Movies like Kissing a Fool (1998)
The best movies like Kissing a Fool (1998) are I Love You, Man (2009), The Wedding Singer (1998) and The Baxter (2005). If Kissing a Fool hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSissi (1955)7.3/10 from 536 votes
- NewestMain Vaapas Aaunga (2026)Released 2026
I Love You, Man (2009)
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."
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Wedding Singer (1998)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Baxter (2005)
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.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisRevenge of the Bridesmaids (2010)
Two women plot revenge against the woman marrying their friend's ex-boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisKeeping the Faith (2000)
Best friends since they were kids, Rabbi Jacob Schram and Father Brian Finn are dynamic and popular young men living and working on New York's Upper West Side. When Anna Reilly, once their childhood friend and now grown into a beautiful corporate executive, suddenly returns to the city, she reenters Jake and Brian's lives and hearts with a vengeance. Sparks fly and an unusual and complicated love triangle ensues.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisShe's Funny That Way (2015)
On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisSaving Silverman (2001)
A pair of buddies conspire to save their best friend from marrying the wrong woman, a cold-hearted beauty who snatches him from them and breaks up their Neil Diamond cover band.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisMy Best Friend's Wedding (1997)
When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisYoh! Bestie (2026)
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Seven Year Hitch (2012)
Jennifer and Kevin are childhood best friends who have lived together, platonically, as adults for many years. When Jennifer decides to marry her cheating, manipulative boyfriend, Bryce Kevin has to stop the wedding to protect her from making, what he believes is, a terrible mistake. With a little help from his brother and neighbor Kevin discovers that he and Jennifer are already legally married due to common law, having lived together for seven years and, as such, Jennifer can not marry Bryce.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisGhosts of Girlfriends Past (2009)
Celebrity photographer Connor Mead lives life in the fast lane, committed to lifelong bachelorhood and simultaneous relationships with multiple women. On the eve of his younger brother Paul's wedding, Connor's mockery of love proves a real buzz-kill for everyone - including his childhood crush, Jenny, the one woman who always seemed immune to his considerable charms. Later that night, he gets a wake-up call from the ghost of his late Uncle Wayne, the hard-partying, legendary ladies' man who was Connor's mentor. Uncle Wayne has an urgent message which he delivers through three ghosts who guide Connor on an eye-opening tour of his romantic past, present and future. Along the way, they attempt to discern whether he will ever be able to change his ways -- and if there is any hope of him finding true love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisZoey 102 (2023)
Pacific Coast Academy alumni return to Malibu for an over-the-top wedding that turns into a high school reunion for the books.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Other Woman (2014)
After discovering her boyfriend is married, Carly soon meets the wife he's been cheating on. And when yet another affair is discovered, all three women team up to plot mutual revenge on the three-timing SOB.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisWhat Happens in Vegas (2008)
During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisEveryone Says I Love You (1996)
A New York girl sets her father up with a beautiful woman in a shaky marriage while her half sister gets engaged.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLittle Manhattan (2005)
Ten-year-old Gabe Burton is just an average kid growing up in Manhattan until Rosemary Telesco walks into his karate class. But before Gabe can tell Rosemary how he feels, she reveals that she won't be going to public school any more. Gabe has a lot more to learn about life, love, and girls.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisThe Wrong Paris (2025)
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Importance of Being Earnest (1952)
Two young gentlemen living in 1890s England use the same pseudonym ('Ernest') on the sly, which is fine until they both fall in love with women using that name, which leads to a comedy of mistaken identities.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBachelor Party (1984)
On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Odd Couple II (1998)
Brucey, the son of Oscar, calls his father to invite him to his wedding to Felix's daughter next Sunday in California. Oscar and Felix meet again at Los Angeles International Airport and rent a car in order to go to San Malina for the wedding.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSissi (1955)
The young Bavarian princess Elisabeth, who all call Sissi, goes with her mother and older sister Néné to Austria where Néné will be wed to an emperor named Franz Joseph, Yet unexpectedly Franz runs into Sissi while out fishing and they fall in love.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisRosa's Dilemma (2025)
Rosa finds herself in a whirlwind of emotions as she navigates an unexpected love triangle between her two coworkers at a fast food joint.
