and often detached from truly connected conversation if with others.

This isn’t an absolute take, but more of an observation of a shift in societal norms. Plenty of people still go out to eat with others, or dine with others at home. It just feels like it’s slipping out of our routines more and more, and I think it’s affecting how we treat each other. There are few things in life I enjoy more than dining with other people, even strangers. It’s the anchor by which I measure my own social battery, a tool that allows me to actively listen while also expressing myself. And, of course, it’s all done over the the very thing that keeps us alive as humans: eating.

The case for dining out more

If you can afford to order food from a restaurant delivered to you, you can afford to dine out. I understand that the cost of living is high and restaurants are exceedingly expensive, but I think that’s also a convenient excuse for people who just don’t want to risk an awkward conversation, or being in a public space when they don’t have to. Another big barrier to dining out, I believe, is having someone to dine with.

But dining alone is not the lonely experience people assume it will be. Sit at the bar, talk to the bartender, ask the person beside you what they ordered. Some conversations will go nowhere, but others may become the most interesting part of your week. Even if you speak to no one, you’ve still placed yourself among other people instead of retreating into another night at home. You may also meet people who become lifelong friends. You just won’t know until you get out there and do it.

And when you do have someone to invite, invite them. Stop waiting for a birthday, a date, or some other occasion worthy of leaving the house. Dinner can be the occasion. We all need to eat anyway. We may as well use that time to look someone in the eyes, hear what’s happening in their life, and remember that we were never meant to experience everything alone or on a screen. Pick up the tab as often as possible to limit the excuses for them to say “no”, and always get desert after.

If you go out to eat with people enough, any people, you will naturally bond with them. Those bonds are much more meaningful than we may be able to see in the moment, but further down the line in life they become priceless memories or even points of emotional clarity. Some of my best memories of my favorite people, including my family, are from dining out together. I can hardly remember the food itself, but I remember the people, the convos, the idiosyncratic gestures and eye-locked moments of verbal silence as you communicate without words.

Learn how to cook, and cook for others as much as possible

Dining with others doesn’t, and shouldn’t have to be exclusively a going out type of event. Some of the best dinners can be had at home, especially if you know how to cook. I thought I knew how to cook until I moved to Rome and lived with Annie Shapero, from “CoMo” Missouri. I was 24, Annie was in her late 20s and just lost her father about a year prior to us meeting. I found her room rental ad on Craigslist and moved into a spare room in her tiny 2-bedroom flat in the Prati neighborhood, just north of the Vatican.

Annie was living her eat, pray, love moment to grieve her father. She inherited some money and decided to take a few years off work and live in Rome to study cooking and write. Upon seeing my freshly removed from Boston college kid cooking skills, she had to intervene and show me a better way. That’s when I learned how to “cook like a Roman”. According to Annie, Romans cook more versatile than other Italians, which other Italians would scoff at, but it does hold some truth.

Everything starts with the olive oil. No matter how broke you are, always buy the best you can find. Source all your ingredients the day of or as close to the day of cooking as possible. Never use more than 4-5 ingredients per dish. Learn how to boil, salt, and time pasta water flawlessly. Have patience. Flavor your oil with garlic, always. Don’t make any sauce (meat, fish, pasta, veg) too soupy or too thick. Serve everything with bread, good wine, and make it snow with parmesan cheese whenever possible, like a good Roman.

Cooking for others then became a love language of mine. I do it weekly for my Mom. I do it for anyone willing to spend time with me at home or even at their homes. Cooking for others is a core part of being human and has been since the existence of humans. What was once a survival gesture has evolved into a gesture of care in the era of (mostly) abundance in the modern world. It’s cost effective, takes time, requires trust, and is by definition intimate. Give me $40 and an Italian market, and I will give you a dinner that rivals Carbone (not joking).

The best excuse to connect with friends, lovers, colleagues, and strangers

Ultimately, eating together is one of the best excuses we have to connect with people we might otherwise keep at a distance. Strangers become friends. Friends become family after enough dinners around the same table. Attraction becomes love somewhere between the first shared appetizer and the tenth time when you already know what the other person is going to order. Even anger can soften into reconciliation when two people sit across from each other long enough to remember the human being behind whatever went wrong.

That is what a screen can never fully replicate. A text can be misread. A photograph can be filtered. A social media profile can make someone seem happier, colder, richer, crueler, or more complete than they really are. But it is much harder to reduce someone to an idea when they are sitting directly in front of you, breaking bread, laughing with their mouth full, telling a story badly, or reaching across the table to let you try what they ordered.

So invite the friend you haven’t seen in months. Call the person you miss. Cook for your mother. Take someone you love to the restaurant you keep saving for a special occasion. Sit at the bar alone and say hello to the stranger beside you. The food may be unforgettable, or it may be completely average. Either way, years from now, you probably won’t remember what you ate. You’ll remember who was sitting across from you, and how being together made both of you feel a little less alone.

Nothing stings quite like asking yourself “what if?” after procrastination has made a decision for you. It’s a natural question, but at best it’s painful and at worst debilitating. How do I know? Lately, I’ve been the “what if?” guy more than I’d like to admit. Hesitation has never protected me from pain or improved the outcome of anything I genuinely wanted. It’s also not my style. It never has been.

I’d love to say that I’m a “do it” kind of guy in all aspects of life, but the truth is I’m not. At least not as much anymore. When I was younger, I would do almost anything regardless of the risk or danger, like many other young men. I loved the rush of spontaneity, the thrill of seeking discomfort to find a hidden joy, and the relief of never having to wonder what might have happened if I hadn’t tried.

At some point, this way of thinking broke down in me. I could analyze and pinpoint where and when, but that’s probably best for a therapist, not my readers. The important realization is that I started hesitating before doing things, and the results ranged from disappointing to devastating. When you overthink, over-plan and overanalyze things, you often stall them. The problem is that these “things” don’t wait for you.

Book the trip, quit your job, tell that girl or guy you like them, and accept the results

Being bold, taking a risk, or “doing something” doesn’t guarantee success. Often, you’ll get a result you don’t like. But taking action at least creates the possibility of getting what you want, or something close to it. Inaction makes the decision for you. And honestly, taking action is the best way to discover what you like, what you don’t like, and what you can tolerate. My life was nothing but “do” for a decade and a half, and despite many mistakes and close calls, it shaped my character and much of what I love and appreciate about myself as a person.

I’m still a risk taker in many aspects of life, so don’t get it twisted. It’s just less dangerous these days. Over the past few years, I’ve invited multiple women to Paris for dinner (they declined) and one to Croatia (“maybe,” then declined) without a plan for what I’d do if they said yes. I told an office job I’d only work fully remote and for 30% more money than they offered (they agreed), while I was in debt, living in Italy and had no other job prospects. I texted an NBA player and told him he was a cunt for cheating on my friend (he replied with a sad emoji). I tried walking into Bosnia from a Serbian border town while having COVID in winter (the border guards said “бр”).

But something happened to me after I turned 40 that seeped in more and more over the past five years and finally reached its peak: I overestimated risk. I started waiting too long to ask difficult questions because I wasn’t ready for the answers. I began to shut down rather than push through tough moments like the death of a friend or my Dad. I felt lied to by someone close to me and walked away instead of trying to work it out. I let anger take the wheel. I let it seep into my life and steer. Not courage, not hope, not acceptance, but ANGER. This is where life falls off the rails for all of us if we let it.

Fear is a motherfucker. That’s what most risk aversion is rooted in. It isn’t always a survival protocol, but rather a barrier to reality. Rejection hurts, but self-rejection through avoidance hurts much more. Death and loss are painful, but they become even more painful when you haven’t closed the emotional wounds you’ve been running from. Staying in a relationship that’s long dead, a career going nowhere, or a physical and mental state you don’t like isn’t noble. It’s a form of cowardice masked as self-care that, in truth, is closer to self-punishment.

The older I get, the more I convince myself that I’ve learned enough from my mistakes to create boundaries that will protect me from repeating them. But that’s all bullshit if you still feel the pain of the same mistakes, only with the flimsy caveat of a delayed result. And it’s not just me. I listen to people vent to me daily about partners they want to break up with but stay with, jobs they hate but tolerate, and trips they want to take but never book. Most of the time, it isn’t circumstance keeping them from booking the trip, dumping the d-bag, or finding a new job. It’s fear of discomfort and the unknown.

Get over your fear of vulnerability

Another hurdle in the never-ending rat race of getting shit done is the delicate nature of vulnerability. Vulnerability is a strength, not a weakness, but only if you’re brave enough to accept yourself as vulnerable. When you open this soft side of yourself to the world, the world often responds with cruelty instead of kindness. That’s the toughest part: pushing through that cruelty without an instant reward and having enough faith in yourself to accept your flaws so they cannot be weaponized against you.

I don’t respect people who hide their vulnerabilities anymore. I was one of them for many years, so I get it, but I don’t respect it now as a 44-year-old man. Vulnerability is strongly tied to accountability, and if neither is part of how you interact with others, I want nothing to do with you. The people I crave being around are the ones who admit their flaws, weaknesses, and fears. They don’t allow themselves to be defined by those things, but instead define themselves despite them.

Accountability is contagious, and that’s where courage becomes something larger than ourselves. When we acknowledge our mistakes and the damage they caused without retreating into self-hatred or blaming everyone else, we make it safer for others to do the same, and they often do. Stoicism has value in the face of adversity, but it becomes a mirage when we use it to avoid emotional pain or pretend not to care when caring is required. To become whole, we need the self-awareness to recognize which moments call for stoicism, which demand vulnerability, and the courage to choose accordingly.

It’s less painful to feel failure than to regret never trying

This is probably the hardest lesson I’ve learned since going sober and dropping almost all of the chaotic behaviors and people out of my life: finding the strength to embrace failure again. When you live in chaos, you eat, sleep and shit failure. It loses its sting, its power and its hold on you. When you try to live a life of comfort and peace, however, failure becomes a frightening reminder of what you’re trying to evolve away from.

The few regrets I’ve had over the past two years of chaos-free living are rooted in inaction, not failure. I regret not setting boundaries around destructive behavior, letting pride get in the way of happiness, and allowing fear of rejection to trap me in obsessive indifference until rejection was forced onto me. Maybe acting sooner wouldn’t have changed the outcomes, but I would have faced them directly instead of spending months trapped in avoidance. There is peace in knowing you said what needed to be said while you still had the chance.

