Hilton and the heart: Summer flings and flops

by Hilton Dresden / Beacon Correspondent • September 16, 2015

This was the summer of my sexual awakening. Or, at the very least, the summer of constant cocktails and weird hookups.

I spent the season in New York, interning by day and slaving away in retail by night. I was determined, going into my time in the Big Apple, to finally blossom into a sexual agent—someone who goes up to other people and charms them into getting naked. And to be quite honest, I did. I’m proud to announce that of the smattering of men I got intimate with, many of them were people I approached and rather assertively told how much I liked their faces.

But to be frank, not all of my summer flings left me feeling warm and sexy afterward—in fact, most produced a sort of empty, even slimy sort of feeling. I often walked away, zipping my fly and wondering if that interaction had made me a happier person.

For starters, there was Alexander, an Upper East Sider from Tinder who aggressively told me that he would only leave his bed that day if he could satiate his “hunger for ass.” Feeling frisky, I wheeled myself over to his neck of the woods after getting drunk at a gay rooftop pool party in the East Village. Why I didn’t just flirt it up with one of the swimsuit models there, I don’t know. Truthfully, it's because there are few things more scary than a pool full of muscular young men in speedos.

Then there was Stephen, a sweet, thirsty young man who responded to my late night “Hey” with an admirably straightforward “Wanna find a shady spot and fool around?” We then met up on a playground on the Upper West Side at 3 a.m.. All I can say is I was drunk and I’m still ashamed, but to write well, you have to be vulnerable and open up. And I must say it was one of the better sexual interactions of the summer. Everyone was happy at the end, and I walked away thinking to myself that I was paying homage to the New York cruising gays of the past. 

Things went deeply south a few weeks later. I was working at Topshop and, due to a horrible hangover, was too delirious to really take in the strange coworker slipping me his number. He took me out for burgers and margaritas, which was nice, but I couldn't help notice upon further inspection that his eyebrows were drawn on and he was wearing bronzer. The eyebrows were throwing me a little, but I’m an open-minded guy. I was willing to embrace them.

That’s when he asked me, “Are you weirded out that I don’t make eye contact?”

“Yeah,” I admitted.

“It’s just not my thing,” he said, as if it’s an acceptable option in life to opt out of a basic component of human interaction. He proceeded to tell me how he hates everything and everyone in his life and how he had quit chain smoking four days ago because his friends were complaining about his odor.

After dinner, we made a pit stop at the convenience store so he could buy two new packs of cigarettes to burn through. “You’re stressing me out too much,” he explained.

 As we drank more, and he smoked more, I realized how much I loathed this man with every fiber of my being. Still, when he invited me back to check out his home in Queens, not wanting to hurt his feelings or say no to life, I nodded solemnly and followed him down a dark, wooded street. We ended up mournfully going to third base.  

Thankfully, later that summer, I met an aspiring designer at fashion week who looked like a more bug-eyed version of an Abercrombie model. He bought wine and cheese that we enjoyed together on a pier in the West Village, gazing out at the night lights glittering on the Hudson. We eventually abandoned all pretense and enthusiastically started making out in the grass. After that he kept saying he had to work on “the project” whenever I asked to hang out, but, hey--I’ll take what I can get. 

My point is, summer flings can be fun. They can be bad. It depends. In the end, I regret none of them. Even as I walked away from that Upper East Side apartment, and that playground, and that large home in Queens, I consoled myself by knowing I now had a great story to tell, and with each uncomfortable sexual experience, I could feel myself becoming closer and closer to writing like the greats: Lena Dunham and Chelsea Handler. So who cares if I was naked on a playground at 3 a.m.? It's a good story.