The Transgender Dating Dilemma
Trans women are taught to feel grateful for any scrap of affection we receive. I’m relegated to the role of teacher and therapist in my dating life — and too often, I fear for my safety.
“I have to tell you something,” I said. He looked at me, eyes narrowing. We’d just met, so I can only imagine the infinite possibilities swirling in his head. He had just moved to Atlanta from Chicago and had this whole stereotypical macho thing about him. He was an amateur MMA fighter, came from the hood — apparently a former gang member, as I learned later.
It wasn’t that he necessarily made me feel threatened, but I knew the statistics. I knew about girls like me. We’re the ones who guys love in the dark. We’re the dirty little secrets who get calls only after hours. No matter how beautiful, intelligent, or successful, we are the ones who have to settle for being nothing more than receptacles for men’s desires and insecurities.
I imagined the worst, but I said it anyway. “I’m a transgender woman.” I emphasized the woman part. That didn’t stop the intense expression of confusion that spread across his face.
“So you’re a man?” he asked. “Do you know how lucky you are that I’m not, like, crazy? Because I know plenty of guys who would really do some shit to you.”
“No, I’m a woman, a transgender woman,” I answered, trying to make him understand.
But I knew it didn’t matter what I said. His entire view of me had changed and there was no going back.
I vowed as I left his place in the middle of the night that I would never put myself in that dangerous of a situation again. And even though I now make sure people know my identity before I’m alone with a potential partner, there are still some aspects of this interaction that seem to show up in my dating life no matter how many precautions I take.
Despite one pervasive misconception that transgender people transition for the approval or acceptance of future sexual partners, when I transitioned there was nothing about the forthcoming experience that assured me I would be seen as desirable. I didn’t know if I’d ever have the chance to be loved. I thought, Who will want you?
Dating is hard for most people. But when you’re trans, it’s hard in a completely different way. It’s all too easy to internalize the assumptions that we are rudimentary facsimiles of the people we actually want to be, or that we take on a lifestyle that’s all about mutilating our “God-given, natural” bodies. Being a person of color that floats between the queer world and the straight world adds all the more pressure. I constantly have to juggle other people’s hangups around gender, sexuality, and race simultaneously.
I’m surprised at how often I encounter people — typically cisgender men — who don’t understand what transgender means, even in a world where Caitlyn Jenner and Laverne Cox make headlines. Despite the slowly turning tides, dealing with these potential partners is difficult because I often have to serve as both a therapist and a teacher.
Like with this one guy — we’ll call him J. He was very much interested in me, but it took a few months for him to admit the full extent. He was pretty homophobic and transphobic when I originally met him, which he attributed to his upbringing. He was a black guy, of Jamaican descent, and he often explained that coming from a single-mother household put more pressure on him to be a certain kind of man.
Though we had a ton of chemistry, he couldn’t understand the ways in which he constantly invalidated my identity. And, to be clear, I don’t need constant validation of my womanhood, but I do need respect — which J wasn’t prepared to give. He made jokes about me and how I “used to be a man,” criticized my writing and activism, and even — the grand offense — used my birth name during arguments. It all got to be too much for me.
Having to constantly define and explain myself is both exhausting and unfair. I feel like I have to share my entire life story early on — a situation in dating that we’re often told to avoid at the risk of being too overwhelming. After a number of dates and situations not too unlike the interaction with the MMA fighter, I had to take a serious look at the risk involved with not disclosing my trans status. I found early disclosure necessary because we live in a world where trans panic is still justification for devaluing and even harming trans women.
So far this year, at least 18 trans women have been killed in the U.S., while countless others have been attacked or have attempted suicide. We rarely discuss the fact that often trans women are killed at the hands of their lovers or romantic or sexual partners, like Ty Underwood, a black trans woman, who was allegedly shot and murdered by a man she’d briefly been dating. Just a week or so later, Yazmin Vash Payne suffered a similar fate in an apparent stabbing by her live-in boyfriend.
A little under a year from now, I’ll be the same age as 25-year-old India Clarke, a recent victim of trans killings. One of my biggest fears is becoming another murder statistic: someone for the media to posthumously misgender, leading the public to believe that I somehow deserved to have my life taken away.
In the wake of these tragedies, I try to to nix my own feelings of dread and shame as soon as I meet a person. Now I typically come out via text message or on my online profiles. It’s not very personal, but it lessens the possibility of a more life-threatening situation.
Sometimes the response has been positive. A few people — both men and women — have had a sense I was trans before I even told them. Other times, potential partners seemed to feel pity for me and quietly congratulated themselves for deigning to date me; I’ve had to check the value I’ve placed on cis people who dared to consider me worthy of their attraction. Still other times, the response — particularly from cis men — has been overwhelmingly negative: “If I had known, I never would have wasted my time” or “How could you think I’d be interested in that?” or the misguided “I’m not gay.”
These misconceptions don’t just negatively affect the trans women involved. Laverne Cox has discussed the stigma around men who love trans women. Though I don’t necessarily agree that they are more stigmatized than the actual trans women they’re involved with, I do know that they deal with their own specific struggle.
When information that rapper Tyga was caught in a scandal with transgender model Mia Isabella, for instance, social media had a field day. Given his presence in the hypermasculine world of hip-hop, that moment highlighted the deep-rooted issues our society has with men being attracted to trans women. Trans women continue to be misgendered and misrepresented as “men in dresses” — so when men love us, there is a concern for their (potentially) complicated sexual identity.
