George (Paul Rudd) is perhaps the last honest man in working in the financial sector. Its not a trait that has done him any good as HOW DO YOU KNOW opens. In fact, his sense of honor has put him in the way of an SEC investigation. The particulars are a mystery to him, but having been in charge when whatever happened occurred makes him, to his way of thinking, responsible. Honesty, as in blurting out with a childlike glee whatever crosses his mind, is also a naggingly persistent trait in Matty (Owen Wilson), a major league baseball player just starting a relationship with Lisa (Reese Witherspoon), an Olympic baseball star. Lisa, the crux of this nascent romantic triangle, has her own issues with honesty, in her case, with herself, after being dropped by her team for having reached the impossibly ripe old age of 31, shes in free-fall with only a plethora of sticky notes full of platitudes to break her fall.
Their paths cross when George calls Lisa after getting her number from a teammate. Hes called to tell her he wont be calling because hes seeing someone who will, to his surprise, shortly dump him for what she claims is the good of their relationship. Its a typically off-kilter development, and one emblematic of writer/director James L. Brooks annual holiday offerings. This is one of his lesser, though worthy efforts. There is nuance and intelligence to a script peopled with characters who are believably flawed, if essentially decent. The story catches none of them at their best, but it does catch them at their truest as they work through their issues without needing to do so at anyone elses expense.
Inevitably, George and Lisa have their first date on what is for each of them the worst day of their respective lives. Her being dropped by her team, and him literally running away from the bad news his father (Jack Nicholson) was set to deliver. After a disastrous start in which they babble about the wisdom of ordering a drink, Lisa suggests total silence. Rather than increasing the awkwardness, the ensuing quiet becomes an oasis of reflection and revelation for George, who falls for her. Alas, Lisa has just gotten serious with Matty after a frank discussion of what constitutes being a good host the morning after a casual hookup. It was a conversation that resulted in a certain amount of reflection and revelation on Mattys part. This doesnt prevent Lisa from bouncing in and out of Georges life as she tries to decide what it is she wants, and George tries to decide if he should make a move, and Matty tries to figure out what it means to be serious about one woman.
What is refreshing about the peculiar triangle, and its ancillary players, is that by the end, everyone is a better person. More or less. Even Georges father, a man so accustomed to manipulating people with an easy, yet lethal mix of charm and intelligence that he can no longer tell when hes sincere, or so he confesses to his son in what may or may not be another attempt at manipulation. Nicholson is perfectly cast, and makes the most of it by not overplaying it.
The script doesnt overplay it either, with crisp dialogue and prescient observations about the nature of human interaction, though there are a few convenient coincidences that the audience is asked to roll with in order for the plot to progress. Its not an onerous request. The performers are engaging, keeping things sharp and thoughtful when saccharine threatens to make a mess of the story. Supporting players provide the proper sounding boards for them without seeming like the expository devices that they are, particularly Kathryn Hahn as Georges pregnant ex-secretary and self-appointed caretaker during his downward spiral. She delivers a refrigerator full of food and a wacky sort of comic relief brought on by hormones, the kind that takes the form of taking an abortive swing at Georges father, or weeping wildly when George wont even try to guess what she knows but contractually cant reveal about the latest legal disaster looming for him.
HOW DO YOU KNOW is a warm and fuzzy film that somehow manages to avoid the trap of becoming cloying. It finds piquant and pithy humor and pathos in watching grown-ups who dont quite know what they want going dealing with the inevitable flux and existential nausea that monumental change brings on. There is nothing particularly challenging here, nor is there is no great energy, but rather an amiable ramble that ends quietly but decisively. As such, its a welcome and diverting tonic to the stress of the season.