Best movies like Head Over Heels

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A unique, carefully handpicked, selection of the best movies like Head Over Heels Starring Monica Potter, Freddie Prinze Jr., Shalom Harlow, Ivana Miličević, and more. If you liked Head Over Heels then you may also like: Two Lovers, 27 Dresses, The Wedding Date, When in Rome, New Year's Eve 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.

Ordinary single girl Amanda Pierce unexpectedly finds herself sharing an awesome Manhattan apartment with four sexy supermodels. Determined to bring Amanda into their world, the models give her the ultimate makeover. The plan works fabulously as Amanda connects with next door charmer Jim Winston. That is, until one night...

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Two Lovers

A depressed man moves back in with his parents following a recent heartbreak and finds himself with two women.

6.4 / 10 2008 Comedy Romance
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27 Dresses

Altruistic Jane finds herself facing her worst nightmare as her younger sister announces her engagement to the man Jane secretly adores.

The Wedding Date

With the wedding of her younger sister fast approaching, Kat Ellis faces the undesirable prospect of traveling alone to London for the ceremony. While this is bad enough, Jeffrey, the man who left her as they moved closer to marriage, happens to be the groom's best man. Determined to show everyone -- most of all Jeffrey -- that her romantic life is as full and thrilling as ever, Kat hires a charming male escort as her date.

When in Rome

After fishing out coins from a water fountain in Italy, cynical New Yorker Beth Harper finds herself being wooed by several ardent suitors. As she deals with the attention, Beth tries to figure out whether a charming reporter really loves her.

New Year's Eve

The lives of several couples and singles in New York intertwine over the course of New Year's Eve.

The Other Woman

After discovering her boyfriend is married, Carly soon meets the wife he's been cheating on. And when yet another affair is discovered, all three women team up to plot mutual revenge on the three-timing SOB.

Just My Luck

Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.

About Last Night

A modern reimagining of the classic romantic comedy, this contemporary version closely follows new love for two couples as they journey from the bar to the bedroom and are eventually put to the test in the real world.

Addicted to Love

Good-natured astronomer Sam is devastated when the love of his life leaves him for a suave Frenchman. He therefore does what every other normal dumpee would do — go to New York and set up home in the abandoned building opposite his ex-girlfriend's apartment, wait until she decides to leave her current lover, and then win her back.

The Back-Up Plan

When Zoe tires of looking for Mr. Right, she decides to have a baby on her own. But on the day she's artificially inseminated, she meets Stan, who seems to be just who she's been searching for all her life. Now, Zoe has to figure out how to make her two life's dreams fit with each other.

Blonde Ambition

A young professional woman (Simpson) unwittingly becomes the pawn of two business executives in their bid to oust the head of a mega-conglomerate.

Booty Call

Rushon is sexually pent-up and ready to take thing things to the next level with his girlfriend, Nikki. But when he calls for a date, she asks to make it a double — bringing along her brash friend, Lysterine, whom Rushon sets up with his lewd buddy, Bunz. Things go better than expected. As the evening transitions from the restaurant to the bedroom, the two men go on a madcap search for what will surely make the night complete: condoms.

Boys' Night Out

Fred, George, Doug and Howie are quickly reaching middle-age. Three of them are married, only Fred is still a bachelor. They want something different than their ordinary marriages, children and TV-dinners. In secret, they get themselves an apartment with a beautiful young woman, Kathy, for romantic rendezvous. But Kathy does not tell them that she is a sociology student researching the sexual life of the white middle-class male.

Breaking Up

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.

Bridget Jones: The Edge of Reason

Bridget Jones is becoming uncomfortable in her relationship with Mark Darcy. Apart from discovering that he's a conservative voter, she has to deal with a new boss, a strange contractor and the worst vacation of her life.

Brown Sugar

Friends since childhood, a magazine editor and a hip-hop record executive stumble into romantic territory.

Ten Inch Hero

Four friends search for love and happiness while working at a California sandwich shop.

Young People Fucking

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?

The Girl Next Door

Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals.

How to Lose a Guy in 10 Days

It’s the battle of wills, as Andie (Kate Hudson) needs to prove she can dump a guy in 10 days, whereas Ben (Matthew McConaughey) needs to prove he can win a girl in 10 days. Now, the clock is ticking - and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks!

He's Just Not That Into You

Remember that really cute girl/guy who said they'd call – and didn't? Maybe they lost your number. Maybe they're in the hospital. Maybe they're awed by your looks, brains or success. Or maybe... They're just not that into you.

Dan in Real Life

Advice columnist, Dan Burns is an expert on relationships, but somehow struggles to succeed as a brother, a son and a single parent to three precocious daughters. Things get even more complicated when Dan finds out that the woman he falls in love with is actually his brother's new girlfriend.

Just Like Heaven

Shortly after David Abbott moves into his new San Francisco digs, he has an unwelcome visitor on his hands: winsome Elizabeth Martinson, who asserts that the apartment is hers -- and promptly vanishes. When she starts appearing and disappearing at will, David thinks she's a ghost, while Elizabeth is convinced she's alive.

The Switch

Kassie is a smart, fun-loving single woman who, despite her neurotic best friend Wally’s objections, decides it’s time to have a baby – even if it means doing it herself…with a little help from a charming sperm donor. But, unbeknownst to her, Kassie’s plans go awry because of a last-minute switch that isn’t discovered until seven years later… when Wally gets acquainted with Kassie’s cute – though slightly neurotic – son.

Down to You

College coeds in New York City, Al, the son of a celebrity chef, and Imogen, a talented artist, become smitten the second they lay eyes on one another at a bar. However, the road to happiness is not a smooth one. Outside forces, including a predatory porn star who wants to lure Al into her bed, threaten to pull apart the young lovers before their romance has a chance to really flourish.

