Movies Like Second Guessing Fate

If you liked Second Guessing Fate (2025), a romance and comedy movie directed by Stefan Brogren, 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
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.
2
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.
3
Prom Pact (2023)
★ 7.2/10Also comedy and romance
It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts…
4
As Luck Would Have It (2021)
★ 6.5/10Also tv movie and comedy
When Lindsey travels to Ireland to acquire land that is perfect for a resort, she decides to enter the town's matchmaking festival to prove her investment—and win over a handsome local.
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
Anything for Love (2016)
★ 6/10Also romance and tv movie
Katherine, a high-powered executive who believes men are intimidated by her career, is persuaded by her friend to create an internet dating profile claiming she is an executive assistant.
7
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.
8
You Cast A Spell On Me (2015)
★ 6.8/10Also comedy and romance
Despite agreeing to an arranged marriage to a childhood friend, a successful businessman tries to track down a beautiful woman that he met at a Halloween party.
9
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.
10
A Christmas Miracle for Daisy (2021)
★ 5.9/10Also romance and comedy
Whitney Alder owns interior design firm Marietta Designs, which she runs with her friend Andi in the small town of Marietta, Montana. Whitney is designing Santa’s float for the annual Marietta Christmas Parade when a…
11
My Favorite Wedding (2017)
★ 6.9/10Also comedy and romance
Potential Northwestern fellow Tess Harper lasers through her best friend's wedding planning like the star doctor she hopes to soon become. In fact, Tess puzzles through any problem - provided it's not her own. When she…
12
Christmas on Windmill Way (2023)
★ 5.9/10Also romance and comedy
Mia Meijer gets ready for the Christmas Market Dutch Bake-Off and suspects that her grandmother, Ann, will walk away with the cherished Golden Rolling Pin thanks to her Kerststol, a traditional Dutch fruited Christmas…
13
About Fate (2022)
★ 7.5/10Also romance and comedy
Two strangers believe in love but never seem to be able to find its true meaning. In a wild twist of events, fate puts each in the other's path on one stormy New Year's Eve.
14
What's Your Number? (2011)
★ 6.5/10Also comedy and romance
Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96…
15
How to Fall in Love (2012)
★ 6/10Also comedy and romance
An accountant, who never quite grew out of his awkward teenage years, finds himself with a dating coach - she happens to be his high school crush as well. Thanks to his coach, he gets a pretty woman he has his sights…
16
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.
17
All Things Valentine (2016)
★ 5.9/10Also romance and comedy
Avery, a blogger with a string of disappointing Valentine’s Days, is ready to give up on love when she meets handsome veterinarian Brenden. When Avery finds out Brenden blames his recent break up on her blog and is the…
18
A Royal Date for Christmas (2023)
★ 5.8/10Also romance and comedy
Bella Sparks, owner of Bella’s Boutique, takes on a demanding new client named Stefan, who needs to be outfitted for a week of high-stakes meetings and events after his luggage goes missing. Imagine Bella’s reaction…
19
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.
20
The Love Hypothesis (2026)
★ 7.9/10Also romance and comedy
Olive Smith, a biology PhD candidate, and Dr. Adam Carlsen, a hotshot professor and well-known tyrant, enter into a fake relationship, seeing each of their carefully calculated theories on love get thrown into chaos.