An odd duck of a romantic comedy from James L. Brooks, How Do You Know strays as far from a barrel of laughs as a writer-director formed by network television can get without losing his grip altogether. The movie's rhythms are loose, disjointed, and peppered with strategic silences or half-finished thoughts. The punch lines are few and there's not much mugging for the camera other than from Jack Nicholson, hamming away as a triumphantly errant parent. And with Janusz Kaminski on board as cinematographer, How Do You Know actually looks like a rainy but inviting downtown Washington, D.C. — exactly what it's supposed to look like — rather than the inside of a sitcom set.
Even with Reese Witherspoon up front in fetchingly scanty frocks, choosing between her sweetly clueless baseball star squeeze (Owen Wilson) and George (Paul Rudd), a straight-arrow businessman upended by a federal investigation, How Do You Know faces uncertain prospects at the box office. But this strange, brave little film deserves to be sent out to sea in a bottle so that future generations may take the measure of just how hair-raisingly indeterminate it was to live and love in early-21st-century America.
In that sense, How Do You Know is the latest memo from a fitfully pungent social commentary that Brooks began in the early 1970s with The Mary Tyler Moore Show and its spin-offs, referenced in his new film by an unmarried mother who reassures her father after she gives birth, "Dad, just remember there are a lot of TV shows with single-mom heroines." Set adrift in a world fragmented by divorce and collapsing families and stripped of social markers, Mary, Rhoda, et al. found emotional solace at work. Brooks is a master of warmly dysfunctional workplace humor — Albert Brooks's sweating scene in Broadcast News is one of the great moments in the comedy of embarrassment and humiliation. But in How Do You Know, even work, that bulwark against the howling uncertainty of a heartless world, is gone.
It's no accident that Lisa (Witherspoon) and George meet at the precise moment their professional lives go into free fall. At 31, Lisa has been cut loose — an inevitability she refused to see coming — from her beloved women's pro sports team, while George, a straight arrow and all-around nice guy, finds himself the target of an investigation for what may be shady business deals carried out by his father, a bullying rascal in the classic Nicholson mold. So floored by adversity is Lisa that on their first blind date, she shushes George just as he launches into a blow-by-blow account of his woes, and they finish their meal in one of the many silences and incomplete sentences that follow as they grope toward, and shy away from, a connection worth having.
Not that How Do You Know doesn't have its moments of shamelessly entertaining shtick, much of it furnished by Nicholson (watch for a very funny visual gag about his proclivities for much younger women) and by Wilson as Lisa's current squeeze, whose idea of being a good host is to stock his bathroom with enough new toothbrushes to accommodate an army of one-night stands. But despite the shtick and the ad campaign, which is clearly trying to market the film as a standard love-triangle rom-com, How Do You Know is one productively shapeless movie whose only real villains are those who use language to dissemble — like George's ambitious girlfriend, who wants to "hit the pause button" on their "intensifying" relationship right after she finds out he's screwed.
The good guys are bewildered, rendered speechless by trying to say what they mean when they're radically unsure of what that is, and whom they should say it to, and how. In one of many terrific ancillary turns, a therapist (played the great Tony Shalhoub) whom Lisa visits all too briefly for enlightenment tells her, "Figure out what you want, and find out how to ask for it." Before it wraps up that question like the obedient Hollywood love story it eventually has to be, How Do You Know takes an unexpectedly candid detour through how incredibly hard just following that directive has become.