Often times when someone is getting out from a long term jail sentence they have a program they enter upon release. They may live in a "half way" house and go through a job program to get back on their feet.
I would tell him to take advantage of all that is offered to him. Tell him to take it slow and get to know himself again as a free man. Tell him that he paid his dues and now he can start fresh to live a good life. Tell him to not be discouraged if family/friends don't know exactly how to treat him and to be forgiving if he or they make mistakes. Tell him that church is a good place to go for support and comfort.
and I do agree. He is not ready for any type of romantic relationship at this point. He should focus only on himself and getting acclimated to life again.
Wish him luck.
I'm not sure of any advice to give him, other than seek counseling. He's going to need a lot of therapy and the desire to become an active member of society.
Personally, I wouldn't have any kind of relationship with a man going through this until he shows major signs of improvement. Think about why he's in there, and remember, he's very likely to do it again.
Good luck to you!