Season 3: Episode 37: The Withholder

Finch returns from Jamaica after a failed attempt at romance with Courtney, who played him, as it turns out. Elliott steps in to try to prove what a friend he is to Finch by giving her a dose of her own medicine--getting her hooked on him and then telling her to kiss off. Meanwhile, Jack makes another bet with Donald Trump--whoever loses less weight has to wear a dress during their golf game.