Lisa Jorgenson's (Reese Witherspoon) entire life has been defined by softball, but at 31, she is deemed too old to play and cut from the team. After being cast adrift, she begins a fling with Matty (Owen Wilson), a charming womanizer who plays professional baseball. About the same time, she goes on a blind date with George (Paul Rudd), a businessman on the hook for stock fraud. Caught in a romantic triangle with the two men, Lisa ponders the meaning of love.