Trial And Error: Dating As A Transgender Woman

It comes with its own set of challenges.

It comes with its own set of challenges. is worth taking precautions when dating, and to remember that you can always stand up for yourself if there is something you don’t want to talk about, or if you sense behavior you aren’t comfortable with, or if the person you are interested in begins trying to manipulate you.

Dating is always weird. This is true regardless of gender or orientation. No matter what you do, there are always expectations and assumptions that come along with going on a date, a pre-packaged set of social givens.

One of these, for cisgender heterosexual men, is that when they decide to go on a date with a woman, they assume the woman is a cisgender female. This isn’t always the case, obviously — I’ve had the good fortune to come across a few cisgender heterosexual men who did not think it at all odd that I was transgender. I will go ahead and say that I haven’t had much success dating, and as such the bulk of this article will be about where things went wrong in a few attempts at finding love and companionship. It should go without saying that names have been altered for the sake of privacy.

Part One: Jim and Obsession

Jim was a man I’d known for about a year before I started to transition from male to female. He admitted to observing my progress and growing more and more attracted to me. I found his bashful interactions to be very endearing, and we would talk on the phone for hours — which, coincidentally, was deeply reassuring given how insecure I am about my voice and how it might sound to others. We both admitted that talking to each other gave us a deep sense of satisfaction so intense that we compared it to feeling high. Although, a few things about him bothered me, like his constant drinking and smoking, as well as a few times he mentioned having a particular interest in transgender women specifically. That’s a very complicated subject, and not one I can go into here, but it ended up foreshadowing what came next.

One day we became physical in my parents’ house, the first time that I ever had to plan around my parents’ absence over a boy. It made me long for a childhood that never was, in a complicated and deeply sad way. That night, he called me drunk and asked if I could set his friend up with one of my underage transgender male friends, someone who still looked very much like a biological female. I was speechless, and broke it off immediately, following many tears. I am extremely protective of my transgender friends, even more so about those who are still very young. That was a transgression that I could not forgive. This is where things took a downward spiral.

He started to call me every few minutes. I explicitly told him to stop calling me, and even then he kept texting and started again the next day. I eventually went to his house to retrieve something of mine; we barely looked at each other for the five seconds it took for him to open the door and hand me the cup I’d lent him. As I got into my car and began to drive away I received a text, it was from Jim. It said “Don’t blame yourself for what is about to happen.”

I admit I have never felt more terrified in my life. My mind immediately went to the worst possible scenario involving an assault of some kind. Then he sent another text, “I won’t be a bother to anyone anymore.” Cue me calling him and desperately pleading with him not to kill himself. I eventually hung up crying at his insistence that life was too hard and he couldn’t live without being around me. I simply couldn’t take it. I told my best friend, and she immediately recognized it as controlling behavior, and told me to block him out of every part of my life at once. I took her advice, and he tried to contact me from various social media accounts before I managed to block him.

I realized that both he and his friend (that he wanted to set up with my underage friend) were acting out a fetish for transgender individuals. The coincidence between the incident above and some of the things he mentioned in passing about transgender women making him feel weirdly excited, all made me realize the reality of the what our relationship would have ended up becoming. That was the end of my fling with Jim.

Part Two: Dick Pics and Tom Hiddleston’s Twin

Online dating is weirder than real life dating, simply because you don’t know who you could be dealing with, as I found out the hard way. First, I should probably make it abundantly clear how much I adore Tom Hiddleston. If you only know him from The Avengers and have not seen Crimson Peak, I would recommend you go educate yourself at once. This is important information to know about me, because on OkCupid — I came across a man who looked exactly like Tom Hiddleston. Needless to say, we chatted for a while and he seemed very sweet and kind...that is, until we started talking about sex; something he assumed I would be OK discussing in explicit detail because I am trans.

I found out that not only would it be impossible to have a non-sexual relationship with him — something that is almost a requirement for me, given the intensity of my dysphoria — but that he engaged in fetish activity that was beyond the pale for most of the BDSM community, and was medically unsafe. It was after he told me all of this, complete with links to explicit pictures that he started bemoaning how he was “a monster.” Right after I tried to cheer him up, he sent me a dick pic...unsolicited. I tried to play it cool, but started to cry nonetheless, given how much I’d hoped this would go well. It is rare to find a man I am very physically attracted to, who is also talented and seemingly kind. I blocked him from Facebook and OkCupid, given that I did not feel safe knowing even more details than I have shared so far about his appetites, and that was the end of my online fling with Tom Hiddleston’s doppelganger.

All this taught me that it is worth taking precautions when dating, and to remember that you can always stand up for yourself if there is something you don’t want to talk about, or if you sense behavior you aren’t comfortable with, or if the person you are interested in begins trying to manipulate you. I still wonder whether or not Jim truly followed through on his threat, and I often wonder if Mr. Faux Tom Hiddleston is still engaging in dangerous behavior and thinking of himself as a monster.

In the end, I have to stop thinking about all of it, because it is unhealthy to dwell on things that have gone wrong, as though they can be fixed. I learned what I could from the experiences, and have accordingly altered how I currently go about dating; but other than that, these memories stay in the past, where they belong.

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