How Do You Know (2010)

Softball player Lisa Jorgenson (Reese Witherspoon) is devastated when she is left off the Team USA roster. Unsure what to do next, Lisa...

Softball player Lisa Jorgenson (Reese Witherspoon) is devastated when she is left off the Team USA roster. Unsure what to do next, Lisa begins dating Matty Reynolds (Owen Wilson), a pitcher for the Washington Nationals. She also receives an intriguing phone call from a young executive, George Madison (Paul Rudd), who was advised by a friend of Lisa's to give her a call. George calls out of politeness because he wants to explain that his relationship with his girlfriend has just become more serious. But life takes an abrupt turn for the worse for George when he suddenly finds himself the target of a federal criminal investigation for corporate malfeasance at a company run by his father, Charles Madison (Jack Nicholson). George is fired from his job and abandoned by the company, with the exception of his father and his pregnant secretary, Annie (Kathryn Hahn).

Still reeling from this blow, George goes to his girlfriend for sympathy and is stunned when she immediately breaks up with him. On a whim, George calls again to invite Lisa to dinner and she accepts. It turns out to be a disaster; George is so overwhelmed with his troubles that Lisa eventually asks that they just eat in silence, and they part ways not expecting to see one another again. Soon, Lisa moves in with Matty, who has a penthouse in the same upscale building where George's father lives. Matty is rich, well-meaning and fun, but is also immature and insensitive, and continues to have casual affairs with other women.

George is indicted and could face prison time. Annie is so loyal that she tries to give him inside information in advance, but he urges her not to lose her own job. 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 then 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 spend at least 25 years — basically, the rest of his life — in prison, whereas George would only do three years at most.

On the night Annie's baby is born and her boyfriend proposes, Lisa begins to reconsider her previous reluctance to settle down. George is clearly smitten with her, but Matty pleads for another chance and she accepts. George makes a proposition to his father: He will take one more shot at persuading Lisa to be with him; If she will, Charles must go to jail, and if she won't, George will take the rap for his dad. At a birthday party that Matty throws for her, George confesses his feelings for Lisa and goes outside to give her time to think it over, Charles looking on from above. Finally, Lisa says goodbye to Matty and joins George outside. At the end of the movie, they are seen boarding a bus together.

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