Gary and I walked out into the cold March air after the three-hour matinee. It was a cloudy day so the sky was already half dark. By then, I pretty much knew I wouldn’t be interested in a second date — he was nice but we didn’t have enough in common — so I didn’t feel any pressure to tell him I’m trans.



“Why don’t I take you out to a nice dinner?” he asked. And when he saw hesitation in my face, he added, “in exchange for taking me to the play. What do you feel like?”

Dinner couldn't hurt. I pondered for a bit and told him I was in the mood for French. There was a bistro in Chelsea I liked. He seemed to enjoy the idea of strolling in the city with me, and put out his arm for me to hold on to as we walked. His biceps were definitely bigger than the boys I usually dated, who tended to be indoorsy artists or scientists.

As we walked the 20 or so blocks down Seventh Avenue, I watched the neighborhood slowly evolve from the chaos of midtown to the more focused energy of Chelsea, its mixture of twee restaurants and the occasional gay bar or adult store. It was early so there were only a few people at the restaurant, a man reading alone and a couple of guys talking intimately. All of a sudden, I felt like a tourist with Gary and his flannels, even though I’d been at the restaurant several times.

Though the restaurant billed itself as a casual bistro, it wasn’t nearly as cheap as I remembered. Gary insisted on wine with dinner, so I imagined the meal was probably still a lot pricier than he was used to. He didn’t seem to mind.

He asked me if I’ve been to France and I told him I used to go reasonably often, back when I lived with a British guy for a few years. The detail I neglected to mention was that my ex-boyfriend is gay, I dated him while I was a guy, and I haven’t been to France as a woman. In a way, I wasn’t the one who traveled there, but my identical male twin.

“I just want to let you know, even if we never see each other again,” Gary said near the end of our meal, “this was a special night for me. Meeting women like you is exactly why I moved closer to the city.”

“That’s really sweet,” I said, as we clinked glasses, his smile already tinged with loneliness. I pitied him a little then. Counter to the stereotype about trans women that’s been drilled into people by movies and TV, it was just as likely for a guy to be more into me than the other way around, even after he knew about my history.

After he paid the bill, he pulled out his chair to go to the restroom, not noticing the guy who had been seated behind him in the meantime. Gary’s chair bumped into the guy’s as he stood up.



“Oh, sorry,” Gary said.

“I don’t mind,” the guy replied. “You can bump into me any time.”

One of his companions added, “You can bump into me, too.”

Gary turned to me with a furrowed brow, which seemed more like confusion than displeasure. He passed the waiter on his way to the bathroom, who smiled at him again. I looked around the restaurant and noticed a couple of other faces, who were clearly amused by the exchange. They looked at me approvingly, as did the guys that Gary bumped into.

It was then when I realized: Gary was not just a gay man’s fantasy, but he was my gay man’s fantasy. Before transition, I used to watch those porn movies where gay men lured or paid straight men to have gay sex for the first time. And those straight guys had these manly jobs like fireman or marine or, actually, park ranger. They symbolized the kind of elusive masculinity that femme gay men like me both aspired to and desired, but couldn't have — yet somehow, there was always something about a guy being actually gay that ruined the image. For me (and a certain cross section of gay men), it was the ultimate thrill to have sex with a guy who isn’t really attracted to men, but somehow gets convinced to do so anyway.