I can forgive myself for taking a chance and being wrong. I can survive rejection, embarrassment, failure and the occasional terrible decision. What I struggle to forgive is surrendering the decision to fear and then watching life make it for me. This isn’t an argument for recklessness or detonating your life every time you feel restless. The lesson isn’t to go balls out and leap everywhere without looking. It’s to recognize when looking has become hiding, caution has become procrastination, and the consequences of doing nothing have become greater than the risk of trying.

So this is the promise I’m making to myself now: when something truly matters, I will act like it matters. I will say the uncomfortable thing, make the appointment, book the trip, set the boundary, ask the question, and accept whatever answer comes back. I will think carefully, but I will not think myself into paralysis. Failure leaves a bruise, but inaction leaves a vacancy that your imagination will spend years trying to fill. I would rather live with the bruise of an honest attempt than the permanent ache of a life I kept postponing.

Get up. Do the thing. Accept the result. Then move on to the next one.

If you care about someone, take them on a trip to Sicily. I’ve found that one of the most misunderstood places on earth is the large, somewhat mysterious island that sits at the bottom of Italy. To the Sicilians, it’s somewhat better that way, and they’ll remind you of that whether at home or abroad. The island is a cornerstone for Italian immigrant culture throughout North America, yet the culture itself largely evades the modern ethos of what it means to be Italian. This is, for lack of a more nuanced explanation, because Sicilians aren’t really Italian. They’re Sicilian, and they’re fiercely proud of it.

That fierce independence has preserved a place whose beauty speaks to you in subtle tones, while also screaming at you profusely. It’s imperfect and remarkably untouched. It lacks the manicured experiences of Positano, or central Rome, or the Amalfi Coast. Its charms emerge from the crumbling facades, chaotic cities, sun-scorched landscapes, ancient traditions and people who welcome you as though hospitality were a matter of personal honor.

Sicily is beautiful not in spite of its flaws, but because of them. Perhaps that’s the biggest appeal, and most convincing argument to bring someone you love there. Much like the people we love most, the destination itself becomes more captivating through its contradictions, its scars, and the parts it has never tried to perfect. It has abundance without opulence, charm without an agenda, culture without curation, and warmth without pretense or the perceived obligation that authenticity comes with a heavy price tag.

Catania doesn’t care if you think it’s beautiful, and that’s why it is

Like most travel decisions I’ve made in my adult life, I picked Catania based on a mix of advice, curiosity, and random obsession. I was sitting on my couch binge-watching The White Lotus with way too many Air France miles in my account and a somewhat naive confidence about my shaky but well-paying job with a luxury travel company. I hit up Irish Dave from the Rome days and asked where I should stay for around 5 weeks. He told me to skip Taormina, where The White Lotus is set, skip Palermo where all the tourists go, and park myself squarely in the center of Catania.

So, I did. I booked a business class ticket with a cheeky stopover in Paris, then rented a room for five weeks in a 100-year-old apartment in San Berillo, Catania’s former drug and red-light district. The neighborhood had since become home to hundreds of murals, eccentric bars, immigrant-run shops and artists who seemed determined to turn every crumbling wall into a declaration of survival. Cliche? Maybe, but worth a shot. It looked grey and gritty, yet oddly beautiful and just dangerous enough to make me wonder whether I had made a terrible mistake. I did not.

From the moment you arrive in Catania you know this isn’t the version of Italy your friends post about on Instagram. It has the commercial chaos of North Africa with outdoor markets that fill otherwise busy streets so deeply that it makes driving impossible. It’s covered in older, abandoned-looking grey buildings in straight lines down grey, moto-heavy streets. It’s got colorful art penetrating the grey in some places, and bulbous string lights lipsticking the broken facades in others.

There’s a rawness to Catania that experienced travelers crave. Nothing, and I mean even the most touristy parts of this city, is refined for the superficial gaze. That, to me, is as sexy as a city gets. Pour a few thousand years of defiant culture on top of its grey and faded golden streets, food so fresh it makes you question what you’ve been eating your entire life, and a smoking volcano looming over everything like a temperamental god, and you have a city that feels dangerous, ancient and completely alive.

Ragusa Ibla is the most romantic city I’ve ever been to in my life

The idea of bringing someone you love to Sicily is not a new one. The summer crowds in Taormina come off the cruise ships in pairs, searching for their high-priced, priceless moment for photo keepsakes. You can hear couples fighting to save the dead relationship in Siracusa as their gelato melts under the Aperol-soaked breath of people who somehow find time to be angry against the backdrop of a 2,000-year-old city glowing gold beside the Ionian Sea. Most of Sicily may be romantic, but it is not a miracle worker.

Ragusa Ibla, however, may be the exception. Sat atop a jagged cliff, surrounded by other jagged cliffs and valleys carved deep into the Sicilian countryside, the town appears less constructed than conjured. Honey-colored Baroque buildings tumble toward quiet piazzas, church domes rise above crooked rooftops, and narrow stone stairways lead everywhere and nowhere at once. At dusk, the limestone turns gold, restaurant tables spill into the streets and the entire town seems to lower its voice. If Sicily cannot save a dying love, Ragusa Ibla might at least make you remember why you fell in love in the first place.

The pace is slow because the pace is steep, which forces you to leave comfort in every step, while juxtaposed with the presence of immense beauty and history built to keep the bad guys out and the good guys in. Ragusa Ibla is romantic because it mimics the best type of human stimulation: authentic, strong, soft in parts, jagged in others, with new things to be uncovered at every turn, but only if you’re brave enough to seek them. I’ve been to Paris when the flowers bloom in spring, and it can’t compare to a 110 degree afternoon that turns into wine and 3-hour pasta dinners in this small cliffside enclave in Sicily.

You’ve never had Sicilian food before, even though you think you have

Ever had horse meatballs? How about ice cream for breakfast? Perhaps I’m an asshole or maybe just a jaded traveler, but I get a particular joy out of visiting places with food that intimidates outsiders. Sicily is one of the few places in Europe that can pull this off. What you think of as Sicilian pizza is called foccacia in Sicily. Your friend’s grandma in New York has been making you American food inspired by Italian ingredients and calling it Sicilian because it’s what her grandma told her. But in Sicily itself, you can throw out all of what you think about Sicilian cuisine.

Due to generations of poverty, conquest and neglect, Sicilians became masters at making very little taste like everything. Stale bread became poor man’s cheese. Eggplant was fried, sweetened and soured until meat felt unnecessary. Sicilian cuisine was created to keep people alive, then perfected by generations who refused to let survival taste like suffering. Every civilization that occupied the island left something behind. Arabs brought citrus, rice and spices. The Spanish brought tomatoes and chocolate.

In Catania, eat pasta alla Norma, grab a cartocciata from a bakery and have granita with brioche for breakfast. If you’re brave, follow the smoke into the streets for horse meat grilled over an open flame. The seafood on the island is the main star of the show, and can win you over at both a novice and expert level of how slimy and tentacally you feel comfortable with creatures from the deep. The fruits and veggies are the most underrated part of Sicilian cuisine, with some of the world’s best pistachios coating everything from pasta to sweet treats to finish things off.

I went to Sicily alone, which I highly recommend too, if you can’t bring someone you love. It’s also a great place for solo travel because Sicily gives you very little room to remain detached. It’s too loud, too beautiful, too frustrating and too generous. You may fight. You’ll definitely sweat. But you’ll also eat three-hour dinners, get drunk on the smell of pistachios and the sea, and see the person beside you against a backdrop that makes ordinary life feel very far away. Take someone you love to Sicily. If you still love each other when you leave, you’ll probably love each other for a long time.

I am an unapologetic romantic. I can sugarcoat that definition into something more complex or dip it in cynicism to sound mysterious and masculine, but I can’t escape the truth. I love dinners, flowers, giving gifts, dressing up for shows and events, and spending weeks or months getting to know a woman as emotionally intimately as she’ll allow. For me, romance is not always connected to sex or physical intimacy, but rather emotions, which may sometimes be problematic, but it’s simply how I am.

One of the most romantic evenings I’ve ever experienced was not with a lover, a girlfriend, or someone I knew before. It was brief and unconventional, but it still resonates with me today. On my third night in Stockholm, Sweden in 2022 I wandered into a pub in Gamla Stan (the old city) and sat beside three people speaking English. After listening to a loud American rant about crypto to his disinterested girlfriend, I turned toward the third person, a visibly bored European woman somewhat disengaged from the conversation entirely but politely participating.

I decided to break the ice and talk to her. Within 30 seconds, I was hooked. Martina was a 29-year-old tour guide from Cagliari, Sardegna (Italy), taking a break from life as a classical orchestra violinist. She had straight brown hair, brown eyes, a petite build, and a toothy smile that seemed to accompany every laugh and reaction. She was quintessentially Italian, beautiful, multilingual, and an artist.

If you capture my attention with your thoughts, you capture me…

Language and cultural exchange is the fastest way to get me engaged in conversation, and often how I break the ice with new people when I travel. I’m fluent in English and Spanish, and speak the other romance languages conversationally, with Italian being my strongest outside of fluency. I spoke to her in Italian to capture her attention, and then we moved into Spanish, Portuguese, French, and English. She tried to teach me some Swedish words, and before long the conversation had turned into one about the arts, the architecture of Stockholm, and the nuances of our favorite things to cook and eat in Italy.

When I’m in this zone with women, the rest of my world goes blank. I didn’t notice the others leave the bar, I didn’t notice the time, nor the bill, nor the cigarettes. I didn’t remember where I was or why. Drink, joke, laughter, eye contact, cigarette, story, eye contact, joke, question, light hand touch, cigarette, drink, repeat. Never look at the phone. Never lose eye contact. Never stop expressing. It was just her and I, spinning around words and gestures, staring at the steepled churches of Gamla Stan in September.

Four hours had passed in the pub and they did last call. We looked up at the brightened lights like an intrusion, an affront to our convo, a painful reminder of reality. But we weren’t done yet, even though she worked the next morning and I had to catch a train to Gothenburg. She told me she lived outside of the city and was going to stay with another Italian friend, Annalisa, and didn’t want to keep her up too late. I pleaded with her to give me two more hours of her time. She agreed, but only if Annalisa was OK to come meet us. She did.

