Oscar Grubman (Aaron Stanford) has sophisticated tastes for a fifteen year old school boy. One of his sophisticated tastes is in love, he refuses the advances of girls his own age because his heart is set on an older woman. He is returning home from Chauncey Academy to spend Thanksgiving with his father Stanely (John Ritter) and stepmother Eve (Sigourney Weaver). At home he tries to make his intentions of love known to the older woman, who turns out to be his stepmother Eve. Things become confused for Oscar when he gets drunk one night and ends up sleeping with Eve's friend Diane Lodder (Bebe Neuwirth). For Oscar, though, Eve is the only one that he wants and he must work his way around Diane to try and get to her.