Bobby Dorfman (Jesse Eisenberg) moves to Hollywood to get a job working with his uncle Phil Stern (Steve Carell), a powerful agent. Bobby falls in love with Phil's secretary Vonnie (Kristen Stewart), who is already engaging in an affair with Phil. Despite falling for Bobby, Vonnie ultimately chooses to marry Phil.
Bobby returns to New York and opens a nightclub with his gangster brother Ben. Bobby marries a woman named Veronica (Blake Lively) and has a daughter with her. Vonnie and Phil appear in New York, briefly rekindling the spark between her and Bobby, but they choose to go on with their proper relationships. In the end, it appears they both regret choosing other people.
A subplot involves Ben's (Corey Stoll) gangster life and his murder of his sister's nasty neighbor. He is found guilty and sentenced to the electric chair.