This is the story of a woman who suffers a crisis of confidence when her sport's career as a softball player get suddenly stopped. Reese Witherspoon plays the character of Lisa Jorgenson who has always been a bit of a tom-boy, playing sports better than boys while she grew up. As an adult she becomes a professional athlete. But, without any warning, she loses her position on her softball team called Team USA. Out of desperation, she starts a casual affair Matty Reynolds (played by Owen Wilson) who is a pitcher on another professional baseball team. Matty is a wild-guy, a womanizer, who has no interest in settling down.
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Lisa meets George (played by Paul Rudd) who knows one of her girlfriends. George tells Lisa that he is very serious about her girlfriend. Suddenly everything in George's life goes wrong. George's father, a big shot businessman, Charles Madison (played by Jack Nicholson) has gotten George in trouble with the feds. George is implicated in crimes that his father did, that George knows nothing about. George loses his job, and is surprised when his girlfriend immediately dumps him. Lisa takes pity on George. She agrees to go out with him. The date is a total disaster because George is unable to cope with all his troubles.
Lisa goes to live with Matty in his luxurious apartment which happens to be in the same high-rise building where George's father lives. The feds come after George. George finally figures out what is happening by getting information from his father's secretary who happens to be pregnant without the father of the baby being around to help her. George's father confesses that he was the one that broke the law, but since he has a record he asks George to take the fall for him. The difference would be that George's father spends the rest of his life in jail, but George would get off with only a few years in prison.
Lisa gets sick of Matty's shenanigans, who cannot stop partying with other women. She goes out with George again. This time they have fun. Matty makes up with Lisa by begging her to let him try to be better. Lisa agrees even though she knows George is the one that really likes her. George is about to give up and give in to his father's request to go to jail for him, when he decides to try one more time to win Lisa over. George tells his father if Lisa stays with Matty, he will go to jail.
There is a birthday party for Lisa at Matty's apartment which is right below the apartment of George's father. George goes to the party. He tells Lisa he loves her and if she loves him to join him outside on the balcony where his father can see them from above. Lisa does not know the stakes are so high, but she makes the right choice and finds herself in love with George after all.
Best part of story, including ending:
It is fun to see the challenges that a woman has who looking for the right man, especially when she is otherwise a very strong person.
Best scene in story:
It is a nice subplot when the secretary of George's father helps George out and we see the scene where the secretary's boyfriend (the one that got her pregnant) proposes to her at the end. That's the hint that everything is going to work out for George as well.
Opinion about the main character:
I like that Lisa finds her inner strength to dump Matty, who is so arrogant, in favor of George who is so sincerely in love with her.