Movies Like It Probably Won't Work Out

If you liked It Probably Won't Work Out, a romance and comedy movie directed by Justin Borland, 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
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.
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
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.
5
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…
6
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.
7
A Hollywood Christmas (2022)
★ 6.1/10Also comedy and romance
Jessica, a young, up-and-coming filmmaker in Hollywood has made a name for herself directing Christmas movies. But when handsome network executive Christopher shows up threatening to halt production on her latest…
8
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.
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
We Broke Up (2021)
★ 5.9/10Also romance and comedy
Lori and Doug break up right before Lori's sister's wedding and decide to pretend they're still together for the weekend as to not disrupt the fun.
11
Playing It Cool (2014)
★ 5.9/10Also comedy and romance
A young man meets and instantly falls in love with an engaged woman.
12
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.
13
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.
14
Picture This (2025)
★ 6/10Also romance and comedy
Single and without a man on the horizon, Pia runs a failing photography studio in London with her best friend Jay. As her sister Sonal prepares for marriage and her mother Laxmi urges her to partner up, a spiritual…
15
Maintenance Required (2025)
★ 6.1/10Also romance and comedy
Charlie, the fiercely independent owner of an all-female mechanic shop, is forced to reevaluate her future when a flashy corporate competitor moves in across the street. Seeking comfort, she turns to an anonymous…
16
The List (2023)
★ 5.9/10Also romance and comedy
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.
17
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.
18
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.
19
The Other End of the Line (2007)
★ 6.5/10Also comedy and romance
An employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone.
20
Puppy Love (2023)
★ 7/10Also comedy and romance
After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched…