Kissing a Fool

Writer Jay and womanizing sportscaster Max have been friends since birth. Jay introduces his editor Samantha to Max and they hit it off. Max wants Jay to try to seduce Sam to test her before their wedding.

Kissing a Fool is a 1998 romance comedy movie directed by Doug Ellin, starring Jason Lee, Bonnie Hunt, David Schwimmer. It holds an IMDb rating of 5.6/10 from 5,312 votes and runs 1h 33m.