Originally Posted by
SparkleKitty 
What was his part of the "working together to get him healthy"?
but if I were you I would let go of holding on to it in the hopes that it will maintain a connection between you. Some distance and time will give you a perspective on the reality of this relationship that you may find very valuable.
His part of getting healthy was going to AA, see a counselor & tried to exercise. But he would go drink after those meetings. He would relapse and would bail to have dinner with me and go drink instead.
I definitely don't want his stuff to have the connection. I just want to give it back cuz its things he probably needs. Its a lot of paperwork and it has created bad vibes the second I told him I had it and I knew how much debt he really was in. His family doesn't know about this but if they saw they would be in shock. And his yearbook probably is not needed but it needs to back to the owner. I know hes going to be mad once I send it, but I have no idea what hes going to say to me next because if I send it, his family may go through it.