I'm a 19-year-old gay transman and I recently met a local guy online. He's a fair bit older than me, but that wasn't a problem for either of us. We started talking and our conversations quickly became sexual and affectionate. We began talking on the phone a lot, emailing and talking about meeting up. It went on for about two weeks. Knowing sex was definitely in the cards at this point, I came out to him. He took it well, at first, said he had a few friends who were struggling with their gender identity, told me I was brave for transitioning so early in life. But he was less talkative and I could tell something was bothering him. We said goodnight, went to bed, and I texted him the next morning. He didn't reply. Next day, same thing. I spoke to my best friend, who advised I give him space for a week, which I did. After a week, I texted again and he told me he had no interest in speaking to me anymore because I had "been dishonest," "purposely misled [him]," and "played with [his] emotions." I felt this was unfair. Does he expect me to tell older men I meet online that I'm trans right away? Does he expect me to tell anyone I'm trans regardless of whether or not I'm comfortable doing so? I'm new at the dating world, Dan, so I don't really know when it's a good time to tell someone I'm trans. Help me out here, was I an asshole or was he? When should I be telling potential boyfriends about my situation?

Honesty Not Always The Best Policy

My response to HNATBP after the jump.


He shouldn't have been such a jerk about your being trans, HNATBP. You flirted with him, you didn't defraud him.

But you should've told him sooner.

Of course you're not obligated to tell anyone you're trans, HNATBP, but a person with whom you're flirting—someone you're hoping to be sexual with at some point—is going to find out you're trans sooner or later. And the sooner you tell that person you're trans, the less likely you are to waste your time on a guy who isn't right for you.

Welcome to the dating world. I would encourage you to come out to guys on this planet right-away-ish. Maybe not during that first interaction, or even the first few e-mails exchanges and telephone calls, but very shortly thereafter. Not to spare the guys you meet on gay hookup sites the trauma of being "misled"—anyone who's traumatized by the thought of being misled has no business on gay hookup sites—but to spare yourself the grief. Look what happened: You wasted two weeks getting to know a guy who wasn't worth your time or trouble, HNATBP, two weeks that you could've spent getting to know a gay guy who's into trans men, open to trans men, or is a trans man himself.

You don't have to come out to "anyone," HNATBP, but a potential boyfriend isn't "anyone." He's someone you're hoping to fuck at some point, right? Why would you wanna make a big emotional investment in a guy who could freak out or bolt when you inevitably disclose to him that you're trans? Wouldn't you rather be rid of those guys before you've invested a lot of time, emotional energy, or sexy sexts in them?

Don't think of coming out as trans to potential boyfriends as something you owe them, HNATBP. Think of it as something you owe yourself.

And, finally, do you know about Buck Angel's dating site for trans men?