If he's not into it, it will hurt, but you'll get the pain over with now rather than later when you have invested even more time in the half-relationship. You know the scene. I then apologized many times and told him it was just a joke and then he cooled down.
He is seeing you and seeing her at the same time but he just hasn't made up his mind. I'm pretty sure he was kidding do guys kid about that kind of thing? We kept in touch while I was overseas for 4 years just as friends.