The two leads meet during a very unhappy period in both of their lives. Reese Witherspoon portrays Lisa, an Olympic caliber softball player past her prime who has just been terminated by the new coach, and Paul Rudd portrays George, a straight-shooting corporate executive who finds out that his company is being investigated by the SEC. Both are about as likable as two actors can be, and their "meet cute" moments are filled with chemistry. We're rooting for them to find true love in the midst of all of their problems. Well, if only it were as simple as that...

The needlessly complex plot was written by James L. Brooks, who also directed the movie. Brooks should have stuck to directing as he did for "As Good as It Gets" and "Terms of Endearment." He could have kept it simple during these times of recession, but it seems obvious that he took all that studio money ($120 million) and spent it in directing what will end up being a very expensive studio flop. This film currently has only a very modest box office gross of about $25 million, falling far short of breaking even on its production costs.  

The budgetary excesses are exemplified by the casting of Jack Nicholson in the minor supporting role of Charles, the father of George. Charles is the founder of the company that his son now runs, the company which is under SEC investigation. George runs the company, but his dad remains Chairman of the Board and a man still pulling the strings from behind the scenes. Nicholson doesn't come cheap, even for a supporting role, and I can only guess at how many millions it took to get him on board. 

Then the noted composer and conductor Hans Zimmer was hired to score the movie. Zimmer did the same for blockbusters like "Sherlock Holmes," "Inception," "The Dark Knight," "Pirates of the Caribbean," "The Da Vinci Code," and "Angels and Demons." Yes, there are a few "small" movies in his repertoire like "Frost/Nixon" and "It's Complicated," but by and large he has to be viewed as a big budget composer. 

They might have pulled it off if, IF, they had the right script. Like many other films, most of the problems with this movie start with the script. The subplots in this film run all over the place, and some are unnecessary. If it had been me, I would have thrown out the entire subplot involving Jack Nicholson. His overwhelming presence mucks up the story, and only a very few people can understand why the company is being investigated by the SEC. Something about payoffs having been made to the wrong people through a foreign subsidiary. There's a plot catcher for you... Many far more simple subplots could have been devised to create the same effect and saved a lot of money in the process. 

Once again, a story of too much money chasing too few good ideas. You have to surmise that nothing was done on the cheap for this movie. What were they thinking? A romantic comedy with a studio budget of $120 million??? It could easily have been done for half that.

There are other subplots whirling around Lisa (Reese Witherspoon), who was a star player for the US Olympic softball team. Now she is 31 years old and past her prime, but she is the player who works the hardest and is the best at rallying the team on to victory during tight moments. However, the new coach doesn't see it that way. He views her as a liability who is preventing a younger player from making the team. Lisa is romantically involved with Matty (Owen Wilson), a star baseball player who just happens to own an expensive Manhattan condo in the same building as corporate bigwig Charles. 

The long dry spells when Matty is on the road allow for a mutual friend to suggest to George that he give Lisa a call. He is in need of a friend, for the only real friend that George has at the moment is Annie (Kathryn Hahn), his loyal and devoted secretary. She realizes that he is being set up to take the fall, but she is legally prohibited from saying anything. Annie is very pregnant and a soon to be an unwed mother, another subplot in this complicated tale.

The "How Do You Know" of the title involves Lisa having to make up her own mind as to which man she loves, but it comes from a question that Matty asks of his teammates. I would have liked this movie more if about 20 minutes, two subplots, a character or two, and about $60 million had been cut from it. 121 minutes, and rated PG-13 for sexual content and strong language.