We Had Fun, Didn’t We? On Living, Dating, and Slaying in NYC

An ode to the city that has given me everything and taken almost as much.

I moved into Rubin Hall on Fifth Avenue and East 10th Street in August 2003. It was my freshman year at New York University, and though I was relegated to a low-cost dorm with two (improbably, for NYU, straight and Republican) roommates, I was fully aware how lucky I was to live in the heart of the West Village, blocks away from Washington Square Park, in a neighborhood populated by any number of celebrities drinking coffee and chatting away on their newfangled Blackberries. On my way to my first day of class I walked by John Leguizamo in a floor-length knit poncho and it took everything inside me not to channel one of my favorite childhood movies, To Wong Foo, and yell out, “Little Latin boy in drag…why are you crying?”

Thus, from my first days here, my life in New York, even at its harshest and most desperate and most depressing (which was often) felt somehow charmed. I could’ve, and maybe should’ve, died on multiple occasions. I made it through 15 years of hardships and setbacks, financial and emotional insecurity, and the general fuckery known as my 20s relatively unscathed; stronger, more confident, and happier than when I came. Through it all I’ve managed, despite dropping out of NYU less than two years after my initial Leguizamo sighting, to build a career doing what I love, maintain the friendships that have bolstered me in the best and worst of times, and, just under the buzzer, find some semblance of a relationship.

My time at NYU was short, but invaluable. I had watched Keri Russell follow that basic bitch Ben to its fictional surrogate, University of New York, on the first season of Felicity during my eighth grade year. That show informed my dreams and expectations of Big Apple college life: I, too, would live a bohemian existence in the Village, fall in and out of love with boys, win a Golden Globe seemingly out of nowhere, only to cut my hair and lose my ratings. Or something like that. The point is I would be in New York City, living the kind of life with which television and the movies had entranced me. Getting there was all that mattered and NYU was my best option. When I finally moved into Rubin months shy of 18, I felt as if I had made it. But as I would learn over and over again, there is no final “made it”—there’s just the constant process of making.

Virgin Megastore, when that was still a thing, was just a few blocks from Rubin and I would take whatever money I had saved from my work study job(s) and buy CDs for my little walkman. My favorite New York pastime then, now, and forever is walking the city’s byzantine streets, music blasting in my ears, floating along on an invisible catwalk scored by “Crazy in Love” or “All Nite (Don’t Stop)” or Kelis’s Tasty, which, for the record, is still one of the best albums of the 21st century. Later, when I discovered marijuana, I only grew to love my favorite pastime even more.

While NYU got me to my end goal, New York, it also provided me with a wellspring of fiercely loyal and just plain fierce friendships that endured long after I unceremoniously left its hallowed halls. My friends, it turned out, were worth far more than the cost of tuition, or the resulting student loan debt—minor compared to most—and have probably proven more important than a degree ever could. With them by my side, I got to be gay in post-9/11 New York, a city, like me, that was rediscovering itself.

We went to college nights at Splash on 18th Street between 5th and 6th, Heaven just a block down the street, Avalon in the old Limelight before it (briefly) became Limelight again, and Stonewall, my first New York gay bar—which I snuck into using a friend’s ID as I had not quite reached the college night minimum age of 18. As we grew older, the dancing kept us together and deepened our bonds; whether it was at MisShapes, the hip party of the early-mid ’00s (pictured at top) or at some gay dive bar like Phoenix or Pieces because all we really needed was music and each other.

We danced in our dorms, which were nothing more than Manhattan starter apartments. We romanced and were romanced by older men, drank and did drugs with strangers, dressed in outrageous clothes, refused to adhere to lines or covers in front of clubs. The city is impossible to own but at that time it felt like we at least had a lease on it. Even after I left NYU, I hung around the dorms and, during a period of housing insecurity, crashed at them too. There’s no more fabulous way to be homeless in New York than in the luxurious Palladium Residence Hall just off Union Square. It had its own pool and gym, for god’s sake. I would never live as poshly again.

