Max Abbott (David Schwimmer) is a womanizing sports broadcaster. His buddy Jay Murphy (Jason Lee) attempts to get Max to change his ways by setting him up with Samantha Andrews (Mili Avital). Samantha is also the editor of the book Jay is writing about having his heart broken by Natasha (Vanessa Angel). Of course Max and Sam hit it off and are soon engaged. The only problem is that Max is afraid she will cheat on him. So he asks Jay to test her by hitting on Sam and see how she responds. Jay eventually agrees. With pressures of a book dead-line Jay and Sam are soon spending every waking hour together and might be developing feelings for each other.
Kissing a Fool is not origional and is not hard to figure out, but it does have some comedic moments. Thank goodness for the humor, otherwise this would be a horrid film. The plot is pointless and dull. The characters are one dimensional and spend most of their time whining while drinking and cursing each other out. None of the actors give a performance worthy of note. If you are desperate for a romantic comedy Kissing a Fool might fill the need but otherwise it does not have much to offer.