Plot

Coming-of-age story about a suave 15-year-old prep school student who falls in love with his stepmother. When her best friend responds to his advances, he suddenly finds himself in way over his head.

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. Oscar is certain that he could be a better mate to Eve than his work-obsessed father. He fails to win Eve's heart and is consequently dejected. Oscar's path to his true love is further crossed by Diane, Eve's best friend who, one night while wearing Eve's borrowed perfumed scarf, offers him temporary comfort in an unconventional tryst. For Diane, Oscar fills a void in her life. For Oscar, Diane is somewhat of a distraction, as his continued pursuit of Eve leads to an unexpected resolution.—Sujit R. Varma

Oscar Grubman (Aaron Stanford) is a 15-year-old teen, portrayed as mature beyond his years, traveling home from school for Thanksgiving. He speaks French fluently, quotes Voltaire and finds girls his own age to be too shallow and superficial, as well as too inexperienced in life. When an attractive girl from his school, Miranda Spear (Kate Mara), who is obviously interested in him, approaches Oscar, he politely brushes her off. Oscar confides in his friend Charlie (Robert Iler) that he is in love with a mature woman and plans to win her heart during Thanksgiving break.

Oscar arrives at the apartment of his father, Columbia University history professor and author, Stanley Grubman (John Ritter), and stepmother, the passionate cardiologist, Eve (Sigourney Weaver). That evening, the Grubmans hold a party where Stanley introduces him to a girl his age, but Oscar rebuffs her as well while staring at the object of his affection: his stepmother. Oscar tries to open up to her, but the unsuspecting Eve doesn't pick up on any of his advances. Stanley tells him to walk the girl home, but he hails her a cab. Depressed from his failure with the older woman, Oscar goes to a bar with a fake ID and gets drunk. He bumps into Eve's best friend, chiropractor Diane Lodder (Bebe Neuwirth), who offers to take him to her own apartment seeing his current condition. Once there, Diane begins to massage him and they end up making love. Oscar wakes the next morning and has an awkward encounter with Diane's boyfriend, Phil.

Back at home, Oscar plans a surprise lunch for Eve but first Stanley inquires about where Oscar spent the night. Oscar makes up a story about meeting Miranda Spear from school. He brings lunch to Eve at her laboratory, where he opens up to her once more, pondering the use of the heart as a symbol for affection. Together, they decide that the liver should be the new symbol for love. Their conversation is interrupted by a phone call from Stanley, who mentions that Diane will be joining them for dinner. Worried that Diane will tell them about their tryst, Oscar finds Diane at a tea room with several of her friends. All behave as though they know about the previous evening, and most of the women twice his age flirt with him. Oscar makes Diane promise to keep last night a secret from Stanley and especially Eve.

At dinner, Diane drinks and behaves coyly. She plays footsie with Oscar and flirts with him in French. After she excuses herself from the table, Oscar follows to confront her. She kisses him while not being totally out of Stanley's view, after which Diane admits to Stanley and Eve that she and Oscar are lovers. The next day, Diane explains to Eve that she found Oscar a charming young man. Eve condemns her for seducing a 15-year-old, but Diane says that many women would have done the same, including possibly Eve. Later that day, Eve and Oscar play a tense round of tennis, lobbing insults at each other, ending up with Oscar getting hit in the head with a ball. Oscar explains that he only did what he did with Diane because he was drunk and she was wearing Eve's scarf. Eve immediately understands that he is in love with her. They share a passionate kiss and Eve eventually breaks away.

At the end of Thanksgiving break, Eve and Stanley take Oscar to the train. Eve asks how his liver feels and he replies that it hurts, but is not broken. She also tells him how much he loves his father. On the train, Oscar meets up with Charlie, and runs into Miranda. Miranda quoted Voltaire, "If we do not find something pleasant, at least we will find something new," and looks longingly at Oscar. Charlie notices this and Oscar tells Charlie that Miranda smells nice. Charlie asks about Eve and Oscar states that his obsession with Eve was not as important as it seemed. Charlie doesn't understand his friend, but Oscar smiles as the train rolls on.