Dating When You’re Trans

Stories, Social, Community + AlliesJames Gardner
Imagery by Rebecca Lieberman

Imagery by Rebecca Lieberman

by James Gardner

Dating is the worst. Part of me is tempted to say this is universal—that everyone kind of hates it. But maybe not. In any case, dating has sucked for me.

Looking back, it seems dating was much easier when I was a cis-gendered female, rather than it is now that I am an out trans guy. Of course, I didn’t self-identify as a woman inside—so that part wasn’t easy. But there’s no denying that the dating part itself presented fewer challenges as a cis-gendered person.

The more I sit with this realization, the more I am convinced that a huge element of the challenge came from the fact that dating sites and other social media groups geared toward dating just aren't that “user-friendly” for trans people.

In my case (and perhaps for many trans folks), going online for potential romance felt like a safe first step in cultivating my new, authentic self—in being able to reach out to others as the man that I was and am. Plus, since I live in a small community, there aren’t many opportunities to date and less of a selection of potential partners.

And yet, the basic tools given to you by most dating sites don’t leave much room for personalization. Most sites allow you to choose between only two genders, male and female. Furthermore, there tends not to be much flexibility when it comes to stating your sexual orientation. Since I identify as a trans male, and my sexual preference is for females, I have been left with only one option in the online dating world: heterosexual.

My foray into the dating world began a couple of years ago while I was still fairly early in my transition. After I came out as trans (FTM), my lesbian relationship was ending, and my first instinct was to stick mainly to gay and lesbian dating sites. Perhaps this was out of a desire to meet and connect with people in the queer community; perhaps it was because I wasn’t totally comfortable identifying as heterosexual, despite the fact that I was a man and was attracted to women.

A little later on in my transition, once I began presenting as male, I set up profiles on two mainstream dating sites, one listing myself as male without stating that I was trans, and the other listing my trans status.

Some people I have spoken with say they think it’s important to disclose that you’re trans right away, while about an equal number of others say it’s better to wait to see if there is any chemistry before sharing such personal information. I tend to agree with the latter. So that’s what I did.

A few months after posting my profiles to both sites, I received a message on the site where I hadn’t disclosed that I was trans. I made a plan to meet the woman I’d been messaging with for a coffee date.

Truth be told, there were no immediate sparks when we met up at our local coffee shop. But we had pleasant enough conversation, and got along.  Our mutually neutral reaction to one another must’ve had some promise, as we planned to go on another date the following weekend.

But on the day of the date I received an angry text.

“When were you going to tell me you are trans?”

She told me she had Googled me. My work in the media and a couple of published articles must have tipped her off. The irony, of course, was that my trans identity was not really something I was trying to keep hidden—from her, or from anyone. We’d just met and were feeling out the situation and our interest in one another, the same way any two people do after a first date. But obviously, the woman felt duped in some way, and she continued with her tirade.

“You tricked me,” she said.

And, while I felt no need to explain myself, I replied.

“My status as a trans person is my personal business, and I feel no need to have to explain it to strangers. I was waiting until we had gotten to know each other better.”

Then she pulled out “the big guns,” or perhaps I should say “gun.”

“Well, I like sex!”

“Yeah…so?” I replied

“Well, you don’t have a cock!”

OK, now she had touched a nerve. Now I really felt the need to explain myself.

“Firstly, you are making assumptions about what I have or don’t have in my pants, which is none of your business, just as I would not ask you if you have a vagina. Secondly, if you think sex is purely genital-to-genital, I feel sorry for you!”

Some of you may find this shocking, but sadly, this kind of gender (and genitalia) policing happens to many transgender people who simply want to go out, have a fun time and meet people.

After this notable dating disaster, I went on other dates that didn’t go as badly; but quite honestly, many people are not as open-minded as they’d like to believe. I recall planning a couple of potential dates in which the person explicitly acknowledged being comfortable about meeting a trans person, and then would politely back out before the date even happened.

But my attitude about dating has become more hopeful, as I’ve gotten more comfortable in my body, and used to making decisions that feel supportive to myself. This June, for instance, I attended the Philadelphia Trans Health Conference for the first time. I planned to meet up with some trans guys who were members of a Facebook page I belonged to. I had not met any of them, but we are a very tight-knit group online, and I was excited about meeting.  I had also planned a date with a woman I had also met via Facebook, in a group for FTMs, butches and femmes. We had been flirting on Facebook for about a year and agreed that if either of us was ever traveling close enough to the other, we would meet. She drove down from New York and we had an enjoyable dinner in Philadelphia.  

There were definitely sparks flying, but she explained that she was just getting over a very difficult relationship and needed time to heal. I was disappointed, but understood. We both agreed it was not our time and that there might be potential for some kind of connection at some point in the future.

However, as I write this, it seems the tides may be turning in my favor. Just weeks ago, I received a message from a local woman on the dating site where I had revealed my trans status. Short on words, the post simply read, “Hi.” I admit, I balked. As a writer, I guess I expect others to be able to write as freely and easily as I do. But instinct guided me to respond.

We agreed to meet at a nearby pub for some eats and to sample some of the local craft beer. Surprisingly, we had both recommended the same place.

As we eased into conversation, she revealed that she was aware of my trans status from my profile, and while she had previously dated women and been married to a man, she wanted to get back to her “Queer roots.”  As we talked, we discovered that we shared some history in the Queer community. She had lived in the city where I had grown up, and was very active in the lesbian community there (which I had been active in years ago). I felt very comfortable with her, and after two hours together we agreed we would like to see each other again

We went on a second date and all is good so far. I am happy, I feel understood and accepted by this person and I am very hopeful that this relationship will continue to blossom.

I guess my dating advice is the same for trans folks as for anyone else. Have faith. We are all worthy of and deserve love in our lives. There is someone out there for us. There’s no denying that trans folks don’t have it as easy because of widespread ignorance and discrimination—and it’s true that we’re most vulnerable in the context of sex and relationships. But there are people out there who understand, who have open minds, and who will see you for you. Not because your gender identity aligns with your genitalia, not because of your bank account, not because of your job or the size of your home. There is power in patience.


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James is a newscaster in British Columbia who made a very public transition while working at a radio station in Victoria. He simply signed on one day as James. When listeners asked what happened to Sheila they were told that Sheila is now James. James says the support he received was overwhelmingly positive. You can learn more about James at the