Once I Came Out, Dating Suddenly Became So Hot... And Complicated

I wanted it all — sex and romance.

by Jamie Valentino
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I entered my first gay bar on the eve of my 21st birthday. I was in between apartments in New York and temporarily staying at my brother's. When I searched for the nearest LGBTQ+-friendly spaces in his Lower East Side neighborhood, a bar called Boiler Room popped up.

My heart started pounding faster as I entered the venue, though I felt relieved by the lack of a doorman. The one time I tried entering a gay bar in the past was the only time my fake ID had ever failed. Still in the closet, I had perceived the bouncer's rejection as a sign I didn't belong inside. But I suppose it didn't traumatize me enough to have the patience to wait another night.

"What are we having?" a bald, muscular bartender asked.

I ordered a gin and soda, and he glanced me up and down.

"First," he said, "Can I see an ID?"

The bartender looked at my real ID, then offered me a drink on the house. "You're lucky it's your birthday in a few hours," he said.

At first, I stayed because I had nowhere else to go — my brother needed me out while he asked his roommate for permission for me to stay — but every free drink from the bartender made me feel more welcomed. Then, I realized he might be interested in me. My experience with men thus far was limited to my brief fling with Jared, a 34-year-old jaded (but ridiculously handsome) New Yorker who couldn't see himself committing to a 20-year-old. Still, though, he slept with me.

My ego couldn't handle another rejection, so I was determined to play it cool with the bartender. He questioned why he had never seen me around, so I joked that he should've looked in the closet. I avoided meeting his relentless gaze as if Medusa was offering me more gin. When I went to the bathroom, the bartender's foot prevented the door from closing. "Did you want to go first?" I asked, but he nudged me inside.

I craved everything: the white picket fence with a sex swing inside the house.

In the past, I had always felt hesitation in my interactions with women, as if there was a wrong way to do intimacy. But now that a strange man locked himself in the bathroom with me, that angst turned into passion. Finally locking eyes, I let the seconds pass between us. I breathed in as he exhaled.

"Don't you want a 21st birthday blow job?" he asked, matter-of-factly, like it was a thing.

It was admittedly the least romantic question I’ve ever heard. But at least dabbling in gay hookup culture online prepared me for this. At first, dating guys felt unexpected, but soon, every chat became like a horny step-and-repeat. However, I didn't expect men to be so straightforward without the veil of the internet. It was incredible how the only difference between a creeper and Prince Charming seemed to be a mutual attraction.

Part of me wanted to reject his advancement, if only because we were inside a dive bar’s public restroom. But then I felt the bartender breathe on me again and, to my surprise, I kissed him first.

"But I'm not 21 yet," I still responded as my lips slowly released his.

Then I checked my phone and saw it was 1:00 a.m. The bartender smiled and unbuckled my pants, performing as promised.

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Previously, I assumed a formal date had to come before physical intimacy. Even watching the most adult shows, I never saw bartenders going down on people in bathrooms or anonymous men inviting guys over online. Even one-night stands got to know each other at the bar before sleeping together, and then they fell in love. But that’s probably because television rarely takes women out of the equation.

Now, it appeared to me that gay men would rather entertain sex without chemistry than the grueling burden of getting to know each other. This was new for me. Being closeted had made my pursuits of vaginal intercourse gradual, to say the least. Usually, a girl would have to throw herself on top of me. I never felt like I had the option to say no then, and to a certain extent, I didn't now.

I wasn’t opposed to casual sex, but I wanted romance, too. I craved everything: the white picket fence with a sex swing inside the house. Or, at the very least, sex and a date. I didn’t necessarily care about the order.

The bartender didn't request my number. The next day, I remembered he had never asked my name. Up to that point, it felt like romance with men was forbidden. Now, it began to feel like it just didn’t exist.

Before I came out, I dated girls. I think they liked that I made engaging conversation and suggested plans beyond the bedroom. When I lost my virginity to a girl named Emily in high school, it felt more like a ceremonial ritual than an exciting pursuit. I remember making small talk during intercourse, which made her laugh. It was our sophomore year, and she had already done anal with a senior. Perhaps her vast experience would've made me nervous if she wasn't a close friend, which is why I chose her. After that, I learned that penises could function regardless of desire, and alcohol served as a great middleman for teenage hookup culture expectations.

After I moved to New York, I felt empowered to contact whoever on the apps without the debilitating fear of being outed. Despite my inexperience, browsing guys online like takeout, I was drawn to taller, muscular men in their 30s who were bottoms. The bottom portion made it feel like kink rather than preference; these men reacted determinedly to reverse the roles as if my desired position was unusual because I was younger and shorter. But being the one to penetrate felt like the only role I knew how to do.

Jared had embraced my preference, and so did Troy, a 33-year-old Londoner who bragged about his accent in his bio. He suggested meeting at a bar in Tribeca, saying, "It's one of my favorites." I countered with an invite to Boiler Room, which had become a safe space amid these abrasive interactions. I liked that the bartender acted neither bothered nor jealous when I brought dates. The only difference was receiving complimentary drinks and sometimes oral when I came alone.

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Troy suggested having a drink at mine first, but I lied that my roommate had already invited a mate over. He didn't need to know my brother was watching TV on our shared bed. I needed to wait another week before moving into a spare room I found in Hell's Kitchen. When we arrived at the bar in Tribeca, I realized I had left my wallet at home. The bouncer refused to let me in, so Troy suggested walking along the pier.

"Are you sure you're 21?" he joked, but it didn’t sound like he cared.

Despite the identification mishap, for once, everything happened like it was supposed to. We bantered and talked about our lives, with me trying to seem as interesting as possible. Our interaction felt a bit forced, but I enjoyed myself because I thought Troy was really cute. He looked like Clark Kent. I learned increasingly more about the power of attraction and what had inspired my brothers to pursue such annoying girlfriends in the past.

