Movies like The Old Maid's Valentine (1900)
The best movies like The Old Maid's Valentine (1900) are ¿Quieres ser mi hijo? (2023), The Prince & Me 4: The Elephant Adventure (2010) and Dinner in America (2022). If The Old Maid's Valentine hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest rated¿Quieres ser mi hijo? (2023)8.4/10 from 378 votes
- NewestYoh! Bestie (2026)Released 2026
¿Quieres ser mi hijo? (2023)
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.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Absolute CinemaMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDinner in America (2022)
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisWhat's Love Got to Do with It? (2023)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisGirl on a Bicycle (2013)
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 turns Paolo's life upside down.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisChampagne Problems (2025)
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisYoh! Bestie (2026)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove Is in the Air (2023)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisI Love You Again (1940)
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisWhat a Way to Go! (1964)
A four-time widow discusses her four marriages, in which all of her husbands became incredibly rich and died prematurely because of their drive to be rich.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisSplendor (1999)
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 biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDesperados (2020)
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Nice Girl Like You (2020)
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisChasing Papi (2003)
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Heart of the World (2000)
Pure fantasia, a race to save the world from a fatal heart attack, juxtaposed against a love rivalry between two brothers - a mortician and an actor playing Christ - for the heart of a scientist studying the earth's core.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisThe Incredible Jessica James (2017)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Right Kind of Wrong (2013)
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisMy Wife's Relations (1922)
Buster and a woman are mistakenly married and her initially unfriendly family begins to treat him nicely when they come to believe he has a large inheritance awaiting him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHigh and Dizzy (1920)
A tipsy doctor encounters his patient sleepwalking on a building ledge, high above the street.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Magic Glass (1914)
A boy uses a professor's liquid to make objects transparent.
Why it matches: Similar story and style · both comedy
April Showers (1923)
Danny O'Rourke is the son of a police officer who was killed in the line of duty. Eager to join the police force, Danny fails his exams. The failure causes him to neglect his sweetheart Maggie, whose father is a police lieutenant. His attentions turn instead towards society girl Miriam Welton. When Danny’s sister, Shannon, is arrested for shoplifting, Danny turns to boxing to save her. He works his way towards the championship but discovers the final bought has been rigged. Danny fights anyhow and he is beaten, but it is discovered that a mistake had been made on his exams and he actually was eligible to join the police force after all. Considered a lost film.
Why it matches: Similar story and style · both romance
Two Old Tars (1913)
Two old tars, retired from service, live alone in a cottage by the sea. They sail along on an even keel, until a buxom and comely widow projects herself on the scene when one old tar breaks one of their unwritten laws and falls in love with her. The other old fellow objects strenuously.
Why it matches: Similar story and style · both comedy
Live Your Life Smiling (1921)
Sitcom for 1920s cinemas about the Winter family.
Why it matches: Similar story and style · both comedy
An Engagement of Convenience (1914)
A man fakes an engagement to a typist to please his rich aunt.
Why it matches: Similar story and style · both comedy
Sunrise: A Song of Two Humans (1927)
A married farmer falls under the spell of a slatternly woman from the city, who tries to convince him to drown his wife.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisExposure (2017)
The pattern-living Paul Fowler has his routines disrupted by the contact-seeking photographer Jane.
Why it matches: Similar story and style · both comedy
The Impossible Voyage (1904)
Using every known means of transportation, several savants from the Geographic Society undertake a journey through the Alps to the Sun which finishes under the sea.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisDeparture of Love (2010)
‘Departure of Love’ was inspired by the silent film comedy of Buster Keaton and the 1920s.
Why it matches: Similar story and style · both romance
Big Buck Bunny (2008)
Follow a day of the life of Big Buck Bunny when he meets three bullying rodents: Frank, Rinky, and Gamera. The rodents amuse themselves by harassing helpless creatures by throwing fruits, nuts and rocks at them. After the deaths of two of Bunny's favorite butterflies, and an offensive attack on Bunny himself, Bunny sets aside his gentle nature and orchestrates a complex plan for revenge.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like this
Like The Old Maid's Valentine and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like The Old Maid's Valentine?
The closest matches to The Old Maid's Valentine are ¿Quieres ser mi hijo? (2023), The Prince & Me 4: The Elephant Adventure (2010) and Dinner in America (2022). Below are 27 more, each with the reason it matches.
What should I watch after The Old Maid's Valentine?
Start with ¿Quieres ser mi hijo? (2023), the closest match to The Old Maid's Valentine.
What is the highest-rated movie like The Old Maid's Valentine?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like The Old Maid's Valentine?
Yoh! Bestie (2026) is the most recent release on this list.
How are movies similar to The Old Maid's Valentine chosen?
First come films that Trakt’s viewers watch alongside The Old Maid's Valentine, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.