Tadpole (2002)

Everyone says he should date girls his own age. Oscar respectfully disagrees.

Beautiful, sophisticated women are all over Oscar Grubman. He is sensitive and compassionate, speaks French fluently, is passionate about Voltaire, and thinks the feature that tells the most about a woman is her hands. On the train home from Chauncey Academy for the Thanksgiving weekend, Oscar confides in his best friend that he has plans for this vacation--he will win the heart of his true love. But there is one major problem--Oscar's true love is his stepmother Eve.