Movies Like Rose & Oscar, Oscar & Rose

If you liked Rose & Oscar, Oscar & Rose, a movie directed by Bennett Valentine, 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 Odd Couple II (1998)
★ 6.3/10
Brucey, the son of Oscar, calls his father to invite him to his wedding to Felix's daughter next Sunday in California. Oscar and Felix meet again at Los Angeles International Airport and rent a car in order to go to…
2
Four Weddings and a Funeral (1994)
★ 6.8/10
Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love.
3
Serendipity (2001)
★ 7/10
Although already in relationships, two strangers realize they have genuine chemistry after a chance encounter – but part company soon after. Years later, they each yearn to reunite, despite being destined for the…
4
Brief Encounter (1945)
★ 7.7/10
Returning home from a shopping trip to a nearby town, bored suburban housewife Laura Jesson is thrown by happenstance into an acquaintance with virtuous doctor Alec Harvey. Their casual friendship soon develops during…
5
The Princess Diaries 2: Royal Engagement (2004)
★ 6.7/10
Mia Thermopolis is now a college graduate and on her way to Genovia to take up her duties as princess. Accompanied by her friend Lilly, Mia continues her 'princess lessons', like riding horses side-saddle and archery…
6
Little Manhattan (2005)
★ 7.2/10
Ten-year-old Gabe Burton is just an average kid growing up in Manhattan until Rosemary Telesco walks into his karate class. But before Gabe can tell Rosemary how he feels, she reveals that she won't be going to public…
7
What's Love Got to Do with It? (2023)
★ 6.1/10
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.
8
The Five-Year Engagement (2012)
★ 5.8/10
Exactly one year after Tom meets Violet, he surprises her with a wedding ring. By all accounts, Tom and Violet are destined for their happily ever after. However, this engaged couple just keep getting tripped up on the…
9
Whatever Works (2009)
★ 7.1/10
Whatever Works explores the relationship between a crotchety misanthrope, Boris and a naïve, impressionable young runaway from the south, Melody. When Melody's uptight parents arrive in New York to rescue her, they are…
10
Run Fatboy Run (2007)
★ 6.2/10
Five years after jilting his pregnant fiancée on their wedding day, out-of-shape Dennis decides to run a marathon to win her back.
11
Not Easily Broken (2009)
★ 6.3/10
A car accident and shifting affections test the bond between a married couple.
12
Girl Shy (1924)
★ 6.9/10
Harold Meadows is a shy, stuttering bachelor working in a tailor shop, who is writing a guidebook, The Secret of Making Love, for other bashful young men. Fate has him meet rich girl Mary, and they fall in love. But…
13
Hello, Goodbye, and Everything in Between (2022)
★ 6.1/10
Clare and Aidan make a pact to break up before college — no regrets, no broken hearts. But will one epic goodbye date offer them a last chance at love?
14
The Wrong Paris (2025)
★ 6.7/10
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.
15
Time Freak (2018)
★ 6.7/10
Stillman, a heartbroken physics student, builds a time machine when his girlfriend breaks up with him. Going back in time, he attempts to save their relationship by fixing every mistake he made—while dragging his best…
16
(500) Days of Summer (2009)
★ 7.3/10
Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went…
17
One Day (2011)
★ 7.4/10
After spending the night together on the eve of their college graduation, Dexter and Emma are shown each year on the same date to see where they are in their lives. They are sometimes together, and sometimes not.
18
Love Me Love Me (2026)
★ 6.1/10
After her brother's death, June moves to Milan for a fresh start, finding comfort in Will, the perfect honor student at her new international school. But when his troubled best friend James—hiding a dangerous life in…
19
Love in the Time of Cholera (2007)
★ 6.6/10
In Colombia just after the Great War, an old man falls from a ladder; dying, he professes great love for his wife. After the funeral, a man calls on the widow - she dismisses him angrily. Flash back more than 50 years…
20
We Live in Time (2024)
★ 7.2/10
An up-and-coming chef and a recent divorcée find their lives forever changed when a chance encounter brings them together, in a decade-spanning, deeply moving romance.