Don't get me wrong I actually enjoyed this film throughout, but its weaknesses are its simply a little lengthy and it just feels so middle of the road. Nothing spectacular ever seems to happen and when I say that I don't mean some shocking and amazing climax, but for a somewhat exception to the rule of romantic comedies there just wasn't that wow moment. There wasn't that one speech, that one look or anything close that even registers this as one of those fluffy rom coms you watch on a rainy Sunday afternoon.
The story here is actually quite intricate though for a genre with such strict guidelines. All revolves around Lisa, played here by Witherspoon in a role that is a departure for her. She is the uncommon woman here, the one not sure that love and the whole settling down thing is for her, thus the point of the film, but never the less it is nice to see her attack a role that doesn't necessarily fold into every one of her personalities little charms. As an aging softball player she is cut from her team and finally forced to come to terms with the fact she is going to have to have a life after the only thing she truly knows comes to an end. Enter Matty and George. Matty, the self-absorbed baseball star seems the logical choice, George the strange guy who she ends up in the most convoluted of ways on a blind date is definitely not the first round draft pick. You know how this is going to end.
And though we of course will have the movie figured out once all the ground rules are laid, it is the performances of Wilson and Rudd that keep us tuned in, that keep us chuckling through the extended run time and keep us rooting for, well, either one would have been fine. Thus the main conflict I have with the film is born and it is one that makes no sense to have in a romantic comedy. It defeats the purpose almost. We don't really hate either of these guys. Yes, Wilson's Matty is interested only in himself and fulfilling his wants and needs, he is ignorant to how to manage a real relationship but has the stability Lisa needs. George on the other hand is caring and completely in love with Lisa from their first silent blind date, but of course he is broke and being investigated at work. Each have their ups and downs but neither one of them makes a hard case for us to root against them. In fact as much as Rudd's George is appealing and sweet, Wilsons Matty is goofy and charming. I don't know if Brooks was trying to change the formula up a bit to make the story more grounded in reality, but lets be honest, everything here completely follows that time-tested formula except for this one aspect and in only changing that one thing it kinda screws up the rest of it.
I have to mention that I was especially impressed with Owen Wilson who plays this role to its fullest and its one of his best as he seems to keep growing in the roles he's taken lately. I look forward to his heavy roster of work in the upcoming months. And one cannot review a film that contains Jack Nicholson without saying something about him, sadly the entire side plot concerning him and his sons business troubles feels forced and in no way affects the story that it severely alters the course of the story. It is a pleasure seeing Nicholson interact with Rudd and he has a couple great moments but I just wish his role would have been more vital. Much like that of the wonderful Kathryn Hahn's. As George's pregnant secretary she not only provides the most touching moment of the film, but she garners laughs every time she is on screen and makes the most out of a role that most likely felt flat on paper.
I enjoyed watching this film once, but can't say that I would do it again. As much as I enjoy the work of its all-star roster it was simply too hard to get into with too little a pay off. I wanted to like it more, I really did, but the truth is, you just know when there is something special about a film and when there's not. 'How Do You Know' just doesn't have it. What a shame.
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