Movies Like Head Over Heels

If you liked Head Over Heels (2010), a comedy movie directed by Roberto Santucci, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
2
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
3
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
4
How to Hack Your Boss (2021)
★ 6.5/10Also comedy
Victor accidentally sends a compromising email to his nagging boss. With the help of his office crush and a clueless friend, he'll try to save his job while having to deal with a rook hacker the porn industry, a…
5
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
6
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
7
Ali Wong: Single Lady (2024)
★ 6.4/10Also comedy
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
8
Seriously Single (2020)
★ 6.8/10Also comedy
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
9
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
10
Me Time (2022)
★ 5.8/10Also comedy
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
11
Eenie Meanie (2025)
★ 6.3/10Also comedy
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
12
Like a Boss (2020)
★ 6.2/10Also comedy
Two female friends with very different ideals decide to start a beauty company together. One is more practical, while the other wants to earn her fortune and live a lavish lifestyle.
13
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
14
A Bad Moms Christmas (2017)
★ 6.3/10Also comedy
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families…
15
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…
16
Pretty Persuasion (2005)
★ 5.8/10Also comedy
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
17
Ladies First (2026)
★ 6/10Also comedy
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.
18
Adult World (2014)
★ 6/10Also comedy
Amy, a naive college graduate who believes she's destined to be a great poet, begrudgingly accepts a job at a sex shop while she pursues a mentorship with reclusive writer Rat Billings.
19
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
20
29th Street (1991)
★ 6.9/10Also comedy
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.