Lisa (Reese Witherspoon) is a woman whose athletic ability is the defining passion of her life, having been her focus since early childhood. When she is cut from her team, everything she has ever known is suddenly taken from her. Not knowing what to do, she stumbles toward regular life. In this mode, she begins a fling with Matty (Owen Wilson), a major league baseball pitcher, a self-centered ladies mana narcissist with a code of honor.
George (Paul Rudd) is a straight-arrow businessman whose complicated relationship with his father, Charles (Jack Nicholson), takes a turn when George is accused of a financial crime, even though he's done nothing wrong. Though he may be headed to jail, George's honesty, integrity, and unceasing optimism may be his only path to keeping his sanity.
Before Lisa's relationship with Matty takes root, she meets George for a first date on the worst evening of each of their lives: she has just been cut, and he has just been served. When everything else seems to be falling apart, they will discover what it means to have something wonderful happen.