Kevin feels guilty after coming between Wayne and his new girlfriend, Sandy (Carla Gugino), after he engages in a secret relationship with her behind his back. He feels that Wayne doesn't deserve her--that's she's too smart and beautiful for him. But when Kevin sees Sandy make Wayne a better person, he backs off. Kevin asks another girl, Alice Pedermeir (Lindsay Sloane) to the school dance, but she's going with someone else, making him dateless. However, Sandy wants to be with the younger more sensitive brother, than the "basic" brother, so she breaks up with Wayne in the parking lot at the dance. Now Kevin is faced with an ultimatum--ditch his brother to be with his ex-girlfriend or comfort his big brother when he needs it the most. Kevin knows family comes first, and leaves Sandy to dance with another guy. Guest starring Michael Ensign as Mr. Finora, Kevin and Wayne's typing teacher.