From legendary director/writer James L. Brooks comes a humorous and romantic look at the "How Do You Know" question. When everything she's ever known is suddenly taken from her, Lisa (Reese Witherspoon) begins a fling with Matty (Owen Wilson), a major league baseball player and self-centered ladies man. Before their relationship takes off, Lisa meets up with George (Paul Rudd) a straight-arrow businessman facing his own serious issues, both with his father (Jack Nicholson) and the law. Just when everything seems to be falling apart it doesn't.