As a gay man, I've had great success with online dating. Recently, I met a cute guy on okcupid. On paper at least, he has a lot of what I'm looking for: he’s a reader, thoughtful, gainfully employed, well traveled. But he may be a female-to-male transgendered person. (I figured this out because his profile pics seem to lack an Adam's apple and because he comes out as very trans affirming.) I’m totally devoted to trans equal rights, but honestly, I'm not sure I’d be comfortable dating an FTM. They just lack the kind of authentic masculinity I’m looking for, which is weird cause I actually find femininity in guys hot.
He Said: When it comes to dating, my view is the more the merrier. I've gone on dates that I doubted would be romantic that turned out to be. The opposite happens just as frequently. Most of all, I find it makes sense to go into what's something of a blind date (since we only know the virtual representation of a person) with the expectation of friendship, and nothing more. In this case, it seems fair to ask about his gender orientation, but I would make it clear that you would like to meet no matter what the answer might be. After all, I'm assuming he would not want to date someone who is unlikely to share an attraction. At any rate, give it a try. You never know what might happen.
She Said: If this guy has all the qualities you look for, then sure, by all means meet him, and you can get around to the transgender issue in person. What fascinates me most about your question, though, is the last sentence. You seek authentic masculinity but find femininity in guys hot. It occurs to me that in reality, there might not be such a big leap between a person born male who displays feminine traits, and a person born female who switches to male. Both are likely to occupy a midway point on the masculine-feminine continuum that you are likely to find sexy. The route each person takes to that midway point might not matter so much in the end; perhaps it only matters “on paper,” as you say. There’s only one way to find out.