For a movie starring Reese Witherspoon and Paul Rudd, you really really want to like this movie. Heck, the two of them in all of their roles that they've every played are so likable that...well, you really want to like this movie played by these likeable people. I mean....Really.
Romantic comedies generally plays to the heartstrings of viewers. They're supposed to touch you and make you smile, and maybe, just maybe, leave you with a small tear forming out of the corner of your eye. How Do You Know just leaves you wondering, Who Cares? Yes, it's a cute story, with a few funny spots here and there (most of which are already in the trailer), but you leave the movie not caring. And that's so hard with Reese Witherspoon and Paul Rudd. Both of whom, like I said before, just seem so likeable.
Writer / Director James L. Brooks teams up again with Jack Nicholson for the first time since As Good As It Gets, which had me hoping for some more great character studies. But Jack was a waste for this role. You could have cast almost anyone for the role and gotten the same effect. And pretty much for any of the characters. There are too many story lines, and too little depth to bring the viewer to care about the story lines. The lone bright spot of the movie came from John Tormey, the doorman...And he had like FIVE lines in the whole movie!
You simply cannot rely on 'cute' to you through a movie that runs almost 2 hours long.