Trans Women Dating Women

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Sex & Relationships

Janelle Villapando has been swiping left and right for years and in that time, she's noticed a few patterns among the men she meets

As a transgender woman, my relationship with online dating is complicated to say the least.

With my accounts on OkCupid, Tinder, Hinge, Coffee Meets Bagel and ChristianMingle, I am subjected to the same kind of messages from Mr. Washboard-Abs-No-Face and unsolicited dick pics that most women, unfortunately, receive. But searching for Mr. Right as a transgender woman (I was born male, but identify and present as female) adds a whole new dimension to digital dating.

Since transitioning in 2014, I haven’t reacted positively to guys who hit on me in person because I haven’t mastered the art of telling them that we have “the same parts.” For the past three years, Tinder has been my gateway into online dating as a transgender woman.

As a 22-year-old grad starting a career in fashion (and hopefully, one day, my own size-inclusive clothing line), I am drawn to guys who are funny and ambitious. There’s no bigger turn-off than someone who does the bare minimum—except maybe body odour. In terms of looks, I prefer taller guys. Being 5’9″, I still like to be able to look up to my man, literally. So, whenever I see 6’2″ or taller on a guy’s profile, it’s almost an automatic right swipe.

(Photo courtesy of Janelle Villapando)

As a trans woman on dating apps, I’ve always made sure that guys are aware that I am transgender. This avoids wasting each other’s time. There have also been many documented cases of trans women being hurt and sometimes even killed when they disclose their status to transphobic men that found them attractive, so being completely transparent is also a way of protecting myself from potentially dangerous situations.

Trans Women Dating Women

As I click, message and swipe through the world of online dating, I’ve quickly learned that there are at least three different types of guys: those who fetishize trans women, those who are curious but cautious, and those who simply don’t read. Unfortunately, these labels don’t appear on their profiles.

The guy who sees me as a fetish

I usually get very forward messages from guys who just want me for my body. They view me as exotic, a kink, something new to try.

These guys want to chill somewhere less public or exclusively at their place so they won’t be seen with me. I have actually “dated” (if you can even call it that) some of these men, including one guy who checked his apartment’s hallway to make sure his neighbours wouldn’t see me leave his place. Another guy made sure even his social media presence wasn’t linked to mine. He lied about not having an Instagram account, then when I “came across it” and liked one of his pictures in spite, he blocked me.

With these kind of guys, I’ve felt like I was their dirty little secret, and at first, I thought this type of interaction was the closest thing to a relationship I was going to have as a trans woman. But I finally reached my limit when one of my dates bumped into someone he knew when we were together. Despite the fact that we were on our third date, he didn’t even acknowledge my existence as I stood there a couple feet from him while he talked to his friend. His silence told me exactly how much I meant to him. After realizing that I deserved so much better and was wasting my time with these guys, I stopped giving them attention.

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The guy who can’t handle that I am trans

After one too many encounters with men who were fetishizing me, I started to spend time on guys who actually wanted to get to know me. These are men who find me attractive, but are initially hesitant because of my trans-ness. With these men, I went on dates in public at the movies, or a chill restaurant, and I was viewed as more than a new sexual experience—but I don’t think I was seen as potential relationship material either. One guy in particular seemed to really like me. We vibed well and there was sexual tension building during our dates. Then poof, he was gone. After a month, he reached out to me saying he couldn’t be with me because I am transgender. He was concerned about how his sexuality would “change.”

I had another similar experience on a first date where a man greeted me, hugged me, then said he left something in his car. After a couple of minutes, I got a text from him while waiting alone at our table that said he had to leave because my transgender status was giving him anxiety. After that, I stopped chasing guys who were too concerned about their feelings to even think about mine. Red flags like continually postponing dates and constantly asking, “When are you getting the surgery?” helped me whittle down the number of guys I talked to by half.

The guy who ignores the (not-so) fine print

Thanks to Tinder, profile pictures say more than a thousand words—and actual words seem to be irrelevant on our profiles. While most people only consider the profile pic before swiping right or left, for me, the text on my profile is crucial. Even since Tinder introduced more genders to choose from than just the binary male and female, it doesn’t show your gender on the swiping screen. I get plenty of matches on Tinder, but within 24 hours around half of them un-match or block me after reading my profile. Whenever I do start talking to guys who “stick around,” I make sure that they know I am transgender before meeting them.

(Screenshot courtesy of Janelle Villapando)

Trans Women Dating Women After Divorce

However, I recently went on a date with a guy who was tall, handsome, funny and had his shit (relatively) together. We met in the late afternoon and enjoyed our frozen yogurt in perfect patio weather. It was going really well! At the end of the date, our first kiss quickly turned into a handsy makeout session in the backseat of my car. Before it went further, I did my routine check of asking, “You know I’m transgender right?” expecting he was going to say yes and carry on. Instead, he looked at me with a blank face.

He started yelling that I never told him. I responded saying it was all over my OkCupid profile, which it turns out he never read. He said, “I’m bouncing; that’s f-cked up,” and jumped out of the car, spat on the ground, slammed the car door and walked away. I sat in the back seat of my car in complete shock.

In that moment, I was mostly concerned about my safety. I stayed in my back seat for probably five minutes to make sure he was gone. When I got back into the front seat to drive home, I still felt uneasy. What if he’s still around? What if he’s going to try to hurt me?

I touched up my makeup, reapplied my lipstick and put the car in drive. Once I got out of the area I started processing what had happened. I knew that it was all going too well for him to even be interested in me. Until that awkward moment, I thought, “Is this how easy dating could be if I were a cisgender woman?” I had gone from the girl that my date was kissing to someone he found disgusting all because of a single word: transgender.

Relationship status: single, but cautious

Not all guys I’ve talked to fall into these three categories. I’ve gone on dates with guys who seem to be genuinely into me and are accepting of my trans identity, but there’s no magical combination of spark, chemistry and attraction.

Trans Women Dating Women After Dating Men

I seem to only be attracted to guys who are no good for me—and I know that I’m not the only woman, trans or not, who feels that way. Since that incident with the guy in my car, I’ve slowed down my activity on dating apps. I thought about deleting all my dating apps, but it’s still my main way of meeting guys. Plus, what if the perfect guy slides into my DM, right? I haven’t lost hope, and my friends continue to encourage me. If I had a dime for every time someone said that I’ll find love when I least expect it, I’d be driving a hot pink Bugatti right now (all white interior, please). If that’s truly the case, I hope he’s 6’4″ and messages me with a cheesy pick-up line.

This article was originally published on August 16, 2017.

Related:

The First Time I Had Sex in My Correct Gender
What It’s Really Like to Be Young and Transgender in Canada
Yes, Men Get Paid More than Women…But What About Trans Women?