Why does he always try to hurt my feelings?

Why are you still talking to this guy again? lol he is a total asshole and you should remove all contact from him. If you really want to drive him crazy and make him want you leave him be and he will come running. If you want to remain in contact with him you need to say something about how he treats you and mean it. If he can continually get away with it, he's going to continue doing it until you make a move.