Lisa Jorgenson's (Reese Witherspoon) entire life has been defined by softball, but, now that she is 31, she is deemed too old to play and cut from the team. Cast adrift, she begins a fling with Matty (Owen Wilson), a charming womanizer who plays professional baseball. Almost at 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 true love.