I’m a cis guy looking to date a trans woman. How do I start?

Dear Kai,

I’m a 55-year-old “mostly” straight guy who’s always been into trans women and sometimes very feminine men, as well as biological women. I’ve stayed on the edges of the LGBTQ2 community for a long, long time trying to figure myself out, and I’ve come to realize that what I really want is to date a transgender woman. I think T-girls are absolutely wonderful, because they are the best of both worlds—male and female all in one! But I have no idea where to find a transgender lady who is looking for love with someone like me.

I’ve seen trans escorts, which has been a mixed experience. I don’t find most of them very sincere or accommodating—and even if they are, things still always feel transactional. I want a real relationship. I’ve also tried to date some trans women I’ve met online, but it seems like most who are on dating apps are too young for me, and some have called me a “chaser” and other nasty names. All I want is a T-girl to love that I can be proud of—is that so wrong? What’s a transamorous guy to do? Am I doomed to be lonely forever?

Transamorous Torontonian

Dear TaT,

I want to begin by telling you that you are right about one thing: There is absolutely nothing wrong with dating and loving trans women. In a world where trans women have historically been hidden, shamed and even killed by men who refuse to admit their attraction to us, there is great beauty and power in the simple act of loving us out loud. So thank you for your courage and willingness to do that.

Congratulations as well on coming into a deeper understanding of your sexuality and romantic desires; this is not an easy thing to do at any age. Transamorous (sometimes also called trans-attracted) straight men in particular tend to be invisibilized, or even pathologized—even in liberal social circles that have started to accept and celebrate homosexuality as part of the mainstream.

That said, this is the part where I have to get a little challenging, because I think it’s worth saying that it seems like you might have a bit more work to do when it comes to really understanding the women you want to date. You write that you think we’re wonderful because we are the “best of both worlds—male and female,” which is a common sentiment among transamorous-identified men. I don’t want to presume too much, but I need to point out that this frames trans women in terms of what we can do and be for our lovers (whether emotionally or sexually), rather than accepting us on our own terms. I’m also curious, TaT, about what you mean when you say you want to date a “trans woman you can be proud of.” Are you looking for a “perfect” trans woman born out of fantasy, or could you be proud of a real, live trans woman, in all of her living beauty and imperfection?


Many trans women do not identify as “male and female,” while others may identify as non-binary. Furthermore, some of us do not appreciate being defined in opposition with so-called “biological women,” because we see our biology as embodying a kind of femininity in its own right. These little distinctions may seem like simple political correctness, but they are deeply important to many trans women and a significant part of transgender culture.

Here is my first suggestion, TaT: Take some time to familiarize yourself with the ways that trans women think, talk and write about ourselves—it’s often very different from the ways that straight men tend to talk about us in popular culture, pornography and the sex industry. For example, the terms “shemale,” and, to a lesser extent, “T-girl,” originally come from the sex trade, and while there’s nothing wrong with that per se, many trans women will get turned off by hearing these words in a dating context. It tends to signal that the person using them is only interested in us as sex objects, rather than as a whole person (who may or may not be interested in sex!).

Thanks to the increasing availability and popularity of trans-made media, it is now easier than ever for people outside the trans community to become familiar with our unique culture. Trans women appear as full, three-dimensional characters in TV shows such as Pose, Euphoria and Orange Is the New Black. Trans women have written award-winning novels, plays and works of non-fiction about our lives. We have started whole movements and revolutions; trans women created the world in which it is possible for straight men to love us in public. Our works of art and contributions to society are everywhere, if only you take the time to look.

To really love a trans woman—or any woman—you have to be able to look beyond your own fantasies and see who she really is. The difference this will make for both you and your prospective partners is enormous, TaT. Everything about love changes when you learn how to really see the other person, because this also allows them to start seeing you as the lover and partner you want to be.

