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.
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, an upright 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 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, 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 by 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.