Synopsis
Kissing a Fool (1998) is an American romantic comedy you can watch online on iFILM, directed by Doug Ellin. David Schwimmer — deep in his Friends years — plays Max, a smug local TV personality who has somehow found a woman worth keeping: Samantha, his smart editor. Jason Lee plays Jay, Max's best friend and a romance novelist who didn't notice Sam until she was already off the market.
Consumed by doubt, Max talks Jay into testing Sam's fidelity. From there the film does exactly what it has to. Bonnie Hunt, Judy Greer, and even Jerry Springer turn up in an ensemble that seems to have genuinely enjoyed shooting in Chicago. No surprises — but a tight 93-minute romantic tangle that knows how to earn its ending. Watch Kissing a Fool (1998) online on iFILM.
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