What the hell happened to James L. Brooks? The man's oeuvre, on TV and film, is filled with classics. Forgive the vitriol, but when Brooks is on, he's the king of broadly appealing human comedy, able to deftly combine witty dialogue and painfully recognizable moments of embarrassment with genuine pathos. No one is better at doing comedy about failure, which is why How Do You Know is so frustrating—it somehow fails at failing.
How Do You Know intertwines two individuals undergoing upheaval: Lisa (Reese Witherspoon), a professional softball player cut from her team, and George (Paul Rudd), an executive under indictment for crimes his Bernie Madoff-like father and boss (Jack Nicholson) may have committed. Unmoored, Lisa throws herself into a relationship with Matty (Owen Wilson), a tomcatting major league pitcher, while George in turn becomes smitten with Lisa and pursues her as a means of avoiding the sword dangling over his head.
There's two interesting ideas for films at work here. One is about a guy avoiding confronting a catastrophe by chasing a girl, and another about a girl losing herself in a fling with a womanizer trying way too hard to be an actual boyfriend. Fused together, the result is a talky mess. It's the kind of film where not only do characters constantly discuss their feelings, but they continue discussing said feelings after stating their point.
The actors are all quite charming. Wilson does his best work in some time as the puppy dog-esque Matty, while Witherspoon and Rudd (whose reunion here will resonate for the two or three people who saw them in the 1998 film Overnight Delivery) can be funny and poignant when they're just required to react, as opposed to spilling Brooks' wordy monologues. It doesn't help that there's overbearing, oboe-heavy romantic comedy music by Hans Zimmer playing over almost every scene.
The film's title evokes the uncertainty faced by the characters, but it could apply to the production: It doesn't know what it wants to be, so it pounds away at vague themes. Brooks has a body of work he can be proud of—perhaps he should pack it in before he lends his name to more embarrassments like this.