“Coming out” on a date
This weekend, for the first time, I went on a date with a guy who didn’t know I was trans. We met on facebook –where we had several trans and trans-friendly friends in common– and he was super cool about trans issues, but I wanted to meet in person before telling him. In previous flirting situations I had disclosed my trans status early on and it ended up being a conversation-stopper, so I was curious about this new strategy. (Besides, I wasn’t sure yet if I was super interested.)
We had dinner and then talked for hours. In person I wasn’t really attracted to him, but I decided to disclose anyway to see how he’d react. I said, “I didn’t always live as male”, which was kind of ambiguous, so then I clarified “I’m a trans man like so-and-so”. He didn’t seem too shocked, although he did stare harder at me for the rest of the conversation. I went on to say, “I thought I should tell you because I know it changes things.” He answered, “It doesn’t change anything for me,” and after a pause, “You’re really cute.”
It was a super positive experience, and it’s too bad I’m not into this guy. I was doubtful about this disclosure-after-meeting strategy because I thought men might feel disappointed: they might still find me attractive after finding out –they might me despite being trans– but I wouldn’t be what they’d expected. I reckoned that if guys knew about my trans status early on and they still wanted to meet me, I’d be sure that they liked the whole package (which is nicer than being liked despite this or that).
But this guy really took it in stride; if anything, he seemed more interested afterwards. I know that not everyone will react this way (some people have a hard time with unexpected surprises of any kind) but it was a huge confidence boost. I feel like more and more doors are opening for me in the dating world; or rather, they were always unlocked but I had never dared to try them.
genderkid 
That’s always a touch one isn’t it. It tends not to come up so much for me because I meet people through friends or at parties where it’s very obvious that I’m trans (no top surgery, and no plans for it). But it seems like there is no ideal solution that works for everyone when it comes to disclosure. Hope you find a way that works for you on an ongoing basis!
That’s really cool! I’ve found that there are more cis gay guys out there than one might imagine who are open to dating passing trans guys (I think things remain more complicated for non-passing trans guys). For dating dating (not sex hook-ups), I like the approach of getting to know the guy enough to know whether or not I and he are interested before dropping the news. Usually, I think there’s no point if I’m not into him. As you’ve just experienced, often, if the guy is into you, he will continue to be interested when you tell him, even if he may never have thought to himself that he’d like to date a trans guy. The felt evidence of attraction is enough for plenty of guys.
I usually hang out in queer worlds in with friends of friends who know that I’m trans, and I usually drop hints once I start getting close with a new friend, but lately I’ve been experiencing a new problem: I have a couple elderly cis gay men who have taken a liking to me (rice queens, probably, but I think the phenomenon is more complicated than people think), and have started gay bonding with me about everything from jock straps to being bullied in high school to hooking up with st8 guys. I get a lot out of talking to gay men from a different generation (I’m talking 70s and 80s), but it does feel inauthentic, because my experience with ALL of these matters are different than if I had been a cis guy like them. One is becoming a close friend, another is just an amusing guy to talk to – in both cases, I’m pretty sure I would have told them by now if they had been my age, but I find myself worrying that, being of a different generation, they wouldn’t get it, or they would suddenly feel distance instead of commonality between us, or they would ask inappropriate questions that would get more personal than I’d want, or also, simply, that it would disturb them to discover that the young man they are attracted to and can’t have is also trans.