20 best movies like Boomerang (1992)

A womanizer meets his match when he falls for the daughter of a gambling addict who is in debt to the mob.

Nightclub manager Darnell Wright is a perpetual playboy who is almost as devoted to his job as he is to the pursuit of beautiful women. After he sets his sights on the ultra-classy Brandi Web, he launches an all-out assault to win her heart. Ultimately, charm, lust and passion prevail, but Darnell learns the hard way that when you play, you pay. Brandi is much harder to get rid of than she was to get--especially when she realizes that she has a rival vying for Darnell's affection. When he finally decides to call it quits, Brandi becomes an obsessed femme fatale stalking the new love of her life.

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.

A washed up golf pro working at a driving range tries to qualify for the US Open in order to win the heart of his succesful rival's girlfriend.

No sooner does Italian-American widow Loretta accept a marriage proposal from her doltish boyfriend, Johnny, than she finds herself falling for his younger brother, Ronny. She tries to resist, but Ronny lost his hand in an accident he blames on his brother, and has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls deeper in love, she comes to learn that she's not the only one in her family with a secret romance.

On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to ... lovers?

Matt falls for Casey, the new girl in school. She's fun-loving and eccentric, but there's a darkness to her whimsy that Matt can't begin to comprehend. When Casey attempts to commit suicide, her parents place her in a mental institution. Matt springs her out, and together the young lovers head on a road trip. They believe their love can "cure" Casey's problems. Matt starts to wonder, though, if are they inspired or misguided.

Alex Whitman (Matthew Perry) is a designer from New York City who is sent to Las Vegas to supervise the construction of a nightclub that his firm has been hired to build. Alex is a straight-laced WASP-ish type who, while enjoying a night on the town, meets Isabel Fuentes (Salma Hayek), a free-spirited Mexican-American photographer. Alex and Isabel are overtaken by lust at first sight and end up sp

Ex-football star Mike Gambril meets Terry McKay on a flight to Sydney, which is forced to land on a small atoll. They become romantic on board a ship sent to take them to a larger island. They agree to meet in New York three months later to see if the attraction is real. One shows up but the other doesn't. However, a chance meeting brings them together again.

Calvin is a young novelist who achieved phenomenal success early in his career but is now struggling with his writing – as well as his romantic life. Finally, he makes a breakthrough and creates a character named Ruby who inspires him. When Calvin finds Ruby, in the flesh, sitting on his couch about a week later, he is completely flabbergasted that his words have turned into a living, breathing person.

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?

Maggie, an alluring free spirit who won't let anyone - or anything - tie her down. But she meets her match in Jamie, whose relentless and nearly infallible charm serve him well with the ladies and in the cutthroat world of pharmaceutical sales. Maggie and Jamie's evolving relationship takes them both by surprise, as they find themselves under the influence of the ultimate drug: love.

Jonas Nightengale is a fraudulent Christian faith healer who makes a living travelling around America holding revival meetings and conducting 'miracles' with the help of his friend and manager, Jane, and their entourage.

A romantic comedy that brings together three disparate characters who are learning to face a challenging and often confusing world as they struggle together against a common demon: sex addiction.

New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.

An art instructor and an English teacher form a rivalry that ends up with a competition at their school in which students decide whether words or pictures are more important.

After a distastrous first date for caterer Holly and network sports director Messer, all they have is common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.

Harry Sanborn is an aged music industry exec with a fondness for younger women like Marin, his latest trophy girlfriend. Things get a little awkward when Harry suffers a heart attack at the home of Marin's mother, Erica. Left in the care of Erica and his doctor, a love triangle starts to take shape.

When new kid in town Ed Wallis is given an assignment to interview an older person, he turns to his mysterious neighbor, Ashby Holt for help. That new connection leads to unexpected journeys for both of them, as Ashby – who turns out to be a retired CIA assassin – deals with a terminal prognosis, and Ed deals with adjusting to life with his newly single mom and developing relationship with a brainy classmate, Eloise.

Book superstore magnate, Joe Fox and independent book shop owner, Kathleen Kelly fall in love in the anonymity of the Internet – both blissfully unaware that he's putting her out of business.

Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.

An aloof, struggling food photographer thinks he has found true love with a fiery grade-school teacher. At first, the relationship is all wine and roses, but as they realize they have little in common besides great sex, the romance wanes, and they struggle through a succession of break-ups and reunions as they try to work things out.

Cheated on, mistreated and stepped on, the women are holding their breath, waiting for the elusive "good man" to break a string of less-than-stellar lovers. Friends and confidants Vannah, Bernie, Glo and Robin talk it all out, determined to find a better way to breathe.

When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, Frankie develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.

Set in the 1920s French Riviera, a master magician is commissioned to try and expose a psychic as a fraud.

A 'Love Guru' assists other males, woos a widowed single mother, but becomes embroiled in controversies.

John Arnold DeMarco is a man who believes he is Don Juan, the greatest lover in the world. Clad in a cape and mask, DeMarco undergoes psychiatric treatment with Dr. Jack Mickler to cure him of his apparent delusion. But the psychiatric sessions have an unexpected effect on the psychiatric staff and, most profoundly, Dr Mickler, who rekindles the romance in his complacent marriage.

