MAJOR boy problem... (quite long, but please take the time to read, it would mean a lot...)?

You should trust your instincts. And, since you don't feel right about this, it's probably not the way to go. If you know he's like that, then there's a pretty good chance he's not going to change, ever. And do you really want to be in a relationship with someone like that? So, no. I think he's just playing with you to see your reaction, I can't say for sure but I don't think he seriously likes you.