Movies Like Trifling with Fate

If you liked Trifling with Fate (2000), a comedy and music movie directed by Michael Bergmann, 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
Let's Make Love (1960)
★ 6.4/10Also comedy and romance
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
2
Romance & Cigarettes (2006)
★ 6/10Also comedy and music
Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval…
3
¿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.
4
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.
5
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…
6
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.
7
The Merry Widow (1934)
★ 6.8/10Also comedy and music
A prince from a small kingdom courts a wealthy widow to keep her money in the country.
8
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.
9
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?
10
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.
11
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.
12
Music and Lyrics (2007)
★ 6.5/10Also comedy and music
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…
13
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…
14
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…
15
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.
16
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.
17
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…
18
Starting Over (1979)
★ 6.4/10Also comedy and romance
After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.
19
In the Good Old Summertime (1949)
★ 6.8/10Also comedy and music
Two co-workers in a music shop dislike one another during business hours but unwittingly carry on an anonymous romance through the mail.
20
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.