Rebecca Romijn, Gabrielle Union, Jamie Kennedy, Thandie Newton
Wesley Deeds, head of the family-owned Deeds Corporation, dresses for work. His fiancée, Natalie, makes breakfast for him, noting his predictable routine. Before work, Wesley picks up his irritable younger brother, Walter, who lost his driver's license after a string of DUIs. They have lunch with their mother, the respectable Wilimena Deeds. After lunch, Wilimena meets Natalie, Natalie's mother, and Natalie's best friend at the bridal shop. The two mothers urge Natalie to think about her future with Wesley.On the impoverished side of town, Lindsey Wakefield, a single mother and cleaner for the Deeds Corporation, finds out she will be evicted if she doesn't pay her bills soon. Lindsey rushes to pick up her check from work and ends up parking in Wesley's reserved spot, leaving her six-year-old daughter, Ariel, in the car. Wesley and Walter find Ariel. Lindsey returns to find her car towed and argues with the two men. Lindsey takes Ariel to school, while Wesley has a meeting with his coworker and best friend, John, over acquiring a company Wesley's father has been competing against for years.After work, Lindsey discovers she has been evicted. Taking her belongings, she picks up Ariel from school and works another shift. Ariel stays in a broom closet during the shift. They then begin to live in their van. Wesley sees them and decides to watch over them until Lindsey's "boyfriend" comes for them. Wesley takes Lindsey and Ariel out for pizza; the trio bonds.Ariel's teacher finds out Lindsey and Ariel are homeless and threatens to call child services. Wesley struggles to expand the business while watching over Walter and developing a more complex love life with Natalie. One night, Natalie returns drunk after a fashion show and tries to initiate sex with her fiancé, but he rejects her. After the child welfare agency takes Ariel, Wesley gives Lindsey a rent-free corporate apartment. Lindsey regains custody of Ariel. When Wesley reveals he has always wanted to ride a motorcycle, Lindsey rents one. The pair ride across the countryside and stops by a pond, where they kiss. Wesley admits he is engaged, and Lindsey leaves.Deeds Corporation takes over the rival company, but Walter ruins the celebration with his outburst. Lindsey attends the party to talk to Wesley, and Walter forces her to stay. Walter suggests to Wilimena that Wesley and Lindsey are having an affair. Wilimena hints to Lindsey that Wesley would not stay with someone poorer for long. Natalie, Wesley, Walter, Wilimena, and Lindsey become trapped in an elevator after Wesley and Walter fight. Natalie and Wilimena notice Lindsey reaching for Wesley's hand, which was injured in the fight.Wesley visits Lindsey that night, but she rejects him. Wesley and Natalie realize that, although they love each other, their marriage would not be happy because they are only together for their parents. They announce their split at their engagement party. Wesley also reveals he is quitting and traveling to see his old friends. He hires John as the new CEO of Deeds. Although initially angry, Walter accepts this. Wesley tells Walter that he sabotages and ruins everything good that comes into his life and he can't help him with it anymore and if that's how he wants to live, then he won't do that with Walter.Wesley tells Lindsey he is going to Nigeria and invites Lindsey and Ariel along. Lindsey again rejects him. Wesley boards his plane. As the plane is taking off, he sees Lindsey and Ariel sitting across the aisle. Wesley and Lindsey kiss, while Ariel looks on happily.