The three of us met up at the metal bar and got a table in the basement by the stage. The bands had left for the night and instead of metal they blasted ABBA and sold beer in Viking-sized glasses. We spoke in mostly Italian to accommodate Annalisa who smirked and moved her eyes when Martina and I flirted. Then the hammer dropped. Martina told me she has a home in Germany. I asked who was staying there while she was in Sweden, and she said “my husband”. Silence. That’s all I could muster before making a somewhat flippant, polite “oh, wow, you’re married?” comment to break the tension.

You don’t make the rules, but you have to accept them

There always seems to be a catch when it comes to me and romance. There’s always a foil, a thorn, an unmentioned detail that derails everything. And maybe that’s why I chase it so much. I’m trying to outwit reality, to out-romance the barriers and boundaries, and it seldom works. This one felt particularly unexpected. Was I misreading the vibe that much? Why not mention this five hours earlier? Was she separated? Is this an open relationship? Was she seeking attention and validation from others where it lacked in her own life? I had no idea, but I had to ask politely.

“Oh, so are you separated while you live in Sweden?” I asked. “No, but we got on each others’ nerves during COVID, so some time apart has felt good, but I miss him.” I accepted that, and though disappointed, kept the conversation going until it was time to part ways. I’d only invested an evening into this stranger, so it was no big deal. There was no heartache, no hurt, no anger, but just a calm acceptance that for whatever reason, these feelings were just a moment to be had by both of us.

I also accepted that the romantic side of this entire encounter could have just been my interpretation, not hers. She flirted, sure, but people flirt when they’re out, people engage. She may have been interested in me in a way that’s totally disconnected from any deeper romantic desire or attraction. I’m not that arrogant to think otherwise. However, I can’t ignore my own feelings, and whether I misread her or not, I know what I felt. This was a pleasant, lightly emotional, deeply intellectual connection and it felt amazing to me.

Then, it was time to say goodbye…

Annalisa said goodbye first with a hug and a double cheek kiss (Italian) in the dimly lit corridor outside of the centuries-old Swedish tavern. She then walked towards the street corner to wait for her friend. Martina approached for the same, but stopped short, inches away from me, before leaning in. She stood there in the cold air, cheeks reddening, eyes open widely, and we looked at each other without a sound or movement for what seemed like a year but was most likely just seconds.

I broke the silence with one last shot. I fired off a hail Mary, you only live once, risk it all type invitation: “Come to Gothenburg with me tomorrow.” She laughed: “You know I can’t.” Of course I knew. I always know. But it never stops me. She then leaned in, put her finger across my lips vertically, and kissed her finger in a way that was so dangerously close to breaking her rules that I could feel the warmth of her breath cut right into mine through the chill Swedish autumn air.

She then said four words that stuck into me like a beautiful dagger: “In another life, Andy”. We smiled, she winked at me, and then she walked away as I froze there staring at two giggling drunk Italian women vanish into the dark, glancing back twice, then gone. I stood alone outside the bar for another five minutes or so, smiling to an audience of no one at the story this evening had given me. I didn’t look at it as a failure, but rather a lesson in attraction, self-awareness, human engagement, and acceptance. It was almost satirical in nature, but still felt good.

That, ultimately, is why I remain an unapologetic romantic. Romance is not always about “getting” the woman, crossing the line into sexual intimacy, or turning a moment into something permanent. Sometimes it is simply the willingness to be completely alive with another person while the world disappears around you. Martina was never going to be the love of my life, but for six hours in Stockholm, she reminded me why I keep risking the awkwardness, the disappointment, and the inevitable return to reality.

Reality was that “another life” never came for us. This one did. And for one cold September night, beneath the steeples of Gamla Stan, it gave us everything it could.

Hey, mate. Missed your death day tribute this year, and though I’d love to say it was deliberate as some sort of ode to your perpetual lateness and missing big events, it wasn’t. The truth is, it’s been a pretty tough ride since your last death day tribute, and it totally slipped my mind. Anyway, enough of the groveling. Here’s a bit of a life update.

The Bucks traded Giannis to Miami, which is probably tempting you to return to life just to protest, but I think it’s cool. I still live in Miami (Beach), and believe it or not, my Mom lives here now too. My Dad died last November somewhat unexpectedly, and though I thought I was prepared for it, it hit me much harder than I was willing to admit. But I’ll get back to that later.

Booze, drugs, and self-destruction are fading memories at this point

I still talk about you all the time in a sort of canonical form when dissecting the madness of humans, eccentricity of artists, and pain of addictions. Speaking of addictions, I’m in year two of sobriety and have no plans on stopping. It’s been an uphill battle to undo a lot of the deep psychological and physical damage that substance reliance did to me, but it’s worth it, and it’s hopefully inspiring to others, although I try to keep from proselytizing or brow beating it into others.

It’s wild to think that at age 44 I’ve lost about two dozen friends and acquaintances to alcohol and drug abuse. There’s a guilt I carry because of that, and I still feel angry that addictions both ruined your life, and then took it. I still talk to some friends from the BA days but none of the old Kilca crew. Guido sold the hostel a while ago, Daniela unfollowed me on social media, but I often wonder how Dan the Man and Joe the performative guitar hipster are doing.

Yes, the country’s still a mess, but I love being back here

I’d like to think that if you had come back to Wisconsin to get help and build a stable life it would have saved you, but that’s no guarantee and parsing through past hypotheticals is a fool’s errand. Needless to say, I love being back in the United States, or at least adjacent to the United States in the wild world of Miami Beach. My career is on a good path here. I’m no longer running from Argentine drug dealers or Panamanian police, or violent girlfriends.

I can’t bring myself to go visit your grave site in Guatemala, mostly because I resent the enablers in Antigua, and the arrogant and pathetic ideologues who call themselves “expats” instead of immigrants and poison themselves while holding local economies hostage with their foreign spending power and cultural ignorance. I’m a bit angry at myself for running from reality for so many years, so a bit of that resentment is rooted in my own past in Latin America. Hope you understand.

Politics are as batshit crazy as always in the US. Trump is senile and his movement has lost the plot even more than it had when you were alive. I tapped out of caring at this point though, because I think the obsession over politics and the culture war is pointless, faux catharsis, and mentally unhealthy. It’s become our most popular sport when the NFL isn’t playing, and I think it’s a distraction from the existential crisis we all have about losing our own humanity, but I’ll leave it at that.

I’m connecting positively with people and places again, and it feels great

I’m not going to sugar coat it, mate, I’ve had a pretty rough year mentally. I went into action mode after my father died to take care of my Mom and help move our family in the right direction, and tried to postpone grief to soften the blow. The result was about six months of stale, apathetic living, highlighted by small glimpses of light through good friendships and growing emotionally closer to a woman I thought and think the world of.

Needless to say, those glimpses of light were more ephemeral than real, and the external validations never came, so reality had to return at some point. These were ultimately distractions that my mind created to soften the blow. At some point I had to face the reality of grief without feeding myself distractions from it. It’s funny because when you’re a drinker like us, you learn how to use booze, and all the excessive dopamine-driving things that come with heavy drinking to fill the pain gaps. When you’re sober, your subconscious reaches for other things in the same way, but it’s hard to spot.

For me it was the impending move of my Mom, new projects in AI to jump the line in my career, and the illusion (delusion) of feeling wanted or chosen, and a subconscious need for external validation. But none of that was a tangible fix to the pain of grief. So, when it all fell apart at once, my grief came back like a sledgehammer and nearly took me out. I think I needed it though. I didn’t stay on the ground for long, mate. I got up, I made a plan to see the places and people I needed to, and I took a 4-week trip by land throughout the entire eastern US.

I got out of the part of my head that runs from difficult things and instead ran towards them. I visited my father’s boy’s school (orphanage) in Philadelphia and broke bread with musicians in Savannah. I walked the streets of Georgetown in DC where he once lived. I spent the weekend with a friend in New York and went to my old schools and our old buildings and Central Park in the summer sun. I hung out at Harvard, and then helped my Mom move from Massachusetts to here. It was great, it was real, and it changed me.

You can’t always get what you want

I still talk about you all the time with friends, most of whom never even met you. I think your story is ultimately a tragedy, but that shouldn’t and doesn’t impede on the brilliance of how you thought and how you impacted people in such a good way. Life is a beautiful torture in that sense. We go through experiences, phases, people, and places that leave indelible marks on our soul in both good and bad ways, and that’s what gives us character. It’s what makes us human.

In a perfect world all of my friends would still be alive. My Dad would live forever, as would my Mom, and my brother, and my cats, and me. All the women I cared about over the years would care about me back. I’d be a millionaire writing my 7th book in the South of France arguing with my friend Brendan about sports and gut laughing over our latest foibles with eccentric women, while threatening the muppets who pissed us off at the local pub.

Life, however, doesn’t work that way, and that’s why life is so beautiful. You can’t value things fully unless you understand the pain of their absence. This is the real core of life and I’m learning to not only accept it, but love it. People come and go, we all die, and we’re all shaped by the hard moments in between. It’s been six years and a few weeks since you were found dead, slumped over a toilet in Antigua, Guatemala. I’ve lost five more friends and a father to death since that day, two of whom you knew.

I’m choosing to live in a way that keeps me sane, alive, and prosperous for many years to come. But I’m also aware that life and death comes through in violent, painful ways at will sometimes, and I’m prepared for whatever happens. Just know that your mark on me, your family, and your many friends all over the world is still shining through us. So, mate, as the cliche goes, you only truly die when people stop talking about you, and as long as I’m alive, that day will never come.

Your Friend,

Andy.

There are no facades in Philadelphia. No veneers to cover up its flaws. No pretense of garish power like some major cities, or sexy and modern opulence like others, or the curated culture and snobbery that historic cities often project. Philly is real. It’s the realest city I’ve ever been to in the United States, and one of its friendliest. The neighborhoods to the North, South, and West are covered in low-rise row houses. Stoops jut out like concrete tongues onto the sidewalk and people move briskly from home to bodega, bodega to bus, or park, or another stoop.

The city center looks like New York and Boston had a baby. There are gleaming glass towers housing mega corporations, and stone and brick buildings that have watched centuries unfold, starting from the founding fathers of the United States and the colonies before that. Office workers stream past churches older than the country, corner delis share blocks with Revolutionary landmarks, and murals explode across walls that have seen generations come and go. Nothing feels polished for tourists. It feels lived in. Worn. Honest. Philadelphia doesn't seem interested in convincing you it's great. It simply is, and somehow that quiet confidence makes it all the more compelling.

I was raised to dismiss Philadelphia, and that was a mistake.

