So I have a crush on this guy named Robby. We have been friends for a good 5 or 6 years but haven't really been close until the past year or so. This has kind of been on and off, but we have flirted a lot in the past, and it's starting up again. Within the last week, we have walked around places hold are arms around each other, and last night we were at this party and we cuddled for the whole night. The thing is that he has had girlfriends, and he's talked to me about me helping him find a girl for him to take to prom. I don't think he knows I'm gay, but he recently started flirting with me again after I had this whole thing with his best friend, and one of my close friends, over whether or not I'm gay. I would think that he would tell him just because they seem to tell each other a lot. So my question is, is it a good idea to figure out if Robby is gay or bi?
By this i presume that you would ask him? if that's the case you must be subtle to avoid seeming impulsive and jeopardizing your friendship as well as any possible relationship , so i wouldn't straight up ask him whether he's gay or bi. Instead maybe just ask him whether he would ever contemplated dating guys, or something along those lines. This way you might just catch him off his guard and because it's a broad question it would avoid the awkwardness of asking whether he's was gay, especially if it turns out that he's not. All i would suggest is be hopeful but prepare for the worst.