At 31 years old Lisa Jorgenson (Reese Witherspoon) is cut from the US national baseball team. She starts dating two men: professional baseball star Matty Reynolds (Owen Wilson) and businessman George Madison (Paul Rudd). Matty is rich, handsome and superficial, but starts to genuinely care about Lisa. George is head of a large corporation, but he is facing a serious fraud investigation related to falsifying tax records. George's pregnant personal assistant Annie (Kathryn Hahn) is loyal, but his domineering father Charles (Jack Nicholson) appears to be behind all that is bad in George's life.
Lisa moves into Matty's swanky apartment, but he misbehaves just enough to push here away and into the waiting arms of George. Meanwhile, Charles is trying to find a way to stay out of trouble with regulators by pushing George deeper into the hole.
Written, directed and co-produced by James L. Brooks, How Do You Know may be the moment a once great filmmaker finally hit the wall with a dull thud. From the uninspired title to the stultifying pacing and abject lack of content, How Do You Know is devoid of laughs, drama or genuine emotion of any kind. The film rolls over and dies early, with neither Brooks nor the cast able to generate even the faintest of pulses.
The one interesting element in the plot would have been Lisa dealing with the rejection of being summarily cut from the sport she loved. Witherspoon tries hard in a couple of scenes to convey the trauma of dealing with the emptiness that resides on the other side of the dream, but Brooks soon loses interest and resumes the ping pong between Matty and George. Witherspoon is reduced to hauling her luggage back and forth between the two men, by buses and taxis, in an unbelievable display of bankrupt writing.
Meanwhile the two men stay at the most superficial level, Matty the playboy athlete and George the honest businessman. Neither progress an inch from their starting positions, and two hours into the movie Matty is still being a dork and George is still all innocent puppy admiration. In a desperate attempt to stretch the proceedings to two hours, Brooks introduces several scenes in which the characters agree to not talk, and then proceed to not communicate, thereby setting up more excruciating scenes to cover the same ground.
How Do You Know is sad late career misfire for Brooks as director and Nicholson as a film star, and they both took a long, possibly permanent hiatus after this debacle.
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