Film - Richie Tenenbaum from The Royal Tenenbaums. He's sweet and shy. I'd want to hear about his world travels and being a child prodigy. Also, one of the few guys that can manage to pull off a beard and still be cute.
TV - Jim Halpert from The Office. He's so funny and sweet! Not to mention hot.
Book - I don't read much fiction so I'm having a hard time coming up with this one. Maybe Hannibal Lecter just because he's so intelligent, fascinating and completely insane.