Oscar wakes the next morning and has an awkward encounter with Dianes boyfriend, Phil ( Adam LeFevre ). Once there, Diane begins to massage him and they end up having sex. He bumps into Eves best friend, chiropractor Diane Lodder ( Bebe Neuwirth ), who offers to take him to her own apartment seeing his current condition. Stanley tells him to walk the girl home, but he hails her a cab.ĭepressed from his failure with the older woman, Oscar goes to a bar with a fake id and gets drunk. 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 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.
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