Best movies like Kissing a Fool

May the best man win.

A unique, carefully handpicked, selection of the best movies like Kissing a Fool Starring David Schwimmer, Jason Lee, Mili Avital, Bonnie Hunt, and more. If you liked Kissing a Fool then you may also like: The Wedding Planner, Never Been Kissed, Revenge of the Bridesmaids, Run, Fatboy, Run, Kiss The Bride and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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?

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The Wedding Planner

San Francisco's premiere wedding planner, Mary Fiore is rescued from an accident by the man of her dreams, paediatrician Steve Edison, only to find he is the fiancé of her latest client. As Mary continues making the wedding arrangements, she and Steve are put into a string of uncomfortable situations that force them to face their mutual attraction.

Never Been Kissed

Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.

Run, Fatboy, Run

Five years after jilting his pregnant fiancée on their wedding day, out-of-shape Dennis decides to run a marathon to win her back.

Kiss The Bride

Sibling drama overshadows the impending nuptials of Danni Sposato and her longtime boyfriend, Geoff Brancato. Television actress Niki brings her manager-boyfriend, Marty, to meet the family for the first time, while spiky youngest sister Toni shows off her bandmate and lover, Amy, and driven Wall Street banker Chrissy flashes the status symbols of her financial success.

Kiss the Bride

In high school, Matt and Ryan were best friends. More than friends, actually. But in the ensuing ten years, they've lost contact. So when Matt receives an invitation to Ryan's wedding he's surprised - especially that Ryan is marrying a woman!

All Over the Guy

A contemporary romantic comedy exploring the unlikely pairing of two 20-somethings thrown together by their respective best friends in hopes of igniting their own romance.

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.

Brown Sugar

Friends since childhood, a magazine editor and a hip-hop record executive stumble into romantic territory.

Century Hotel

David Weaver makes his feature debut with this omnibus film in which each tale is told during different points during the 20th century, but in the same hotel room -- room 720. The film opens during the swinging '20s when a beautiful young woman, married against her will to a brutish thug of a man, endures a tension-fraught honeymoon. During the Depression segment, a mail-order bride from China meets her husband for the first time. Following the end of WWII, a soldier returns home to meet his girlfriend and his best friend. During the paranoia of the 1950s, a professor searches for his wife. During the 1980s, a lawyer has too much sex and debt, and during the dawn of the millennium, a woman comes to a newly refurbished room 720 to meet her Internet lover. Such acclaimed Canadian actors as Tom McCamus, Sandrine Holt, and Colm Feore star in this film, which was screened at the 2001 Toronto Film Festival.

Chained for Life

A Siamese twin kills the husband who left her. The courts have to decide if she is convicted of murder, how can they punish her sister, who had nothing to do with the crime?

Chaos Theory

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.

Committed

After her husband, Carl, suddenly leaves, Joline travels from New York to Texas to track him down. Although Joline tries to remain upbeat, she is discouraged when she discovers that Carl already has a new girlfriend, the lovely Carmen. Familiarizing herself with Carl's new home and friends, Joline gets company in the form of her brother, Jay. Will Joline win Carl back, or are there other romantic possibilities on her horizon?

A Night in the Life of Jimmy Reardon

A recent high school graduate is faced with two options, either go to a business school where his father wants him to go to, or get a full time job. However he decides to defy his father and go to Hawaii. Trouble is he has no money. Along the way he comes to understand his parents and eventually bonds with his father.

When Ladies Meet

Mary, a writer working on a novel about a love triangle, is attracted to her publisher. Her suitor Jimmy is determined to break them up; he introduces Mary to the publisher's wife without telling Mary who she is.

Desire Me

A war widow falls in love with the man who informed her of her husband's death.

Mr. Malcolm's List

When she fails to meet an item on his list of requirements for a bride, Julia Thistlewaite is jilted by London’s most eligible bachelor, Mr. Malcolm. Feeling humiliated and determined to exact revenge, she convinces her friend Selina Dalton to play the role of his ideal match. Soon, Mr. Malcolm wonders whether he’s found the perfect woman...or the perfect hoax.

