The Transgender Woman’s Field Guide to Dating

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STYLECASTER | A Dating Guide for Trans Women
Photo: Allison Kahler

Dating is tough for everyone, but dating as a transgender woman is even harder. I’ve been on more dates than I can count. Starting from the early stages of my transition at age 15, through sexual reassignment surgery at 19, to being an out and proud transgender woman at 24—I can say with certainty that I’ve gone out with pretty much every personality type.

Some of my most entertaining stories have come from my dating chronicles, but so have some of my worst. Through these experiences, both hot and not, I’ve found there are four main types of guys I run into, being an out transgender woman. They go as follows:

The Unaccepting Guy

Profile: This guy is most likely a Republican or comes from a conservative-leaning family.

The Encounter

We were three dates in, and for first time in years, I was starting to really like someone. One night, we were out dancing in Hollywood and stepped outside to catch some air. I was leaning against the wall, close enough that I could play with the necklace hidden in his shirt. I expressed relief that it wasn’t a cross (a red flag of someone with a more conservative background), and he told me that his father was conservative and voted for Trump, and while he himself didn’t vote, he hated Hillary Clinton. I could tell he was uncomfortable talking about politics, but as someone who needs to protect themselves from the get-go, I pressed him on his personal views. He admitted to being financially conservative and otherwise liberal. I asked, “What about LGBT rights?” He replied, “What’s that?”

Shocked, I said, “Lesbian Gay Bisexual Transgender.” His response: “Oh, I’m fine with everything but the T.” My face dropped. I asked why he had an issue with the “T.” He said, “I just don’t believe you can be a man one day and then a woman the next, you either have XY or XX chromosomes and that’s it.” Until that moment, I wasn’t sure if he knew I was transgender, and that’s when I dropped the bomb. His mouth agape, he backed away and said, “But we kissed! Oh my god, I have a fear about this happening, you should have told me.”

I went on to tell him my entire story, including how abnormally normal my life has been as a transgender woman. At one point, he got confused during my explanation of the gender spectrum and thought I was hermaphrodite, which he would have been okay with because in that case, ”I couldn’t help it.”  The conversation ended when I said, “I don’t need to explain myself to you. I want someone who likes me even more because of the courage I had as a young teen.” His rebuttal: “Well, for the next guy you should probably tell him first.” I walked away.

Frustrated, I met up with a new but great friend of mine who was nearby, spewing, “Here I am, opening up and sharing my story for the world, so that I can change how our society perceives transgender people, and I couldn’t change the mind of someone I have a genuine attraction and connection with.” My friend said, “Corey, that boy will never look at transgender people the same after tonight. He is going to go home and think on this and whether you know it or not, you have changed how he views a transgender person—at least, a transgender woman.”

The Takeaway

Initially, I felt defeated. I needed my friend’s words to realize that even though I didn’t visibly change his ideals in front of my eyes, I did make an impact and he’ll never see trans women the same way. A few days later, I went on a hike with a dear friend. After telling her the story, she said, “Every single person you meet or come in contact with, you change their perception. By being your genuine self, I’ve watched even the shortest interactions between you and a new person change the way they think about a transgender person.”

It was another reminder of how far I’ve come and the accomplishments I’ve already made. I don’t blame these types of guys who didn’t receive the proper education or weren’t given the resources to be accepting of non-binary people. When meeting these men, remind yourself that they’re not the one for you, and it has nothing to do with you doing anything wrong—it’s just about their own ignorance. 

MORE: Why We Need to Fight to Destigmatize Transgender Beauty Standards Now

The Semi-Accepting Guy

Profile: This man respects me and may admit attraction, but isn’t able to overcome the perceived or feared oddities of what it would be like to be with a trans woman.

The Encounter

Right after I brushed off the conservative guy, in walked another dreamboat. At 6’8,” he was smart, funny, ambitious, well-rounded, and had overcome a struggle of his own. After meeting twice, we went on what was supposed to be a quick coffee and hiking date. Instead, our effortless connection led to a two-hour breakfast, long hike, and two-hour dinner in one day. I even opened up to him about my fear of men dating me to “see what it’s like” to be with a trans woman.

At some point during our hike, he expressed that he was extremely attracted to me, and in some ways scared to like me. He told me he was trying his hardest to restrain himself from kissing me for a few reasons. The first is that he was scared we’d have such a strong bond that we’d become a couple. The second is that if it didn’t work in the bedroom and he didn’t want to see me again, he wouldn’t want me to think, after sex, that he was using me as a science experiment. He asked my permission to take a day to think about us moving forward.

After much thought, our conversation for closure came down to two things: His mother and friends would accept me, but his Serbian father never would; and he was afraid of experiencing me sexually. He told me if I hadn’t been open and honest with him (which he was thankful for regardless) that he wouldn’t have cared, but because he already knew, he wasn’t willing to look past it.