So many trans women grow into their sexuality feeling ashamed and exploited. We learn to be wary of “chasers” because their affections are rarely genuine. They don’t really care about how we feel or what we want, only about our bodies and what they want to do with them. A skilled, savvy trans sex worker might learn how to turn this into a profitable business venture, but the truth is that very few trans women actually enjoy dating chasers without getting paid because it’s usually a lot of work with little reward. Think about it: How much would you enjoy having sex with someone who was only thinking about their own needs and interests?

It’s worth noting as well, TaT, that many trans sex workers live in precarity and are subject to police profiling and abuse. If you’ve had some less-than-stellar encounters with trans women escorts, try to remember that trans women have restricted opportunities in most sectors of employment—sex work included. The job can be very demanding, and not every sex worker is selling an emotional experience as well as a physical one. The surest way to have a good sexual encounter is to be caring, patient, attentive and open-minded—whether or not you’re paying your partner.

When it comes to finding trans women within an appropriate age range, I happen to know that there are plenty of trans women in their 30s, 40s, 50s and older who are looking for romance in their lives. You may want to consider which online platforms are most likely to help you find such women: It might be more difficult on hook-up apps like Grindr, for example, because trans women who use them tend to be swarmed with the kind of chasers described above. Others, such as Tinder, may actually disproportionately ban trans people since they are designed primarily for cisgender users.

Some apps, such as OKCupid, explicitly welcome trans people by offering a wide range of gender designations to choose from—you might find more luck there. There are also a few apps that are specifically made for cis people to meet trans women, though I haven’t heard of any that have been really successful so far.

Remember, too, that once the current COVID-19 pandemic subsides, there will also be a whole IRL world to explore. Long before dating sites and apps were the norm, straight men met trans women in specific trans-friendly bars, clubs and other community venues. While such venues are sadly shrinking in number due to the ongoing pressures of gentrification (not to mention the economic impact of the pandemic), there are still many community events where you could meet the woman of your dreams. Better yet, why not host your own? Organizing trans-friendly parties, mixers and speed-dating events could be an excellent way to become part of the community.

Don’t give up hope, TaT. Being a transamorous man looking for love can be a challenging road—but then, being a trans woman is difficult in pretty much every possible way. The best advice I can give you is to join us in the struggle. Get to know trans women as we live our day-to-day lives, independent of the fantasies that the dominant culture projects onto us. Fight for our rights, our lives, our happiness. In doing so, you may discover a whole new side of us (and yourself) that is deeply lovable in ways you hadn’t imagined before. Fantasy is a wonderful thing, TaT, but real life—fierce, unyielding, many-textured—is so much more.

Need advice in a hurry? In our video series “Ask Kai: Quick Tips for the Apocalypse,” Kai Cheng Thom offers concrete suggestions to help keep your relationship happy and healthy in these harrowing times. In our latest, Kai answers how to figure out if monogamy is right for you, and how to bring up an open relationship—and how not to do it. Watch the episode below.

Kai Cheng Thom is no longer a registered or practicing mental health professional. The opinions expressed in this column are not intended or implied to be a substitute for professional medical advice, diagnosis or treatment. All content in this column, including, but not limited to, all text, graphics, videos and images, is for general information purposes only. This column, its author, Xtra (including its parent and affiliated companies, as well as their directors, officers, employees, successors and assigns) and any guest authors are not responsible for the accuracy of the information contained in this column or the outcome of following any information provided directly or indirectly from it.

Kai Cheng Thom is a writer, performer, and social worker who divides her heart between Montreal and Toronto, unceded Indigenous territories. She is the author of the Lambda Award-nominated novel Fierce Femmes and Notorious Liars: A Dangerous Trans Girl's Confabulous Memoir (Metonymy Press), as well as the poetry collection a place called No Homeland (Arsenal Pulp Press). Her latest book, Falling Back in Love with Being Human, a collection of letters and poetry, is out now from Penguin Random House Canada.

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