Most Similar Movies to Don't Go Breaking My Heart (1999)
If you are looking for movies like Don't Go Breaking My Heart (1999), you might like movies tagged with keyword : romance, comedy, urban romance, modern love, love triangle, city life, 1990s, romantic comedy, emotional conflict, relationship, love story, humor, light-hearted, sweet, romantic, emotions, urban romance, romantic comedy, emotional drama, hong kong cinema .
The Perfect Match (2016), Love Is in the Air (2013), Valentine's Again (2017), Baby, Baby, Baby (2015), Eloïse's Lover (2009), Just a Walk in the Park (2002), Almost Love (2019) ... Let's take a look at the following list...

The Perfect Match (2016)
Complications arise when a lifelong playboy (Terrence J) bets his friends that he can date the same woman (Cassie Ventura) for one month without falling in love.
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Love Is in the Air (2013)
Antoine is a lawyer living in New York. On his way back to France for the final round of a job interview, Antoine finds himself sitting right next to his ex-girlfriend Julie. With a seven-hour flight ahead of them, they are going to have to speak to each other.
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Valentine's Again (2017)
Katherine, an ad executive, endures the worst Valentine's Day date of her life. On her walk home, a gypsy weaves a magical spell on her. When she wakes up the next morning, she realizes she's reliving the day until she finds the right man.
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Baby, Baby, Baby (2015)
The relationship between two mismatched people who try to move past their baggage to make their love work.
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Eloïse's Lover (2009)
A beautiful woman (Ariadna Cabrol) begins a lesbian affair with an 18-year-old high-school student (Diana Gómez).
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Just a Walk in the Park (2002)
A group of thirtysomethings having problems with fidelity gets an opportunity to turn back the clock.
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Almost Love (2019)
A couple are about to find out if their relationship has an expiration date.
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Talk of the Town (1995)
Monika, the host of a daily radio call-in show on the verge of beco- ming a thirtysomething, has almost given up all hopes of finding the man of her dreams when her gay brother convinces her to try it one last time -- via a contact advertisement. Suprisingly, she finds some- one she instantly falls in love with, only to find out that her "Mr. Perfect" is already marri...Read all
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If Lucy Fell (1996)
Two NYC roomies have a pact to jump off Brooklyn Bridge, if they haven't found life partners before she's 30. That's less than a month away.
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Singles (1992)
A group of twenty-something friends, most of whom live in the same apartment complex, search for love and success in grunge-era Seattle.
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Hotel de Love (1996)
Twin brothers meet a childhood sweetheart at a tacky hotel and rediscover their love as they renew their competition for her affection.
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Splendor (1999)
Veronica, 22, meets a writer and a drummer hunk at a club on Halloween. Why choose when she can have both? 3some? But then a third man comes along.
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Seven Girlfriends (1999)
A guy proposing is told that he has no idea how to have a relationship. On the way to the funeral of another ex, he goes on a road trip to find out what went wrong with the 7 girlfriends in his life by contacting them.
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A Case of You (2013)
A young writer tries to impress a girl he meets online with an embellished profile, but he finds himself in a real mess when she falls for him and he has to keep up the act.
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Happy Ending (2014)
A confused writer goes on the search of inspiration for his next story and falls in love with a best seller author who doesn't believe in love.
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My Online Valentine (2019)
My Online Valentine follows, Cozette "Cozi" Newton (Taja V. Simpson) and Blaze Maddox (Blue Kimble) who find romance through an online dating site, blazedates.com. But, just as Cozi decides to take a risk and give dating Blaze a chance, her ex-boyfriend Ajax Booker (Robert Christopher Riley) pops back into her life with plans of his own. As Ajax has a plan of his own ...Read all
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The Matchbreaker (2016)
A rich merchant, Antonio is depressed for no good reason, until his good friend Bassanio comes to tell him how he's in love with Portia. Portia's father has died and left a very strange will: only the man that picks the correct casket out of three (silver, gold, and lead) can marry her. Bassanio, unfortunately, is strapped for cash with which to go wooing, and Antonio...Read all
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Cafe Ole (2000)
Malcolm's (28) new love, Alicia (25), an illegal Chilean refugee, will be short-lived if he does not make the right choice.
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