I spent half my childhood just 90 minutes from Philadelphia in NYC, and the other half just 90 minutes farther. I visited the city once before last week. My Dad was born in the Philly suburbs, then moved to Philly against his will at age 7, finally leaving after college at age 22. He was put in a school for orphaned and fatherless boys in 1940, went to The Wharton School at Penn after that, and when he left, he never looked back.

He took our family there once in 1990, but I remember none of it. For me, this trip was a fresh look at a city I’d subconsciously hated and feared for no reason, other than generational “trauma”. When we’d ask Dad about his childhood he’d fire off a line or two about getting bullied in an orphanage then change the subject. If we asked what the city was like he’d talk about Penn, and Pat’s cheesesteaks, and then look away or change the subject again.

In his later life I begged him to come on a trip with me to re-visit his hometown, and rather than a “no” he’d simply say “not right now, Andy” and move on. I never had a reason to visit the city by myself. Never had any work there, or event I wanted to go to, or friends I wanted to see there. For all intents and purposes, it was just a poorer, smaller, tougher New York in my mind. A place that gave my Dad horrors just to think about. A place to be avoided.

Confronting the demons I couldn’t kill in Miami

I had to go to Philadelphia. It wasn’t a choice in my mind anymore, but rather a mandate. A mandate from myself, from my own desire to be happy again. The pressures of grieving my Dad’s death weighed heavy on me all year. The greyness of life during grief left me feeling without purpose, without hope. It left me in a state of numbness after the initial pain. And that numbness cascaded into near madness.

My mind raced for months through “what ifs” to try and feel good again but none of them worked. My career felt boring and stagnant. My urge to be social fell off. My fitness journey stalled. My will to keep living a “normal” human life was propped up by helping my Mom with her widowed move to Miami, writing, planning elaborate trips, and projecting emotional intimacy on people who never shared those feelings back. Everything from November to May in my life was a projection, both good and bad…until it all crashed in succession.

Then, as reality returned into vision, I saw the path closing out this grief, this grey, this need for love and validation from people or places or things I project it on. I decided to do the heavy lifting that my Dad never got to do. I decided to end his torment with this boys home, this school, this city I was told was not worth visiting. I decided to go to Philly and embrace whatever it was that I would find there. To forgive the school, the home, and his Mom for putting him in there. Through this I wanted to find my own peace again too. My own emotional setation that had been eluding me for all of 2026.

What I found was love. What I found was a beautiful city. What I found were people, strangers who went out of their way to be kind. People who embraced this grandson of Philly and allow me to stare these demons straight in the eye, because my father was too hurt to do it himself.

Do yourself a favor, and go to Philadelphia…

As a professional travel writer who’s lived in four countries, visited over 30, and seen every type of city this world has to offer, I can say without hesitation that Philly is one of my favorites. This city is abundant with good vibes that are so authentic it may catch you off guard if you have your spidey senses set for the showiness of Miami or the grandeur of New York or Paris. Philly has so much soul it gushes out of the food halls, basketball courts, and office buildings, and onto your sleeve as you walk.

Philadelphia is ethnically diverse without the visible tension. There are accents and languages everywhere. The city is also noticeably black, with a wide range of dark-skinned American, African, and Caribbean people working at shops, going to school, managing the offices, driving the buses, or hanging out at the parks. You don’t get stared at for being white in Philly, or for being clearly from out of town. You get a “what’s good cuz?” when you walk into a store, or wait next to people at a crosswalk.

People in Philly are friendlier than almost any other city I’ve visited of comparable size and economy. There’s a politeness there that I didn’t expect, even with my emotional, cynical baggage worn on my shoulder coming in. I ate chicken and sausage grinders on the hotel rooftop and talked sports with Ock behind the counter. I got a tour of the world’s most prestigious business school (my Dad’s alma matter) just by asking and telling them my story. I howl laughed with the Uber driver when the models who were in there before me left a box of muffins that we turned into a story about what it must be like to eat carbs at that weight.

The price of a weekend in Philadelphia is about HALF of what it would be in Miami, Chicago, New York, or San Francisco. You never feel ripped off or overwhelmed as a guest. The city is extremely walkable and relatively safe during the day. The historic parts of the city are all clustered into the center, and the outlying neighborhoods are all different yet share the same energy: authentic, run-down, yet charming in a “this is home for someone” type of way.

I stayed in University City and walked the campus where both my Dad and the first girl I fell in love with went to school. It was 70+ years since he left and 20+ since she left, yet I could picture both of them there. From Chestnut to Market St. there was life all over the Ivy League campus, even in summer. Bars and pizza places made way for ramen and dumpling shops, student housing, parks and playgrounds built by the institution to be good neighbors with the West Philly locals.

As I boarded the train to New York, I realized I’d never really come to Philadelphia to understand my father. I’d come to understand that I didn’t have to inherit every wound he carried. Some stories are meant to be remembered. Others are meant to end with us. I left with a deeper appreciation for the man who raised me, but also for the city he couldn’t bear to love again. In forgiving Philadelphia, I think I forgave a small part of myself too.

The hope had come in waves, accompanied by the colors and sounds of things and people and places that were almost there, but not. It arrived without warning, glowing brightly enough to make the distance disappear. For a moment, the future felt close enough to touch. Then the wave would pull back, taking its warmth with it, leaving only the cold uncertainty of waiting for the next one.

The waves moved like fireflies in the dark, burning, drifting, vanishing, then returning somewhere else. He could never predict when they would arrive, only that they always left. But the hope remained. Small, restless, impossible to hold. It lingered long after the waves had gone, demanding a place to live.

So he built a castle to keep it still, to keep it real, to keep it there.

Brick by brick the walls grew, with hope inside, moving from finished room to empty space. The madness of the movement kept him building, day in and day out, so the hope would never escape.

The space between the hope was choking. It glowed in brightness that blinded like the sun, then vanished into dark lines etched onto walls, it whispered, flickered, then returned to silence again. He had to fill the space, he had to fill the silence, he had to keep the hope alive. The castle was built too big to let it go, so he started to build stories to keep it alive.

The stories about the castle started to grow faster than the castle did.

The storyteller built the walls with action, but he painted them with words. Thousands of words and stories, some real, some fantasy. The words kept the hope from moving, from fleeing to another place. But he couldn’t build the castle strong enough to keep up. The walls and words were cracking under the pressure. The castle started to crumble.

Beneath the space between the hope there lived doubt.

The doubt was strong and grew even stronger under the castle’s foundation. It crept through the cracks like weeds and blurred out the words on the painted castle walls. The doubt wasn’t built, it was just there, it was real, immortal. The castle wasn’t. It was built too fast, too big, too brightly painted to notice.

The doubt started to live in the castle built for hope. It painted over the walls of words. It broke and tarnished the thick foundation. It sat in the rooms built for hope, where hope was now gone, fled, and vanished. And one day, in an instant, the castle fell. It fell on hope, it fell on doubt, it fell on him.

He stood in the ruins of castle he built, angry at doubt, and even angrier at hope. How could they both be so cruel? How could they not see the castle he had built, the words on the painted walls? Where would hope live now that it was gone? How would he live without hope? He cursed the castle, the words, the walls, the paint, then himself and the space that lived between them.

But hope doesn’t need a castle to survive, and neither does doubt. The castle had never been built for either of them. It was built for him.

They existed long before the first brick was laid and would remain long after the dust settled. Hope would find another room, another face, another dream. Doubt would find another crack, another silence, another dark corner to call home.

The castle had never been built for neither hope nor doubt. It was built for him.

Built to contain the endless movement between wanting and knowing, between possibility and reality, between the stories he told himself and the truths he was afraid to face. He mistook the castle for safety, and the hope inside it for purpose.

Standing in the ruins, he finally understood what the collapse had revealed, and what the castle never could.

The space between hope was never empty.

It was where hope and doubt had always lived together. Not as enemies, but as companions. Neither trying to conquer the other. Neither demanding more room. They simply existed, side by side, beneath the noise of the walls, the paint, and the stories.

He never needed to build a castle for hope, nor defend it from doubt. He only needed to accept the space between them. The space where fantasy gives way to truth, where silence becomes something to listen to rather than escape, where life unfolds without permission from either hope or fear.

The castle was never the destination. The space beyond it was. And it was there that life had been waiting for him all along.

Somewhere beneath the booze-stained stones on River St. you can feel the screams of the slaves who picked the cotton that was sold there. The grey alleys and harsh brick buildings that press up to the river shores are starkly beautiful, built from the riches of the American south and chattel slavery. Like any old port from colonial times, where there was once trade in cotton, grains, and human beings, there now sit sports bars, candy shops, and souvenir stores. The 18th and 19th Century British architecture frames the river like a lifeline to opulence for some, and terror for others, and you can feel it in Savannah if you’re paying attention.

Beyond the port the city whispers instead of screams. The perfectly symmetric public squares anchor rows of former mansions, some chopped into apartments for multiple families, others left in tact for the wealthy and cultured class of Georgia. The Southern Live Oak trees provide shade from the southern heat, and the city’s greenery is so lush you can hear the hum of bugs louder than you can hear traffic. You can feel the money in this town through centuries, not decades, much like Boston, or in Old Towns across Europe and the Americas.

The charm often outlasts the skepticism in the American South

Like any well-read arrogant New Yorker, I’ve always thought of the South with a tinge of disdain. Some of that is unfair, but a lot of it comes from what we were taught about the region’s history. History, however, cannot define a place in the modern sense. At least not if you’re a traveler. If it did, then you could never go anywhere without inheriting their guilt or sin. Conquests are part of life. Death, slavery, economic disparity, and political upheaval are native to all places in the world.

You can appreciate the gold-lined churches in Mexico while simultaneously acknowledging the torture and murder involved in getting enough to paint an ornate cherub on the ceiling. It’s part of the experience, and Savannah is just an American version of the same complex dichotomy. The beauty of the place is so overwhelming that maybe our brains choose to forget how it was forged. Or maybe we just accept that what it is now is its absolution.

The people in the American South are friendly by default. It’s baked into their culture. There’s a politeness that’s been commodified in tourism and popular culture, but it’s still authentic and resonates immediately. Southerners aren’t dumb, they just talk slower. There are racists here, but there are racists in New York too. The biting arrogance of the Yank is hushed subtly by the Southern charm, rather than exposed by it. This is one of my favorite parts of traveling through here: the manners, kindness, and grace of the people.

