Ben King for BuzzFeed News
A couple of years ago I found myself messaging guys on OKCupid, asking if anyone wanted to see a matinée of Twelfth Night with me at two that same afternoon. I had lined up earlier in the day to get rush tickets, but the friend I was supposed to go with ended up canceling, so I needed to find someone else.
“I’ll go with you,” one of the guys immediately wrote back. “By the way, my name’s Gary.”
I enjoy the randomness of dating online. I didn’t even look closely at Gary’s profile before I asked him out after his initial message, just gleaned from his use of “you” instead of “u” and his curiosity about literature that he was a decent enough guy. He was beardier than my usual, clean-cut nerdy type, but if anything else, I figured it would be fun to spend the afternoon with someone I would have never met otherwise.
More than a decade after medical transition, I was a lot more relaxed about dating and being trans. It used to be at the forefront of my mind every time I went out with a guy — when to tell him and how so that he wouldn’t freak out. But over the years, I learned that most men have never dated a trans woman before, and disclosing to them also meant that I was teaching them how to react to me. If I acted like it was something to be ashamed of, then that was what I was teaching them. But if presented it as one of many parts that made me interesting, then they were a lot less likely to care.
When I first saw Gary, I wondered if I should be a little embarrassed because of his outfit. He wore a puffy blue vest over red flannels, and his beard had flecks of gray I didn’t notice from his pictures, though his alert, deep-set eyes and ruddy cheeks communicated an open disposition. He stooped down to hug me and I felt his back muscles flex, though I didn’t feel the pull of attraction; I was too distracted by the thought of being in the theater with a guy dressed like a lumberjack.
“I’m excited,” Gary told me. “I’ve never been to a Broadway show. Do you know the play?”
“I studied it in college,” I said, trying to keep my Shakespeare fandom in check.
Having lived as both a man and a woman, I've learned that it’s all an act — everyone is performing their gender all the time.
Gary’s sweetness made me reprimand myself for being snobby about his clothes. As soon as we got to our standing-only places in the back of the orchestra section, I couldn’t help but tell him about how I saw several productions back when I lived in London. Rather than glazing over, his eyes widened as I kept talking about Shakespeare. Most guys in the city find my nerdy interests cute, yet boring. Gary found them impressive, a taste of the urbane New York culture he craved. (He had moved to Inwood to be closer to the city, and drove upstate four days a week to work as a ranger for one of the state parks.)
“And even the women’s parts are played by men?” Gary asked at one point, his eyebrow arched. It hadn't even occurred to me until then that it might be awkward for someone like me to see a play on a date where half the cast was in female drag. I cooly told him how women were banned from the theater in Shakespeare’s time, so men normally played all the women’s roles back then.
In Twelfth Night, the main character Viola spends a lot of the play pretending to be a man, so the actor who plays her has to be a man who plays a woman playing a man — and by the end, we learn she also has an identical boy twin, Sebastian. All this gender-shifting was a big part of why it was my favorite Shakespeare play, since I have a history of gender-shifting myself. I didn’t mention that part to Gary, as the house lights dimmed and the play started.
“I can tell they’re men playing women but they’re really convincing,” Gary whispered to me after a few minutes. “How do they do that?”
“They’re great actors,” I whispered back, amused by the irony, knowing by his tone that he had no inkling of my history. I wondered if he would think of my womanhood as an act. Yet having lived as both a man and a woman, I've learned that it’s all an act; everyone is performing their gender all the time, and some of us are just more talented or convincing than others in our respective roles — so convincing even to ourselves that we often forget we’re playing them. If I’m rare, it’s only that I’ve played both parts.
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 twenty 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.
Straight men symbolized the kind of elusive masculinity that femme gay men like me both aspired to and desired, but couldn't have.
As Gary meandered his way through the restaurant and other pairs of eyes trained on him, I noticed things I didn’t before. His jaw was stronger than I remembered, his chest broader. His expression, which up to then I thought of as a bit clueless, seemed rugged in this new light. I remembered that thrill of long ago: the fantasy of being with a guy who wasn’t really into men.
“Shall we go?” he asked.
We were going to different subways. Gary offered to walk me, but I was too confused by my newfound attraction to take the offer, so I told him it was fine. I hugged him good night as he kissed me on the cheek, and I enjoyed the brush of his beard against my skin.
As I walked to the station, I thought about those fleeting moments when my body was in contact with Gary’s, and felt the old excitement of my gay man’s fantasy. I remembered, in my early days of transition, the thrill of straight guys hitting on me who would have never given me the time of day when I still lived as a gay man, and how I happily had sex with them for fun. I didn’t transition to fulfill the fantasy of sleeping with lots of straight guys — my desire to be a woman was so much more encompassing and complicated than that — but the knowledge that men wanted me as a woman definitely sped up the process.
As time went on, I craved the random sex less and less, got more excited by shared interests and the prospects of future companionship. Not feeling objectified just for my looks became a priority for me, after being consistently seen by men as nothing but a body to fuck, and it became more important for me to feel safe with guys I dated. As my core group of friends shifted from gay men to cisgender women, I began to adopt social attitudes that were more typical of my new role. I might have an identical twin who’s a man, but even though we’re both attracted to men, the type of guy I fantasized about when I was still a guy, I suddenly realized, was no longer the type of guy I wanted in my role of woman.
For a moment, I saw Gary through the eyes of the men in the restaurant. I recovered some of that old lust, and thought about texting Gary to tell him I wanted him to walk me to the subway after all. Maybe I would bring him all the way to bed, relive the fantasies of my past. And the whole time we’re together, I would imagine those gay men who lusted after him but couldn’t have him. Those men, who used to eye me with disdain as too femme, would now envy me for being able to have not just Gary, but as many straight guys like him as I wanted.
Except I no longer wanted guys like Gary. So I let the envy of those men trail off behind me as I entered the bright fluorescent light of the subway station, walked through the turnstile, and took the train home.
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