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Plot

Lisa Jorgenson (Reese Witherspoon) is a softball player, popular with teammates but over 30 and, to her dismay, left off the Team USA roster.

Unsure what to do next, Lisa has begun dating a handsome, hard-partying pitcher for the Washington Nationals baseball team, Matty Reynolds (Owen Wilson), and also receives an intriguing phone call from a young executive, George Madison (Paul Rudd), who was advised by a girlfriend of Lisa's to give her a call.

George calls out of politeness because he wants to explain that his relationship with another woman has just become more serious. But life takes an abrupt turn for the worse for George when he finds himself the target of a criminal investigaton for corporate malfeasance at a company run by Charles Madison, his father.

Although his pregnant assistant Annie is sympathetic because George can do no wrong in her eyes, George is dismissed from his job and all contact with colleagues other than his father is cut off. Still reeling from this blow, George goes to his girlfriend for sympathy and is stunned when she immediately breaks up with him.

Lisa isn't quite sure what to make of Matty, who has a penthouse in the same Washington, D.C., upscale building where George's dad lives. Matty means well, makes millions of dollars and is fun to be with, so she moves in with him, but Matty is also immature, uninterested in Lisa's own feelings and continues to have casual affairs with other women.

On a whim, George calls again to invite Lisa to dinner and she accepts. It turns out to be a disaster, George so overwhelmed with his troubles that Lisa asks they just eat their food in silence. They part ways not expecting to see one another again.

George doubts things could get worse, but they do. He is indicted and could face jail. Annie is so loyal that she tries to give him inside information in advance, but he urges her not to lose her own job, particularly since her boyfriend can't find one and with a baby on the way.

Matty tries to do better in Lisa's eyes, promising to consider seeing fewer women on the side. He inadvertently offends her, so Lisa moves out and spends a pleasant, tipsy evening at George's modest new apartment.

George's father drops one last bombshell on his son. It was he who committed the illegal act for which George is being charged. Due to a previous conviction, Charles would need to serve a sentence of "25 years to dead," whereas George would only do three years, tops.

On the night Annie's baby is born and her boyfriend proposes, Lisa begins to reconsider her previous reluctance to a future of marriage and kids. George is clearly smitten with her, but Matty pleads for another chance and she accepts.

George makes a proposition to his dad. He will take one more shot at persuading Lisa to be with him. If she will, Charles must go to jail. If she won't, George will take the rap for his dad.

At a birthday party the baseball player throws for her, George makes his pitch. It's up to her now. George goes outside to give her time to think it over, Charles looking on from above. Lisa comes outside and its clear that she has chosen him.