Written and directed by James L. Brooks, How Do You Know is a romantic comedy that decided to go on a roundabout manner in presenting its many messages about love and life rather than cutting to the chase, having many indecisive characters figuring just what to do at important milestones, and basically having them stuck there to bloat this close to two hours. It's a little frustrating to watch plenty of whining going all round, and I felt that much can be salvaged if the pace was kept snappy and succinct.
Two narrative threads run through the film, revolving around a growing romantic triangle between the characters of Lisa (Reese Whiterspoon), a baseball player on the national team who discovers that her life thus far has been unceremoniously cut down after it's decided by the head coach that it's time for her to make way for new blood, George (Paul Rudd) the CEO of his father's company who has been charged by the Federal Court for a Sarbanes-Oxley type of fraud that can see him potentially facing jail time, though of no fault of his own other than to assume things are coasting along, and Matty (Owen Wilson) the successful sportsman whom Lisa is dating in an on-off-on manner.
While it may seem like a character study of all three, everyone shares a basic characteristic of being excessively whiny, and at times needy, wanting things to go their way, and requiring listening ears to hear them out. I understand that most are at major crossroads - one not knowing what to do coming out of a sports career her whole life to date, the other facing felony charges through no fault of his own, with the suspicion that his dad (Jack Nicholson) may be responsible for the whole shebang and he's the scapegoat being set up for the fall, coupled with being ostracized by the people he knows, and Wilson's Matty deciding to no longer become the playboy Casanova and go monogamous for Lisa - but observing them go through their mood swings sometimes don't always make for a good comedy.
And too much of something makes this extremely tired to sit through, and it's a painful endurance to the final act where things get pieced together and a semblance of a certain direction Brooks wants to take with this. Don't get me wrong, I enjoyed each and every nugget of experience and advice that Brooks wanted to dispense through the characters, especially that between Lisa and George where they ultimately learn and share through their conversations, even though Lisa tries hard to keep things platonic, and we the audience know that George secretly desires more. Moments I thought had plenty of substance belonged to the tale about Playdoh - presents becoming meaningful when they come with a morale lifting story - and that involving shutting up to think rather than to engage in verbal barrage that will probably serve more bad than good.
Owen Wilson may be sleepwalking in this role here since he doesn't offer much as the alpha male jock who's none too bright though possessing enough to surprise sporadically, while Reese Whiterspoon probably needed a meatier role than this one, having to play a character gone neurotic when realizing she's out of her own comfort zone like fish out of water. Paul Rudd though continues to grow from strength to strength, showing he has what it takes to shine in serious dramatic moments, laced with that likability of being an everyday Joe that you'll probably root for. However, all three stars get outshone by the presence of Jack Nicholson each time he comes onto the scene, and frankly his last few scenes opposite Paul Rudd was some of the best this film had to offer.
Still, the performance of the cast failed to steer this film out of its self-indulgence, deciding to run on the spot rather than to move the story along. It's one thing dispensing good advice, but it's another if one likes to listen to one's own voice. I would like to love this film as I did James L. Brooks' Spanglish which remains amongst one of my favourites, but alas it went on aimlessly for far too long and wasn't able to salvage the damage done.