Q: When is the right time to reveal your kink to a potential partner? In my case, I’m a hetero male X-dresser. At what point does it become “unfair” to the girls I date not to tell them? I realize this is a potential deal-breaker for many women. How do you even open up the topic? I’m newly single and haven’t had to worry about dating and kink in 20 years!
Dating is complicated and having a kink adds an extra element of excitement. It can save a lot of time and heartbreak if we have a clear goal. I don’t mean vague ideas like: fun, companionship or love. I mean you need to figure out what your next partner’s relationship will be to your kink.
A fun part of being a sexuality educator is that I frequently am entrusted with the fantasies and fears of absolute strangers: secrets they are unwilling to share with their friends and even long-term partners. Airplane seatmates, fellow waiting room attendees, and even elevator ride companions have spilled some real juicy stuff to me over the years, and let me be clear: I LOVE IT. I also understand it.
Talking about this stuff is hard and scary, especially if you feel like rejection or ridicule are potential outcomes. Sometimes people delay talking up the point where it feels impossible to bring up without starting a fight for having not mentioned it sooner. A surprised partner might feel lied to, confused about how to react, or simply freak out in the moment, and if you’re not able to create space for those reactions, it can escalate into something much bigger than necessary.
So often I will get questions like “how do I bring up my fetish to my wife of 20 years?” or hear “I’ve always wanted to try an open relationship, but there’s never a good time to talk about it.” And my answer to them is some variation on: How do you talk to them about anything? Literally.
“Airplane seatmates, fellow waiting room attendees, and even elevator ride companions have spilled some real juicy stuff to me over the years, and let me be clear: I LOVE IT. I also understand it.”
You’ve had to have tough money discussions in those two decades, no doubt. You’ve had dumb roommate arguments, awkward family situations, plus they had that super annoying habit you had to either squash or learn to live with. In loving, mutually respectful relationships partners talk openly and honestly about hard shit. Work together as teammates: being clear about your needs and boundaries and listening to theirs, not trying to argue a case. It requires multiple conversations, usually. It takes a lot of patience, compassion and hard work. We give our lovers the chance to be cool with our vulnerabilities, to be the rad, loving, kind human that we chose.
But you’re not talking about how to bring it up to a spouse of 20 years. You’re in the dating pool, and that means you have it even easier. You can decide right now that your next partner is not only going to accept your cross-dressing, but they are going to be absolutely cool with it, maybe even come to love indulging in it with you.
Because you, my friend, have the benefit of living in 20goddamn20, a year where anything can happen, nothing is off the table and kink-specific dating sites are absolutely a thing.
Sure, you can go on Plenty of Fish and chat about Game of Thrones and the election for two weeks with a cute lady, finally meeting up for some wine in Rittenhouse Park on a Tuesday night, and after a couple hours, gather up the gumption to mention your fetish, only to find out your date is relentlessly, intractably vanilla. Or you can head to the kink community, put up a profile on Fetlife, knki, fetish.com, whplr, kinky zoo, kinkd, fuck.com, kinksters, open…. (you get the idea) and save everyone a ton of time.
“You can decide right now that your next partner is not only going to accept your cross-dressing, but they are going to be absolutely cool with it, maybe even come to love indulging in it with you.”
Maybe you already have an IRL target in mind, though. Perhaps that friendly woman from down the hall, the cute redhead you always see at the dog park or a friend of a friend. If so, keep building rapport. Once you’ve spent a handful of dates getting to know this human, providing context for who you both are and how you exist in the world, then you can start to casually bring up fetishes, nerdy obsessions, odd collections, or any other potential “deal-breakers.”
You can straight up ask, “what’s the weirdest thing about you?” or just say, “what’s a thing you love that very few people share with you?” Then it’s a mutually intimate situation and you can suss out their threshold.
Because it’s not just a potential impasse for them – something that they may decide they can’t learn to deal with – it’s also a dealbreaker for you: if they can’t get down with thing that is a part of who you are and brings you great pleasure, they’re not the right one for you either.
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