The First Time I Told A Date I Was Trans, This Is What Happened
After three-and-a-half years of being in a relationship, I found myself single again when I was 25. Heartbroken, alone, and terrified of dating. My mind would race with all the thoughts of having to explain my transition to another person with walls-down honesty. To try to open myself up to someone after building years of trust. I didn’t know if I could do it again. I spent eight months pretending I was too good for commitment, throwing myself into new friendships, and making some questionable decisions along the way. I learned a lot about myself and I thought after being single for a while that I was ready to get back out there.
I was terrified because, frankly, I knew NOTHING about really going out on dates. This was the first time I had been single since college. My dating life often feels like it's caught between two worlds: one is filled with a community of queer folks who cannot see me because I pass; in the other, a world of cis, I'm surrounded by a world of straight folks who do not understand me. It almost feels like being stuck in queer purgatory.
I had no time to go out and meet people, so I figured I would start where everyone starts: dating apps. I meticulously picked photos, wrote a bio, and dreamed up a perfect opening line. I always thought of myself as a direct person, so I decided to put on my profile that I was a trans man. Because I had never been worried about people knowing I’m trans, why start now?
Well I swiped and swiped and swiped and swiped and then waited and NOTHING. Not a single match. It was really an ego kill. I mean, I’m not People magazine’s Sexiest Man Alive (lookin’ at you, Blake Shelton), but I didn’t think I was hideous. I was curious as to what women thought when they saw “trans man” in my profile. I decided to take it off as an experiment — not to trick or to lie, but to see if doing so opened me up to meeting more people.
And then I matched with Emily*. She was cute and holding a beer in her picture. I wanted to make a good first impression, so I obviously started our conversation with a Broad City gif.
“Tell me about the cat in your picture,” she wrote back. It felt like a good sign. We exchanged numbers and she gushed over how cute my cat was. We were both sarcastic, love bourbon, and I geekily told her about my favorite band, The Head and the Heart, and why everyone should be listening to them.
We texted for a few days and I started to feel good about trying to date again. I suggested we go to this cool bourbon distillery that she had mentioned in an earlier conversation. She enthusiastically agreed. Was it really that easy? It was a date. My first date after my break up. I was so excited until a friend asked, “Does she know you’re trans?”
She didn’t. This was the first time I was faced with having to tell someone that I’m trans before going out with them. When I dated in college, people knew I was trans. I didn't have to "come out" to potential new partners. I kept going back and forth about whether or not I should tell her before the date, during, or after it had ended. I didn’t know the rules. Are there even rules to this? I didn’t know why I was so nervous. I had come out hundreds of times at this point, so why did I care this time around?
After a night of liquid courage, I texted her asking if me being trans was a problem. I waited what felt like hours (but was probably really only 10 minutes or so) for her to respond. That’s when it got weird. “Thanks for being honest,” she said, “In all honesty I don’t know if I can make any promises about my intentions at this point moving forward. Does that make sense? I just want to be honest with you, too.” I felt like my throat dropped into my stomach. I thought that was going to be the end of it, until she followed up with, “Does this mean you don’t want to go on the date?”
I thought it was important for me to put myself back out there. I told her I’d still like to go out. I took her to the bourbon distillery, thinking there would be many people on the tour — but it ended up being literally just the two of us. I was trying hard to focus on having a good time, but not even the bourbon could calm my nerves. I was hyper-aware of how I was presenting myself. We made pleasant conversation about where we work, what we like to do for fun. After two hours of sitting in this small distillery, she told me she needed to go to meet up with her parents. I walked her to her car and said something along the lines of, "We should hang out again." She smiled and agreed. We hugged and parted ways.
When I tried to set up another date, I was ghosted. It left me feeling upset. First of all, no one likes to be ghosted. We’re all adults, why can’t we just say when we’re not interested? I wasn't broken up about Emily, though. I barely knew her. I was broken up because before I told her that I was trans, she acted like she really liked me. After, it was as if a switch flipped. Like I was no longer desirable. It was not because of the way I dress or difference of political opinions or even because I’m mean. It was because of who I am. Something I have zero control over. I was so consumed with her liking me and trying to prove to her that I’m just a guy that I lost sight of myself. I sold myself out just for one stupid date.
It messed with my head for a couple of weeks. Dating now, compared to dating four years ago, is so different and difficult. Every time I tell a potential new date I’m trans, I have to brace for disappointment. I have to argue with myself all the time over when I think it's the right time to tell people I'm trans. Do I do it right away, but risk being too intense? Do I wait and risk wasting my time or potentially starting to like someone only to discover they aren't OK with dating a trans guy?
I wish I knew the answer. I wish I could say any of this is easy, but I know in my heart that I really don't want to be with someone who isn't comfortable with me being trans or thinks my identity is a deal breaker. I want to be with someone who celebrates who I am. I want to be with someone who sees me.