you excellent approach and attitude has brought him closer. Of course he is afraid of how things will turn out if he did come back, I am sure you are too. You were amazing the way you handled the convo and yes I agree he was trying to figure out something with that line of questions that had to do with the OW.
I know you want clear actions from him but please make sure your list is optimistic. He needs encouragement that HE IS capable of doing the right things. Maybe next you talk give him some exmaples of things he previously did that you think were great?