From legendary director/writer James L. Brooks comes a humorous and romantic look at the “How Do You Know” question. When everything she’s ever known is suddenly taken from her, Lisa (Reese Witherspoon) begins a fling with Matty (Owen Wilson), a major league baseball player and self-centered ladies man. Before their relationship takes off, Lisa meets up with George (Paul Rudd) a straight-arrow businessman facing his own serious issues, both with his father (Jack Nicholson) and the law. Just when everything seems to be falling apart it doesn't.
Compared to previous James L. Brooks dramedies, like As Good As It Gets, How Do You Know feels slight, but it still marks an improvement over the ill-conceived Spanglish. The setup begins with a newly minted couple and a brand-new single. Lisa (Reese Witherspoon), a pro softball player, dates Matty (Owen Wilson), a major-league pitcher, who lives in the same Washington, D.C., high rise as financial exec Charles (Jack Nicholson, looking ill at ease), whose son and employee, George (Paul Rudd), gets the boot from his girlfriend after he loses his job. When George meets Lisa, who didn't make the team, sparks fly, but she's unavailable, so they get on with their lives. Hardly the brightest bulb, Matty raises Lisa's spirits with his goofy antics, so she moves in with him. Then George finds out he faces charges for tax fraud, even though he broke no laws. While his pregnant assistant, Annie (Crossing Jordan's Kathryn Hahn), supports him through the crisis, he can't stop thinking about the blonde from the elevator, so he tries to get to know Lisa better. Throughout the rest of this glossy entertainment, their friendship verges on romance, but Lisa stays with Matty, until Annie helps her to see George clearly for the first time. As love triangles go, Brooks isn't reinventing the wheel, making this underwritten affair one of his less inspired creations, but Witherspoon, Rudd, and Wilson are good company--even if the latter is essentially reprising his vacuous Zoolander character (just substitute baseball for modeling). --Kathleen C. Fennessy