Movies Like Two-Sided Ride

If you liked Two-Sided Ride (2016), a movie directed by Jason Karman, 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 Object of My Affection (1998)
★ 5.8/10
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
2
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
3
Girl on a Bicycle (2013)
★ 5.9/10
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…
4
Sabrina (1954)
★ 7.5/10
After two years in Paris, chauffeur's daughter Sabrina returns home elegantly transformed and immediately catches the attention of David, the playboy son of her father's rich employers. David woos and wins Sabrina, who…
5
People We Meet on Vacation (2026)
★ 6.9/10
Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.
6
Meet Me Next Christmas (2024)
★ 6.3/10
On a quest to reconnect with the man of her dreams, Layla races across New York City to find a ticket to a sold-out Pentatonix Christmas Eve concert.
7
My Fake Boyfriend (2022)
★ 5.9/10
A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets…
8
That Touch of Mink (1962)
★ 6.5/10
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
9
Leaving Las Vegas (1995)
★ 7.2/10
Ben Sanderson, an alcoholic Hollywood screenwriter who lost everything because of his drinking, arrives in Las Vegas to drink himself to death. There, he meets and forms an uneasy friendship and non-interference pact…
10
Driver's Ed (2026)
★ 6.9/10
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
11
Bros (2022)
★ 6.6/10
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
12
Naomi and Ely's No Kiss List (2015)
★ 5.9/10
The bonds between Naomi and Ely are tested when they fall for the same guy.
13
The Lost Husband (2020)
★ 6.7/10
Trying to put her life back together after the death of her husband, Libby and her children move to her estranged Aunt's goat farm in central Texas.
14
The AI Doc: Or How I Became an Apocaloptimist (2026)
★ 7/10
A father-to-be tries to figure out what is happening with all this AI insanity, and explores the most powerful technology humanity has ever created... and what's at stake if we get it wrong.
15
Yoh! Bestie (2026)
★ 6.3/10
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.
16
A Place in the Sun (1951)
★ 7.3/10
A young social climber wins the heart of a beautiful heiress but his former girlfriend's pregnancy stands in the way of his ambition.
17
The Lonely Guy (1984)
★ 6.2/10
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.
18
Alex Strangelove (2018)
★ 6.6/10
Alex Truelove is on a quest to lose his virginity, an event eagerly awaited by his patient girlfriend and cheered on with welcome advice by his rowdy friends. But Alex, a super gregarious dude, is oddly unmotivated. A…
19
The Great Gatsby (2013)
★ 7.3/10
Nick Carraway arrives in New York in 1922, an era of loose morals, glittering jazz and bootleg kings. Chasing his own American Dream, Nick encounters the mysterious millionaire Gatsby and his bewitching cousin Daisy…
20
Life in a Year (2020)
★ 8.2/10
A 17 year old finds out that his girlfriend is dying, so he sets out to give her an entire life, in the last year she has left.