Best movies like The Heartbreak Kid

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A unique, carefully handpicked, selection of the best movies like The Heartbreak Kid Starring Charles Grodin, Cybill Shepherd, Jeannie Berlin, Audra Lindley, and more. If you liked The Heartbreak Kid then you may also like: The Four Seasons, Waitress, Wedding Bell Blues, The Oh in Ohio, The Only Game in Town 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.

Three days into his Miami honeymoon, Lenny meets tall, blonde Kelly. This confirms his fear that he has made a serious mistake and he decides he wants Kelly instead.

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The Four Seasons

Three middle-aged wealthy couples take vacations together in Spring, Summer, Autumn and Winter. Along the way we are treated to mid-life, marital, parental and other crises.

Waitress

Jenna is a pregnant, unhappily married waitress in the deep south. She meets a newcomer to her town and falls into an unlikely relationship as a last attempt at happiness.

Wedding Bell Blues

Micki, Tanya and Jasmine have 24 hours to get divorced. There's just one problem...They're still single. When Jasmine, Tanya and Micki decide they'd rather be divorced than unmarried, they take off to Las Vegas in search of the perfect ex.

The Oh in Ohio

Priscilla and Jack appear to be the perfect couple, but they have a secret: She is sexually frustrated. They separate in the hope of resolving the situation. While Jack moves into a bachelor pad and begins an affair with a student, Priscilla discovers the joys of self-pleasuring and finds an unusual bed-mate.

The Only Game in Town

Fran walks into a piano bar for pizza. She comes back home with Joe, the piano player. Joe plans on winning $5,000 and leave Las Vegas. Fran waits for something else. Meanwhile, he moves in with her.

Just Between Friends

Holly and Sandy strike up an instant friendship; they don't know however that they have more in common than they'd like. When tragedy strikes, their relationship is tested.

5.9 / 10 2013 Comedy
suggested by: user638mohblfl9

The Big Wedding

To the amusement of their adult children and friends, long divorced couple Don and Ellie Griffin are once again forced to play the happy couple for the sake of their adopted son's wedding after his ultra conservative biological mother unexpectedly decides to fly halfway across the world to attend. With all of the wedding guests looking on, the Griffins are hilariously forced to confront their past, present and future - and hopefully avoid killing each other in the process.

Blume in Love

Lawyer Stephen Blume, specialized in divorces, lives a paradoxical situation when, having his own marriage break up, is still in love with his ex-wife.

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?

Seems Like Old Times

Writer Nick Gardenia is kidnapped from his California cliffhouse and forced to rob a bank. Now a fugitive, he seeks help from his ex-wife who is now a public defender and has remarried — to a prosecutor.

From Justin to Kelly

A waitress from Texas and a college student from Pennsylvania meet during spring break in Fort Lauderdale, Florida and come together through their shared love of singing.

The Crew

Four retired mobsters plan one last crime to save their retirement home.

Same Time, Next Year

A man and woman meet by chance at a romantic inn over dinner and, although both are married to others, they find themselves in the same bed the next morning questioning how this could have happened. They agree to meet on the same weekend each year—in the same hotel room—and the years pass each has some personal crisis that the other helps them through, often without both of them understanding what is going on.

Plaza Suite

Film version of the Neil Simon play has three separate acts set in the same hotel suite in New York's Plaza Hotel with Walter Matthau in a triple role. In the first, Karen Nash tries to get her inattentive husband Sam's attention to spruce up their failing marriage. In the second, brash film producer Jesse Kiplinger tries to get his former one-time flame Muriel to see him for what he stands for. In the third, Roy Hubley and his wife Norma try and try to get their uncertain-of-herself daughter out of the bathroom before her approaching wedding.

Denial

Couples split up after a comment at an LA dinner party sets up arguments about how truthful partners are in their relationships.

The Heartbreak Kid

Eddie, the 40-year-old confirmed bachelor finally says "I do" to the beautiful and sexy Lila. But during their honeymoon in Mexico, the woman of his dreams turns out to be a total nightmare, and the guy who could never pull the trigger realizes he’s jumped the gun.

Diary of a Mad Housewife

Tina Balser is a bored New York housewife-mother married to Jonathan, a pompous, social-climbing lawyer who ridicules her in front of their children, criticizing everything she does or wears. She begins an affair with George Prager, a dashing, successful, and blatantly sadistic writer.

