Oscar wakes the next morning and has an awkward encounter with Diane's boyfriend, Phil ( Adam LeFevre).īack at home, Oscar plans a surprise lunch for Eve but first Stanley inquires about where Oscar spent the night. Once there, Diane begins to massage him and they end up having sex. 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. Depressed from his failure with the older woman, Oscar goes to a bar with a fake id and gets drunk. Stanley tells him to walk the girl home, but he hails her a cab.
Oscar tries to open up to her, but the unsuspecting Eve doesn't pick up on any of his advances. That evening, the Grubmans hold a party where Stanley introduces him to a girl of his age, but Oscar rebuffs her as well while staring at the object of his affection: his stepmother. 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). 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. When an attractive girl from his school, Miranda Spear ( Kate Mara), who is obviously interested in him, approaches Oscar, he politely brushes her off. He speaks fluent French, quotes Voltaire and finds girls of his own age to be too shallow and superficial, as well as too inexperienced in life.
Oscar Grubman ( Aaron Stanford) is a 15-year-old boy, portrayed as mature beyond his years, traveling home from school for Thanksgiving.
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