Does he regret his decisions or is he playing me? (long, sorry)?

Dump him. Sounds like he's keeping you around just in case things don't work out with the gf. Really do you want to plan a life with a guy who has a pregnant gf? Honestly if this guy cared about you at all or was any kind of a man he would leave you alone until he resolved his issues. I think he might feel a little sorry for himself but I don't think he has the kind of regrets you're thinking of. Sorry, you asked...short answer? Dump him.