Movies Like The Sadness of Sex

If you liked The Sadness of Sex (1998), a comedy and romance movie directed by Rupert Wainwright, 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
Yoh! Bestie (2026)
★ 6.2/10Also romance and comedy
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
2
Sex Appeal (2022)
★ 6.6/10Also comedy and romance
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
3
Desperados (2020)
★ 6/10Also comedy and romance
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
4
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romance
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
5
The Prince & Me 4: The Elephant Adventure (2010)
★ 6.1/10Also comedy and romance
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged…
6
How I Got Into College (1989)
★ 6/10Also comedy and romance
High school senior Marlon Bowne is smitten with overachieving classmate Jessica Kailo. But, if he wants to have a shot with her, he'll have to find a way to get into Ramsey College, Jessica's top choice of schools. It…
7
Little Italy (2018)
★ 6.6/10Also comedy and romance
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
8
Chasing Papi (2003)
★ 6.7/10Also comedy and romance
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored…
9
Players (2024)
★ 6.1/10Also romance and comedy
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
10
What's Love Got to Do with It? (2023)
★ 6.1/10Also romance and comedy
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
11
Easy Virtue (2008)
★ 6.5/10Also comedy and romance
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
12
Someone Like You... (2001)
★ 6/10Also comedy and romance
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…
13
Splendor (1999)
★ 6.2/10Also comedy and romance
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…
14
Bye Bye Love (1995)
★ 6.1/10Also comedy and romance
With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter…
15
One Night Only (2026)
★ 6.4/10Also romance and comedy
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
16
Love, Weddings & Other Disasters (2020)
★ 6/10Also romance and comedy
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
17
Dean (2016)
★ 5.9/10Also romance and comedy
A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family home in the wake of his mother's death.
18
The Incredible Jessica James (2017)
★ 6.1/10Also romance and comedy
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
19
Cuban Fury (2014)
★ 6.1/10Also comedy and romance
Beneath Bruce Garrett's under-confident, overweight exterior, the passionate heart of a salsa king lies dormant. Now, one woman is about to reignite his Latin fire.
20
Girl on a Bicycle (2013)
★ 5.9/10Also comedy and romance
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day…