Nearing 30 And Single, I Decided To Date 4 Men From My Past. Here's How It Went.

"I had met a lot of eligible bachelors, and after four years of being off the market, I started to wonder if I had met them at the wrong time."
The author.
The author.
Courtesy Of Jamie Valentino

I’ve lived in New York for nearly 10 years, meaning many random men have my phone number.

A scroll through my contacts was proof I had seen more penises than names I could remember. Sure, the treasure trove of lovers in my phone are fewer “missed connections” than “doors I never fully closed because I wanted attention” or someone convenient to text when I was horny.

But I prided myself on having met a lot of eligible bachelors, and after four years of being off the market, I started to wonder if I had met them at the wrong time. A time when I was younger and unprepared, perhaps too immature, and usually too drunk for something more. Approaching 30, I became infatuated with the possibility that the past could hold my future.

This is how I gaslit myself into the idea that rekindling old flames was smarter than starting from scratch on the apps.

Niko wasn’t precisely the catalyst for what happened next, but he was the first name crossed off the list. Our dynamic had been unique in seamlessly shifting between romance and friendship, but a lot happened in the five years since we last saw each other.

I got stuck in a destructive, co-dependent relationship, and he fell in love ― with other people, respectively. Regardless, both roads brought us back to singledom, and I assumed we were now older, wiser, and therefore better equipped to be together.

Until I had the experience of waking up held tightly by him as his boner pressed against my skin, and wondering why he didn’t want me. When I tried to go down on him, he pushed my head away and pulled me toward him to cuddle.

“I don’t really care for blow jobs,” he said, but I heard from you like a silent vowel.

“You’re my special friend,” Niko always told me. Reminiscing on this, I was still young enough to spiral.

As my presence in his life unexpectedly morphed from lover to body pillow, I realized I was too old to believe I could force a man to desire me.

Next, I messaged Adrian. We had met while he was bartending at a now-defunct gay bar called Therapy and had sex a handful of times. Our text exchanges were reliably brief but effective, typically leading to him in my bed.

While Niko and I had an unparalleled mental chemistry, Adrian and I were like wild animals. I couldn’t be in a room with him without penetration happening. We’d lay in bed, and he’d say something like, “I forgot how beautiful you are.” Then, the next day, he’d forget about me again until the next sultry full moon.

As physically passionate as we were, I wondered why our dynamic never developed beyond great sex. I liked everything about him, even if I remembered the contours of his face and body more than the personality underneath. But when I messaged him, for the first time ever, he responded with disinterest. He had reached out in the past when I was miserably taken and then when I was traveling abroad as an expat. Now that I was available and in his zip code, he seemed to forget we were uncontrollably aroused by each other.

When I messaged Lawrence the next day, I realized I was going through my contacts like the ghosts of gay flings past. Even though Lawrence never called me his boyfriend, he invited me to Christmas with his family. He worked as an on-the-call makeup artist for a famous diva pop star. I initially saw him through her Instagram, and then recognized him at the bar in person and wasted no time picking him up.

We were more than lovers but never took our relationship beyond dating. Maybe because he cut ties with me shortly after the holidays, apparently not impressed with me getting wasted with his mother. I knew his ex was an alcoholic, but I had thought his mom and I were bonding. We had gotten back in touch when he coincidently read about my quest to quit drinking.

I met Lawrence for lunch at Waverly Diner, and at last, it was like nothing changed between us. The dialogue went back and forth from seriousness to irreverence, and he was as clever and cynical as I remembered. As much as I still cared about him, the butterflies had flown too far to return. After lunch, we walked through Washington Square Park, but it didn’t feel amorous. It felt like I was with a beloved friend.

I started to feel like Goldilocks, except I was running out of bears.

I thought I had found a hack to dating, but maybe the past was too comfortable of a place to find the thrill of love. It’s not like people (usually) fall in love on first dates, but there’s a chemical reaction that happens when a new person captures your attention. I couldn’t alter the dopamine receptors in the men who already knew me and make them fall into crippling lust again ― or myself, for that matter. And I had already learned the insurmountable consequences of prolonging a relationship that had run its course.

Still, I decided to give it one more shot with Dan Cute Lawyer, which is how I still had him saved on my phone since we first met on Grindr. Dan Cute Lawyer was everything I wanted on paper. Our personal lives never intersected, which is often the trick in sustaining long-term sexual relationships.

This time, when I messaged, I invited him to a gallery opening, but he had already made plans with his friends. I offered to join them, and he responded to come after ― at 12 a.m. I begrudgingly agreed and then flaked at the last minute as his rejection angered me. I had never wanted to meet his friends before, but it was different knowing it wasn’t an option.

It’s not like I was looking to get married, but I felt the urge to tap into the potential of these men who seemingly got away. But despite being older and wiser, I was still talented at diving head first into romance and landing on concrete.

So, I stopped using my phone like a time machine and resumed looking forward to new encounters. Niko invited me to a popular circuit party, Horse Meat Disco, and I jumped at the chance to throw myself in a strobe light sea of shirtless gay men.

I spent the night dancing freely with Niko, flirting with strangers but always returning to each other like the platonic lovers we were. I would’ve compared him to a brother, except I never cuddled naked with mine for fun.

I was happy to have him. He taught me to accept a good thing without projecting where my life was falling short.

The next day, we met up again for breakfast, and I coincidentally received a text from Adrian. But our previous exchange had left a bad taste in my mouth. If I hadn’t been so caught up in my mission to screw Adrian into something more, I would’ve remembered it was running into each other by chance that typically led to our scandalous nights. And I always hosted because he was in an open relationship.

Niko and I took a walk in Chelsea afterward, and he kissed me on the lips goodbye, and I remembered how lucky I was to have such a special relationship that wasn’t constrained by labels. In fact, I didn’t regret any of the relationships I had with these men from my past until I started approaching them with expectations.

There’s an entire spectrum of fondness, friendship and love that most people don’t get to enjoy, conditioned to live in black and white. But I could experience the rainbow without forcing anything, keeping my eyes on the future without throwing out the past. You just never know how your relationships may evolve.

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