The Takeaway

With this type of guy, I tend to go into education mode and talk about the normalcy of my hand-crafted vulva. Their concerns usually include what their friends and family would say, how they’d react to me, what it means for his sexuality, and difficulties comprehending the idea of a sexual encounter with me. All these fears show that he simply isn’t the right one for me. In this situation, I remind myself that I want someone who doesn’t need to take time to think , but is willing to move forward based on our innate chemistry and attraction. This leads to man number three.

MORE: How Fashion Helped Me Figure out Who I Am as a Trans Woman

The Over-Accepting Guy

Profile: This guy either has a fetish for trans women, prefers them over cis women (i.e. people who identify as the sex they were born with) for varied reasons, or has slept with one either without knowing or for the one-time experience.

The Encounter

I’ve been getting to know a work colleague. He’s the bad boy my mom definitely does not want me dating. Even with tattoos everywhere, I’ve learned he’s rough on the outside but sensitive on the inside. After almost two months of playing coy, we finally went on a date. We decided to act like a couple for the evening, holding hands on the sidewalk and over dinner. During our night together, we had one of our deep conversations. He asked me about being trans, something I really wasn’t sure if he had picked up on or not.

He told me, “I’ve seen your hashtags—of course I knew, but I wanted you to tell me.” Having an irregular past of his own, he opened up to me about a night where he was on hard drugs in a hotel room. His friend invited over two prostitute friends of theirs, and those two girls each brought another sex-worker friend, one of whom was a pre-operative trans woman, whom he proceeded to have sex with while high on heroine.

Situations like this turn me off. I don’t like knowing I wouldn’t be a man’s first sexual transgender experience. Because I feel so feminine and identify as a woman before identifying as transgender, so I tend to want to be every guy’s first.

The Takeaway

I don’t want to throw myself at a guy just because he’s okay with dating transgender women. In part, my instant reduction of attraction towards this guy stems from skepticism about why they want to pursue things with a trans woman. When I transitioned, transgenderism was not discussed in mainstream media, and men attracted to trans women were either ill-intentioned, harmful, or ostracized.  There are men who seek out trans women to fulfill a kink or fetish, and I’ve also been out with guys who simply prefer transgender women for reasons I’m not sure of. There are circumstances where I can get over not being a man’s first transgender date, like the guy I work with. I understood that he wasn’t in his typical mindset and have looked past it.

Unless you feel compatible with this type of kinky partner, please do not feel the need to entertain their sexual desires or their objectifying you. You’re not a societal experiment; you’re a human being who deserves to be with someone who accepts you for the entire person you are, not one aspect that helps to define you. This brings me to the ideal man.

MORE: What to Do When You’re Dating a Guy Who’s Seriously Hung

The Unicorn

Profile: This guy is respectful, interested in learning more, forward-thinking, and has a progressive attitude.

The Encounter

My ex is one of these rare species of men. I’ll save the full tale for another time, but the abbreviated version is that we were perfect for one another, but met at the wrong time. If he and I met or rekindled our relationship a year from now, things would be different. It was a mature relationship at an age where we had much to learn. We were each other’s first serious partner, both friends and lovers, and mutually felt we were each other’s perfect person. We broke up with the hopes of being together again someday, if and when we were in the same city at the same time.

After college graduation, he lived in the DC area, and I lived in New York. After our breakup, I told him over the phone during our final goodbye that I was transgender, to which he said, “That doesn’t change anything for me.” I asked if we had still been dating, whether he would care. “I’m not sure. I can’t go back and put myself in the situation, but it doesn’t change how I think of you or our relationship,” he said.

This man was intelligent, sexy, kind, caring, selfless, athletic, social, calm, sweet, sensitive, and the most beautiful person inside and out that I’ve experienced. I fell in the love with his being, his soul, the person that he was, and I know he felt the same. He once told me, “You know me better than I know myself. I know you’re the best possible person for me, but right now, we can’t be together.”  We both needed to live our lives, travel, and experience highs and lows separate from one another. He’s so logical, that even during our breakup I couldn’t be mad at him. I wish, at times, that he cared enough to not let me go completely, but I am thankful for it now. I’ve learned to love myself, even at my loneliest.

The Takeaway

This type of guy exists, and I am so lucky to have met and experienced one of these rare “unicorns.” For a transgender woman, that blessing is few and far between. This is the man I look for when I consider any potential prospect. All trans women looking to date a cisgender man should look out for this type of gentleman.

Having the opportunity to date men I’m attracted to is humbling. I know I’m blessed with an abnormally normal life for a transgender person during this time in history. I hope this gives a glimpse into a transgender woman’s dating life, as well as insight for transgender women who are out there doing the same. I am reminded that I do not need to rely on any man to feel whole. Between these men and dating ruts, I’ve become fun and carefree again, and for now I’m focusing on loving myself completely, and taking in the smaller accomplishments I make everyday as an out transgender woman.

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