20 best movies like Kissing a Fool (1998)

When Dustin's girlfriend, Alexis, breaks up with him, he employs his best buddy, Tank, to take her out on the worst rebound date imaginable in the hopes that it will send her running back into his arms. But when Tank begins to really fall for Alexis, he finds himself in an impossible position.

A sudden loss disrupts Carol’s orderly life, propelling her into the dating world for the first time in 20 years. Finally living in the present tense, she finds herself swept up in not one, but two unexpected relationships that challenge her assumptions about what it means to grow old.

Seven close friends reunite for the wedding of two of their friends. Problems arise because the bride and the maid of honor have had a long rivalry over the groom.

Two top CIA operatives wage an epic battle against one another after they discover they are dating the same woman.

Iris invites her friend Jack to stay at her family's island getaway after the death of his brother. At their remote cabin, Jack's drunken encounter with Hannah, Iris' sister, kicks off a revealing stretch of days.

Sam and Gray are such a well-matched pair that it is difficult to believe they are brother and sister rather than husband and wife. They both share a love of 1940s movies and dancing, and when they meet Charlie, they have something else in common: They both fall in love with her. Sam must deal with unexpected feelings of jealousy, while Gray struggles to come to terms with her sexual orientation.

Inspired by his fiancée (who dumped him), a man publishes a break-up handbook for men, becoming a bestselling author in the process.

Pat Pemberton is a brilliant athlete, except when her domineering fiancé is around. The ladies golf championship is in her reach until she gets flustered by his presence at the final holes. He wants them to get married and forget the whole thing, but she cannot give up on herself that easily. She enlists the help of Mike Conovan, a slightly shady sports promoter. Together they face mobsters, a jealous boxer, and a growing mutual attraction.

A successful veterinarian and radio show host with low self-esteem asks her model friend to impersonate her when a handsome man wants to see her.

When he hears that the new female employee digs ambitious men who are the store employee of the month, a slacker gets his act together but finds himself in competition with his rival, an ambitious co-worker.

After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.

Though Rachel (Ginnifer Goodwin) is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy (Kate Hudson). Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan (John Krasinski), Rachel's confidant, harbors a potentially explosive secret of his own.

An independent woman can't chose between the two men she loves.

A man with a "doormat" personality tries standing up for himself for a change in this comedy. 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.

Sam and George strike gold in Alaska. George sends Sam to Seattle to bring George's fiancé back to Alaska. Sam finds she is already married, and returns instead with Angel. Sam, after trying to get George and Angel together, finally romances Angel, who, in the meantime, is busy fighting off the advances of George's younger brother, Billy.

When a chance encounter brings together the cynical Dell and the quick-witted Kimberly, the stage is set for a tempestuous love affair that unfolds like a puzzle. As the film zigzags back and forth in time-from a meteor shower in LA, to an encounter in a Paris hotel room, to a fateful phone call-an unforgettable portrait of a relationship emerges.

Yu Akahane (Nana Komatsu) moves to a dormitory room after her father's transfer from work. She is excited that she will live in the same dorm as Takumi Shirakawa (Yudai Chiba) aka "White Prince." Yet, Haruto Kurosaki (Kento Nakajima) aka "Black Devil" kisses her as punishment for going against him. It is Yu Akahane’s first kiss. Since then, she becomes obedient to Haruto Kurosaki.

With a new iPhone, an apartment near the Grove, and a comfortable bank account left to her by her beloved late husband, Marnie Minervini has happily relocated from New Jersey to Los Angeles to be near her daughter Lori, a successful (but still single) screenwriter, and smother her with motherly love. But when the dozens of texts, unexpected visits, and conversations dominated by unsolicited advice force Lori to draw strict personal boundaries, Marnie finds ways to channel her eternal optimism and forceful generosity to change the lives of others - as well as her own - and find a new purpose in life.

This is a fast-paced comedy about a 40-year-old gay man who finds himself dating two equally lovable men - a secure 50-year-old who came out later in life, and an adventurous 30-year-old who wasn't looking for a relationship. What he doesn't find out right away is that the two men are, in fact, father and son. And as they say, wackiness ensues.

As soon as they meet Ari and Sam get into a pretty passionate - and combustible - relationship. Indeed, the scenes of their rendezvous often seem reminiscent of the Chicago Fire. But the course of true flaming lust never runs true, and as they try to handle their all-consuming passion their two best friends endlessly meet to compare notes on developments.

When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.

The separation of a long married couple goes awry when they fall for each other again.

As the Best Exotic Marigold Hotel has only a single remaining vacancy - posing a rooming predicament for two fresh arrivals - Sonny pursues his expansionist dream of opening a second hotel.

Otto Wall is just a little unlucky in life, and unbeknownst to him, in love. When his wife suddenly asks for a divorce, he bounces between a search for answers, desperate attempts to stay connected to his daughter, and his fateful reentry into the dating pool.

