Most Similar Movies to Head Over Heels (2001)
If you are looking for movies like Head Over Heels (2001), you might like movies tagged with keyword : romance, comedy, fashion, new york, art, workplace, misunderstanding, fake marriage, romantic comedy, light comedy, urban, female lead, male lead, dating, cultural differences, humor, lighthearted, modern, emotion, growth .
Monster-in-Law (2005), Love in Design (2018), Just Wright (2010), Blonde Ambition (2007), Down to You (2000), The Seat Filler (2004), The Proposal (2009) ... Let's take a look at the following list...

Monster-in-Law (2005)
The love life of Charlotte is reduced to an endless string of disastrous blind dates, until she meets the perfect man, Kevin. Unfortunately, his merciless mother will do anything to destroy their relationship.
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Love in Design (2018)
A hitman in Koreatown meets a Karaoke hostess only to find out she is his next target.
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Just Wright (2010)
A physical therapist falls for the basketball player she is helping recover from a career-threatening injury.
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Blonde Ambition (2007)
A young professional woman (Simpson) unwittingly becomes the pawn of two business executives in their bid to oust the head of a mega-conglomerate.
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Down to You (2000)
A young man wins and loses the first serious love of his life. Al Connelly falls in love with the girl of his dreams. After the summer she breaks up with him. As he tries to recover Al goes to desperate measures.
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The Seat Filler (2004)
A law student (Duane Martin) pretends to work in show business after starting a romance with a singer (Kelly Rowland) he met at an awards show.
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The Proposal (2009)
A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada.
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Set It Up (2018)
Two corporate executive assistants hatch a plan to match-make their two bosses.
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How to Lose a Guy in 10 Days (2003)
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days. Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 days." They meet in a bar shortly after the bet is made.
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My Sassy Girl (2008)
A sweet Midwestern guy with his life planned out for himself is wooed, groomed, and ultimately dumped by a complicated, elusive gal.
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What Happens in Vegas (2008)
A man and a woman are compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
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Love Birds (2011)
Doug's girlfriend leaves him and he falls apart. He finds a hurt "not duck" on the roof and ends looking after it. He meets cute, single bird specialist Holly at the zoo.
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Must Love Dogs (2005)
A forty-something preschool teacher looks to the personals for a change of pace and a relationship, with hilarious results.
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Made of Honor (2008)
A guy in love with an engaged woman tries to win her over after she asks him to be her maid of honor.
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Tere Naal Love Ho Gaya (2012)
Mini isn't eager to wed the rich suitor who's been chosen for her, so she stages her own kidnapping and runs off with a man who works for her father.
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Because I Said So (2007)
A meddling mother tries to set her daughter up with the right man so her kid won't follow in her footsteps.
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A Guy Thing (2003)
A soon-to-be husband wakes up on the morning after his bachelor party in bed with another woman.
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It Had to Be You (2015)
Sonia, a neurotic and charming jingle writer, dreams of having an exciting life. The sudden marriage proposal from her boyfriend forces Sonia to confront whether she wants to join the ranks of her married friends or pursue her fantasies.
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