After college, I leveraged the NYU name to secure an office assistant job at Cornell Medical College in the Upper East Side, while living deep in Brooklyn in the neighborhood of Kensington, precariously close to Coney Island. Office jobs were always easy for me—I have an exacting attention to detail that makes menial tasks a minor delight—but once I got a promotion with benefits and an enviable salary (for a 21-year-old college dropout) and the possibility to advance further in a career I had no desire to pursue, I was miserable. I drank and did drugs to excess—this was also around the time my co-worker got me into cocaine, which we would sometimes do after (and occasionally during) the work day to cope with our mutual unhappiness.

Out of frustration, I decided to quit to pursue what I actually wanted to do: write. Looking back on it, I was either incredibly brave or incredibly foolish: to drop out of college then quit a stable job simply because it made me sad. But I guess I believed in myself, or in my ability to survive as I had been doing so, more or less on my own, for quite some time. Things always seemed to end up okay after awhile. I just didn’t realize that this pattern of course correction could take far longer than I expected or was comfortable with. It’s not like I quit college or the Cornell job without a plan. It’s just that the plan was to “make it.” I knew I had talent, but New York is a city overrun with talent.

Making money off your talent: that’s the rub. Upon quitting my job, I had saved up some money, enough to last me a few months, I reckoned, as I figured myself out. However, if the best laid plans go awry, you can imagine how my half-assedly laid plan fared. My luck ran out and so did my money. I ended up having to move back to my hometown of Poughkeepsie in New York’s Hudson Valley near the end of the 2007 summer, just as my friends had graduated NYU. I was not yet 22 and felt as if I had already lived a lifetime.

I languished on the vine in Poughkeepsie for two years. Though it was only a 90-minute train ride outside of New York, I felt a world away. And what’s worse, the gossamer of city life clung to me. Whereas in my youth I longed for New York without having experienced it, the city had become a part of me and I craved it. So I plotted my way back, only to have luck or something like it intervene.

In the fall of 2009, I moved to the Bronx, while still working my job at a nonprofit art organization in Poughkeepsie, reverse commuting three days of the week, to the tune of three hours each way. But it was worth it to live in the city again. It was even worth it when I was mugged on my way home one Friday afternoon from the Marble Hill stop on the Metro-North. Strangely, that felt as if I had taken one step closer to becoming a real New Yorker. You can’t call yourself one if you haven’t been mugged at least once. It’s a cruel but necessary rite of passage, one that tests your will to live in a city that will repeatedly threaten your safety. It was a threat I was ready, willing, and able to accept.

Some time in the spring of 2010 I started writing for a now-defunct fashion blog after answering an ad on Craigslist. [Sidebar: Craigslist gifted me with a lot, from jobs to apartments to hookups, and while I wouldn’t be caught dead on it now, it was integral in my development as both a New Yorker and an adult.] I only got paid a whopping one dollar per post but I got to write, which I did in my free time at work. Among the limited perks was the occasional invite to third-tier fashion shows back when New York Fashion Week was still at Bryant Park—i.e. when it was still good. It was a decent side-hustle and then the darnedest thing happened.

Through some shady machinations I don’t have the time or patience to get into, the blog was bought by a millionaire/former male model and I was among the writers hired full time to run it. There were five of us, all 25 and under, and we moved the operation into the millionaire playboy’s apartment, and subsequently ran roughshod all over the city. If that isn’t luck, or something like it, I don’t know what is. And so I quit my job in Poughkeepsie and returned to life full time in New York with renewed vigor, determined to Mary Tyler Moore my way through this time—I was going to “make it” after all.

I would wake up before dawn, go to the gym, come back home and write for a few hours, then head into Manhattan to our office in the garment district, always wearing a lewk because I was in fashion now. My dedication to the art of gagging the children led me down some strange and wild sartorial roads, usually for the best, occasionally for the worst. Since my days in Kensington, Brooklyn, I’ve been identifiable as the neighborhood faggot, either by my dress or the way I walk, empowered by the music blasting through my headphones from the moment I touched down in New York. That music also guarded me from any possible detractors I might have encountered in those hoods that by now have at least brushed up against gentrification. However, more often than not, when I met someone’s gaze on the street, it was accompanied by an affirmation of “WORK!”