Love in the Time of Cholera

In Colombia just after the Great War, an old man falls from a ladder; dying, he professes great love for his wife. After the funeral, a man calls on the widow - she dismisses him angrily. Flash back more than 50 years to the day Florentino Ariza, a telegraph boy, falls in love with Fermina Daza, the daughter of a mule trader.

Simon Birch

Simon Birch and Joe Wenteworth are boys who have a reputation for being oddballs. Joe never knew his father, and his mother, Rebecca, is keeping her lips sealed no matter how much he protests. Simon, meanwhile, is an 11-year-old dwarf whose outsize personality belies his small stature. Indeed, he often assails the local reverend with thorny theological questions and joins Joe on his quest to find his biological father.

Made of Honor

Tom and Hannah have been platonic friends for 10 years. He's a serial dater, while she wants marriage but hasn't found Mr. Right. Just as Tom is starting to think that he is relationship material after all, Hannah gets engaged. When she asks Tom to be her 'maid' of honor, he reluctantly agrees just so he can attempt to stop the wedding and woo her.

The Hurricane

A Polynesian sailor is separated from his wife when he's unjustly imprisoned for defending himself against a colonial bully. Members of the community petition the governor for clemency but all pretense of law and order are soon shattered by an incoming tropical storm.

Love & Sex

When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.

Mad at the Moon

A young woman on the frontier marries a meek farmer who has an annoying habit of going through a rather drastic change every full moon.

The Manxman

A fisherman and a rising lawyer who grew up together as brothers fall in love with the same woman.

Mortal Thoughts

A loathsome man ends up dead, but it's not clear who's to blame. If ever a person got what he deserved, it's James Urbanksi, an abusive drunk who steals from his wife, Joyce, and promises her close friend Cynthia Kellogg that she'll be the next target of his rage. At a group outing, James bleeds to death after someone cuts his throat. But because he's such a terrible human being, police aren't sure which of his acquaintances decided to kill him.

My Favorite Year

Fledgling comic Benjy Stone can't believe his luck when his childhood hero, the swashbuckling matinee idol Alan Swann, gets booked to appear on the variety show he writes for. But when Swann arrives, he fails to live up to his silver screen image. Instead, he's a drunken womanizer who suffers from stage fright. Benjy is assigned to look after him before the show, and it's all he can do to keep his former idol from going completely off the rails.

Seeing Other People

Ed and Alice are two months shy of getting married when she realizes that she wishes she'd had a more active love life while still single. Reluctantly, Ed agrees to have an open relationship in the months before their wedding, and initially this seems to improve their connection, particularly in the bedroom. However, as Ed and Alice get more involved in their own flings, the experiment goes awry.

Take Me Home Tonight

Recent MIT grad Matt Franklin should be well on his way to a successful career at a Fortune 500 company, but instead he rebels against maturity by taking a job at a video store. Matt rethinks his position when his unrequited high-school crush, Tori, walks in and invites him to an end-of-summer party. With the help of his twin sister and his best friend, Matt hatches a plan to change the course of his life.

Tangled

A young man is found bruised, beaten and stumbling down a secluded road. As the police try to piece together what happened, the convoluted relationship between a young woman and her two suitors gradually emerges.

The Marrying Kind

Florence and Chet Keefer have had a troublesome marriage. Whilst in the middle of a divorce hearing the judge encourages them to remember the good times they have had hoping that the marriage can be saved.

Leap Year

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.

From This Day Forward

A young American soldier, with an honorable discharge, returns home from World War II to his bride, whom he married after a short courtship and has not seen for several years. The two come together with many trials and tribulations in trying to preserve their marriage in the post-war years.

The Falling

Karis (Nicole Oliver) is a clothing store owner who picks up a handsome music executive, Lars (Christopher Shyer), in a bar and immediately engages him in some very hot sex that leads to an ongoing physical relationship. One morning Lars encounters Morgan (Rob Lee) in Karis' kitchen; Morgan is her future ex-husband and a policeman with a violent temper who begins a campaign of intimidation to make Lars stop seeing Karis. But wait: 30 minutes into the movie the point-of-view changes to Morgan's, and we see he's not such a bad guy after all and that Lars is the hot-tempered villain. But wait: 30 minutes later the point of view switches to Karis, and it turns out that she hasn't been completely honest about things. Whose story is the real one?

