Charlie calls a college buddy to defend Randall in a lawsuit after he ruins a model's coiffure at a charity fashion show, but the man has eyes for Caitlin. Carter coaches Paul on wooing an attractive new hire before Stuart goes after her.

Charlie gets trapped in a stalled train before his date with a woman he's desperate to impress. Carter's weird neighbor Kurt hits on him, and Paul helps by getting Carter reservations at a posh restaurant.