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Sarah Nolan is a newly divorced woman cautiously rediscovering romance with the enthusiastic but often misguided help of her well-meaning family. As she braves a series of hilarious disastrous mismatches and first dates, Sarah begins to trust her own instincts again and learns that, no matter what, it's never a good idea to give up on love.

Three very different people in their twenties try to figure out love, sex, identity and friendship in Los Angeles.

Left broke and homeless by his wealthy parents' divorce, a young man moves in with an old friend and finally meets the woman of his dreams -- only to discover she's already dating his friend.

The film tells the story of quick-witted teen Mark, contentedly living the same day in an endless loop whose world is turned upside-down when he meets mysterious Margaret also stuck in the time loop. Mark and Margaret form a magnetic partnership, setting out to find all the tiny things that make that one day perfect. What follows is a love story with a fantastical twist, as the two struggle to figure out how -- and whether -- to escape their never-ending day.

Seenu loves Sunaina but they're chased by a stalking cop, an infatuated beauty and her mafia don dad - can Seenu's heroics work?

A man and woman meet and try to have a romantic affair, despite their personal problems and the interference of their disapproving friends.

While on holiday, Avi meets Naina and falls in love with her. Smitten, he decides to stay and work in her cafe. He confesses his love in a letter, however it's Naina's mother who mistakenly reads it.

Celeste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered businesswoman and budding novelist; he, a free spirit who keeps things from getting boring. Their only problem is that they have decided to get divorced. Can their perfect relationship withstand this minor setback?

Victor Bukowski is an out-of-work actor with problems. He's got a lousy agent, he has a habit of falling out with directors and he's still in love with his ex-girlfriend. However, Victor is about to embark on an unexpected emotional journey which will make him confront his future and his past mistakes.

A film adaptation of Shakespeare's comedy about lovers whose romantic affections are manipulated by fairy magic. The setting is updated to a Tuscan hill town in the late 19th century.

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

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.

Weekend trips, office parties, late night conversations, drinking on the job, marriage pressure, biological clocks, holding eye contact a second too long… you know what makes the line between “friends” and “more than friends” really blurry? Beer.

A lovestruck, lounge-singing darts champion finds his prayers are answered -- literally -- when he mysteriously receives a box of love-inducing darts.

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

Former prom king and college freshman Scott returns home for Thanksgiving break and gets dumped by his long-term girlfriend. With his world turned upside down, Scott strikes an unlikely friendship with former classmate Tori, an ugly duckling who blossomed in her first semester of college, and they embark on an outrageous adventure through their hometown. But when Scott and Tori start falling in love, they realize that a few months away may have changed them more than they realized.

A small town waitress gets a nail accidentally lodged in her head causing unpredictable behavior that leads her to Washington, DC. Sparks fly when she meets a clueless young senator who takes up her cause - but what happens when love interferes with what you stand for?

Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another.

After being cut from the USA softball team and feeling a bit past her prime, Lisa finds herself evaluating her life and in the middle of a love triangle, as a corporate guy in crisis competes with her current, baseball-playing beau.

Calamity Jane and Wild Bill Hickok fuss, feud and fall in love. At first, Calamity is too busy fighting Indians and cracking a bullwhip to pay attention to such girlie things as dresses and perfume. She soon changes her mind when Katie Brown arrives in town.

Developed from a radio program which began in 1941, hyperactive teenager Judy challenges and is challeged by her overly proper parents, pest of a brother Randolph and boyfriend Oogie.

Set to the music of popular hit songs from the 1980s. A beautiful coastal village, present day Italy. After a whirlwind romance, Maddie is preparing to marry gorgeous Italian Raf, and has invited her sister Taylor to the wedding. Unbeknownst to Maddie, however, Raf is Taylor's ex-holiday flame, and the love of her life...

Gray Wheeler just lost everything. But it could be the best thing that ever happened to her. After the death of her fiancé, Gray moves in with her late love's best friends. While Sam and Dennis do their best to cheer Gray up, Fritz doesn't seem to care. Once Gray breaks through Fritz's defenses, however, she finally sees why her fiancé thought so highly of him. As they spend more time together, Gray learns that her chances for love have not died out with her fiancé. But when some surprise guests show up on their doorstep, it'll take the love of all of her new friends to help Gray learn that life may be messy, but love is messier.

Dave, a high school senior, spends most of his time pining away over a girl he can’t have. Aubrey, a junior with artistic aspirations, has a hot boyfriend who doesn’t quite understand her or seem to care. Although they go to different schools, Dave and Aubrey find themselves at the same party. When both head outside to get some air, they meet. A casual conversation sparks an instant connection, and, over the course of a weekend, things turn magical, romantic, complicated, and funny as Aubrey and Dave discover what it's like to fall in love for the first time.

A young woman who dreams of being a children's author makes an unlikely friendship with a cantankerous, rich old widower.