Well that's something interesting, humor. His sense of humor is odd, mostly slapstick humor. but I think his biggest problem is that he doesn't know what to say first time out, the icebreaker sort of thing. He's told me that he's tried all sorts of things, but I believe that his confidence comes off as cocky, though some women have told me that he comes off as being very creepy.
Though he says he can't understand why women won't accept somebody who is willing to provide a house, a car and what not. He's heavily into classic cars, and won't drive anything newer than 1970. And while all the cars he has do run, IMHO they look like junk, but I'm not a big car fanatic. I did try to get him interested in knitting though that went over like a lead balloon. :D Anyway, keep the advice rolling in, I appreciate all the comments, and I'm pretty sure he'll appreciate it when he can get a date.