Alright VHS Heaven faithful, let’s rewind to 1998. Bill Clinton was facing impeachment, Saving Private Ryan was dominating the box office, and somewhere in the video store, nestled between the bigger hits, you might have stumbled upon a rom-com with a familiar face and a slightly… questionable premise. I’m talking about Kissing a Fool, a film that tried to leverage David Schwimmer’s monumental Friends fame into big-screen success, with decidedly mixed results. But pop that tape in, ignore the tracking lines for a moment, and let’s talk about this curious Chicago-set love triangle.
### Testing... Testing... Is This Love On?
The setup is pure high-concept 90s: Max Abbitt (David Schwimmer), a commitment-phobic sports broadcaster prone to dramatic neuroses (sound familiar?), is finally getting married to the intelligent and lovely Sam Andrews (Mili Avital). Plagued by insecurity, Max hatches a truly boneheaded scheme: he asks his best friend, cynical novelist Jay Murphy (Jason Lee), to hit on Sam, essentially testing her fidelity before the wedding. What could possibly go wrong? Well, strap in.
This premise walks a tightrope between darkly funny and just plain uncomfortable, and the film, directed and co-written by Doug Ellin, definitely wobbles. Ellin, who would later find massive success creating HBO's slick Hollywood satire Entourage, shows flashes of sharp observational humor here, particularly in the banter between Max and Jay. But it’s the other co-writer credit that raises eyebrows today: James Frey. Yes, that James Frey, years before the A Million Little Pieces controversy exploded. Knowing his name is attached adds a fascinating, almost bizarre layer of retro-trivia to the viewing experience, doesn't it? Suddenly, a standard rom-com plot feels touched by something stranger.
### Friends, Lovers, and That Guy from 'Mallrats'
Schwimmer, also serving as an executive producer, clearly saw this as a chance to stretch beyond Ross Geller. Max is certainly neurotic, echoing his TV counterpart, but he's also possessive, manipulative, and often deeply unlikeable. It’s a tricky role, and while Schwimmer commits, the character sometimes feels more grating than tragically flawed. You can almost feel the pressure of trying to transition from Must See TV stardom to leading man charisma, a path many sitcom stars found rocky. Remember the buzz around any project a Friends cast member did outside the show back then? This one didn't quite land with the splash perhaps hoped for; Kissing a Fool reportedly cost around $4 million and barely recouped that at the box office, meeting with rather indifferent critical reviews.
The real spark, however, comes from Jason Lee. Riding high on his indie cred from collaborations with Kevin Smith like Mallrats (1995) and the brilliant Chasing Amy (1997), Lee effortlessly steals scenes as Jay. He’s got that laid-back charm, the wry delivery, and crucially, believable chemistry with Mili Avital. Avital, an Israeli actress who had turned heads in Stargate (1994), does admirable work as Sam, grounding the increasingly absurd situation with a degree of emotional honesty. You genuinely understand why Jay might fall for her, and why she might find herself drawn to his straightforward appeal compared to Max's exhausting theatrics. Their connection feels more organic and compelling than the central relationship the film ostensibly wants us to root for.
### That Late-90s Sheen
Watching Kissing a Fool now is like opening a time capsule to the specific anxieties and aesthetics of the late Clinton era. The dialogue snaps with a certain pre-internet rhythm, the apartments look lived-in yet stylishly "urban," and the relationship dynamics feel… well, very 1998. There's a cynicism lurking beneath the surface, a willingness to explore the messier aspects of love and friendship that feels slightly more adult than some of its fluffier contemporaries, even if the execution is uneven.
The Chicago setting provides a nice backdrop, less fairytale New York and more grounded Midwest metropolis. There aren't any huge, pyrotechnic action sequences here, obviously, but the "practical effects" are the real human interactions, the close-ups capturing shifting allegiances and dawning realisations. It feels refreshingly analogue compared to today's often hyper-stylized rom-coms. The emotional beats land through performance and dialogue, not slick editing montages set to the latest pop hit (though the soundtrack is quite 90s).
### So, Worth the Rewind?
Look, Kissing a Fool isn't a lost masterpiece. Schwimmer’s Max pushes the boundaries of sympathetic protagonists, and the central premise requires you to check your logic at the door (seriously, who does that?!). But there's an undeniable charm here, largely thanks to Jason Lee and Mili Avital. It captures a specific moment in time, both culturally and in the careers of its stars. It's the kind of film you'd rent on a whim, maybe catch late at night, and find yourself surprisingly engaged by the Jay/Sam storyline, even while rolling your eyes at Max.
It tackles themes of trust, insecurity, and the terrifying leap of faith that is true commitment, albeit through a somewhat contrived lens. There are some genuinely funny moments, and the dynamic between the three leads keeps things interesting.
Rating: 6/10
Justification: While the central premise is shaky and Schwimmer's character can be frustrating, strong performances from Jason Lee and Mili Avital, along with some sharp dialogue and that unmistakable late-90s vibe (plus the fascinating James Frey connection), make it an interesting curio worth revisiting for fans of the era's romantic comedies. It's flawed but has more personality than you might expect.
Final Thought: Kissing a Fool might test your patience like Max tested Sam's fidelity, but it’s a reminder that sometimes, the most interesting parts of a 90s rom-com weren't the grand gestures, but the messy, relatable human bits hiding underneath the Hollywood gloss. A flawed gem from the shelf, indeed.