Modern Savannah is the best of what America can offer because its adaptive

Savannah has a beautiful modern menagerie of American culture and that’s what draws you in. Black people are everywhere in Georgia. But now instead of being sold they’re selling pizza to tourists, and real estate to retirees. They’re managing Wet Willies on River St. and giving ghost tours in the Victorian District alongside whites, and other races that couldn’t point to the city on a map 50 years ago. The culture here is not opaque but rather brilliantly bright in all of its faces.

The art scene in Savannah is immense thanks to the “Savannah College of Art & Design” (SCAD). There are lots of young people pushing their limits of self discovery through well-funded galleries, hipster coffee shops, multi-unit brick apartment blocks, and dive bars that are far enough away from tourists to be authentic. There are very few murals in Savannah, unlike most modern cities, but you don’t have to look for to find the spoils of self expression from young artists, and I love that.

Nothing here feels accidental, but nothing feels over-curated or over-framed outside of the commercialized cluster of bars and gift shops on River St. Even River St. has its authentic charm if you look deep enough. Packs of drunken middle aged men who look like they just stepped off a golf course collide with bachelorette parties of screaming white women with penis cups, stumbling on cobblestones with flip flops and plastic cups. They don’t sell slaves or cotton here anymore, but they sell distraction, and the deep irony of that has brought a smile to my face more than once.

There are a lot of couples here seeking a romantic setting for their anniversary, their first trip during “new love”, or their last trip trying to save the marriage that was never meant to be. Savannah is a smaller, safer New Orleans where people can drive to and still feel like they’re thousands of miles away. It’s inexpensive compared to Miami, but pricey when compared to the rest of the region. Unlike Miami, however, the money spent seems worth it. The history, whichever history you choose to feel, is felt in every corner of this colonial city.

The parties are loud and spill outside in some quarters. In others the human silence is mesmerizing, with the willowed oaks and bugs whispering back and forth almost symphonically. The food is heavy but good, with authentic Southern cooking and modern pub grub in abundance and fairly priced. The vibe is warm like the thick, humid, Georgia air, and you can walk anywhere, and at almost any time of day or night safely. Savannah is complex, modern, old, detailed, and yet widely open for interpretation. I’d recommend going alone or with your loved one(s). Set no expectations and just let it breathe with you.

In the world of travel, there are some cities that call your attention purely from their own romantic mystique, thrust upon us through popular culture and wherever you’re from village lore. The more these cities get romanticized, the more the cynics and “haters” will talk them down, misdefine them, and put them in a box. No one place represents this dichotomy more than New York City (Paris being a close 2nd). They say you either love it or hate it, but I think there’s way more nuance to it than that explanation allows. Then again, I’m from there. I’m biased.

New York City is an American institution while simultaneously being the country’s most culturally and economically diverse place. Some purists may even say it’s “un-American” because of that. The truth is New York allows you to define it yourself, and that’s its magic. It’s chaotic yet calming, bold yet subtle, sexy and ugly all at once. If you care about someone and give a shit about experiences, take them to New York.

Take them to the place where in any given decade the zeitgeist can call it either a communist hellhole or fascist fortress. Take them to the place where you can spend $1 on a slice of pizza or $90 on a hotel cheeseburger. Take them to where fashion trends start in all-black rugged Robert Moses projects and bleed into Chelsea gay bars and boutiques, five years before they make it to the rest of the world. Take someone you love to New York City because humanity is one sneeze away from becoming extinct, and the robots can’t replicate a summer day in Central Park.

What to do in New York as a tourist who doesn’t want to be a tourist

Don’t overthink this part. Everyone seems to overthink this part, and as a native New Yorker I can tell you with authority that no one cares. Also, I can tell you as a native New Yorker that we like to think of ourselves as authorities on everything, so bare with me fam, and buckle up for some opinions. The first thing you should plot out for your New York experience is finding a place to stay that is not in Times Square. The next thing you should do is take your budget and double it. It’s America, greed is good, and what’s the point if you don’t max out some credit to have fun.

I recommend staying in a hotel on the Upper East Side or Upper West Side if you’re over 40. If you’re young, stay anywhere downtown in and around the Village. The older hotel the better, as these places have so many ghosts in their walls the aura points alone will change your disposition without you even realizing it. Walk or take the subway for most of your trip, and mix in some taxi rides for dinner dates, bar nights, or any events if you attend them. The allure of the subway is a daytime thing, and only if you can get to your destination without a transfer.

Go to some museums. The Met is a must, as is the Guggenheim for art. The Natural History Museum is also a must, and has so much history you can spend most of an afternoon there learning about the world AND the museum itself. As kids we got the privilege of going to these places in after school groups or during class time itself. They are institutions from a bygone era of public-accessible education to create a civilized society, and in the TikTok era are as refreshing as they are culturally relevant and important in the modern age.

Spend a full afternoon in Central Park. Start in the middle by the Reservoir and work your way down to where it meets Midtown Manhattan. Check out the lawns and stop to breath a bit, make out, chat about life at home (wherever you’re from), and whine about the price of everything. Then marvel at Olmsted’s masterpiece as you traverse the megacity tree by tree rather than block by block. As you go south, head to the East Village for boutique shopping, then Chelsea for some gay shit (respectfully) like a cat cafe, queer bookstore, or true real local art gallery.

What to eat in New York with your loved one(s)

By the time you rubbed the brown New York haze out of your eyes on day one, you’ll have already tried the pizza. We get it. Now go for bagels with lox and a schmear. If you hate Jews, visit Cleveland. If you’re not a cunt, go to a Jewish deli anywhere in the city and do it more than once during your trip. Pastrami on anything is my favorite, but don’t be scared to try the other various pastes and pates of fish, blending Russian flavors with Middle Eastern ones, smashed between unique New York carbs.

Go to a nice restaurant too. The names change over the years, but if you follow the Michelin guide you’ll do fine. Don’t penny pinch here. I know it sounds gauche and maybe even tone deaf to say, but this is a “take someone you love” article, and believe me, you’ll never regret splurging on a nice dinner in NYC, even if it’s bad. It’s an experience. Share it. Whatever cuisine or style of dining you like, there’s a nice version of it in New York that will make core memories for you and whoever you love.

Find the most Chinese Chinese place in Chinatown and order a Peking Duck, cold sesame noodles, and as many dumplings as you can handle. There’s only once place in the US with better Chinese food than NYC Chinatown and it’s San Francisco. So, don’t be shy and dive right into whatever level of authenticity you have the balls for in New York. Look for restaurants with cheap square signs and banquet style round table seating. The fewer “Gweilo” a Cantonese slang term used to describe white people or, more broadly, foreigners, the better.

Catch a Broadway show, a basketball game, an exhibition, or a concert

Taking someone you love anywhere should always involve a show type of event. Unlike the corny substanceless trappings of Las Vegas, New York shows are fun, engaging, easy to reach, authentic, and unmistakable. There’s nothing quite like a Knicks game at the Garden, or Les Mis or Lion King or whatever on Broadway. There are lots of local music scenes and venues to, so do a little digging and find something you can’t normally find where you’re from. Dress up a bit too. New Yorkers wear a lot of black, but do you broski. Just remember to skip the shorts and hoodie for the show, and dress up more than you normally would. Thank me later.

Event hopping in New York is somewhat of a lost art due to the price and volume of things, but it’s still possible and you should do it. Go to an early musical in Midtown, then a gallery party in SoHo. Eat at 10PM and then walk to a bar with live music. Push your credit card to the limits because let’s be honest, you could be spending a G in Nashville on BBQ and some horseshit by Post Fucking Malone but you’re not. You’re in Manhattan, and even the worst venue and worst show and worst art is better here. If you have any creative juice inside you, it will rise to the surface in New York City.

Don’t overthink it, just GO!

Travel takes planning, but I find that the more intimidating the destination, the more people overthink the plan and fail to launch. You can handle New York, sweetheart. Millions of people just like you do it everyday. It’s safer and more orderly than your Fox News Dad says it is. It’s more fun than your neighbors who are too scared to go there say it is. It’s everything you’ve imagined while being nothing like you thought it would be. New York City is truly undefinable, and that’s its allure.

Take someone you love to New York City because love exists best when balanced with the noise of the world around it. Love exists best when you show them a world that’s both you and not you at the same time. Travel works best when you go with someone you love. No gimmicks, no forced romanticism, no trying to impress. Take them to New York to have fun, to stay out way too late, to have morning sex to the sound of car horns and people yelling in a language you don’t know but sounds like something near Pakistan.

Take someone you love to New York and live in the moment, every moment. The smells, the noise, the elegance, the stark economic disparities, the wind gusts that use the towers like sails. It’s all part of being alive, of being free from your comfort zone, of re-discovering why you love a world that exists beyond phone and TV screens. A world that has no white picket fences or strip mall Cheesecake Factory. Take yourself to New York because you love yourself too, and the world is moving so fast, you don’t know when you’ll have the chance to do it again.

San Telmo is my favorite neighborhood in Buenos Aires, and it’s not even close. On the southern end of the city, it captures the raw struggle, romance, fallen decadence, and artistic might of the City of Fury in a paradoxically neat and organized 10 x 10 blocks. It’s best known for the Sunday Feria (open air market) that draws tourists and some hip locals out for artisan crafts, greasy sausage sandwiches, and the voyeuristic pleasures of watching street tango and hippies doing acrobatics at crosswalks.

San Telmo isn’t just an artists’ neighborhood, it IS art in and of itself. The murals aren’t curated and commissioned by marketing teams or city improvement budgets. The antique stores hold relics from rich families who lost it all in the 2002 crash, like dark personal histories woven through dusty lamps, hand-carved wooden furniture, and silverware that’s been untouched for decades. Meat is grilled on open flames adjacent to boutique hotels, where the cigarette plumes billow with the laughter of partially-toothed taxi drivers gossiping over fernet.

The charm of preserved authenticity in a world with too much soulless modernism

I have a deep affinity for “Old Town” sections of once-colonized cities. They’re mostly European-influenced, though one could make the argument that the Ottoman and Arabic-influenced Old Towns in Turkey and Andalusia are just as charming. I’ve lived in two of these places. One was in Panama, a UNESCO World Heritage Site called Casco Viejo. The other is San Telmo, the Old Town in Buenos Aires. Both were my favorite neighborhoods in each respective country, and both highly complex.

Modern development champions cost efficiency, technology, and space efficiency over seemingly everything else. Old Town infrastructure does not. That’s its strongest appeal. The Spanish built the cores of their conquered cities to mimic their own. There’s always a central plaza that acts as the beating heart of commerce, leisure, religion, governance, and protest. San Telmo’s central plaza is no exception.

