Kissing a Fool (1998)

In the light-hearted comedy-drama "Kissing a Fool," we delve into the contrasting worlds of childhood best friends Max and Jay. Max, a local sports broadcaster, is a charismatic womanizer, navigating through life with a revolving door of romantic encounters, while Jay, an introspective writer, is the hopeless romantic, still nursing a heartbreak from a year-old breakup with Natasha. Their lives take a surprising turn when Jay introduces his enigmatic editor, Sam, to Max. In a whirlwind of emotion, Max and Sam, drawn to each other like magnets, find themselves engaged after a single date. Despite this rash decision, Max's insecurities begin to bubble to the surface, leaving him uncertain about his impending nuptials. In a twisted ploy to test Sam's fidelity, Max cajoles Jay into attempting to seduce his soon-to-be wife. Reluctantly, Jay finds himself entangled in this bizarre test of trust. As weeks pass and their professional and personal lives become increasingly intertwined, Jay and Sam begin to discover an unexpected spark between them. This intricate dance of love and friendship leads to a captivating journey of unexpected feelings, as they grapple with their evolving relationships and the looming question of fidelity. "Kissing a Fool" is a riveting exploration of love, friendship, and trust, where the lines between loyalty and love blur, unraveling a tale that is as unpredictable as love itself.

Kissing a Fool is a comedy movie featuring David Schwimmer and directed by Doug Ellin.

Kissing a Fool is currently streaming on Starz Roku Premium Channel.