The love triangle consists of Lisa (Reese Witherspoon), an Olympic softball player facing the end of her career; Matty (Owen Wilson), a slutty pro baseball player; and George (Paul Rudd), a schmoopy, upstanding professional falsely accused of insider trading. This is where the trouble starts. The directing of Lisa and George is extremely off, and the script doesn't flesh George out beyond his watery, romantic eyes and vague sense of morality. In Lisa, Reese Witherspoon is trying to do this tough, fast-talkin' broad, and boy, is it a disastrous attempt. George is directed to just be in awe of Lisa (why, we never really figure out), creepily latching his eyes onto her and just being desperately in love with her from the moment they meet. This is disingenuous for two reasons. One, it feels like some condescending female wish fulfillment bullshit. Yes, all ladies love Paul Rudd, but just watching him be head over heels for Reese Witherspoon for no damn reason isn't going to make us automatically like your movie. And two, there is nothing that great about Lisa. She talks only in inspirational mantras (like Charlotte did on Private Practice post-rape, which was a little unsettling for me to see again), and she's hung up on a mentally deficient guy who cheats on her (Matty) because he's rich. She's kind of a worthless asshole, actually.

Then there's the issue of how the movie's title question is woven into the story. All the characters are confused about one thing or another. George doesn't know whether to take the blame for the insider trading so someone else with priors can avoid a lengthy sentence (that's one of the stupid ones -- the answer is don't go to jail for a crime you didn't commit, ya dummy!). Lisa doesn't know what she wants to do with her life. Matty doesn't know how to tell if he's in love, or, hilariously, how to apologize to a girl properly. Jack Nicholson doesn't know whether to play his scenes as "raspy old toad" or "really raspy old toad." They're all at a crossroads. I didn't find any of them to be particularly compelling crossroads, but it was still a clever gimmick anyhow.

The comedy largely falls flat, and Reese Witherspoon didn't have any chemistry with either guy, but such is Reese Witherspoon these days, I suppose. I think she was a casting mistake, but then again, with James L. Brooks spacing on directing this thing competently, it probably would have been a mess either way.

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