Movies Like Kiss Me, Stupid

If you liked Kiss Me, Stupid (1964), a comedy and romance movie directed by Billy Wilder, 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
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.
2
Music and Lyrics (2007)
★ 6.5/10Also comedy and romance
A washed-up '80s pop star gets a chance at a comeback when reigning pop diva Cora Corman invites him to write & record a duet with her, but there's a problem--Alex hasn't written a song in years; he's never written…
3
Watching the Detectives (2007)
★ 6.3/10Also comedy and romance
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets…
4
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?
5
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.
6
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.
7
The Right Kind of Wrong (2013)
★ 5.9/10Also romance and comedy
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
8
The Wrong Paris (2025)
★ 6.7/10Also romance and comedy
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.
9
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…
10
How to Marry a Millionaire (1953)
★ 6.8/10Also comedy and romance
Three women set out to find eligible millionaires to marry, but find true love in the process.
11
Hollywood Stargirl (2022)
★ 6.6/10Also comedy and romance
When Stargirl's mother is hired as the costume designer on a movie, they relocate to L.A., where Stargirl quickly becomes involved with an eclectic assortment of characters.
12
Silk Stockings (1957)
★ 6.8/10Also comedy and romance
After three bumbling Soviet agents fail in their mission to retrieve a straying Soviet composer from Paris, the beautiful, ultra-serious Ninotchka is sent to complete their mission and to retrieve them. She starts out…
13
A Touch of Class (1973)
★ 6.1/10Also comedy and romance
Steve, a happily married American man living in London meets Vicki, an English divorcée and run off to Marbella for a rollicking week of sex. They then return to London to set up a cozy menage, despite the fact that he…
14
Pillow Talk (1959)
★ 7.1/10Also comedy and romance
Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a…
15
5 to 7 (2014)
★ 7.1/10Also comedy and romance
A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.
16
This Little Love of Mine (2021)
★ 6.1/10Also romance and comedy
Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the firm’s biggest client – Chip’s…
17
Boot Camp (2024)
★ 6.1/10Also romance and comedy
Unathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self and ignore the others' expectations.
18
Love Is in the Air (2023)
★ 6.2/10Also romance and comedy
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
19
Only the Lonely (1991)
★ 6.2/10Also comedy and romance
Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna, whose father owns the local funeral parlour. Naturally, his mother objects to the…
20
Relationship Goals (2026)
★ 6.4/10Also romance and comedy
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her…