Plaza Dorrego feels less like a tourist attraction and more like a living room for the city’s collective subconscious. Elderly men debate politics and football beneath the trees while tango music drifts through the square and artists sketch quietly at café tables. The architecture itself encourages life to spill outward. Narrow sidewalks, wrought iron balconies, tiled entryways, and aging facades create a kind of forced intimacy that modern cities seem designed to eliminate.

Layer upon layer of Argentine history stacked in a small, semi-rundown neighborhood

The contradictions and layered scars of San Telmo are why it’s so beautiful to me. San Telmo carries the ghost of Argentina’s rise and collapse simultaneously. Once home to Buenos Aires’ aristocracy, the neighborhood changed after yellow fever outbreaks pushed the wealthy north toward Recoleta. The grand homes left behind were subdivided into communal immigrant housing, layering elegance with hardship in a way that still defines the neighborhood today.

That contradiction is what makes San Telmo so complexly appealing and even aesthetically iconic. The chipped paint, cracked marble, rusting balconies, and fading storefronts don’t diminish its charm; they create it. In modern neighborhoods, aesthetics often feel manufactured. In San Telmo, these things feel more earned, more difficult to find through the maze of a mega city. The gringos love it because it feels real. The Argies have a love/hate relationship with it, but the artists among them are addicted to that charm, and in their own way, create it.

It’s no surprise the neighborhood became a refuge for artists, musicians, antique dealers, chefs, and drifters obsessed with self-expression. Restaurants feel personal rather than corporate. Galleries exist beside butcher shops and corner stores. Boutique hotels occupy decaying colonial buildings that still feel haunted by another era. San Telmo resists becoming polished or sanitized. It remains emotional, expressive, imperfect, and deeply alive.

A city within a city that still feels human

I think what I ultimately love about San Telmo is that it still feels human in a world increasingly designed to feel efficient. The neighborhood isn’t optimized. It doesn’t move particularly fast. Things break. Buildings lean a little. Sidewalks crack. Waiters disappear for twenty minutes at a time. Weed smoke billows from the alleys and patios of hostels. Nothing feels streamlined for maximum convenience, and somehow that’s exactly why it works.

There’s a strange dignity in places that don’t erase their imperfections. San Telmo feels comfortable with its own contradictions. Beautiful but rough. Romantic but gritty. European but unmistakably Latin American. You can drink natural wine beneath chandeliers in a crumbling mansion and then walk outside into graffiti, stray dogs, political posters, and the smell of grilled chorizo smoke hanging in the air. None of it clashes. It all belongs.

That’s the part that I think modern cities keep getting wrong. Soul cannot be master planned. You cannot algorithm your way into authenticity. The best neighborhoods in the world usually emerge from struggle, immigration, artistic obsession, economic collapse, resilience, and time. San Telmo has all of it layered into every block.

And maybe that’s why I keep romanticizing it years later. Not because it’s perfect, but because it isn’t. San Telmo feels like a neighborhood that survived something. And in a strange way, so do the people who love it.

Buenos Aires, Argentina has no formidable comparison that I’ve ever seen, and I’ve seen a lot of places up close. It is a truly unique city. There is an energy there that’s overwhelming. There’s this enraging type of beauty that the city and its people exude that can be maddening, euphoric, manic, and addictive, and it never leaves. You could call Buenos Aires the “Paris of the south” or some other lazily coined “New York of….” but neither would be apt descriptions, and anyone who’s spend more than a week there could tell you that. I spent four years there.

The allure of Buenos Aires is fairly simple on its surface, particularly for tourism. It’s exotic, distant, and affordable. It’s in the lower half of South America, but European looking enough to dull the edge of developed world fear of visiting what they’ve always been told was a scary continent. The people are stunningly beautiful, they dine on steak, drink wine ‘til sunrise, and invented the Tango. Buenos Aires is unmistakably seductive, and both the casual tourist and veteran expat would be lying to you if they said that wasn’t part of what drew them there.

Fist impressions can be tricky here

The first thing you notice when you arrive to Buenos Aires is just how massive the city is. There are layers and layers of sprawling suburbs with a few major-trafficked highways cutting right into the north, south, and central hubs of the city. The city itself is dense. It’s packed with brick and concrete towers, many faded and painted white, with every square inch of space used for living or small commerce. In most of urban Buenos Aires, you have people living in small apartments in 10-15 floors above boutique shops, Chinese-run bodegas (Chinos), “kioskos” (smoke shops), and quick food stores.

To be in a city of this size can be overwhelming, even to New Yorkers like me. There is constant noise in the urban centers of Buenos Aires. Their downtown looks like a run-down Hong Kong hawker district. Their posh monied urban neighborhoods reek of mismanaged money with a little upper class decay, but it makes them sexy because of the architecture and the educated class that bring their more open ideas into the subculture. You can feel this on DAY ONE, too. There is movement of pedestrians at all hours, and traffic filled with black and yellow cabs, horribly maintained buses, and Renault and Fiat cars owned by the privileged.

Porteños are much kinder than their reputation

People from Buenos Aires, or “Porteños” as they’re called locally, have a somewhat bad reputation that I think is mostly overblown. The stereotype is arrogant, loud, slick talkers who are racist, womanizers (men), “hysterical” (women), and cheap. Do these people exist in Buenos Aires? Yes. Do you see these traits more than you would in neighboring South American countries? Yes. Are these people the norm or the outliers? They are unequivocally the outliers, and the reputation comes more from the Argie tourists abroad rather than just the Porteños themselves.

Porteños are some of the most generous, kind, and deeply compassionate people I have ever met, and it’s not even close. It takes a lot to live in Buenos Aires. It takes a mental fortitude that forces you to harden yourself to survive. Yet balanced with this, Porteños never lack emotion and passion, and rarely lack empathy, kindness, kinship, and loyalty. I’ve met Porteños at a park and ended up joining an asado (Argie bbq party) at their home within minutes. They love to feed friends and even strangers. They love to tell you vulnerable things about themselves and open up about love and anger and desire and all the shit people in places like Boston are scared to.

The most underrated cultural capitol of the world

Buenos Aires is soaked in culture. The city is overflowing with creative people chasing their art for art’s sake. The music scene is massive, with as many rock shows as New York, a thriving local hip hop scene, a charming foklore music scene, and the beating heart of the world of Tango. You could go to a show of basically any genre or scene of music you want every day of the week. You can see new art exhibits just as often. There is a fashion scene with bold designers and out-of-this-world gorgeous models who take breaks from Milan to come walk on in Palermo and see Mom and Dad.

Because of its size, like any mega city, Buenos Aires has a lot of neighborhood cultural markings. At least when I was there, it wasn’t as gentrified as other cities that size. When you’re in San Telmo, you FEEL San Telmo. You feel the hustle culture of the markets and Sunday Feria. You feel the Spanish Colonial architecture pull at your mind in every restaurant and shop, and all the things they sell. In Palermo you feel like you made it. The hot girls in yoga pants with gay guys and small dog accessories chat up nonsense the makes a buzz over the Plaza Serrano patios mixing with traffic and clinking coffee spoons.

The outer barrios of Buenos Aires are like another planet. They’re developed with massive mid-20th Century housing blocks for the working class. They’re rows of tiny little boxes with lights dominating the street view but not quite tall enough to dominate the sky. Down below it’s South America at its finest. There are old men tailors and butchers who smoke while working and sit outside the shoebox-sized stores to get a break from the heat or to catch up on gossip. There are smoking sausages at street corner cafeterias, tire shops, and young people kicking soccer balls, smoking together, and making out.

Chaos is gorgeous in Buenos Aires

The most undeniable description of Buenos Aires that literally anyone who’s ever been there would attest to is that it’s chaotic. The city moans with noise day and night, both human and machine made. The money feels worthless no matter how much you make, and the government ire causes daily protests and cop clashes. There are constant workers strikes, tear gassed avenues on the way to work, soccer riots, parades, and national holidays.

Dating in Buenos Aires is is chaotic too, as are jobs, friendships, and your own personal sanity. Porteños get used to this, which is what makes them so resilient. Things go wrong all the time, but yet, life moves on. They’re constantly heartbroken in love, and by their favorite soccer team, and by the government, and the economy. But they always put that shit behind them and play life the way it was meant to be played. They love hard and they’re proud of their resiliency, and it’s so powerful that you feel this while you’re there, and even learn to do it yourself.

You can never truly describe Buenos Aires until you’ve seen it. And even then, you’re just searching for order to describe the orderless. Spend a few weeks there and see for yourself. I did, and I overstayed by 4 years.

When a great artist draws or paints, they convey as much meaning in the absence of what you can’t see as the presence of what you can. The gaps in between the colors, the lines, the expressions, stimulate the emotions in your interpretation. That’s how I look at life these days, and how I want to start intentionally approaching travel. I want to pay more attention to the details, the innocuous moments, the beauty, the chaos, and the inspiration in the subtleties.

When you start to look between where the brush strokes, you start to see the world’s uniqueness again. When you go somewhere new, somewhere that isn’t home, your mind instinctively looks for similarities that make you feel comfort and safety. It’s a natural instinct and a grounding one. Once that’s set, your mind often looks for differences. You want to feel the adventure and excitement of new tastes, new sounds, new rhythms. People and places that look different enough to notice, but similar enough to console you.

When you travel as much as I do, the need for that consolation exits, but it exists in a far more abstract way

My own personal grounding while I travel comes with a lot of layers of potential discomfort on top of it, and therein lies the fun. It’s the challenge of feeling safe, in control, and focused in places where it doesn’t come easy. This is why I love going to places like Honduras, Bogota, Serbia, and Ukraine. You’re forced to see the details. You’re forced to stop overthinking and adjust on the fly, and do it all while soaking in culture, and art, and architecture, and human movement.

You don’t need to go that far to live within the subtle details and margins when you travel, however. You just need to know where to look. You can feel it in Paris in the loosely-overheard convos on the metro, or in front of a cigarette kiosk late at night. You can feel it in Mexico City when it pours rain, as the deep green-treed avenues clear of pedestrians and leave a stark contrast between the bright colors and the grey below, connected by raindrops pounding over car roofs in traffic. You can feel it on a Tuesday after a holiday weekend in Miami, with the tired service staff longing for a break and the birds being the only visitors to the beach.

