Cosby (1996)

Season 2: Episode 6

Pauline is absolutely thrilled that after years of being the single friend, she has finally become a couple with her new boyfriend, Gregory, a self-absorbed, self-proclaimed genius who disturbs Hilton. So when she decides to dump him because he's too uptight, Ruth thinks that Hilton is really the one to blame and sends him off to remedy the situation. But when Hilton, Griffin and Gregory team up at The Steinway Street Pub, they end up good buddies, and big, big winners too, in a trivia game.