Movies Like Tripping Through

If you liked Tripping Through (2016), a comedy and romance movie directed by Malcolm Ellis, 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
¿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.
2
Yoh! Bestie (2026)
★ 6.3/10Also 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.
3
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.
4
Players (2024)
★ 6/10Also 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…
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
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.
7
Playing It Cool (2014)
★ 5.9/10Also comedy and romance
A young man meets and instantly falls in love with an engaged woman.
8
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.
9
One Night Only (2026)
★ 6.5/10Also romance and comedy
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
10
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.
11
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…
12
My Sassy Girl (2008)
★ 6.8/10Also comedy and romance
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
13
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…
14
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.
15
The Lonely Guy (1984)
★ 6.2/10Also comedy and romance
A writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.
16
Splendor (1999)
★ 6.2/10Also comedy and romance
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible…
17
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.
18
The Woman in Red (1984)
★ 6.3/10Also comedy and romance
When a happily married family man, who would never consider an affair, meets a beautiful woman in red, he is totally infatuated and desperate to make her acquaintance. However, as he tries out various schemes to sneak…
19
Along Came Polly (2004)
★ 6/10Also comedy and romance
Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's…
20
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…