Enemies, a Love Story

A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.

The Favor

Kathy is married to Peter. Now she can't help but wonder how things could have been if she got together with her old boyfriend, Tom. Being married prevents from doing that so she asks her friend, Emily to go to him and see if she can sleep with him then tell Kathy how it was. When Emily tells Kathy that things were awesome, their friendship suffers, at the same so does Kathy's marriage. Things get even more complicated when Emily learns she's pregnant, and she's not certain if it's Tom's or her boyfriend, Elliot.

Feeling Minnesota

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.

Forever Mine

A hotel cabana boy falls for the wife of a powerful politico. But when she confesses to the affair, her husband determines to end it forever.

The Lonely Guy

A writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.

Last Wedding

Three couples in Vancouver navigate their relationships: first jobs, first crises, professional jealousy, an affair, and lack of communication. Noah and Zipporah marry after a brief courtship. She wants to be a singer and stalls out when she fails. He's working hard at a business that may go under. Sarah and Shane are architects; he can't handle her success at a downtown firm. Leslie is a librarian, sour and prickly; her mate, Peter, is a college teacher whose head is turned by a student. Can any of these couples sort things out and stay together? Should they?

How to Make an American Quilt

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.

I Think I Love My Wife

Richard Cooper is a married man and father of two who is just plain bored with married life. Not getting any sex from his wife, he resorts to ogling random women on the street to the point that he takes lunch late to look at them. When old crush Nikki Tru visits his office to get a reference letter, she becomes obsessed with Cooper and they begin a complicated relationship.

Making Mr. Right

When image consultant Frankie Stone is hired by a tech company to teach a scientist’s “Ulysses Robot” how to be a man, she winds up developing very real feelings for the faux human.

5.5 / 10 1995 Comedy Romance
suggested by: user4834nhioebh

Miami Rhapsody

Gwyn Marcus has always wanted a marriage like her parents. She has just accepted the proposal of her boyfriend Matt, but she has misgivings about their future together. Her fear of commitment grows as she learns of the various affairs that her family is having. With her sister getting married and her brother already married, her mother is growing concerned about Gwyn's being the last single person in the family. But the more she thinks about marriage, the more she must search for the balance between career, marriage and family.

Micki & Maude

TV reporter Rob Salinger is married to Micki, but because she's always busy working, they hardly ever spend time together. One night at which he got stood up by Micki again, Rob meets cellist Maude and they soon get romanticly involved. When it turns out Maude is pregnant with his baby, Rob decides to marry Maude. When he's on the verge of telling Micki, she tells him she's pregnant, so he doesn't have the heart to leave her, but he marries Maude anyway. Now married to two pregnant women who don't know about each other, Rob has a busy time taking care of both and keep them from finding out.

Monsoon Wedding

As the romantic monsoon rains loom, the extended Verma family reunites from around the globe for a last-minute arranged marriage in New Delhi. This film traces five intersecting stories, each navigating different aspects of love as they cross boundaries of class, continent and morality.

Serious Moonlight

A high-powered attorney duct tapes her adulterous husband to the toilet ... right before their home is invaded by burglars.

Sleep with Me

Six different writers wrote a scene each of this romantic comedy featuring the marriage and turbulent relationship of Joseph and Sarah, with Joseph's best friend Frank trying hard to cope with letting the love of his life marry his best friend.

Something to Talk About

Grace King 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.

Take This Waltz

Twenty-eight-year-old Margot is happily married to Lou, a good-natured cookbook author. But when Margot meets Daniel, a handsome artist who lives across the street, their mutual attraction is undeniable.

The Taming of the Shrew

Italy, 16th century. Petruchio, a choleric, lying and poor rural landowner from Verona, arrives in Padua in search of fortune and a wife, while Baptista, a wealthy merchant, announces that he will not allow Bianca, his youngest daughter, to marry until the temperamental and unruly Katherina, his eldest daughter, does.

That Old Feeling

A bride's divorced parents find their old feelings for each other during the wedding reception and over the course of the next few days upsetting the newlywed's honeymoon.

That's Life!

A wealthy architect struggles with a severe case of male menopause at the approach of his 60th birthday.

