It's good to have an old-fashioned gossip with him. After he told me two thoroughly abysmal jokes, and apologized that that's why he warned people before he told those to them, because they were so bad, I told him sternly that the only jokes of his that I would ever not want to hear would be the ones that would leave me feeling like crying in a corner. Other than the jokes that would hurt me, bad jokes don't bother me...
We got off into Weird Al and then discussion of my exes, a little.
Let him know that these conversations with him are reminding me more of the good days with Shawn. Got into a discussion of how hard I slapped when I was in high school. Told that story about slapping Shawn.
...He eventually had to get to bed. Learned that his "Anything else?" is ... well, if we don't have anything to talk about, we can't really be talking, right? Let him know that even when I don't have anything to talk about, I still desire to talk with him. So we found things.
Then it was his bedtime.
...votania and marxdarx find my smile after I've been talking to him very unnerving.