Review: How Do You Know

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James L. Brooks has earned the right to call himself a comedy directing and writing legend, even if the majority of his credits come from his television work on programs like Mary Tyler Moore, Taxi, and most notably, The Simpsons. Brooks has made only a handful of movies over the course of his career, two of which became classic comedy dramas and multi-award winners. First, Brooks offered the world some Terms of Endearment (1983), and received many awards in return (Best Picture, Director, Actress, Supporting Actor, Adapted Screenplay), then gave As Good As it Gets in 1997, another multi-award winner, with laurels going to leads Jack Nicholson and Helen Hunt.

With How Do You Know, Brooks hasn’t retired his leading man yet, playing Nicholson as a non-romantic lead alongside a new generation of talent, namely Reese Witherspoon, Paul Rudd, and Owen Wilson. How Do You Know is here in time for the holidays, just as As Good it Gets was, and similar romantic comedies like Nancy Meyers’s It’s Complicatedbefore it. This movie aims to raise your spirits, and does eventually, only after a lot of good-natured turmoil. People may expect a little more than they get…

James L. Brooks has earned the right to call himself a comedy directing and writing legend, even if the majority of his credits come from his television work on programs like Mary Tyler Moore, Taxi, and most notably, The Simpsons. Brooks has made only a handful of movies over the course of his career, two of which became classic comedy dramas and multi-award winners. First, Brooks offered the world some Terms of Endearment (1983), and received many awards in return (Best Picture, Director, Actress, Supporting Actor, Adapted Screenplay), then gave As Good As it Gets in 1997, another multi-award winner, with laurels going to leads Jack Nicholson and Helen Hunt.

With How Do You Know, Brooks hasn't retired his leading man yet, playing Nicholson as a non-romantic lead alongside a new generation of talent, namely Reese Witherspoon, Paul Rudd, and Owen Wilson. How Do You Know is here in time for the holidays, just as As Good it Gets was, and similar romantic comedies like Nancy Meyers's It's Complicated before it. This movie aims to raise your spirits, and does eventually, only after a lot of good-natured turmoil. People may expect a little more than they get from Brooks this time around, but should not walk away totally disappointed.

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The title of this film is in the form of a question, and the movie asks many questions, as do the characters, and probably the viewers too. How do you know when it's the right time for love? — is the main, long-winded query the film poses. The film captures the romantic leads at cross roads in their lives: Lisa (Witherspoon), a professional baseball player, is cut from the team after ten years at the top and stares down an uncertain future; completely ignorant of the cause, George (Rudd) is charged with a federal offense and is forced to leave the company he runs with his father Charles (Nicholson) for the duration of the investigation. When the leads first speak, they are oblivious to the trials ahead and continue on after a brief telephone encounter completely independent and ignorant of the other's doings. However, an overly convenient plot setting — Matty (Wilson), the pro ball player and 'playa' Lisa is casually dating, and George's father live in the same condo — allows the leads to run into one another on a semi-frequent basis.

Playing hapless, but reserved, Witherspoon is appropriately dazed in the wake of her job loss, making light of big decisions, such as moving in with the easygoing Matty, only to move out, in, and out again. The usually chipper actress is refreshingly bitter, playing a strong, independent woman at her weakest. Rudd is dumbstruck in the face of federal indictment, and borderline feckless, a character trait alluded to more than once by Charles, and which Rudd inhabits effortlessly.

Kathryn Hahn is an actress you may recognize as always the bridesmaid never the lead in movies (see: How to Lose a Guy in 10 Days; Win a Date with Tad Hamilton!), but in How Do You Know, plays a more important role in the overall story. Let's call her the surrogate mother, and she is literally pregnant with the bundle of joy that will reign down sunshine on the conclusion of the film in the place of typical romance genre fair, like a wedding. Pregnant herself during the movie's production, Hahn plays George's bewildered assistant and close friend. Her hormonal performance isn't exaggerated, but rather authentic for a pregnant-to-the-point-of-bursting woman who does the worrying for everyone else. 

Nicholson is the stern father figure, there for his son, but also somewhat of an antagonistic character for his association with the company that George is no longer a part of. The father-son moments are sincere and carry a lot of the interest of the film, while the romantic story dilly-dallies. Between Rudd's open-face, goof factor, and Witherspoon's crooked-smile cynicism, not much is accomplished between these two for a large part of the movie. Like I said, a lot of questioning, and subtle rephrasing drives the dialog, and in turn, the wheels of the movie. Brooks builds an ill-fitting friendship story first, which for the most part lives up to the bond we accept as formed between Lisa and George at the end of the movie. We believe in George's pursuit of Lisa against all odds, which are those curve balls that put them in awkward positions to one another, because she's like a vision at the darkest time in his life, beautiful and as helpless as he is.

Ultimately, Lisa and George must decide what life they want to lead now that they've left their respective folds. Both can either choose a life connected to their past — Lisa living an athlete's life vicariously through Matty; George taking the fall for his company — or face the unknown together, without any answers. The message is strong, if tediously built, benefiting by its own anti-climactic end. Events seem to only happen on the periphery of the narrative, since the leads are isolated from their former life roles. As a result How Do You Know plays like a thinking person's romantic comedy, worth the trip to the theatre for some, but best saved for a rainy day with loved ones.

Overall Score: 6.95 – Okay. (6s are just okay. These movies usually have many flaws, didn’t try to do anything special, or were poorly executed. Some will still love 6s, but most prefer to just rent them. Watch more trailers and read more reviews before you decide.)