Trusting, I think the man needs someone to talk to who knows him and his past. Listen and validate (you know this already). He's bound to slip up and accidentally tell you what is on his mind. I suspect he's got some issues that he may need your assistance with at some point.
Hang in there.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.
