Transgender Friend?

Dear Bill:

A strange question: I have a friend whom I've known for about four years. He is a man, but I have a fairly strong idea that he might be transgender. He's a great person and I value the friendship very much, so I don't want to rock the boat, but he has never brought up the subject that he hasn't always been a man.

I wouldn't say it's vital for me to know for sure...I would definitely want him as a friend, regardless. I'm gay but romantic considerations aren't really a factor here...he has a girlfriend and is thinking of marriage. It's just that I'm curious, it seems to be limiting the conversation -- there is an invisible elephant in the room that neither of us is talking about.

Should I just wait for him to bring it up? Clearly, I can't just say, "You're transgender, aren't you?" It would be amazingly awkward, even more so if I'm wrong.

It's understandable that you're curious about this situation but you're right that it would be awkward -- and worse if he's not transgender. If he is a Trans Man he may be thinking or hoping that he completely "passes" so you'd also risk shattering his illusions or confidence. I would wait until he brings it up, which he may eventually do as you grow closer as friends. Does he know that you're gay? If not, coming out would be a start -- you're both members of the LGBT community even if he isn't gay apparently. Have you met the woman he's going to marry? She may turn out to be transgender as well, which would be another sign. Not that all transgender people pair up with other Trans Men or Women, but it does happen, especially if they want a partner who will understand them and be non-judgmental.

Just hope that some day he'll take you into his confidence.