Two And A Half Men: Season 2, Episode 12

2 - 12: A Lung Full of Alan

Alan is jealous of Charlie when an old classmate, Jamie Eckelberry (Paget Brewster), who's now a beautiful woman, seems to be more interested in Charlie, before it is revealed that she hates him and worked hard to make herself a beautiful woman to rub his nose in it. She reveals that she used to be interested in Alan when they were younger, but shoots him down after he asks if they could try to go back to that now. Title quotation from: Charlie, when trying to prove to Jamie that Alan is a better man than he is, after Alan tells Charlie to talk him up.