How should I handle this? Sorta long?

Girl, in all honesty, you should quit wasting your time on this loser. He's stringing you along as a safety net for when he feels lonely. Sorry if that sounds harsh, but it's better to get some perspective on this relationship. I think you should find someone else to hang out with and forget about this guy. If he can't even be straight with you when you ask him questions, then don't waste time on him. You deserve better.