Bobby Dorfman (Jesse Eisenberg) is the youngest son of a Jewish family in New York City in the 1930s; his elder sister Evelyn is a married school teacher, while his elder brother Ben is a gangster. Discontented with working for his father, a jeweler, Bobby decides to move to Hollywood, where he takes a job running menial errands for his uncle Phil (Steve Carell), a powerhouse talent agent.
Phil introduces Bobby to his secretary Veronica, nicknamed Vonnie (Kristen Stewart), who is tasked with helping Bobby settle into Hollywood. Bobby is drawn to her unpretentiousness as opposed to most young women living in Hollywood, and falls deeply in love with her. She rebuffs his advances, telling him she has a journalist boyfriend named Doug. In reality, "Doug" is Phil, with whom Vonnie is carrying on an illicit romance; he promises to divorce his wife and marry her.
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