Here’s something that every New Yorker knows like a sacred truth: You can get drunk in this city for free and/or cheap. There used to be a weekly email newsletter, My Open Bar, that told you where every open bar was in the city and it saved my life. Or ruined it, depending on how you look at it. Once I was in fashion, however, drinking for free became not only a routine, but an expectation, thanks to all of the random parties celebrating this, that, and who-the-hell-cares. Any open bar less than two hours was an affront to my very nature. I took to double-fisting cocktails like an alcoholic fish to firewater. Hungry from my upstate sabbatical, I took in all that the city had to offer. “Empire State of Mind” had come out shortly before I moved back and I took its lyrics to heart: There’s nothing you can’t do now you’re in New York.

I would dance late into the night—on a school night!—with my friends again, either at Su Casa, a weekly party above the old Qdoba in the West Village, or the late Sugarland (R.I.P.) in Williamsburg where seemingly every gay in the city eventually ended up. One time, I went to the soft opening of Catch in the Meatpacking District during Fashion Week and my favorite DJ, DJ Marshall from Su Casa, was spinning. My friend and co-fashion kween Mac and I were dancing our respective faces off when a tall, beefy gentleman came up to us and said, “Serena would like to dance with you.” That man was Andy Roddick and that Serena was Serena Fucking Willams, resplendent in an afro. We air-kissed, dropped it like it was scorchingly hot, and hugged at the end of the night. And I learned that Andy Roddick is surprisingly buff in person. Sure, I may have fallen asleep on the subway ride home, got robbed of my costume jewelry, and had to sleep in the office that night—but, hey, that’s the price you pay for twerking with an icon.

Actual footage of me and Serena

That was New York, and that was why I wanted so desperately to come back here. Crazy nights like those that can’t or don’t happen anywhere else. After those crazy nights I’d wake up early the next morning and do the whole thing again. I wasn’t exhausted, though the thought of all that activity now exhausts the living fuck out of me. As does the thought of my capacity for drinking 10 years ago.

God, I’ve passed out in every corner of this town. There’s no worse feeling than waking up on the subway in Coney Island at 3 am when you live on literally the opposite end of the line, all the way in the Bronx. This problem was remedied when I moved into a shitty studio in the slightly more conveniently located neighborhood of Bedford Stuyvesant—a.k.a. “The Livest One”—Brooklyn in the fall of 2011. It may have been shitty–and trust me, it was—but it was mine. Living alone is the greatest feeling any New Yorker will ever experience. In a city of roommates (many of them found on Craigslist) and crowded streets and crowded subway cars and crowds everywhere, true solitude is priceless. But everything has its price and my halcyon days of living alone were numbered.

By this time, I had moved on from trolling Craigslist M4M to Adam4Adam and this new doodad, Grindr. This, then, marked the beginning of my “ho phase.” As soon as I moved back to the city, I had dedicated myself to bodybuilding—a childhood obsession for what seems like very obvious reasons in hindsight—and found my way to David Barton Gym in Astor Place. David Barton was what I imagined being gay in the ’90s was like: tawdry and delightfully tacky. If a jacked white dude wearing ripped jean shorts, Calvin Klein briefs, and Doc Martin boots became a place, it would be David Barton Gym. It had a disco ball DJ booth, mood lighting, and an infamous steam room I may have enjoyed on one or two special occasions.

Going to a gay gym seems like a good idea—there’s a lot of toxic masculinity in most “straight” gyms that I find particularly off-putting—but it also brings with it its fair share of bullshit. If you think gay men are competitive in the everyday world, throw in some weights, an abundance of mirrors, and towel service and you’ve got yourself a hornet’s nest ready to blow. That mix of testosterone, pheromones, and designer cologne was intoxicating. I couldn’t really afford the hefty monthly membership dues, but I liked going there, I felt comfortable among all that ostentatious faggotry, and there was no end of hot boys. I still managed, however, not to hook up with them; that whole shitting where you eat scenario made it kinda weird. Besides, I was never good at making eye contact or performing common social graces, so instead, I used Grindr to find men around the gym.

In the spring of 2012, I bid farewell to the fashion blog and worked remotely for a gay site based out west. I could work from home, or, as I often did, from the gym, punctuating my days with the occasional hook-up. My time at David Barton paid off and I found myself being able to wrangle men I had only masturbated to. It was like discovering a new superpower. But how would I use it? Would I let it corrupt me as all power inevitably does to those who wield it? I was 26 and horny, so the answer is obviously yes. I abused it. A lot.

