Review of Kissing a Fool (1998) by Caleb C — 09 Apr 2011

David Schwimmer plays Max, a womanizing Chicago TV sportscaster who falls for Sam played by Israel native Mili Avital, his attractive young publisher but who he feels is too good to be true. Max and Sam seem perfect for each other but Max wonders if he can really keep Sam "satisfied" long-term and tries to get his best friend Jay (Jason Lee) to see if she can become unfaithful.

Jay is hesitant to do this being the sensitive soul that he is plus he is still grieving over the breakup of his slutty model girlfriend but things become complicated when Jay also succumbs to Sam's charms and begins to fall in love with her.