Reese Witherspoon as Lisa
Paul Rudd as George
Owen Wilson as Matty
Jack Nicholson as Charles
Kathryn Hahn as Annie
Mark Linn-Baker as Ron
Lenny Venito as Al
Molly Price as Coach Sally
Ron McLarty as George's Lawyer
Shelley Conn as Terry
Domenick Lombardozzi as Bullpen Pitcher
John Tormey as Doorman
Teyonah Parris as Riva
Tony Shalhoub as Psychiatrist
Directed by James L. Brooks
30-something Olympic-level softball player Lisa Jorgenson (Reese Witherspoon) has reached a crossroads in her life after being retired from her team, as has George Madison (Paul Rudd), a businessman who has been indicted for financial crimes he didn't commit but that his boss/father (Jack Nicholson) seems to know more about than he's letting on. By the time the two of them meet, Lisa has already moved in with a self-involved baseball player named Matty (Owen Wilson), making her wonder if she's made the right decision.
There are so many jokes that can be made around the title of James L. Brooks' sixth movie, another meet-cute romantic comedy like the kind he helped originate while generally avoiding all the cliches that have come with that dubious honor. The most obvious joke goes something like: "How do you know this bland rom-com was done by Brooks as a response to the poor reaction to 'Spanglish,' trying to create a populist piece of tripe with stars coasting through roles that require them to show very little variety or range?"
But maybe we're getting ahead of ourselves here.
"How Do You Know" is first and foremost a vehicle for Reese Witherspoon to return to the type of female-friendly fare that helped establish her career. Whether or not you're able to endure her whining for more than 30 minutes at a stretch might give you some idea whether or not this movie is going to be for you. The only real difference between Lisa and most of her previous roles is that she's a softball player; otherwise, it's basically the same role you'd expect from any movie trying to win over the female crowd with a strong mostly self-assured female lead.
Concurrently with our introduction to Lisa, we watch as Paul Rudd's character George Madison is dealing with his own crisis as he's being forced out of the family business by an indictment for financial crimes. Both of them are put into a situation where they must reassess their lives when they end up being set up on a blind date. By then, Lisa has already started dating a successful baseball player, who seems oblivious to her needs, and George is having a similar conflict with his father. Rudd's characterization is that of a mopey and dopey guy who lacks much of the charisma he's brought to previous characters.
Rudd's first scene with Jack Nicholson involves the veteran trying to chew up scenery with a raspy voice that seems half-gone and lacking the commanding presence it's had in the past, making one feel as if Jack is phoning this one in. Later in the movie, Nicholson successfully tones things down a bit and actually gets a couple big laughs, one from just walking into a room and another merely from a facial expression, but it takes way too long for that Nicholson to emerge.
Wilson's baseball player is the least developed of the characters, possibly intentionally, because he's basically a shallow chauvinist pig with very little respect for women and very little concern towards Lisa's need for a more supportive partner. In one scene, he's talking to his fellow ball players asking how one knows they're in love and they give all sorts of sexist answers. To be honest, it's not a very interesting character even when compared to the similarly-shallow Kevin from "Meet the Parents."
As one might imagine from the title, much of the movie revolves around indecisiveness both in Lisa and George, but the rom-com aspect of the story is constantly sidetracked by the shift in focus to George's legal problems and his relationship with his father. Considering the lack of depth in the men in her life, Lisa's decisions just don't make much sense. There's nothing about either of these guys that could possibly appeal to any woman, so when she moves out on Matty and decides to go visit George, you might wonder what she's thinking but that's generally par for the course with the movie.
The slightly unnecessary fifth wheel in the equation is Kathryn Hahn as George's pregnant receptionist and personal assistant who offers a nice counterpoint to all the dud performances from the big name stars. She's a nice addition to the cast but an extended scene of her in the hospital as she's about to have her baby seems to have been shoehorned in to try to give a secondary character more depth than necessary.
Throughout all these developments--and we use that term loosely, because not a lot really happens in terms of plot--the film constantly tries to get all deep and philosophical about life and love, but that just contributes to the worst thing about the movie... that it's just plain dull. There are very few actual laughs, the cast's timing generally being off, nor is there very much about any of the character that might keep you even remotely invested in what they have to say or what is going on with them. Brooks has too many strong films under his belt to fully blame him for this dud, but it's hard not to feel as if he allowed his star cast to run all over his movie rather than trying to control them or force them to work outside their comfort zone rather than just delivering uninspired and routine performances.
The Bottom Line:
There are good romantic comedies and there are bad, but the former master of the genre has somehow managed to make one that lacks romance and laughs. Considering how many great films have been influenced by Brooks' earlier work, it's hard to believe how badly this movie fails. The results are grueling and it's hard to believe any women would want to buy what Brooks and his cast are trying to sell.