Dating While Trans

Dating in the 21st century is complicated and challenging. Dating as a transgender person in the 21st century is complicated, challenging, and at times downright terrifying. I think almost everyone, transgender or cisgender, fears rejection, at least on some level. Rejection for a transgender person can be accompanied by violence; verbal assault or physical assault. In fact, according to a FORGE report, 50% of transgender people have experienced sexual violence. And a review of research by Williams Institute reveals that 30%-50% of transgender people will experience intimate partner violence at some point in their life. Dating as a transgender person can be life threatening. And even when it’s not, it’s still scary.

Personally, I have experienced both emotional and physical abuse from a significant other, though it was not in reaction to me coming out as transgender. I have been lucky to receive generally positive responses from women I’ve come out to on dates. (Let me point out how screwy it is that I think I’m lucky that I was met with relatively kind reactions.) I’m also very aware that if I were a transwoman and/or a transperson of color my chances of being a victim of violence or harassment would increase.

There are lots of different ways to come out to dates. If you’re online dating, you can choose to come out before you ever meet the person in real life or come out in your dating profile. You can come out on the first date or wait for the second or third date. I have often come out on the 1st or 2nd date. I want to make sure I have a connection with the person, because if I am not going to continue seeing them, then I don’t need to sweat the anxiety over how they’ll react. The difficult part is that there really is no natural way to slip it into a conversation. And a lot of early dating topics can require creative answers if I don’t want to come out in my answer. Even the classic question about careers can lead to awkward situations, if I’m not ready to come out.

            Her (within 5 minutes of us meeting): What do you do for work?

     Me: (Should I just say I work at the local LGBT center? What if she asks follow up          questions?) I work at a local nonprofit. What do you do? (Please don’t ask me                more questions.)

    Her: What nonprofit?

    Me: (well, here we go) The LGBT center in town.

    Her: Wait. Are you gay?

    Me: (Oh my—is she serious? That’s the conclusion she jumps to. I’m on a date with         her and she thinks my job means I’m gay?) Um, no. I’m not…are you? (Wait, what           did I just say? Why did I say that? Smooth move.)

   Her: Noooo…and are you sure?

   Me: Pretty sure. (Okay, I’m ready to go.)

Now, I acknowledge that I could have cut the confusion by explaining that my interest in advocating for the LGBTQ community was the T not the G, but something told me that if she couldn’t fathom a guy having any reason to work at an LGBT center unless he was gay, she wouldn’t handle me being transgender well. I did not come out to her on that date and there were no future dates.

Another subject that can quickly get awkward navigating is when dates want to ask questions about growing up. I went on a date with a woman I had met online—the site said we were an 85% match, so I was hopeful that she was progressive. Halfway through dinner she asked me if I had played sports in high school and without thinking I said “No—I mean I tried out for the basketball team but I got cut.” She looked at me confused, “Aren’t you a little short to play basketball?” I had forgotten that she wouldn’t have known that in high school I would have actually been trying out for the women’s team. And while yes, I’m still short to play women’s basketball, it wasn’t as much of a reach. I smiled awkwardly and replied, “Probably why I got cut.” She nodded, signaling to me that my story checked out. I asked her if she played sports and she replied “No, I went with theater and performed in school plays. I’m a total theater nerd!” Before I could contain my excitement I exclaimed “Me too!” and watched a piece of pasta fly out of my mouth in her direction. Horrified I watched it soar in slow motion and then it disappeared. Oh no, had it landed on her!? Did it disappear in her open smiling mouth? She didn’t seem to react, so I left it alone.

She inquired what plays and roles I had performed. I didn’t know how to get out of this one. The majority of the roles I had played were female roles, because in high school I hadn’t come out as trans yet. “I played Boy George once. And I was the bellhop in Lend Me a Tenor.” I let my answer trail off. “What was your favorite role to play?” I added to move the spotlight off of me before I started telling her about playing Gretel and a drunk grandma and Tinkerbell. She started telling me about playing Mrs. Pot in Beauty and the Beast.

I ended up seeing her again. I chose to come out to her on our second date because I felt a connection and wanted to keep seeing her, but I didn’t want to waste either of our time if me being transgender was going to be a deal breaker for her. “I should probably tell you something about myself.” I started. She looked like I was about to tell her that I was a werewolf. Maybe I could have used a softer introduction. “I’m transgender, I was assigned female at birth but I identify as a man. I wanted to tell you now because I like you and would like to see you again, but don’t want to waste either of our time if this is a deal breaker for you.” She looked at me without saying anything. Which provided enough time for me to jump to the worst of conclusions. Then she broke her silence, “Thank you for sharing that with me. Your honesty is impressive and an attractive quality. Though, that’s a lot to take in. Not bad, just a lot because it’s different than what I’ve imagined or been able to see for myself. I might need to sit with it for awhile.” She did and she concluded that it was too big of a curveball for her and was as polite as someone can be when delivering that news.

Some other gems of immediate reactions from women I’ve told on dates include:

  • “Oh my gawd! That’s why you’re so pretty. I thought you were too pretty to be a regular guy.” (we did not go on any more dates. I actually got the waiter’s attention and mouthed “Check please.”)
  • “That’s so cool!” Then she high-fived me.
  • “You’re that Jay!”
  • “Wait, were you GQ Joe?” GQ Joe was my drag king persona before I transitioned, so yes, I was GQ Joe.
  • “Okay, but do you want to split a dessert or each get our own?” We each got our own AND shared.

Dating is complicated. Dating while trans adds another layer or two of complications. Rejection is scary on its own but the addition of being trans makes the fear of rejection even scarier because you can’t control people’s reactions. Dating while trans involves a lot of unknowns, but one thing is for sure, it’s an act of brave self-love and resistance to the world that says we aren’t worthy of love just because we’re trans. No matter what anyone says, trans people deserve love. We deserve to experience all the awkward, fun, cringe-worthy, exciting, infuriating, exciting, and blog-worthy dating stories that any cisgender person experiences.


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