Movies Like Kissing a Fool
If you loved Kissing a Fool's Comedy and Romance storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
Materialists
A young, ambitious New York City matchmaker finds herself torn between the perfect match and her imperfect ex.
Table 19
Eloise, having been relieved of maid of honor duties after being unceremoniously dumped by the best man via text, decides to attend the wedding anyway – only to find herself seated with five fellow-unwanted guests at the dreaded Table 19.
I Love You, Man
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
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.
The Wood
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.
The Wedding Ringer
Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO of Best Man, Inc., a company that provides flattering best men for socially challenged guys in need. What ensues is a hilarious wedding charade as they try to pull off the big con, and an unexpected budding bromance between Doug and his fake best man Jimmy.
Broadcast News
A high-strung news producer finds herself in a love triangle between a talented but self-doubting reporter and a charming news anchor who embodies the growing trivialization of news that she is determined to fight against.
Bridesmaids
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.
More Movies Like Kissing a Fool
A Guy Thing
Paul Morse is a good guy. When his friends throw him a wild bachelor party, he just wants to keep his conscience clean -- which is why he's shocked when he wakes up in bed with a beautiful girl named Becky and can't remember the night before. Desperate to keep his fiancée, Karen, from finding out what may or may not be the truth, he tells her a teensy lie. Soon his lies are spiraling out of control and his life is a series of comical misunderstandings.
Plus One
Longtime single friends, Ben and Alice, agree to be each other's respective plus one at every wedding they're invited to, during a busy summer of wedding fever.
The Best Man
After writing a soon-to-be bestselling novel, writer and committed bachelor Harper attempts to hide the fact that his saucy new book is loosely based on the lives and loves of his tight-knit group of friends. Harper is set to be best man at his friend Lance's wedding, and all his friends will be in attendance. When an advance copy of the book makes its way into the hands of his ex-flame, Jordan, Harper attempts to keep it under wraps.
Vanilla Sky
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.
Friends with Kids
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.
American Wedding
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.
How to Date Billy Walsh
Archie has been in love with his best friend Amelia for as long as he can remember. Just when he builds up the courage to declare his feelings, she falls head over heels for Billy Walsh, a new American transfer student.
Keeping the Faith
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.
Bull Durham
Veteran catcher Crash Davis is brought to the minor league Durham Bulls to help their up and coming pitching prospect, "Nuke" Laloosh. Their relationship gets off to a rocky start and is further complicated when baseball groupie Annie Savoy sets her sights on the two men.
The Wedding Year
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
Revenge of the Bridesmaids
Two women plot revenge against the woman marrying their friend's ex-boyfriend.
Everybody Loves Somebody
On the surface, Clara Barron seems to have it all: a job as an OB-GYN; a great house in LA; and a loving family. But, the one thing Clara doesn't have figured out is her love life. Pressured by a family wedding in Mexico, Clara asks a co-worker to pose as her boyfriend for the weekend festivities,- only to be caught by surprise when her ex- boyfriend (and family favorite) suddenly shows up after disappearing from her life completely. Torn, Clara must decide between going back to the past or open her heart to new and unexpected possibilities.
Why These Movies Are Similar
These recommendations share core qualities with Kissing a Fool (1998): Comedy and Romance themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Kissing a Fool.
See full details for Kissing a Fool (1998)