For two years, I had, for me, a lot of sex. Even after I had been kicked out of my apartment in December 2013, then subsequently fired from my job weeks later in January 2014. I was collecting unemployment and living in the giant abandoned loft apartment in Bushwick that a friend had acquired as part of a drug deal. That, really, was my sexual peak. I worked out all the time—not to toot my own horn, but beep-beep, I was ripped—had a crazy quintessentially New York place all to myself, and I was building up my confidence again by taking up freelance writing. In effect, I was living my best life, or at the very least my best fuckboy life.

There were, of course, some dark times. While I enjoyed all my canoodling, the sex left me feeling empty once it was over and the boy with whom I had shared such intimate passion disappeared never to be seen again. And the sting of rejection—having fully bought into the fantasy that I was one of The Desirables, that elite class of New York homosexual—never failed to devastate me. Around this time I fell in and out of what I thought was love for the first time. Though he turned out only to be a footnote in my romantic life, the experience served as a reminder to nut up and to take a chance on telling someone how you feel even if they don’t reciprocate.

The sex, as it does, got boring. The search was exhausting and, for some gays, the search was the goal. What remained was my writing. I had gotten enough freelance work to get off unemployment and through my favorite strategy for success—sticking around—I got an editor position at Out, a magazine I had clandestinely read as a baby gay in Borders Bookstores before they too went the way of the dinosaur and R. Kelly’s career. Once I hit 30 in 2015, things took a decidedly calmer turn. I had done my 20s—to the max. I don’t even have time to talk about the time I got arrested, taken to the hospital in handcuffs, and spent the night in jail. That was how I devoured New York: By having it devour me. Now I can safely say we’ve both had enough of each other.

New York is constantly changing so I think it pointless to lament about “Old New York” or how things used to be. Everyone’s Old New York was someone else’s New New York, that is, what felt fresh and new for you felt like someone’s way of life was being upended, brushed under a rug. That being said, New York’s not what it used to be. It’s no longer mine or my friends’, insofar as it ever was. Our lease ran out. There’s nowhere to dance anymore, or I don’t have it in me to find those places hidden off the radar, in dark basements, or in deep pockets in the outer boroughs. The life of the city feels like it has withered, or maybe I’m just tired. I thought I had experienced everything, or at least everything I wanted to experience, in New York, except I’d been single since day one.

I never really dated anyone and then, weeks before I was set to leave, suddenly there he was. We met on Scruff, he came over one night, I made him dinner, and that was it. The next thing I know, it’s Valentine’s Day and he surprises me with a romantic night in a hotel room. I had never had a Valentine. I regarded Valentine’s Day as annual torture designed for the perpetually single like myself. But we fell into a comfortable groove, both fully aware that our time together was limited. I think that may have made it all the better. There was nothing to lose so we could like each other and be open about it without consequence. That this happened as I was preparing my exit from this city was unfortunate, but it also felt like a fitting way to end this chapter of my life. I experienced what I had never known before.

New York has given me everything and taken almost as much, but as the painfully true cliché goes, I made it here so I can make it anywhere. Moreover, I made it on my own terms, as frustrating and seemingly self-defeating as that occasionally was. I leave this intense, romantic, anarchic, sprawling, ugly, beautiful, epic city not as I did in 2007, with my tail betwixt my legs, but I leave knowing that I didn’t let it beat me. New York was everything I wanted and more—and a whole lot of what I wasn’t expecting, and more.

But New York is also something of a trap. If you’re here long enough, you start to believe that there is nowhere else—that this city is the center of the universe. You get trapped in patterns, you get stuck within yourself because this city demands you to guard against all outside forces. I want nothing more than to get out of town, get out of myself, and see what the rest of the world has to offer. It’s as if this whole time New York was just a cocoon from which only now I am escaping, fully formed. The process was painful at times, but ultimately I lived the life that I wanted.

New York, you’ve given me everything, and for that I say, Thank you—next.

Lester Fabian Brathwaite is an LA-based writer, editor, bon vivant, and all-around sassbag. He's formerly Senior Editor of Out Magazine and is currently hungry. Insta: @lefabrat