SimilarScreen
Kissing a Fool

Kissing a Fool

May the best man win.

19985.51h 33m

Overview

An egotistical television personality enlists the assistance of his best friend in putting the fidelity of his fiancé to the test in this amiable comedy of the sexes. Told in flashback, the film takes a familiar love-triangle scenario and gives it a bitter twist. With a bride who seems too good for either suitor, the film is sustained by one question - who will she choose?

Directed by Doug Ellin
Written by James Frey, Doug Ellin
Produced by Rick Lashbrook, Andrew Form, Tag Mendillo
0

Top Cast

David Schwimmer

David Schwimmer

Max Abbitt

Jason Lee

Jason Lee

Jay Murphy

Mili Avital

Mili Avital

Samantha Andrews

Bonnie Hunt

Bonnie Hunt

Linda Streicher

Vanessa Angel

Vanessa Angel

Natasha

Judy Greer

Judy Greer

Andrea

Kari Wührer

Kari Wührer

Dara

Frank Medrano

Frank Medrano

Cliff Randal

Bitty Schram

Bitty Schram

Vicki Pelam

Jerry Springer

Jerry Springer

Self

Themes & Keywords

marriage proposallove trianglefiancémarriagebrideflashbackbest friendgroomtold in flashbackegotism

About Kissing a Fool

Kissing a Fool is a comedy, romance film released in 1998 exploring themes of marriage proposal, love triangle, fiancé, marriage, bride, flashback. Directed by Doug Ellin, it stars David Schwimmer, Jason Lee, Mili Avital. An egotistical television personality enlists the assistance of his best friend in putting the fidelity of his fiancé to the test in this amiable comedy of the sexes. Told in flashback, the film takes a familiar love-triangle scenario and gives it a bitter twist. With a bride who seems too good for either suitor, the film is sustained by one question - who will she choose?

Movies Similar to Kissing a Fool

Discover titles like Kissing a Fool — ranked by similarity and community votes

We found 15 movies similar to Kissing a Fool

If you enjoyed Kissing a Fool, you'll love these handpicked recommendations. Each title below shares similar themes, tone, and storytelling style. Our algorithm analyzes genres, keywords, director filmography, and cast connections to find the closest matches. Whether you're looking for the same emotional depth, narrative structure, or visual style, these picks are curated to deliver the best viewing experience for fans of Kissing a Fool.

The Groomsmen
33% Match

Blue-collar Paulie prepares for fatherhood and his forthcoming wedding to Sue by hanging out with his groomsmen. Brother Jimbo, cousin Mike, and his pals fill the reunion with drinking, boys-will-be-boys antics and a few unexpected personal confessions. But, when the bonding devolves into accusations and regret, Paulie has to decide whether he's ready to tie the knot and take this big step into adulthood.

The Wedding Singer
32% Match

Robbie, a local rock star turned wedding singer, is dumped on the day of his wedding. Meanwhile, waitress Julia finally sets a wedding date with her fiancée Glenn. When Julia and Robbie meet and hit it off, they find that things are more complicated than anybody thought.

The Sweetest Thing
29% Match

Christina's love life is stuck in neutral. After years of avoiding the hazards of a meaningful relationship, one night while club-hopping with her girlfriends, she meets Peter, her perfect match. Fed up with playing games, she finally gets the courage to let her guard down and follow her heart, only to discover that Peter has suddenly left town. Accompanied by Courtney, she sets out to capture the one that got away.

I Love You, Man
29% Match

Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates."

The Baxter
29% Match

The Baxter(2005)

Movie6.0/10

Mild mannered tax accountant Elliot Sherman is what he calls a "Baxter": the kind of calm, unexciting fellow who "wears sock garters" and "enjoys raking leaves." Loved by bosses and parents, Elliot is a perfectly nice guy. And that's his problem.

In Her Shoes
28% Match

Irresponsible party girl Maggie is kicked out of her father's and stepmother's home—where she lives for free—and is taken in by her hard-working sister, Philadelphia lawyer Rose. After Maggie's disruptive ways ruin her sister's love life, Rose turns her out as well. But when their grandmother, who they never knew existed, comes into their lives, the sisters face some complicated truths about themselves and their family.

The Wood
27% Match

The Wood(1999)

Movie6.6/10

In the panicky, uncertain hours before his wedding, a groom with prenuptial jitters and his two best friends reminisce about growing up together in the middle-class African-American neighborhood of Inglewood, California. Flashing back to the twenty-something trio's childhood exploits, the memories capture the mood and nostalgia of the '80s era.

Chaos Theory
26% Match

Frank Allen, a professional speaker who lectures on time management has a perfectly ordered and scheduled life, down to the minute. When his wife sets his clock forward 10 minutes as a joke, his day is thrown off. Deciding that his strictly ordered life has done him little good, he begins to make multiple choice index cards, choosing one at random and doing what is written on the card.

Sweet Home Alabama
26% Match

New York fashion designer, Melanie Carmichael suddenly finds herself engaged to the city's most eligible bachelor. But her past holds many secrets—including Jake, the redneck husband she married in high school, who refuses to divorce her. Bound and determined to end their contentious relationship once and for all, Melanie sneaks back home to Alabama to confront her past.

American Wedding
26% Match

With high school a distant memory, Jim and Michelle are getting married — and in a hurry, since Jim's grandmother is sick and wants to see him walk down the aisle — prompting Stifler to throw the ultimate bachelor party. And Jim's dad is reliable as ever, doling out advice no one wants to hear.

Café Society
25% Match

The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.

Bridesmaids
25% Match

Annie's life is a mess. But when she finds out her lifetime best friend is engaged, she simply must serve as Lillian's maid of honor. Though lovelorn and broke, Annie bluffs her way through the expensive and bizarre rituals. With one chance to get it perfect, she’ll show Lillian and her bridesmaids just how far you’ll go for someone you love.

Good Luck Chuck
25% Match

Cursed since childhood, dentist Charlie Logan cannot find the right woman. Even worse, he learns that each of his ex-girlfriends finds true love with the man she meets after her relationship with him ends. Hearing of Charlie's reputation as a good-luck charm, women from all over line up for a quick tryst. But when Charlie meets the woman of his dreams, he must find a way to break the curse or risk losing her to the next man she meets.

Leap Year
25% Match

Leap Year(2010)

Movie6.9/10

When yet another anniversary passes without a marriage proposal from her boyfriend, Anna decides to take action. Aware of a Celtic tradition that allows women to pop the question on Feb. 29, she plans to follow her lover to Dublin and ask him to marry her. Fate has other plans, however, and Anna winds up on the other side of the Emerald Isle with handsome, but surly, Declan -- an Irishman who may just lead Anna down the road to true love.