Less than Perfect (2002)

Season 2: Episode 23

Claude is heartbroken when Mitch goes on assignment to Budapest, so Owen and Carl try to lift her spirits with a game of "Pimp Hat," where everyone picks a name out of a hat and sets up a date for them. Kipp joins in the game, secretly plotting to ruin everyone's evening, and Lydia becomes jealous that she and Jeb don't have a good "first date story."