For example, I invited him to a BBQ at my friend's parent's house. (He was my roommate at the time, and had met my other friend a few times so this was not a random thing)
He talked to my friend's mother for maybe 15 minutes at the BBQ. She is a cheerful and loopy sort of person, and that was exactly the sort of conversation they had. On the drive home he asked me, "that family has been through a lot of tragedy, haven't they?". Indeed, it would break your heart to hear about them.