NoBadPicks

Movies Like Head Over Heels

If you loved Head Over Heels's Romance and Comedy storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.

Top Picks

Someone Great
6.4

Someone Great

2019

An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one outrageous last adventure in New York City.

Good Dick
5.9

Good Dick

2008

A fidgety, wisecracking video store clerk develops a fixation on a particularly reclusive customer, a frequent visitor to the pornography section of Cinefile, the video store where he works in Los Angeles. After multiple failures to impress her during their brief daily transactions, he finds her street address in the store's database, drives to her apartment building and initiates an unconventional campaign to win her affections.

My Sassy Girl
6.7

My Sassy Girl

2008

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

Someone Like You...
5.9

Someone Like You...

2001

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.

How to Be Single
6.3

How to Be Single

2016

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.

The List
6.0

The List

2023

After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with someone from hers.

Happy Together
5.9

Happy Together

1989

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

Alfie
5.8

Alfie

2004

A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.

More Movies Like Head Over Heels

Isn't It Romantic
6.2

Isn't It Romantic

2019

For a long time, Natalie, an Australian architect living in New York City, had always believed that what she had seen in rom-coms is all fantasy. But after thwarting a mugger at a subway station only to be knocked out while fleeing, Natalie wakes up and discovers that her life has suddenly become her worst nightmare—a romantic comedy—and she is the leading lady.

She's Funny That Way
5.9

She's Funny That Way

2015

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.

The Wrong Paris
6.7

The Wrong Paris

2025

Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.

Drive Me Crazy
6.5

Drive Me Crazy

1999

Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.

The Broken Hearts Gallery
7.2

The Broken Hearts Gallery

2020

Lucy is a young gallery assistant who collects mementos from her relationships. She discovers that she must let go of her past to move forward, and comes up with a lovely, artistic way to help herself and others who have suffered heartbreak.

Love at First Bite
5.9

Love at First Bite

1979

Dracula and Renfield relocate to '70s era New York in search of Cindy Sondheim, the reincarnation of Dracula's one true love, Mina Harker. "Trouble adjusting" is a wild understatement for the Count as he battles Cindy's psychiatrist, Jeffrey Rosenberg, a descendant of Van Helsing, who may be in love with Cindy too.

Splendor
6.1

Splendor

1999

Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?

Never Been Kissed
6.2

Never Been Kissed

1999

Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.

West Side Story
7.2

West Side Story

1961

In Manhattan’s Upper West Side, rival gangs of Polish-Americans and newly arrived Puerto Ricans clash for control of the neighborhood, even as two young members from opposite sides fall dangerously in love.

Sex and the Single Girl
6.5

Sex and the Single Girl

1964

A womanizing reporter for a sleazy tabloid magazine impersonates his hen-pecked neighbor in order to get an expose on renowned psychologist Helen Gurley Brown.

Heights
6.3

Heights

2005

Spanning twenty-four hours, HEIGHTS follows five New Yorkers challenged to choose their destiny before the sun comes up the next day.

Bullets Over Broadway
7.1

Bullets Over Broadway

1994

After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a psychiatrist—she's a dreadful actress. David puts up with the leading man who is a compulsive eater, the grand dame who wants her part jazzed up, and Olive's interfering hitman/bodyguard—but, eventually he must decide whether art or life is more important.

Why These Movies Are Similar

These recommendations share core qualities with Head Over Heels (2001): Romance and Comedy themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Head Over Heels.

See full details for Head Over Heels (2001)

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