@longgone…I have tried to joke with him on occasion, but without much success. When we talk, he often shares about how stressed he is at work (I work with him). Needless to say, I don’t try to joke with him then because it wouldn’t seem appropriate.
Lately his stress is through the roof, and he doesn’t have much time to talk, but I know things are getting to him more and more.
@Coloma…I have tried that (see above), but with not much success. I would worry that he doesn’t see me as a friend who he can lighten up with, except that he shares a lot with me.