No, no you make a lot of sense. Indeed I don't trust him.
I don't know if that helps to understand but:

- he has lost a dear person and he thinks he is responsible for his death because he was mean and he thinks that caused the disease. Silly in my opinion. Not that fast!
-he had no real relationship in the past years or ever actually.
-he says he misses the time when he had no care in this world
-he said once he thought he was ready but he isn't, the next minute he says he doesn't love me enough.
-when my character (see first post) said : "ok you didn't love her" he answered "I never said that!"
"But if I did love her enough I wouldn't doubt". He doesn't even KNOW.
-I always had the feeling he wanted a girl who treats him badly, because he feels so much guilt and he wants to be punished.
-he said he never opened up like he did with me, not even to his family. It sounded like "you were important. I am not a jerk. I didn't take advantage!"

So yes, he wanted it very badly to be possible between us but it just wasn't good enough. Or he's just not ready.
Do you think guilt alone can explain the fact that he has trouble getting over it?

Yes, as it is, no real relationship is possible. In the last year he has started coming out of his shell and now he feels the need to find someone. That seems to be new. But of course it is only the first step.

I just wonder if even if he gets a grasp on his life, if I would be the right person.
He says he wants an intelligent woman, strong... but he always felt bad when I knew something he didn't.

Voilà I don't know what to do next. Keep an eye on him from a safe distance to see how things go? What behavior on my side would make sense here? Maybe I am blind, maybe I am clinging on too little. But even my friends say he is very weird and they can't explain this.