How Do You Know may have underperformed when it was first released in theaters, but the James L. Brooks romantic comedy holds up on its 15th anniversary.

Professional softball star Lisa Jorgenson (Reese Witherspoon) begins dating Washington Nationals pitcher Matty Reynolds (Owen Wilson) while receiving an unexpected call from young executive George Madison (Paul Rudd). George, trying to be polite, explains that his relationship with his girlfriend has grown more serious. But life takes a dramatic turn when George is implicated in corporate wrongdoing at his father Charles Madison’s (Jack Nicholson) company, losing his job and facing federal scrutiny, with only his father and pregnant secretary Annie (Kathryn Hahn) standing by him.

Both struggling with personal setbacks, George and Lisa’s first lunch together ends awkwardly, leaving them unsure if they’ll cross paths again. Meanwhile, Lisa moves in with the wealthy but immature Matty, whose casual affairs and insensitivity begin to strain their relationship. George wrestles with legal peril as he navigates his father’s betrayal and his own conscience, while Lisa contemplates her career and romantic choices.

An unexpected reunion in Matty’s building sparks connection between George and Lisa, culminating in a night spent together in George’s modest apartment. When Charles confesses that he committed the crime George is accused of, the stakes rise: George must decide whether to protect his father or pursue a chance at love with Lisa.

At a birthday party, George declares his feelings, giving Lisa the choice to follow her heart. After thoughtful reflection, Lisa realizes her love for George outweighs everything else. How Do You Know concludes with Lisa joining him outside, ready to embrace a future together, while Charles faces the consequences of his actions.

When I first saw How Do You Know towards the end of December 2010, my initial thought was that it was way too long and could probably shave off maybe 20 minutes of run time. But maybe that was also because of sitting through G-d knows how many minutes of previews. In rewatching 15 years later, it could probably still stand to lose a few minutes, but the comedy should have performed way better than it did.

I mean, look at the cast that Brooks is directing in How Do You Know. Reese Witherspoon, Owen Wilson, Paul Rudd, Jack Nicholson, and Kathryn Hahn! What’s not to enjoy about the cast?! Hell, both Rudd and Hahn reunited not long thereafter on Parks and Recreation in a very different environment. Of course, the main cast is the reason why the budget was so expensive at the time. It should have recouped its budget with that kind of name talent attached. Alas, that wasn’t the case.

Brooks does in How Do You Know what George Clooney did a number of years later with Suburbicon. He merged two different ideas into one. Maybe that wasn’t the best idea—I don’t know. The fact that Lisa Jorgenson is a professional athlete is too compelling of a story arc to ignore. Brooks could have chosen to focus on the fallout of being cut by USA Softball and how this impacts her. But instead, he’s equally invested in an arc relating to corporate executives and accountability when it comes to breaking the law. There are compelling stories to be told either way. Maybe putting two into one film was just too much for audiences.

As I rewatched the film earlier in December, Brooks was launching a political dramedy, Ella McCay. Much like How Do You Know, it was also getting slammed as people first started to watch the film. I was not one of those slamming it because I personally thought it was good. Maybe not Top 10 of the year good, but good enough to at least deserve a rewatch down the road.

Fifteen years later, How Do You Know still isn’t perfect, but it’s far more charming and thoughtful than its early reputation suggests. The film’s uneven structure keeps it from fully soaring, yet the performances and Brooks’s unmistakable touch give it a warmth that lingers. It’s a movie that rewards a second look, especially when viewed outside the expectations that greeted it in 2010. For all its imperfections, it remains an appealing, quietly affecting romantic comedy well worth revisiting.

DIRECTOR/SCREENWRITER: James L. Brooks
CAST: Reese Witherspoon, Owen Wilson, Paul Rudd, and Jack Nicholson, Kathryn Hahn, Mark Linn-Baker, Lenny Venito, Molly Price, Ron McLarty, Shelley Conn, Dominick Lombardozzi

Columbia Pictures releases How Do You Know in theaters on December 17, 2010. Grade: 3.5/5

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