True Love

Donna and Michael are getting married. But first, they have to plan the reception, get the tux, buy the rings, and cope with their own uncertainty about the decision. Michael fears commitment. Donna has her doubts about Michael's immaturity. Both are getting cold feet.

The Leading Man

Successful playwright Felix Webb has a new play, 'The Hit Man', in rehearsal. Directed by his old friend Humphrey, it is already being hailed as a masterpiece; but Felix can't enjoy his success. He has fallen passionately in love with Hilary, a beautiful, fiesty young actress, and is preparing to desert his perfect family, his wife Elena and three lively children. His intolerable situation is further complicated when Humphrey casts Hilary as one of the leads in 'The Hit Man'. Enter Robin Grange, a charismatic young Hollywood actor making his London theatre debut. Robin is attractive, charming and dangerous, and soon inveigles his way into everyone's life. He ingratiates himself with the cast and, quickly grasping Felix's dilemma, sets about weaving his web of mischief. He suggests that if he were to seduce Elena, she would be distracted from Felix's affair, regain her self respect, and perhaps even willingly part from the unfaithful husband to whom she clings...

Married Life

A very gentle middle-aged man is married, but when he falls in love with another woman, he decides that to divorce his wife would humiliate her too much – so instead he decides to kill her.

You Can Thank Me Later

In this Canadian comedy-drama, Shirley Cooperberg heads a Montreal Jewish family. During her husband's operation, her brood arrives at the hospital -- failed writer Eli, neurotic Susan, and successful theatrical producer Edward. An onslaught of one-liners find targets amid sibling rivalries and angst-ridden animosities.

The Marriage of a Young Stockbroker

A stockbroker is stuck in a dreary job and a marriage that's become a dull routine. To cope with the boredom and frustration, he resorts to voyeurism and extramarital love affairs.

Say Nothing

Housewife Grace Needham (Nastassja Kinski) has a one-night stand with Julian Grant (William Baldwin), who then becomes obsessed with sinking her marriage to husband Matt (Hart Bochner). The twist here is that Julian is a millionaire global powerbroker, and Matt works for him! It's a titanic battle of testosterone as the guys duke it out while Grace simmers angrily.

Second Honeymoon

Raoul McLish stops over in Miami Beach where he runs into his ex-wife, Vicky Benton, and her new husband Bob, a belt manufacturer. At first Bob enjoys Raoul's presence - in part because Vicky is his not Raoul's and in part because Raoul is a lot of fun. The fun wears thin for Bob as his seriousness and possessiveness take over. When Bob leaves for a few days to settle a labor dispute at his factory, Vicky and Raoul spend time together, Winchell's column implies untoward behavior, Bob barks at Vicky, and that gets her back up. Can things be sorted out? Help comes from Raoul's upright valet, McTavish, and a principled cigarette girl, Joy, whom Raoul picks up.

5.3 / 10 2001 Comedy Drama
suggested by: user220ln0r5brs

Dinner with Friends

A husband and wife reevaluate their marriage after their closest friends, another couple decide to split up after twelve years.

A Guide for the Married Woman

A seriocomic look at the life of Julie Walker. Bored with her marriage, and encouraged by her friends, she contemplates an affair. Fantasy and reality mix often, leading to complications and headaches.

Dostana

Two straight guys who pretend to be a couple to secure a posh Miami apartment fall for their gorgeous roommate. Hilarity ensures as Kunal and Sameer strive to convince everyone they are a couple while secretly trying to win Neha's heart.

My New Gun

Debbie and Gerald's lives drastically change after they get a gun. Their mysterious neighbor, Skippy, becomes an important and transforming figure in their lives.

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.

Chasing Papi

Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?

The Freebie

Annie and Darren have been married for seven years, and they love each other as much as the day they were wed; they're affectionate, have fun together, and enjoy games such as crossword puzzle races. They would seem to have a perfect relationship, except for one thing -- they haven't had sex in ages, and seem to have lost all interest in making love with one another, no matter how they try to put each other in the mood. Hoping to put some adventure back into their lives, Annie and Darren come up with an unusual idea -- they each get one night in which they're free to find someone and have sex with them, scot-free. But is this going to help their relationship, or is it just going to turn a small problem into a big problem?

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