How Do You Know drags out Lisa's decision-making process, as if she's got a real decision to make.
Do you ever want to delete every sentence that you're saying even as you're saying them?
-- George (Paul Rudd)
As a child, Lisa is perky and confident. With her hair pulled back beneath her baseball helmet, she wears a "Girls Rule" t-shirt and smacks the hell out of a ball of the tee, not incidentally intimidating the redheaded boy who's just whiffed on the ball. When she grows up to be a glorious softball player, Lisa (played by Reese Witherspoon), helps her team win championships. And then, as a 31-year-old, she's cut. And she's not confident anymore.
She's still perky, though.
Lisa's earnest efforts to pull through her crisis are at the center of How Do You Know. Another of James L. Brooks' ostensible romantic comedies for adults, it sets her up with a depressing lack of options, essentially, Boy #1 or Boy #2. (Think: Holly Hunter in Broadcast News, Adam Sandler in Spanglish, Helen Hunt in As Good as it Gets.) This time the formula provides the protagonist two exceptionally limited love objects, the fatuous Nationals pitcher Matty (Owen Wilson) and the neurotic business executive George (Paul Rudd). As Lisa ponders whom to choose -- that is, how she can "know" who's right for her -- she wears cute designer dresses and covers her mirror covered with uplifting post-its ("Courage is mastery of fear," "You got the swagger, better let it show!"). And she frets. Eventually, she comes to the decision that will end the movie.
Lisa's route to that end is not so much roundabout as it is slow-moving and, frankly, dull. For a woman who's apparently spent her life and career around other women, her teammates, she's remarkably bereft of friends. When the grouchy male softball coach (Dean Norris) tells an assembly of women coaches that Lisa won't make the team, they all know it will affect her deeply and worry for her. They also know that it's what happens in professional sports (except, apparently, in the movie version of men's sports, where Matty can still be pitching for $14 million a year in his 40s, not to mention indulging in "anonymous sex" on road trips). And so they let her go, following a brief gathering at her DC apartment to lament her passing. ("We should protest," offers one teammate, unhopefully.)
It's How Do You Know's contrivance that just as Lisa is facing a life change, so too is George. His is slightly less regular: the financial company he's sort of inheriting from his father Charles (Jack Nicholson) has been targeted for a federal investigation, and George, who insists he knows nothing, is the presumptive scapegoat. Having always done what Charles expects him to do, George doesn't question that he's cast out and not allowed to speak to anyone at the company or even that he'll have to pay his own gigantic legal fees. He takes his dad's lawyer's word for it.
George, unlike Lisa, does have a friend, his former assistant Annie (Kathryn Hahn, playing one of those best friends who steals the movie). She points out that he's being poorly used by Charles (most vividly in a moment when she leaps from her chair to strike at the self-serving old man, then wonders aloud at her own fit of vehemence), finds him a new, post-income apartment in her neighborhood, and brings him homecooked meals in tupperware.
As you'll no doubt guess, Annie provides the film's lone voice of passionate reason. As welcome as this is, it is also too easily attributed to her pregnancy (yes, yes, "hormones") and status as a mostly regular worker. Unlike her boss and Lisa and Matty, she's worried about health care insurance and her boyfriend Al's (Lenny Venito) recent layoff. At the same time, she has sense of resolve that's less perky than wise (she reassures her father that her own decision is fine, based on what he knows: "Dad, just remember there are a lot of TV shows with single mom heroines”).
In addition, Annie reveals a moral sensibility that seems to elude the privileged folks around her: her anger at Charles and affection for George frame the film's sympathy for the son, and so makes him into the correct choice for Lisa. Annie even provides Lisa with a model of good womanhood: just before they meet, Lisa tells George that she's never understood women who aspire to marry and have children: "I think they're pretending," she says during one of those romcom-engineered drunken confessionals.
Yes, Lisa has been leading a lonely, if self-affirming existence. And yes, that sadness is most plainly reflected in her fellow ball player Matty, as shallow a guy as has ever showed up in a Brooks movie. Still, and even after she learns he keeps a collection of pink Nationals sweatshirts in a closet for girls to wear on mornings-after, Lisa moves in with him, imagining he's a decent boyfriend. Still, she's surprised when she finds out he's texting a girl for a date on the road while talking to her, and still, she's not sure she wants to give up the sorts of presents he offers, say, a pre-pre-engagement gift of a diamond-encrusted watch for her birthday -- late, at a party populated by his teammates and their girls, and not her friends.
Nothing about Matty makes him an appropriate match for Lisa, and really, very little about George makes him a likely match. And yet How Do You Know drags out her decision-making process, as if she's got a real decision to make. The trouble is, she doesn't. Her choice is foregone, despite occasional moments of lucidity, as when she walks out on Matty (more than once) or, exasperated by George's insta-dedication to her, she erupts: "What the hell do you now except looking at me like Bambi?" If Lisa does have such moments, the movie forgets them in the end, leaving her to "pretend," after all.