Many straight men continue to think their attraction to trans women means they’re gay (or, they think they can’t be attracted to trans women because they insist they aren’t gay). But in reality, people are attracted to a person before they even know what genitalia they have. Most cisgender people don’t walk around actively looking for a specific set or kind of genitalia — they just happen to typically be interested in, and start dating, people who have the kind that they’re accustomed to. By extension, cisgender straight men who are attracted to trans women are attracted to them because trans women are women. When we conflate gender and sex, it’s damaging to all of us.
Early on I had this whole idea — as many trans folks do — that if you just let a potential partner get to know you, then the fact that you’re trans would just fade away. And sometimes that’s the case, for sure. Often, it’s not. Most commonly, there’s this lofty mountain of stigma and shame to climb with a person before there’s even a glimmer of a chance of true connection.
Conditional passing privilege has typically played in my favor. Living up to conventional cisnormative beauty standards has given me more social access to potential partners than many other trans people have had. There are definitely guys who encounter me who express at least being open to talking to me further. They’ll say, “Wow, you don’t look like any trans woman I’ve ever seen” or “Well, you’re still pretty, though.” I’d be lying if I didn’t admit that, on some level, these comments make me feel good — but when I think about the narrow box I have to crouch inside in order to be desired and loved, it doesn’t make me feel good at all.
It might seem like I’d find more success if I avoided the straight dating world, but dating isn’t easy in queer spaces either. There are definitely queer people (both cis and trans) who openly aren’t interested in trans women — or they claim to be for political or social clout, but don’t actively pursue us.
Queer women’s circles are particularly plagued by transmisogyny. Being a “gold star lesbian” means never having had sex with a man or with a penis — that status is viewed as an achievement. Lesbians have to have a certain body, and only have sex with certain bodies, in order to be the “best” queer women — which doesn’t only shame trans women, but also shames the women who have loved them.
Both queer and straight people who refuse to date trans people rely upon the argument that everyone is allowed to prefer certain sets of genitalia. Sure, everyone is entitled to sexual preference, but it’s reckless to categorically dismiss all trans women under this premise. As a society, we should all urge each other to consider why these preferences exist, particularly with regard to trans people.
When I hear that someone doesn’t want to have sex with a trans woman because of her penis — say, a lesbian who wants to maintain her gold star status or a straight man who insists he isn’t “gay” — I hear assumptions about how that sex would play out. Many trans women who have penises are not interested in acknowledging that body part during sex, and there are many ways to be respectful of that. Trans women don’t all have the same genital configuration or surgical history, either — our bodies are all different. When it comes to queer women’s culture, in particular, many lesbians misguidedly deal with trauma from the patriarchy by attacking essentialist notions of manhood. But the penis is not an essential element of manhood — it can beautifully and comfortably coexist with womanhood in one body.
Just as I would push someone who categorically dismisses potential partners based on race to consider where those “preferences”come from, I’d encourage self-reflection from anyone who automatically writes off all trans people.
I’ve had conversations with people over the years who suggest I just pursue the kinds of people who are particularly interested in trans women. Many of them are what we call “chasers.” While there are plenty of people who are capable of valuing a trans woman in her totality, many others value only the sexual element of their potential relationships with us. Trans chasers are often guided in their desire by the porn industry, trans oversexualization in the media, and the long history of trans women being relegated to sex work. Regardless of whether a trans woman exists in one of these realms or not, she deserves to be considered as more than a living, breathing sex toy.
I’ve encountered a few chasers, and the experience is almost always the same. They love to ask questions about your genitalia, and they assume that you have a penis you’re willing to use. There’s very little regard for the very real issue of dysphoria that many trans people experience. Cisheterosexual couples who proposition trans women to be their “special unicorn” in the sack are not uncommon. Now, I’m certainly not against threesomes — but grappling with the fact that you’re an accessory to someone’s experience because of your body is intense.
Then there are the “experimenters.” The ones who say, “I’ve never been with a girl like you, but I’ve always wanted to.” I knew one guy who hoped to hook up with me as his first-time fetish, but when we discussed if he’d ever seriously date a trans woman, it was a whole different story. He had no problem having sex with or hanging out with a trans woman, but didn’t really see their value as actual partners. Aside from worrying about what his family and friends would think, he had decided that since trans women couldn’t have children, he didn’t want to date one. I’ve always found it difficult to believe these kinds of men would treat cis women the same way if they were unable to birth children.
Though it may seem like dating as a trans woman involves nothing but tragedy and heartache, that’s not always the case. Even in the last year, I’m finding more potential partners who value me for me and not for their preconceived stereotypes. Now dating is starting to be more about general compatibility than about what may or may not be in my pants.
One guy I dated for a few months actually did a lot of work to get over his hangups. We argued a lot, but in time he was able to understand some of the finer points about gender identity and sexual orientation. On one date, we went to a bookstore and he surprised me by picking up Janet Mock’s Redefining Realness and reading it from cover to cover. He came back asking questions to prove just how much he’d changed since when we first met. It’s people like him — those willing to learn — who give me hope.
It helps that so many trans people are coming out from the dark and letting their skin soak up the sun. Now there are actually models for trans people in healthy relationships who are working to reverse the narrative that we’re unlovable. The world is seeing our fully realized selves and society is realizing that trans people are not cut from a monolithic cloth. We are just as diverse as any other population.
And not to cause mass trans hysteria, but for anyone who might have thought otherwise: Trans people can go anywhere a cis person can go. We’re everywhere. That trans person you just met, who you might be attracted to, probably has a rich and interesting story, as well as a unique and enlightening view of the world. They’ve probably trekked through an intense journey of self-discovery that shouldn’t be downplayed or outright dismissed.
In time, I imagine we’ll see a world that overwhelmingly values our authenticity and strikes down the xenophobic shame it throws onto us and those who love us. If we continue to empower trans people, we will also empower humanity as a whole. No one should have to live or love in the dark.