it sounds like only he can change his what if mentality or you would become his psychologist. As per one of your other answers I also think you need to talk about the practicalities of the relationship if it is to work out and see if there is a next step that will make it easier like one of you moving, etc. as your current situation is obviously not working if you have broken up. Sounds like you have something good but timing and having same priorities can often make or break a relationship even more than the connection I find.