Movies Like Trouble Date

If you liked Trouble Date (2023), a comedy movie directed by Robert Therrell, 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
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
2
Ali Wong: Single Lady (2024)
★ 6.4/10Also comedy
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
3
Switching Channels (1988)
★ 6.1/10Also comedy
A television news chief courts his anchorwoman ex-wife with an eleventh-hour story.
4
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
5
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
6
Seriously Single (2020)
★ 6.8/10Also comedy
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
7
I Love My Dad (2022)
★ 5.9/10Also comedy
A hopelessly estranged father catfishes his son in an attempt to reconnect.
8
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
9
The Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
10
Footlight Parade (1933)
★ 6.8/10Also comedy
A fledgling producer finds himself at odds with his workers, financiers and his greedy ex-wife when he tries to produce live musicals for movie-going audiences.
11
21 & Over (2013)
★ 5.8/10Also comedy
Brilliant student Jeff Chang has the most important interview of his life tomorrow. But today is still his birthday, what starts off as a casual celebration with friends evolves into a night of debauchery that risks to…
12
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
13
Impractical Jokers: The Movie (2020)
★ 6.5/10Also comedy
The story of a humiliating high school mishap from 1992 that sends the Impractical Jokers on the road competing in hidden-camera challenges for the chance to turn back the clock and redeem three of the four Jokers.
14
Love Happy (1949)
★ 5.8/10Also comedy
The Marx Brothers help young Broadway hopefuls when they get mixed up with gangsters due to a tin of sardines containing Romanoff diamonds.
15
Tommy Boy (1995)
★ 6.8/10Also comedy
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
16
The 12 Days of Christmas Eve (2022)
★ 6/10Also comedy
When Brian Conway, a successful businessman whose family relationships have suffered, gets in a car accident on Christmas Eve, Santa gives him twelve chances to redo the day and repair the relationships in his life…
17
One Night at McCool's (2001)
★ 5.9/10Also comedy
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
18
The F**k-It List (2020)
★ 6/10Also comedy
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
19
St. Vincent (2014)
★ 7.1/10Also comedy
A young boy whose parents just divorced finds an unlikely friend and mentor in the misanthropic, bawdy, hedonistic, war veteran who lives next door.
20
29th Street (1991)
★ 6.9/10Also comedy
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.