Maybe it’s just me but I don’t remember the museums I’ve seen in Europe as much as the people who went out for a beer with me. I can see the Blue Mosque in Istanbul on YouTube. I can’t watch over a crowd of taxi drivers moaning in mourning on their phones as they watch TikTok news reports of an earthquake that took out their cities. Anyone can tell you pasta is better in Italy, but I can still taste the aglio oglio Annie Shapero taught me how to make in our kitchen in Rome 20 years ago. I can still smell the damp hallways from my Casco apartment in Panama.

The details are what make the journey worth going on

I find beauty in the details when I’m at home, too. I think of the off-days more than the championed moments of success often. I remember power outs from Boston in the summer and escaping the heat on the tar-filled roof. I remember the same in Buenos Aires, watching our cocktail ice melt into drinks while Pako played acoustic guitar with the lights out to the ornery young crowd.

I get joy from walking past the pink-colored flowers on 2nd street in South Beach. I remember how hard I laughed at karaoke with the Lobster Shack crew for someone’s birthday. I smile when I see my friend bike around wearing rainbow-colored Christmas lights around his neck. I’ll never forget how my friend took soy sauce holders from dinner and turned them into paint pallets. I still smile with a coy grin when I remember my 41st birthday at a metal bar in Sweden. I still feel a sting of pain when I remember getting screamed at in front of Ted’s in front of everyone.

The little details in life are what make it interesting. Seeing the world around you or the world far away requires a patience for these details that can be elusive in the trappings of your own overthoughts or fantastical madness. The mundane afternoons are the best. The waiting between trains, or texts, or dinner dates, or reuniting with old friends. I live for these moments, and they’re why I can’t stop traveling, and hopefully never will. The details let me know I’m home, wherever I am, because home lives within those details. Home lives within our memories, and are hopes to make new ones.

There’s no way to plan for grief. You can tell yourself there is, like I did, but it never feels planned, even after losing dozens of people you know and love. I drank a bottle of vodka and screamed at the walls when my brother Guatemala Jon died in 2014. When Brendan died in 2020 I did the same, scrolling through pictures from our adventures in Buenos Aires, eulogizing him online, comforting his family I’d never met until that day. When my Dad died I had to sit with it. I still sit with it six months later.

For most of my dead friends, there was no plan but there was a pattern: drink, yell, cry, sleep endlessly, and push on. With my Dad it’s been different. He was my best friend. More than just a father, he was a man I talked to almost every day. We fought a lot when I was younger, mostly because our egos clashed and he saw some of his worst features in me. He also saw some of his best features in me, and highlighted those both explicitly and subtly with his words.

When you accept mortality, you can truly appreciate and love people without fear

The last 10 years of my father’s life weren’t easy, but our relationship during that time was still mostly beautiful. He read as much of my writing as he could, with age stripping him each year of his cognitive abilities, fighting back to hold onto pieces of his beautiful mind. We’d spend hours together watching Anthony Bourdain in the basement, cooking elaborate 3AM meals, and discussing the depths of our acute opinions on humanity, art, women, culture, and life.

The time I spent with him in these 10 years wasn’t rooted in proximity or circumstance. It was rooted with intention. I made the conscious decision to connect with him as much as possible once I accepted his mortality. I tried to call and visit as much as possible. I said “I love you” to end every phone call, embraced every hug deeply, and often wept on my way to the airport after every goodbye, knowing it could be my last and making peace with it. It was exhausting but worth it. It’s the only thing keeping my mind and my heart together now.

My last visit with him was scarred by his anger and emotional abuse, but it doesn’t define him, nor his relationship with me. He must have known he was about to die, and in the pain of not wanting or accepting it, lashed out at the world in spite. I plead for him to subside his anger, but his mind was already gone. His mind was not the beautiful place it once was, but that pain couldn’t invalidate the depths of a lifetime full of that beauty. His death released him from the madness, and kept that beauty alive through me, and my Mom, and my brother.

The side effects of grief and the brutal awareness of self

Self doubt is the most debilitating thought you can have. Before my Dad died, it started subtly. I was in the midst of what was to be an incredible year of self awareness, self discovery, happiness, and hope. The transformativeness of 2025 was so refreshing it gave me a confidence and energy that I saw as the path to what I wanted for the rest of my life. Then it crashed. It crashed when I was in Massachusetts in September and watched my Dad scream at my Mom for no reason, and then at me for defending her, and my brother for just being there. I lived in a type of doubt I’d never experienced before.

I felt a loss of control. I felt like nothing I could do would change fate, but maybe if I was a better man I could ease the pain of that fate on others. I lived in doubt as a standard, not an exception. I’m human. I want a peaceful life like anyone else. My ego tells me I can control that. Fate tells me I can’t. The clash of that juxtaposition sent me spiraling, and unlike other spirals in life so far, I didn’t have fast-track dopamine triggers to ease the pain. No alcohol, no running to South America, no ignoring it, no scapegoat for the feelings.

I crashed out in a hotel room in Utah in October on a layover that turned into a week of sober mind-fuck madness alone near the airport. I got back to Miami feeling like I was suffocating under the weight of my own thoughts. I started to withdraw from the kava bars, from friends, from going outside. Two weeks later my father died, and for a month or so my mind shifted to immediate grief, and care for my mother. Then, in early spring, grief shifted from pain and purpose to a numbness, a lack of hope, a lack of care.

Nothing is more dangerous than a person who lacks hope or care. I was self aware of this danger, yet couldn’t bend my mind back into purpose again. The months flew by like days, patterned with work, walking alone, reading, writing, phone scrolling, and sleeping. Life was back to normal, so to speak, but it didn’t feel normal to me yet. I developed insecurities I never had before, feeling like an imposition on the world and the people in it rather than an asset to them.

You can never define yourself by your fears or insecurities

Realizing your way through post-traumatic insecurities is challenging but necessary. The thing about insecurities is that they’re almost always rooted in fantasy, and in some cases even absurdity. Mine came out through a fear of abandonment, tied into the fear of rejection. I suppose this was somewhere buried in me for a while, but I only noticed it after my Dad died. These fears don’t control or define me, but I am aware of their presence as they pop up. My Dad taught me that. You confront them by acknowledging them and you decide not to let them change you.

You have to laugh at them sometimes too, because they’re not rooted in reality, they’re rooted in emotions. The absurdity is almost comical in my case. Analyzing and overthinking behaviors in others or myself. Assuming rejection from things that haven’t happened yet. Assuming failure from things I routinely succeed at. Believing I am all alone in this world while simultaneously receiving attention and love from people across the map from every stage in life. None of this is real. This is just the mind coping through pain, and though absurd in nature, real in how it feels in the moment.

Now, six months later, the fears and insecurities are melting away and turning to presence. Not a return to the presence of before, but a new presence. I see my own mortality now through the loss of my father. I see what my idea of purpose can evolve into. For me it’s people. It’s love. It’s expression through acknowledgement of the beauty we see around us without fear of acknowledging it or embracing it, or (most importantly) being afraid to lose it. Nothing is permanent in life. That doesn’t mean we should fear losing the people, places, and things we love, but rather celebrate them as often as we can, and with as much sincerity as we can.

This shift hasn’t come easy for me but it’s coming, and I’m grateful for that. Six months after my father died, and I’m still here. I write every day. I swim in the ocean, and take walks for miles in the sun. I go to dinners with a person whose beauty and creativity inspires every type of beautiful thought my mind can handle. I sit by the pool with another who’s wisdom and humor brings me levity. I send piles of back and forth texts with another about deep thoughts, bar gossip, and shared hope. I talk, and I listen to friends and family I love who are just like me, and whose presence is a gift just by showing up.

I get to spend time with my Mom remembering all of the great things my father was to us. I get to hear her fears and comfort her, like she did for me when I’ve felt alone or weak. The grief doesn’t end in six months. The absence of my father is real. But it’s part of the normalcy of life, not a marker of failure. It’s humbling to see the fragility of life and how important the beautiful things in it are to me. Not from a position of fear of losing them, but an acceptance of their temporary place. And in that temporary place of acceptance, I’ve found to peace to love to live again, and live to love again.

I want you to ask yourself a question and pause for a second to think about it. What attracts you to other people? Why are you attracted to people at any level? Human attraction is innate to our existence. It’s the overarching basis by how we reproduce, how we survive adversity, how we learn, and how we live within the brutal wild of nature. Attraction can be complex or simple. It can be the height of our human emotions or an animalistic instinct that throws us off course if we’re not careful.

But what is it that defines attraction? There are the obvious answers, of course. Beauty. Chemistry. Sex appeal. A certain kind of face, body, voice, style, confidence, mystery, or chaos that pulls us in before we have time to ask whether it should. Sometimes attraction arrives before thought. It bypasses logic, walks straight into the room, sits down, and starts making decisions for us. And that’s where things get interesting.

Attraction is not bad. In fact, at its best, attraction is one of the purest forces we have. It can guide us toward people who make us feel alive, seen, inspired, and more like ourselves. It can open doors we were too afraid to knock on. It can turn strangers into lovers, friends, collaborators, muses, and chosen family. It can remind us that we are still capable of wonder. Attraction also has its flaws. And those flaws can blind us from a reality that we not only seek but need. That’s the sort of paradox of attraction.

Modern distortion and the pull before the proof

Attraction can make us mistake intensity for intimacy. It can make beauty look like character. It can make status feel like safety. It can convince us that someone is deep because they are distant, or special because they are hard to reach. It can make us project entire personalities onto people we barely know, then feel betrayed when they fail to become the fantasy we created. This is less of an exception these days and more of a status quo, and the reason is simple: insecurities.

We are bombarded with the notion, both online and in person, that we can always do better, that we can always upgrade, that we deserve more than whatever we’re getting from the people we surround ourselves with. This can apply to both romantic and platonic relationships, and even work relationships. But it’s not really about “better.” It’s about perception. We all CAN do better, and should all strive to be the best version of ourselves, but there’s a lot of nuance in that journey.

When you’re constantly measuring yourself against curated lives, filtered faces, and highlight reels, your sense of value shifts. You start to believe that what you have isn’t enough, or worse, that you aren’t enough. And from that place, attraction stops being a genuine pull toward connection and becomes a reaction to insecurity. Nothing hurts more than the feeling of not being enough. It puts people into a mental prison where they feel so unattractive that they often give up on themselves entirely.