Why it matches: Similar story and style · both romance & comedy
Tinsel Town (2025)
A washed-up Hollywood action hero is tricked into starring in a small English town’s chaotic Christmas pantomime, where a straight-talking dance instructor and his estranged daughter just might help him rediscover the magic of the season.
Why it matches: Similar story and style · both comedy & romance
A Week in Paradise (2022)
Actress Maggie's world collapses when her director husband is outed by the paparazzi when it’s discovered his new leading lady is pregnant with his baby. Seeking solace and healing, Maggie escapes to her ex-pat cousin’s beautiful hotel in Nevis. After a week in paradise, she discovers herself and meets a new love interest. Then reality comes crashing back in.
Why it matches: Similar story and style · both romance & comedy
Lover Loser (2025)
As graduation approaches, Ewan is consumed by the quiet ache of his unspoken love. His emotions fluctuate between tenderness and frustration, as he grapples with the pain of being in love with someone who will never love him back. His longing is nuanced: moments of joy and intimacy with Gabe are bittersweet, filled with the hope of something more that will never be.
Why it matches: Similar story and style · both romance & comedy
Moonstruck (1987)
37-year-old Italian-American widow Loretta Castorini believes she is unlucky in love, and so accepts a marriage proposal from her boyfriend Johnny, even though she doesn't love him. When she meets his estranged younger brother Ronny, an emotional and passionate man, she finds herself drawn to him. She tries to resist, but Ronny, who blames his brother for the loss of his hand, has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls for Ronny, she learns that she's not the only one in her family with a secret romance.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisVanilla Sky (2001)
David Aames has it all: wealth, good looks and gorgeous women on his arm. But just as he begins falling for the warmhearted Sofia, his face is horribly disfigured in a car accident. That's just the beginning of his troubles as the lines between illusion and reality, between life and death, are blurred.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisAway from Her (2007)
Fiona and Grant have been married for nearly 50 years. They have to face the fact that Fiona’s absent-mindedness is a symptom of Alzheimer’s disease. She must go to a specialized nursing home, where she slowly forgets Grant and turns her affection to Aubrey, another patient in the home.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisThe Last Mistress (2007)
Secrets, rumors and betrayals surround the upcoming marriage between a young dissolute man and virtuous woman of the French aristocracy.
Why it matches: Similar story and style · both romance
SnoozefestMovies like thisMain Vaapas Aaunga (2026)
Haunted by a childhood romance and recollections of love lost during the 1947 Partition of India, 95-year-old Ishar Singh Grewal shares his story with his grandson Nirvair, the past unfolding through memories of migration, longing, and a romance that endures across generations.
Why it matches: Similar story and style · both romance
Like Kissing a Fool and something else?
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Frequently asked questions
What are the best movies like Kissing a Fool?
The closest matches to Kissing a Fool are I Love You, Man (2009), The Wedding Singer (1998) and The Baxter (2005). Below are 27 more, each with the reason it matches.
What should I watch after Kissing a Fool?
Start with I Love You, Man (2009), the closest match to Kissing a Fool.
What is the highest-rated movie like Kissing a Fool?
Sissi (1955), rated 7.3/10 by 536 TMDB users.
What is the newest movie like Kissing a Fool?
Main Vaapas Aaunga (2026) is the most recent release on this list.
Are there English movies like Kissing a Fool?
Yes: I Love You, Man (2009), The Wedding Singer (1998) and The Baxter (2005).
How are movies similar to Kissing a Fool chosen?
First come films that Trakt’s viewers watch alongside Kissing a Fool, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.