In How Do You Know, Lisa (Reese Witherspoon) has a choice: does she want to spend her time with the happy-go-lucky, super-rich baseball player bimbo (Owen Wilson) who may sleep with other girls while on road trips, but offers no-conflict easy times and great sex? Or will she opt for George (Paul Rubb), a neurotic misfit who is in the midst of an existential breakdown now that he is under investigation for a federal crime he neither committed nor (seemingly) can get out from under?
Well, for Lisa, the answer is obvious. The man behind door No. 1: Owen Wilson’s usual flirty self, full of pursed lips, puppy dog eyes, laid-back charm, and that wonderful crooked nose. But wait! There’s more to it. How Do You Know tells the tale of how George makes his bid for Lisa, learning how to love living in the process.
The movie, which also features a bit role for Jack Nicholson as George’s father Charles, is mostly your run-of-the-mill well-meaning relationship comedy, full of romantic twists and turns and a few well-realized moments of identifiable farce. The quartet of actors don’t bring their best chops to the tale, but they can pull off this kind of story half-asleep, while making the laughs roll on the cue. Some of the best bits are the one’s the trailer has already spoiled for you: Paul Rudd literally running away from bad news and Owen Wilson overreacting when Rudd’s character happens to walk Lisa into his apartment. Other enjoyable moments include Lisa and George’s charming — and completely silent — first date, an idea I wish I had thought of a long time ago.
At its most sincere, How Do You Know is about a girl learning the courage to dive into a committed relationship and not see marriage and motherhood as paths to a life of misery. But it’s Rudd’s story that dominates our interest, and in order for Lisa to find the right man, he must first work through some clever double-talk double crossings with his father. Ol’ Jack pulls some charm into the picture in these scenes, but he mostly comes across like a caged lion, prowling about and munching on spoon-fed zoo food.