As I focus in on this man, I feel he is a dreamer more than a doer. He enjoys talking about things but is not certain if he will actually ever do the things he dreams/talks about. I also feel there is someone else in his life. Not a very stable situation; it may even be a past relationship that he is trying to hang on to; it is keeping him from actually living his life. As dysfunctional as this may seem, he is not in a hurry to change things. The term “emotionally lazy” keeps coming to mind as I focus in on him more closely. He enjoys you but he is a bit of a drifter at heart. I do not see a high probability of this turning into something stable and long term. The only chance you will have of accomplishing this would be to completely distance yourself from him. Then there would be a slightly increased chance of him getting over whatever it is that keeps him in limbo. Then he would get a clearer picture to himself of what he wants next in his life and where you fit in. Even in this case, him going through this and contacting you at a later date with a more solid offer… I see about a 40% chance. But that is the only way I can see as I focus in on him and what he is feeling that you would have chance to take the relationship to a higher level. At the rate you’re going right now, I don’t see it happening. The climate he is creating is not right for the cultivation of a stable healthy relationship.
I don’t know how these factors fit in but I see a younger female friend-just a friend who he is obsessed with and the death of someone very close to him that he constantly thinks about and misses. His mind is adrift, not with the present time most of the time. He is not grounded nor does he want to be.