If he's cheated on you, I'd say that's a deal breaker. Cheaters are scum. Find someone else before you become too invested in this boy.

Ohhhh I got it now, I had misread it before.

If you are actually falling in love with this guy, tell him how you really feel. But if you don't want to lose him as a best friend, then maybe getting into a relationship with him isn't the best thing to do. I'm not sure, I suck with dating so I'm not really one to give advice.

Seriously, it's hard to say. I mean every guy thinks different, but I believe sharing intimate moments is a pretty save way. So do not only meet him in class.

I don't know your relationship, but due to the fact that you play that kind of joke, maybe try to be more yourself, be more the person you really are and he should fall in love with and not the person you play concerning the joke.

Love is something you can only get if you take risks. So if you are scared that your relationship can suffer, you are maybe right, but I think the real question is, which fear is stronger, to lose him as a friend or not to know whether he has the same feelings you have. At the end it's your decision, and nobody knows what will happen anyway, but I was in the same situation and though it didn't worked out we are still really good friend. I can't remember a day I regret this decision, because I know now that it wasn't meant to be, and that is ok to.