I've never actually dated. I still can't get a DATE WITH MY WIFE. Oops, I hit the cap key, but okay.But as a gift for someone I can't figure out what to give, The Onion books are always good--it's a mock newspaper in Madison, very funny. Funny headlines and news stories written in deadpan parody of journalese. Once someone finds favorite things to laugh about, shared jokes, it seems personal enough.
If he has no sense of humor, dump him. Women dating guys like that is tragic, a waste of our natural resources.