Outgoing Max (Schwimmer) is considering marrying his girlfriend of two weeks, Sam (Avital), but is unsure she can be trusted, so asks best mate Jay (Lee) to try and seduce her. He refuses, but when Sam and Jay are brought together professionally, they discover just how much they like each other.
David Schwimmer (he's one of the Friends, you know) goes for a change of pace by playing a womanising, four-letter word using TV sports guy. In other words, the anti-Ross. It's a very brave attempt but, like the film in total, he can't quite pull it off. He plays Max, a misogynistic, serial womaniser with an over-inflated sense of self importance given that he works as a local TV sportscaster making him at best a big fish in small pond. (We know this, also, because he delivers his catchphrase - "What up?" about 500 times in the movie).
This all changes, however, when Max meets Sam (Avital), the editor of his oh-so-sensitive best buddy Jay (Lee)'s impending novel. Within 24 hours they have pet names for each other, within two weeks they've moved in and become engaged. In fact, everything's racing along nicely until Max has something of a panic attack. Judging everyone by his own somewhat lax standards, Max has to know if his wife-to-be can possibly remain faithful tohim, so he enlists Jay to try and sleep with her, just to check. Needless to say, complicated romance is soon in the air. Kissing A Fool is a film that has its cake and damn well wants to eat it, too. It fancies itself as a light breezy comedy but also wants to display a sharp cynical edge, and struggling awkwardly with both, it ultimately achieves neither. Similarly, Schwimmer wants to show us there's more to him than just being a girly-man. Sadly, there isn't.
Chasing Amy's Jason Lee, on the other hand, is rather good, although in keeping with the general tone of the film, him being the shy sensitive one is overdone to the point where ultimately it's hard to care who gets the girl.
Kissing A Fool tries too hard to shake things up just a little, but falls between rather too many stools.