The Great Depression (S01E12)

Jennifer is overseeing Tiffany’s spring dance, which Tiffany has been organizing by putting the budget into military-related stocks. Unfortunately, when peace unexpectedly arrives, her investments tank. To help cover the dance costs, Jack must return his new J. Bean outfits, which Mr. Floppy teases makes him look "like a gay-boy." Jennifer persuades Jack to accompany her to the dance. Meanwhile, Ryan ends up with ten dates since the football players' girlfriends want revenge after the guys hired a stripper the previous week. The dance theme is "The O.J. Trial Under the Stars," and Barry ends up winning Prom Queen.