Kissing A Fool (1998)

Max and Jay have been best friends since childhood. Jay has recently broken up with the love of his life while Max has a revolving door for a love-life. Jay, currently writing a book and unable to shake the blues, sets Max up with his editor Samantha. Although they share few interests, they are engaged within two weeks. Still, Max's roving eye is in operation and when confronted with the fact that Sam will be the last woman he will sleep with, he proposes a test. Jay will hit on Sam. If she shows no interest, then Max will be confident enough in her loyalty to go ahead with the marriage. Jay rejects the plan, but the pressures of editing thrust him and Sam together constantly. They are forced to deal with their true feelings when Max is away on a business trip where his own inability to resist temptation is confirmed.