I've never liked those books/films/plays where the nebbish guy longs for a woman way out of his league, and ends up deceiving her by pretending to be someone she does find attractive. (Think various Shakespeare plays, Revenge of the Nerds, Nutty Professor). It's almost as if the guy is punishing the woman for turning him down. Classic pick up artist behaviour. Of course, being Hollywood it all ends up happily ever after, the woman falls for his nebbish charm and overlooks the deception, when really the nerd is just as cruel and manipulative as the jocks and popular guys he despises.