I assumed only the gender of my romantic partners would change after coming out — not that I would have to relearn what it means to fall in love.

Troy kissed me, so naturally, I kissed him back. This, too, was romantic, especially considering the waterfront and the stillness of the night above us, as if we were alone in the world. The moment felt like the beginning of something. But unfortunately, it only took him 15 minutes before he began unbuckling my pants without warning. Apparently, Troy took us feeling alone in the world too literally.

Ironically, now that I wanted to experience romance with desperation like never before, I couldn't express interest in a man without him immediately trying to take my clothes off. I's not that I didn't want to engage, but every rom-com I had been brainwashed with abruptly seemed like sci-fi. I mean, Julia Roberts would never!

"But we're in public!" I said.

He shrugged, assuring me no one would see us. I had figured out that prudeness seemed like kryptonite of gay dating. Since I didn’t want to kill my potential Superman, I closed my eyes and let him go down on me. Within my first month of coming out, I managed to be offered and accept public oral twice.

I invited myself to drop Troy off at his building, thinking I was sneaky. We kissed goodbye in front of his doorstep, but I suggested continuing upstairs. "Ugh, I wish," he said, "I'm living with my ex. It's late, though. How about you blow me in the stairwell?"

Sex was great, but I wanted more than that. I walked home frustrated with blue balls and the realization my new queer reality wasn’t as easy as I had once expected it to be. I had never really considered the dynamics of a gay man’s sex life. I assumed only the gender of my romantic partners would change after coming out — not that I would have to relearn what it means to fall in love. I was discovering that my new community seemed fun and exciting, lawless and sexually uninhibited. It felt like we were empowered to do whatever we wanted — as long as we kept our expectations casual.

I had heard people preach about self-love and dealing with prejudice, but no one ever told me about the sharp lifestyle differences that happen when you pass through the rainbow. I quickly learned the best practices for attaining sex. However, mastering the colorful idiosyncrasies of pursuing queer love seemed impossible.

It turned out dating for love among men was more complicated than dating a female beard. This could've been karma. After years of breadcrumbing girls and doing the bare minimum to sustain some form of a girlfriend to avoid setting off any gay flags, it seemed like men were only interested in my body. The trope of the bachelor only interested in sex had become my burden; it felt like I had taken on the woman's role. Why couldn't I have my cake and sleep with it too? Online, I could find a man to tie me up or pee on me faster than I could land a romantic date. (Not that I tried the former two, but both were offered several times.) So, I decided to go the old-fashioned route and meet the one at the club.

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The Australian caught my eye across the dance floor at Le Bain. I noticed him like people do in movies. Our gaze met unexpectedly, then often. He kept looking at me, and so I stared at him. The next moment, we found ourselves dancing together. I promptly forgot about the friends I came with who I had met at my beloved Boiler Room.

He paid for all my drinks, held my hand whenever we walked, and he wouldn't stop kissing me. I followed his lead like a stray puppy. Then, when the club's lights turned on, he suggested getting food at a diner.

The Australian ordered pasta at 4:30 a.m. I had been told gays don't eat before anal sex, so I felt rejected. But, of course, I still had a lot to learn about how our bodies work. His friends ate similarly hearty meals. I didn't feel sexy eating in front of him, so finally, I ordered a smoothie, and then wine. He said to put my order on his tab, and from my hetero experience, I knew men offered to pay for you when they liked you.

Afterward, he brought me and a friend back to a studio apartment. (The friend and I had briefly spoken earlier when he heard I was also Colombian. He called me handsome in Spanish. Flirting with him didn’t feel like an option since I had already committed to the Australian.)

"You guys are boyfriends?" I asked.

The Australian said no, he was crashing at his friend's apartment. He never mentioned that he lived in Australia. He cheated me out of our future one-of-a-kind relationship that I had so carefully planned in my head. The bastard wasn't falling madly in love with me but just in lust for the night. I guess my first ménage-à-trois wouldn't hurt, I thought. I had a threesome in the past with two girls at their suggestion, but this seemed like way more fun.

"Don't worry," the Australian said. "The couch pulls out, and we can sleep on the bed." His friend complained that it was his turn but allowed it. I shrugged, trying to emulate indifference.

Ultimately, I would've said yes to marrying the Australian or his tall, dark, and handsome friend joining us. In the silence of the early morning, the Australian and I fooled around under the covers until he suggested I top him. It was excellent, and I sneakily threw away the used condom in the trash can. His friend had heard us anyway; it was the first thing he mentioned. We laughed and chatted for an hour while the Australian slept.

"We didn't really get to meet, but I'm Michael," he said.

Seeing my new crush Michael's incredible smile, I regretted not putting my eggs in the local basket. He said goodbye because he was supposed to meet a date, specifying from Tinder. (I soon would learn this is what gay men use for "serious dating," to the shock of straight people everywhere.)

"You're going to have sex?" I instinctively asked without thinking.

"No," he replied, amused, "No offense, but I don't sleep with guys I don't know."

How badly I wanted to answer, Me neither.

"We should go out and wingman each other sometimes," he said before leaving, placing me squarely in the friend zone.

The Australian eventually woke up. He was so hot, he convinced me to slip back under the covers again. I was disappointed that he lived abroad, but I figured sleeping with him twice made it more significant than a one-night stand. And I enjoyed it. He suggested adding me on Facebook to stay in touch, but I responded, "What's the point?" Gay or straight, I knew the long-distance route was not for me.

In time, I would learn that desiring a relationship didn’t make me a gay unicorn. I just needed to practice patience to meet compatible partners — like any other person — which became easier after I let myself indulge a little. After all, isn’t that what every gay man deserves after a life of restraint?