When relaxed and charming Ben Wrightman meets workaholic Lindsey Meeks she finds him sweet and charming, they hit it off and when it is winter Ben can spend every waking hour with Lindsey, but when summer comes around the corner Lindsey discovers Ben's obsession with the Boston Red Sox. She thinks it is perfect until everything goes downhill for them.

On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?

With a reputation for seducing members of the opposite sex, regardless of their marital status, a notorious womanizer discovers a beauty who seems impervious to his charms. However, as he continues to pursue the indifferent lady, he finds himself falling in love.

Dr. Henry Harriston is a successful psychoanalyst in New York City. When he is near a nervous breakdown, he arranges to change his flat with Beatrice Saulnier from France for a while. Both don't know each other and both find themselves deeply involved into the social settings of the other, because the decision to change their flats is made overnight. Could be the perfect amusement, but suddenly Henry finds himself beaten up by Beatrice' lover and Beatrice is considered to be Dr. Harriston's substitute by his clients...

To inherit a million dollars, an egotistical man must find the women he's betrayed and convince them to forgive him.

Kenya McQueen, a corporate lawyer finds love in the most unexpected place when she agrees to go on a blind date with Brian Kelly, a sexy and free-spirited landscaper.

Johnny, a freewheeling, motorcycle-riding musician, rolls into a small town with his band, and meets Kathy, an honor student who catches his eye. Meanwhile, Kathy's father, after being in the Witness Protection Program, is finally found by the two corrupt cops he escaped from years ago, who claim he owes them a lot of money.

Reunited at a wedding after many years, former lovers again feel the pull of a mutual attraction neither is willing to admit. Escaping the reception for the privacy of a hotel room, the unnamed pair explore the choices of the past that led them to the present.

Sam Clayton's marriage to ex-stripper Freddie comes about when she's strong-armed into the match by Red, a club proprietor who once did her a favor. But Freddie falls in love with Jjaks, Sam's brother, and the pair tries to escape the situation together. It isn't long before both Sam and Red catch up with them, resulting in threats against the two of them -- although tension also starts to build between Sam and Red.

Grace Bichon, who is managing her father's riding-stable, discovers that her husband Eddie is deceiving her with another woman. After confronting him in the middle of the night on the streets of their small home town, she decides to stay at her sister Emma Rae's house for a while to make up her mind. Breaking out of her everyday life, she starts to question the authority of everyone.

It's New York City in 1981, and various twentysomethings are converging on a New Year's Eve party.

Melanie Parker, an architect and mother of Sammy, and Jack Taylor, a newspaper columnist and father of Maggie, are both divorced. They meet one morning when overwhelmed Jack is left unexpectedly with Maggie and forgets that Melanie was to take her to school. As a result, both children miss their school field trip and are stuck with the parents. The two adults project their negative stereotypes of ex-spouses on each other, but end up needing to rely on each other to watch the children as each must save his job. Humor is added by Sammy's propensity for lodging objects in his nose and Maggie's tendency to wander.

During a snowy winter in the small fictional town of Knight's Ridge, Massachusetts, a group of lifelong buddies hang out, drink and struggle to connect with the women who affect their decisions, dreams and desires.

Rose Morgan, who still lives with her mother, is a professor of Romantic Literature who desperately longs for passion in her life. Gregory Larkin, a mathematics professor, has been burned by passionate relationships and longs for a sexless union based on friendship and respect.

Advertising execs Melanie Welsh and Donovan Goodwin disagree on a cellphone Christmas commercial they’re pitching. He says his sleek design will win over the client but she knows it lacks holiday spirit.

After thirty years of marriage, a middle-aged couple attends an intense, week-long counseling session to work on their relationship.

A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.

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.

Soon-to-be-wed graduate student Finn Dodd develops cold feet when she suspects her fiancé is cheating on her. In order to clear her head, Finn visits her grandmother, Hy, and great aunt, Glady Joe Cleary, in Grasse, Calif. There, Finn learns that Hy and Glady Joe are members of a group of passionate quilters, and over the course of her visit she is regaled with tales of love and life by women who have collected rich experiences and much wisdom.

With the help of a talking freeway billboard, a "wacky weatherman" tries to win the heart of an English newspaper reporter, who is struggling to make sense of the strange world of early-90s Los Angeles.

Rival Chicago reporters Sabrina Peterson and Peter Brackett join forces to uncover a train wreck conspiracy.

Marisa Ventura is a struggling single mom who works at a posh Manhattan hotel and dreams of a better life for her and her young son. One fateful day, hotel guest and senatorial candidate Christopher Marshall meets Marisa and mistakes her for a wealthy socialite. After an enchanting evening together, the two fall madly in love. But when Marisa's true identity is revealed, issues of class and social status threaten to separate them. Can two people from very different worlds overcome their differences and live happily ever after?

Longtime friends Ronny and Nick are partners in an auto-design firm. They are hard at work on a presentation for a dream project that would really launch their company. Then Ronny spots Nick's wife out with another man, and in the process of investigating the possible affair, he learns that Nick has a few secrets of his own. As the presentation nears, Ronny agonizes over what might happen if the truth gets out.