I would definitely go out with Howard, if only because he tries sooo hard to get attention that he deserves a break. Plus I think once he stopped feeling like he had to impress you he would be a genuinely nice guy.

*pretends to faint on the floor* EWWWWW!!! He still live with his mother! No, in any guy older than me, I don't like that (by older I mean waaaaaaay older.)