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Sam (Chris Pine), a struggling corporate barterer in New York, is in trouble after one of his deals violates federal law, and the Federal Trade Commission threatens him with investigation. Sam's boss (Jon Favreau) tells him to bribe federal officials at Sam's expense. Returning home, Sam learns from his girlfriend Hannah (Olivia Wilde) that his estranged record-producer father, Jerry, has died in L.A. of cancer. Sam tries to avoid attending the funeral, but Hannah insists on making arrangements. After flying home to L.A., he stays with Hannah at Jerry's house and has a tense reunion with his mother Lillian (Michelle Pfeiffer). Sam meets with his father's lawyer (Philip Baker Hall), who tells him that the will leaves Sam no money. Sam receives Jerry's shaving kit and discovers that it contains $150,000 in cash, with a note stipulating that the money be delivered to "Josh Davis." Josh (Michael Hall D'Addario) turns out to be a troubled 11-year old. His single-mother Frankie (Elizabeth Banks) is a recovering-alcoholic and bartender. Sam secretly follows Frankie to an AA meeting, during which she reveals to the group that she is Jerry's illegitimate daughter, unmentioned in the newspapers. Sam realizes that Frankie is his half-sister and Josh is his nephew. Sam tells Hannah the news and his intention of keeping the money for himself. This disgusts Hannah, and she returns to New York, leaving Sam with Lillian. Sam introduces himself to Frankie as a fellow alcoholic visiting from New York and becomes involved in her and Josh's lives, giving encouragement and social advice to Josh, while platonically dating Frankie. He learns that Jerry would visit Frankie and her mother on Sundays and that Frankie has never met his "real" wife and son. Growing close to Frankie and Josh, Sam broods over what to do while receiving mounting phone calls from federal officials warning him of his deepening legal trouble. Frankie tells him that she does not want him around Josh since Sam will leave Josh and return to New York. Sam decides to leave but returns to pick up Josh from school when he receives Frankie's phone call at the airport, telling him Josh has been in a fight. One night, after watching Sam put Josh to bed, Frankie embraces Sam and tells him to stay. Sam reveals his true identity, and Frankie explodes in anger, throwing him out of the apartment. Lillian is hospitalized following a heart condition, and in the waiting room, Hannah finds Sam, and they reconcile. Hannah tells Sam that she has transferred to UCLA and will stay with him. Meanwhile, Frankie receives Jerry's money through a lawyer. Attempting to contact her, Sam finds that she has quit her job and moved with Josh without telling anyone. After she returns from the hospital, Lillian tells Sam that she made Jerry choose their family over Frankie and her mother. She thought she was protecting Sam, but Jerry rejected Sam, since he was always reminded of the daughter he abandoned. One day Josh, now living in a suburban neighborhood with Frankie, tracks down Lillian's house, and through his grandmother passes on his home address to Sam. When Sam visits Frankie, she is angry. He begs for forgiveness and asks for a chance to be her sibling. He shows her an old film reel Jerry shot of a young Sam at a playground. In the film, a girl joins Sam, and Frankie realizes that Jerry had united her and Sam to play together. At this recognition, Frankie accepts Sam as her brother.