Worth Winning

Taylor is a man who has no problems with women. So confident is he that he accepts a challenge from his friends: he has to secure proposals of marriage from three women of their choice.

Betting On The Bride

A womanizer bets that he can get someone to accept his marriage proposal after dating them for just 30 days. What he doesn't know is that the woman he targeted has some serious commitment issues.

Twisted Little Lies

A college professor with an overzealous student must escape his twisted game of cat and mouse before her life is ruined forever.

Hanging by a Thread

A group of old friends on an outing re-live various traumas and tragedies via flashback whilst trapped high above a ravine in a disabled cable-car.

Campfire Christmas

Romance rekindles for Peyton and her closest friends when her parents decide to host a holiday themed reunion before selling their family owned summer camp.

A Bride for Christmas

Bride-to-be Jessie Patterson calls off her third engagement - during the ceremony! She swears off serious relationships, until she meets and is pursued by Aiden MacTiernan. Aiden, on the other hand, has bet his friends he is marriage material, and can find a fiancé in the four weeks leading up to Christmas. When Jessie and Aiden begin to fall for each other, Jessie must decide if she is ready for serious love, and Aiden must decide if his bet is worth risking his relationship with Jessie.

The Romantics

Alliances are tested when seven college pals reunite to watch two of their own say “I do” at a seaside wedding. But the maid of honor and the groom share a passionate history, and the bride isn’t the only one who’s wondering if it’s all in the past.

Perfect Harmony

A pop singer and a professor must put aside their differences when their best friends decide to get married. However, working together as best man and maid of honor soon leads to the duet of a lifetime.

A December Bride

Aspiring interior designer Layla is dreading the Christmastime wedding of her cousin who’s marrying Layla’s ex-fiancé. Although Seth is the one responsible for introducing the bride and groom, she begrudgingly accepts his offer to be her date as she’s out of options. Seth gets carried away at the reception and announces they’re engaged, forcing a mortified Layla to keep up the pretense.

The Four-Faced Liar

A story of love and lies for four twenty-somethings looking to find themselves in New York City. A pair of best friends and a seemingly perfect couple meet at a local Irish pub tucked in the winding streets of the West Village. Through their chance meeting, the four bond and over time all of their relationships with one another morph into love, betrayal and heartbreak for all.

The Convenient Groom

Dr. Kate Lawrence, a celebrity relationship expert, plans to publicly announce her engagement to Bryan, a handsome and perfectly polished businessman. As Kate prepares to share the news, Bryan shocks her by breaking up with her and calling off the wedding. Wanting to save her from humiliation and protect her public image, Lucas Wright, Kate's childhood friend steps in and pretends to be Kate's fiancé.

Love at the Christmas Table

Family friends Sam and Kat spend every Christmas Eve at the Children's Table. They grow up together, sharing the highs and lows of young adulthood. And at thirty, Sam realizes that Kat is the one... but he's afraid that the past will get in the way.

Honeymoon for One

A woman finds out her fiancé has been cheating on her so she ends her engagement just a week before the wedding. She embarks on an unexpected adventure when she goes on her honeymoon to a beautiful Irish castle estate - alone.

The Bride Walks Out

Carolyn Martin is a fashion model who hastily marries her boyfriend, engineer Michael Martin. But part of the marriage arrangement requires that Carolyn quit her $50-per-week modeling job to be a full-time housewife; the couple will instead live on Michael’s $35-per-week job.

Soccer Mom Madam

After a bitter breakup leaves her and her young children without any support, Anna goes to work for her cousin at a massage parlour known for "happy endings." As soon as she learns the ropes, Anna branches out on her own.

The Gal Who Took the West

In order to gain passage to the West, a woman poses as an opera singer, and causes a feud between two cousins.

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