Having struck out in her career, professional softball player Lisa (Reese Witherspoon) begins dating self-centred baseball star Matty (Owen Wilson). Meanwhile, working for his father's business, executive George (Paul Rudd) finds himself in hot water when the company is investigated for corporate malpractice. As George is ostracised by his colleagues and shunned by his girlfriend, his shiftily loveable dad Charles (Jack Nicholson) isn't much help.
Early in her relationship with the womanising Matty, Lisa finds herself on a semi-disastrous date with George. Equally depressed by their downward career trajectories, the two strike up a chemistry that will lead to a tricky love triangle and cause George, Lisa and Matty to question everything they know about love.