The nuances of high standards

I’ve found that the modern standards for attraction lean far too heavily on superficial attributes. Many women prioritize their attraction to men with money, looks, status, and access. Many men prioritize women’s youth, beauty, sexual availability, and agreeability. None of these are inherently bad—in fact, they’re highly attractive traits—but none are rooted in character, which makes them unstable foundations for anything deeper. Looks fade. Status shifts. People want more autonomy. Money comes and goes, and even when it stays, the excitement of it often doesn’t.

Here’s the harder truth: when men build their appeal primarily around looks or money, it often functions to attract sexual attention and desire more than connection. This isn’t always said out loud in front of women, but it’s spoken of and bragged about amongst the men who live it as a reality. The man with a yacht and a Rolex wants to attract as many sexual options as possible, not a soulmate. So does the man who carefully crafts his physical image to distract from what’s missing underneath. And it works…for a while. But what looks like “high value” on the surface is often low in character, which is why so many of these relationships end in cheating, boredom, or replacement.

Don’t believe me? Look at the pattern. CEOs, lawyers, athletes, entertainers, hedge funders; men society labels “high value”. These men often move through relationships quickly, driven more by access and attraction than depth. Not always, but often enough to notice. The dynamic rewards it. Attraction stays strong even when the behavior doesn’t justify it, and that imbalance is where people get hurt. The pull is real, but it isn’t grounded. And without that grounding, it doesn’t last. Attraction becomes an asset to desire, but a liability to the heart.

On the other side, women who rely heavily on beauty and sex appeal can end up being valued more as an idea than a person. That’s often what gets them attention, access, and opportunity. It’s not inherently bad, but it can create misaligned expectations on both sides. They’re pursued, desired, and elevated, but not always truly known or taken seriously. And in a system that rewards that, it can be used as leverage, and even become a path to success beyond being seen as a ‘trophy’.”

But the disconnect isn’t one-sided. Many men say they want depth, loyalty, and emotional intelligence, yet prioritize attraction to women who are primarily valued for their appearance. They project character onto beauty, then feel disappointed when it was never there to begin with. In doing so, they often overlook women who actually embody those deeper qualities because they don’t trigger the same immediate pull. Attraction narrows the field, and sometimes it narrows it in the wrong direction. How do I know? I’ve done it myself, and learned the hard way.

This isn’t to say that everyone is superficial when it comes to standards. I recently discussed this topic with someone I deeply care about who embodies high standards in their purest form, and lives it. It’s refreshing, attractive, and inspirational, but it’s so rare. She doesn’t settle. She doesn’t tolerate low character traits in men or women, and I admire that. But it doesn’t always get rewarded the way it should. People like her seem to be the exception rather than the norm, and I think it frustrates her. It certainly frustrates me, because I’ve wasted years of my own life chasing depth in shallow waters, and am only now setting the bar where it should have been all along.

The reality check

The truth is, attraction without discernment is just impulse dressed up as intention. If you’re not paying attention to character, patterns, and how someone actually shows up over time, then attraction will keep leading you into the same situations with different faces. It will feel new every time, but the outcome will be familiar. The same confusion. The same disappointment. The same realization that you ignored what was right in front of you because something about them felt too good to walk away from.

At some point, the responsibility needs to shift in order to make it work. Not in a self-blaming way, but in an honest one. You start to realize that the problem isn’t that good people don’t exist. It’s that you weren’t choosing them. Or maybe you weren’t even attracted to them, because they didn’t trigger the same emotional intensity you’ve learned to associate with connection.

And that’s the real flaw of attraction. Not that it pulls you in, but that it can keep you stuck, repeating patterns that feel meaningful in the moment but leave you empty in the end. Until you learn to separate what excites you from what actually sustains you, attraction will keep feeling powerful, but rarely fulfilling.

I’d be lying if I told you that seeing women covered head to toe in burqas didn’t evoke a visceral sense of fear in me most of my life. To be fair, most full-bodied religious garb triggers some sort of reaction in me because it feels alien, forced, antiquated. It’s just how my subconscious was visually taught to connect clothing with human control mechanisms. Much like a military uniform, except burqas are what the wives of the bad guys wear, not the heroes who we’re taught will come and save us from them.

Bursa, Turkey broke down this narrative for me in less than a day. Not by design but rather by happenstance. Ironically juxtaposed with a terrible experience in Istanbul, where Christian women and Gucci-laden Muslim Kurds had taken a thousand dollars from me at gunpoint in Istanbul. Bursa was my temporary salvation from a side of Turkey that appalled me. Bursa, a city of mosques. and burqas, and tradition, brought beauty into my soul when most of it was stripped out over Valentine’s day through the prism of 30 drinks, fake night clubs, and Slavic sex appeal.

How to get to Bursa

Getting to Bursa is harder than it looks on a map. It’s a decently-sized city that sits almost majestically at the foot of Mount Uludağ, just a short drive from the shores of the Sea of Marmara. Like most things in Istanbul, your journey starts with a rip off taxi ride and a chaotic ferry boat. I took a large “high speed” ferry from the busy Yenikapi docks in Fatih to Mudanya on the other side of the sea. The ferry was packed with people and their luggage, saving hours of travel time by sea as they head into the mainland of Turkey.

From Mudanya it’s about a 30-minute taxi ride to the heart of Bursa’s old city. The trip feels much longer than it is because of the changes in land and topography. The Sea of Marmara separates the sprawl of Istanbul from a mountain range on its other side. Once across, you feel the altitude changing with each minute of your drive. There are modern suburbs that line the way with Turkish chain restaurants, tire stores, roadside cafeterias, and residential enclaves. As you pull into Bursa you see the snowcaps of Mount Uludağ, the weather gets cooler and dryer, and the sights of people get denser.

A city of Mosques, masks, and sweet treats

There are hundreds of mosques in Bursa, and in the old town they are literally on every other block. There’s the stunning 14th Century-built Grand Mosque (Ulu Cami), the Green Mosque (Yeşil Camii) with it’s green/blue tile interior, the Emir Sultan Mosque, and dozens more all within walking distance of each other. This city was the first Ottoman capital, and in its ancient core you’ll find signs of a bygone time around every corner.

The entire district acts as one big market, both open air and indoors. This is typical of Turkey and one of the country’s biggest cultural appeals. Walking around Bursa is like walking through a market. Stalls spill into the street, where other vendors compete with tables and hand-held product displays. Women are almost all covered in burqas and walking in groups or with men, seldom alone. The more modern storefronts don’t clash but rather compliment the street pop ups with clothes electronics, perfumes. These commercial rows give way to a labyrinth of more, busy even during the cold days of February.

Separate from the home goods and clothing are rows and rows of fresh fruit and nuts, and then a smell corner of fish and meat. The city is basically dry due to the Mosques, so rather than booze bars you’ll find soda clubs (yes, really). These clubs have a corniness that is more appealing than offputting. Strings of bright colored flashing lights lead to colorful menus of sugary drinks, some with candy in them, excitement for the senses on a night out. They blast heavy Turkish pop music and host pop-idol decorations like the Japanese do in Roppongi to get your attention.

Teenagers and adults sit at tables on dates drinking bright blue and chemically altered pink drinks from fishbowls with more flare than good flavor, flirting, dancing, scrolling. No alcohol needed, no buqas indoors, but all pracicing Muslims who abstain from drinking, and if you stay long enough, pray on the mats in the corner facing Mecca.

From Bursa to Boston, I always find the party…

Though cute for the first night, the alcoholic in me needed more than candy soda on my three-day Bursa journey, so I went to the internet to figure it out. I spent my second day walking through the labyrinth of mosques and markets to discover the city’s charm, but with the ulterior motive of finding a drink and some “good trouble”. The internet told me a BBQ place on the outskirts of the old city sold beer so I walked there, traipesing through cat-filled alleys, a bohemian hostel cafe, and a plaza with a flag so big, and a picture of Erdogan so large, I thought I was on a movie set.

The BBQ joint was closed, so I opted for some booze free “brunch” of the most famous dish in the region: the Iskander Kebab. If you like kebabs, or just salty meat in general, this is your dish. It’s famous in Turkey for its decadence. Kebab meat shaved and skewered, then covered in its own boiling oil on a metal plate to finish, set over rice with a white yogurt sauce dolloped to dip on the side. You wash it down with an “ayran”, which is a yogurt drink meant to keep the oils from overcoming you.

I then did some deep diving on the booze situation and discovered that there was one restaurant in the fish market by my hotel that served beer. So I went there. Walking through blocks of big fish killing floors with overpowering smells and the humidity of slow melting ice in 40 degrees made the mission more poignant. I found the fish restaurant tucked into the back, and when I asked for beer like a teen buying a joint in a park, the fish monger owner’s eyes lit up.

He took me inside and told me I needed to pick some food first. I pointed at some iced shrimp and a fish. He muttered some words in Turkish through a smile and a cigarette, then put 6 bottles of warm Danish Tuborg beer into the ice below the fish, and handed me a warm one. This was heaven. I sat behind the ice display out front, fish juice bleeding with cold ice water at my feet towards the drain, smoking a cigarette I was given and volleying bites between swigs of this warm beer.

Culture shock is normal, but shouldn’t be a barrier to shared humanity

Being in Bursa taught me that most of what I thought I understood about Islam, and Turkey, was built from a distance. From headlines, from movies, from imagery that only ever showed the extremes. From a crazy night out in Istanbul that felt like a movie. It’s easy to assign meaning to something when you’ve never had to exist inside of it, and I realized how much of my perspective came from that gap.

What I saw didn’t match the narrative I’d been carrying. The women in burqas weren’t moving like prisoners. They were talking, laughing, shopping, scrolling their phones, living their lives like anyone else. The clothing didn’t disappear, but the meaning behind it shifted. Even the things that felt restrictive on paper didn’t play out that way. No alcohol didn’t mean no nightlife. It just meant a different version of it. Music, lights, flirting, energy. Prayer wasn’t looming over everything. It was just part of the rhythm.

None of this erases the harder truths that exist in parts of the world where religion and control intersect in real ways. But it forced me to confront how quickly I had taken those truths and applied them broadly without question. I had reduced something complex into something easy to judge. Bursa didn’t feel foreign or threatening, but rather a relief, a respite, a reset. It reminded me of the brightness of travel, just after hitting one of the darkest travel moments of my life. It was humbling, kind, and gave me space. These are the reasons to go, to learn more about your own prejudices and the madness of your internal intrusive thoughts. Bursa is beautiful.