The Tinder Transsexual Conundrum

As online dating apps have evolved, they have refined shallowness to a fine art. Whereas before there might have been a nominal risk of learning about someone’s personality before judging their desirability, newer generations of dating apps have shifted the emphasis even more overwhelmingly onto the initial reaction to the first photo. So, if you’re looking for matches you’d better look good, or at least know which angles can temporarily dupe your prospects into thinking you do. And in Southeast Asia, especially in places like Manila and Bangkok, many of the women with the prettiest faces, the most flattering filters and the nicest angles are transsexuals. (I’m not sure if the word “ladyboy” is appropriate, although many of these individuals do self-identify in that way.)

And because these apps discourage you from knowing much about your prospective partners aside from what’s in their pictures, it’s quite easy to distractedly swipe right on a pretty woman and later realize, after the dust has settled and you’ve actually taken a look at her profile, that she’s a transsexual. To be honest, I’ve done this a lot, not least of all because a lot of these trans women look good. And why not? Considering the effort and money involved in transforming yourself from a man to a woman, the extra effort involved in making yourself into a really sexy woman seems like a minimum additional investment.

And yet, I find it hard to wrap my head around the idea of being sexually attracted to someone who used to be a man. To be fair, I’m happy to report that I’ve come a long way from my old transphobia – A decade ago I remember being quite squeamish about the notion of a trans woman (or man), and I vividly remember pointedly using the word “him” when talking about my friend Ruby’s trans female friend (who wasn’t present), much to Ruby’s obvious annoyance. Since then, I’ve adopted the sort of live-and-let-live attitude that most decent human beings eventually grow into if they don’t end up curdled and bitter. (To be fair, a lot of people do end up curdled and bitter.)

And yet, I still have trouble wrapping my head around the idea of being sexually attracted to a woman who was born a man, no matter how charming and pretty they are. So after I realize my oversight, I unmatch. Back when I started making these mistakes – when dating apps were still more oriented toward matching based on anything other than a gut reaction to a photo – I would sometimes tell these women how pretty they were, but that I wasn’t really used to dating a trans woman. In retrospect, I have no idea whether this was nice or appallingly rude and inconsiderate. Now I just unmatch without a word.

But with that strain of hyperactive empathy that weirdly intermingles with my borderline sociopathy, I can’t help but imagine what it must be like for them. Occasionally I will match women (especially western women) who are so unattainably attractive that I assume they must have made a mistake in matching me. Unfortunately, this is often the case, as I watch their profile disappear from my list of matches without a word. Not that I’m comparing myself to a hot babe, but I can relate to those initial, hesitant feelings of hope, wondering if you’ve really found someone who’s cool and open-minded, only to have their picture disappear forever without a word – and to have it happen over and over again, all because a bunch of morons on the Internet thought you were a babe until they realized you weren’t a cis babe.

I can imagine that in a few decades, people will find it downright quaint that older generations were so concerned about a person’s sex at birth. It may well seem insignificant, like whether someone was delivered naturally or by C-section. And so I find myself in the position of being just a little bit of a curmudgeon, while also aware that I am, as everyone has been at times, on the wrong side of history. I comfort myself with the thought that my current mild prejudice is fairly harmless compared to my earlier transphobia, but I still nurse some guilt over the number of times I’ve been that disappearing face on the list of matches in some lovely, kind-hearted trans woman’s Tinder app. But the real beauty of the brief human lifespan is that regressive opinions will naturally die out, to be replaced by younger generations who wonder why anyone ever really gave a shit in the first place. And until then, I wish everyone out there, whoever they are, all the best of luck in finding love.


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