What do you think this boy is trying to get at?

He could just be playing around, if he likes you the dare could have been his way of trying to express himself, or he could be just playing mind games. He could be annoyed that you trapped him like that, maybe because he was only looking for a little fun. Just talk to him, if he won't give you a straight answer then he really isn't worth your time, pull back from him and give him some space and see if he still wants to play games, and if he does then leave him alone. There is someone better out there for you.