Failure to Launch

Tripp, an attractive man in his thirties, is still living with his parents Al and Sue. Tripp's best friends Demo and Ace are also still living in their parents' homes and seem proud of it. Al and Sue are not happy, however, and are fascinated when friends whose adult son has recently moved away from home reveal they hired an expert to arrange the matter and couldn't be happier with the result.

Going the Distance

Erin and Garrett are very much in love. When Erin moves to San Francisco to finish her journalism degree and Garrett stays behind in New York to work in the music industry, they gamely keep the romance alive with webcams and frequent-flyer miles. But just when it seems the lovers will soon be reunited, they each score a big break that could separate them for good.

The Sweetest Thing

Christina's love life is stuck in neutral. After years of avoiding the hazards of a meaningful relationship, one night while club-hopping with her girlfriends, she meets Peter, her perfect match. Fed up with playing games, she finally gets the courage to let her guard down and follow her heart, only to discover that Peter has suddenly left town. Accompanied by Courtney, she sets out to capture the one that got away.

Happy Together

Christopher is an ambitious college freshman, striving to become a writer. Through a computer fault he's assigned the same room as Alex, a real party freak and... a girl! He's annoyed and tries to get a different room as soon as possible, but when he learns to know her, he also starts to like her. She not only improves his sexual life, but also his writing skills

Letters to Juliet

An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by the "secretaries of Juliet" -- and she goes on a quest to find the lovers referenced in the letter.

Monster-in-Law

Office temp Charlotte Cantilini thinks she's found Mr. Right when she starts dating gorgeous surgeon Dr. Kevin Fields. But there's a problem standing in the way of everlasting bliss: Kevin's overbearing and controlling mother, Viola. Fearing she'll lose her son's affections forever, Viola decides to break up the happy couple by becoming the world's worst mother-in-law.

A Guy Thing

Paul Morse is a good guy. When his friends throw him a wild bachelor party, he just wants to keep his conscience clean -- which is why he's shocked when he wakes up in bed with a beautiful girl named Becky and can't remember the night before. Desperate to keep his fiancée, Karen, from finding out what may or may not be the truth, he tells her a teensy lie. Soon his lies are spiraling out of control and his life is a series of comical misunderstandings.

Heartbreakers

Max and Page are a brilliant mother/daughter con team who have their grift down to a fine science. Max targets wealthy, willing men and marries them. Page then seduces them, and Max catches her husband in the act. Then it's off to palimony city and the next easy mark.

My Best Friend's Girl

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.

Mystery Date

Tom McHugh quickly learns that his perfect big brother Craig isn't all he's cracked up to be while on a night on the town with the girl next door, during which Tom is harassed by unpleasant strangers, threatened by mobsters, pursued by police, attacked by an irate florist, accused of murder, and has his date kidnapped—all because everyone thinks he's Craig...and the classic 1959 DeSoto Firesweep he borrowed off his brother has two dead bodies in the trunk.

Secret Admirer

An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who come in contact with it.

Someone Like You...

Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.

The Truth About Cats & Dogs

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.

Two Night Stand

After an extremely regrettable one night stand, two strangers wake up to find themselves snowed in after sleeping through a blizzard that put all of Manhattan on ice. They're now trapped together in a tiny apartment, forced to get to know each other way more than any one night stand should.

That Awkward Moment

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.

She's Funny That Way

On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.

So Fine

While trying to get his father out of a financial jam, a man comes up with an idea that turns into an unexpected overnight financial fashion success - the bottomless pants.

Fall

For Michael Shiver, life as an easy-going cab driver in New York suddenly changes when he picks up supermodel Sarah Easton and falls head over heels in love. But Sarah has more than just passion on her mind; she also has a husband and a glamorous lifestyle that she can't seem to leave behind. Torn between her feelings for Michael and the security of her marriage, Sarah is forced to make a realistic decision about the sacrifices that must be made to be truly and totally in love.

Christmas Catch

Detective Mackenzie Bennett is hot on the trail of Carson, a suspected diamond thief, and goes undercover to catch him in the act. While undercover, Mack not only falls for Carson, but begins to suspect that he's been framed. Are feelings clouding Mack's judgment or are they focusing on the wrong suspect?

The Accidental Husband

Emma, a radio host, is about to be married to Richard, her perfect match. But right before her wedding, she learns she's already married to Patrick, a charming but irresponsible fireman. Furthermore, Patrick has a secret: he has arranged this little trick because Emma advised Patrick's ex-fiancée to end their relationship. However, Patrick may find that the trick is on him, for he soon begins to fall in love with his uptight adversary.

Cross My Heart

A man and a woman go out on a "big" third date. He's ashamed to admit he just lost his job, and she's afraid he'll run away if he finds out that she has a kid. Small lies lead to bigger ones and the night gets crazy very soon.

Beauty & the Briefcase

A freelance writer looking for romance sells a story to Cosmopolitan magazine about finding love in the workplace and goes undercover at a Finance Company.

Love in the Forecast

After swearing off dating for a full year, Leah quickly learns her new commitment has made her a magnet for men.

A Christmas Kiss II

At a Christmastime event, Jenna shares an impromptu, unforgettable kiss with the dashing billionaire, Cooper Montgomery. Unaware of his intentions and fearful of getting hurt in another relationship, Jenna vows to resist his charms, but begins to realize his affection is real as the two spend more time together.

Irish Wish

Maddie's dream guy is days away from marrying her best friend when a wish for true love made on an ancient stone in Ireland magically alters her fate.

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