I’ve been dating since I was fourteen, several years before my transition and before the guys I dated would see me as a woman. But even back then, I was cognizant of the way men reacted to me instantly—usually it was a cute guy in class that seemed to immediately take a liking to me. The issue was that, as a girl who didn’t present as such, I was often kept a secret, relegated to late-night phone calls and texts or one-on-one hangouts.
As I got older and the men around me became less constrained by the rigidity of small-town surroundings and conservative societal norms, I began to date them more publicly; they’d meet my friends and family and ask me to meet theirs. Still, I knew none of these partners were what I really saw for myself. Now an adult woman who still didn’t present as such, I ultimately wasn’t going out with the kind of men that I wanted. Instead, I was dating dudes on the DL—bi men who were keenly interested in the fact that my body was male and others who were in their “experimental” phase.
But I wanted to experience sex and love as a woman—ultimately, I wanted to experience everything as a woman. That would mean not dating men who were trying to repress latent homosexual desires, but dating those who were looking for a woman as a partner. I wanted to be courted properly while wearing something fabulous. I wanted autonomy.
During the pandemic, many of us thought about how we wanted to live our lives post-COVID. Trans people came out publicly and began their medical transitions. I happened to be one of them. I came out on my 30th birthday to both my friends and family. I would do the same at work the following week. And, once I’d grown my hair and had it braided in an African salon around the corner from my apartment, I decided it was time to come out in my dating life as well—to present as myself on the apps.
That’s when I realized, fairly immediately, something a certain kind of Bud Light-Boycotting member of society would hate to hear about trans dating: Men are not only open to, but actively pursuing trans women. And no, I’m not talking about the ones who saw me as some kind of novelty—I had zero interest in being an experiment or tourist attraction for dudes who were clearly fetishizing me or looking to recreate a scene from a porno. I’d suffered enough of that already, thanks.
Sure, I encountered a few of those, the ones who’d open with intrusive and inappropriate questions. (“Pre- or post-op?” Block!) But by and large, most men I connected with seemed surprisingly well-versed in being with trans women. These were people who had actual experience dating women like me and wanted more of it, guys who knew how to navigate my body. There’s a stigma that comes with dating while transgender—this idea that it somehow narrows your options or makes you less widely desirable. But as soon as I changed my photos on the apps to reflect my transitioned self, the massive uptick in engagement was instant. In fact, even the dating apps themselves, not just the men on them, were suddenly more interested in me. Raya, which I’d been on a two-year wait list for, let me in the day after I reapplied with new photos in which I presented as my female self.
Not long after the first week or two on the apps, I'd built up a roster of men I was dating regularly—and yes, they all knew about each other (thanks polyamory). There was Eli the lawyer/writer in an open marriage, Dave the finance bro who lived in a fabulous Upper East Side building and sent Uber Blacks to pick me up, and the NFL player who couldn’t keep his hands off me. Date nights became inventive and impressive, like a food crawl through Chinatown or cocktails at The Carlyle. I garnered attention everywhere I went. Finally, I was dating the way I’d always wanted to date, just like my cis girlfriends and acquaintances.
Pre-transition, I was still getting hit on and my inbox held messages from men on social media, but it always felt like I was something to be embarrassed of. That was no longer the case. Now men were taking me out to crowded, well-known restaurants, picking me up from my apartment, and shooting the breeze with my cis male roommates like a real-life version of New Girl.
I was seeing the way men treated women when they wanted them firsthand. I’d watch the ways my dates would try to impress me; flexing their biceps as I held on, walking to an enviably hard-to-get dinner reservation or the Guggenheim. I’d wake up to music in my Instagram DMs—songs that made an admirer think of me.
What really changed, though, was that these suitors were asking me to be their girlfriend—no more closeted, casual, half-hearted dating. And, eventually, one of them won me over. Nearly four years since my whirlwind dating life began, my now-boyfriend and true love of my life is everything I’d wished for. He’s classically handsome, rugged, tall (in my highest heels we still aren’t eye level; he’s 6'3"), and while I’ve seen him hoist furniture and move it around like it was nothing (*swoon*), he handles me with such grace and care. We share traditional sensibilities—he wouldn’t let me pay for our meals out for most of our first year together and I always made sure I was in lingerie and coquette-coded dresses when we were together. (Though, of course. he’d be just as happy to see me “sweatpants, hair tied, chillin’ with no makeup on.”)
I mention all of this to say that I got everything I wanted from transitioning. I live as my authentic self, the one I always pictured somewhere lounging in a man’s lap, a diaphanous dress spread out over my legs, his big arms around me while he kissed me on the forehead. In a world where you can be whatever you want, choose it and chase it.
Nicky Josephine is a writer living and loving in Brooklyn, New York. She is currently working on her first book, a collection of essays, diaristic short stories, and screenshots of real interactions.
