The story of Kissing a Fool is framed in a flashback, in which a publisher, Linda (Bonnie Hunt), while hosting a wedding at her house, relates to two over-eager wedding guests the story of how the bride and groom got together.
The bride in question is Sam (Mili Avital), an editor who works for Linda. She's currently editing the novel of Jay (Jason Lee), whose best friend is Chicago sportscaster Max Abbott (David Schwimmer). Jay sets up Sam and Max, and before you know it, the couple is engaged to be married.
However, the womanizing Max has doubts about the loyalties of his bride-to-be. He tries to get his pal Jay to seduce her as a test. If she bites, Max will call off the wedding...otherwise, he's found the right girl. Of course, Jay is reluctant, coming off a bad relationship with Natasha (Vanessa Angel), but he soon finds himself falling in love with Sam.
The heart of any romantic comedy is its characters, and Kissing the Fool runs the gamut from good to not so good. In the "good" category: Jason Lee. His is the most developed character in the film, and he handles it well. To top it off, he's funny, and gets most of the film's good lines.
Mili Avital sits somewhere in the middle of the road. Her character is nice, but flavorless. We never learn that much about her, and she doesn't express a strong presence that might transcend her mundane character.
Playing out of type, and without much success, is David Schwimmer. As much as he tries, his suave sportscaster is never quite believable. He's at his best during his "pathetic" moments, or, in other words, when he seems to be in more familiar territory. It just goes to show that a change of pace isn't necessarily good.
And then there's Bonnie Hunt. She barely registers a presence as a minor character throughout the flashbacks, but when she's the narrator, you wish she would just go away. It certainly doesn't help that the entire awkward flashback structure kills the story (for some reason it reveals the answers to the film's central questions right at the beginning). But any time the film begins to gain momentum on its own, WHAM! We're thrust back to Bonnie Hunt and her over-eager guests, and everything falls apart.
The story itself is a bit light. Even without the revealing framework, you can see exactly where the film is going. But the film's saving graces are its humorous moments. There are some wonderful exchanges between characters, and plenty of amusingly awkward situations throughout Kissing a Fool. However, while the humor makes Kissing a Fool palatable, its many flaws keep it from being completely enjoyable.
[R - strong language] (Universal)