I have a 28 year old friend who has been single for the past six years I know of. I have hooked him with some two hot girls, but he does not seem interested in them, and had rather work out with me in the gym than spend time with them. He never talks about girls, except the rare times he mentions what he considers sexy, he describes the typical blonde girl, the same kind that every red blooded American boy is suppose to like. He never talks about sexual conquests and acts disgusted whenever sex is mentioned. He asked me if I was "a friend of dorothy" and that was before I told him I am gay. When I did tell him, he said he is homophobic and my sexuality makes him uncomfortable, but he still wants to hang out with me. I've noticed that he initiates contact with me, wanting to me to workout with him, and he gets upset if I break away from him because I think sometimes he is uncomfortable around me. He seems to know quite a bit about gay slang and some of the music we listen to. I get the feeling he is a closet case, but I'm not sure.

If you are gay, wouldn't you be able to tell better than us? If you think he's gay, he probably is and doesn't want anyone else to know.

Does it really matter?

Are you upset that he might be, and is just acting straight?

I never have heard the friend of Dorothy phrase before. Is that like Judy Garland?

Did he tell you he's gay?

Did you catch him in bed with another man?

No?

Then there's no way to know for sure.

Except, just maybe---you could ASK him.

It doesn't upset me if he is. I just don't like his attitude he has sometimes and it frustrates me because I'm not sure what the best course of action is.

Your options would seem to be:

Ask him about his orientation.

Drop the subject altogether.

Distance yourself from the boy.

Your choice.