Unhappily Ever After - Season 1 Episode 12 The Great Depression

Jennifer is chaperoning Tiffany's spring dance. Tiffany is in charge of planning the dance, and has invested the funds into war-oriented stocks. Unfortunately, peace breaks out and her investments go bad. Jack has to return his new J. Bean wardrobe (that Mr. Floppy says makes him look like a gay-boy) in order to help fund the dance. Jennifer makes Jack help her with and take her to the dance. Ryan ends up with 10 dates because the girlfriends of the football team want to get even with the team for getting a stripper the week before. The theme of the dance is ""The O.J. Trial Under the Stars,"" and Barry wins Queen of the Prom.