Reese Witherspoon, Owen Wilson, Paul Rudd and Jack Nicholson all star in the new comedy written and directed by James L. Brooks, that takes a contemporary and romantic look at the question “How Do You Know?”

Lisa (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 (Wilson), a major league baseball pitcher, a self-centred ladies man – a narcissist with a code of honour.
George Madison (Rudd) is a straight–arrow businessman whose complicated relationship with his father, Charles (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 honestly, 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 had just been served. When everything else seems to be falling apart, they will discover what it means to have something wonderful happen.