Fifteen-year-old Prep student Oscar Grubman (Aaron Stanford) feels that girls his own age haven't lived enough, which is why he's coming home to Manhattan's Upper East Side for Thanksgiving to profess his love to his stepmother, Eve (Sigourney Weaver)--whose marriage to his professor father (John Ritter) has become routine and uninspiring. Unable to find the right moment to express himself, Oscar slips out to a bar after dinner and finds himself drunk and missing his wallet. Walking home, he bumps into Eve's best friend, Diane (Bebe Neuwirth), a sexy chiropractor who offers to take him home to detox. A backrub leads to a kiss, which results in Oscar and Diane spending the night together. Oscar, feeling he has betrayed his true love, must now prevent Diane--who laughs at the whole situation--from telling Eve what has happened between them.