Movies like When I Was The Prettiest (2012)
The best movies like When I Was The Prettiest (2012) are Christmas in August (1998), All My Life (2020) and Five Feet Apart (2019). If When I Was The Prettiest hooked you with its drama and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Pianist (2002)8.4/10 from 10,624 votes
- NewestBaby Udon (2026)Released 2026
- In KoreanChristmas in August (1998)Also in Korean
Christmas in August (1998)
It's a sweltering summer, but Jung-won, a terminally ill, thirty-something photographer, is already in the winter of his life when he begins a tentative romance with a young traffic cop who doesn't know about his condition. Is their relationship doomed before it even begins?
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisAll My Life (2020)
It was a chance meeting started by one of Sol’s friends trying to chat up Jennifer. However, in the end, it was those two who hit it off. Sol enjoyed Jen’s smile, her effort, and how silly she could be. Jen enjoyed Sol’s cooking, his athleticism, and that he would join her in fun moments. As you can imagine, love bloomed, and things got serious. Jen’s investment in Sol led to her pushing him to follow his dreams and even move in to save money. Sol’s investment in Jen well, it led to him proposing. But what started as a liver tumor grew into full-on cancer, so with a diagnosis of 6 months to live, Sol and Jennifer try to make the best of it.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisFive Feet Apart (2019)
Seventeen-year-old Stella spends most of her time in the hospital as a cystic fibrosis patient. Her life is full of routines, boundaries and self-control — all of which get put to the test when she meets Will, an impossibly charming teen who has the same illness. There's an instant flirtation, though restrictions dictate that they must maintain a safe distance between them. As their connection intensifies, so does the temptation to throw the rules out the window and embrace that attraction.
Why it matches: Recommended by TMDB viewers · both romance & drama
Absolute CinemaMovies like thisApril Snow (2005)
A man and a woman are brought together after their spouses, who were having an affair, are hospitalized after a car crash.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisDying Young (1991)
After she discovers that her boyfriend has betrayed her, Hilary O'Neil is looking for a new start and a new job. She begins to work as a private nurse for a young man suffering from blood cancer. Slowly, they fall in love, but they always know their love cannot last because he is destined to die.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisOur Friend (2019)
After learning that his terminally ill wife has six months to live, a man welcomes the support of his best friend who moves into their home to help out.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisOrdinary Love (2019)
An extraordinary look at the lives of a middle-aged couple in the midst of the wife's breast cancer diagnosis.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisWe Live in Time (2024)
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.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisMan in Love (2014)
Tae-il lives a fast life as low level thug. He then learns that he has a terminal illness and not much time left to live. Then, for the first time in his life, he falls in love.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisNot Easily Broken (2009)
A car accident and shifting affections test the bond between a married couple.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisHappy End (1999)
When a wife becomes the breadwinner of her family after her husband loses his job, adultery becomes part of her life.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisUntil Forever (2016)
Until Forever: The Michael Boyum Story is a powerful, true account of one young man's courageous battle with leukemia and his journey of faith.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisKeith (2008)
Natalie is high school royalty, but her queen bee status falls apart when she falls for the new guy at school. Although Keith ignores her at first, they soon become friends -- even though Natalie suspects that Keith has something to hide. As the free-spirited Keith shows Natalie how to embrace what life offers, they grow closer -- until a secret tests the bounds of their relationship
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisMore Than Blue (2009)
A terminally ill man tries to find a suitable husband for the friend he has loved since childhood.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisLove Story (1970)
Harvard Law student Oliver Barrett IV and music student Jennifer Cavilleri share a chemistry they cannot deny - and a love they cannot ignore. Despite their opposite backgrounds, the young couple put their hearts on the line for each other. When they marry, Oliver's wealthy father threatens to disown him. Jenny tries to reconcile the Barrett men, but to no avail.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisA Moment to Remember (2004)
A young couple's love is tested when Sun-jin is diagnosed with a rare form of Alzheimer's disease.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisStrangers When We Meet (1960)
A suburban architect loves his wife but is bored with his marriage and with his work, so he takes up with the neglected, married beauty who lives down the street.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisFreeheld (2015)
New Jersey car mechanic Stacie Andree and her police detective girlfriend Laurel Hester both battle to secure Hester's pension benefits after she was diagnosed with a terminal illness.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisAll That Heaven Allows (1955)
Two different social classes collide when Cary Scott, a wealthy upper-class widow, falls in love with her much younger and down-to-earth gardener, prompting disapproval and criticism from her children and country club friends.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisLullaby (2014)
Estranged from his family, Jonathan (Hedlund) discovers his father has decided to take himself off life support in forty-eight hours’ time. During this intensely condensed period, a lifetime of drama plays out. Robert (Jenkins) fights a zero sum game to reclaim all that his illness stole from his family. A debate rages on patients’ rights and what it truly means to be free. Jonathan reconciles with his father, reconnects with his mother (Archer), sister (Brown-Findlay), and his love (Adams) and reclaims his voice through two unlikely catalysts – a young, wise-beyond-her-years patient (Barden) and a no-nonsense nurse (Hudson). Through this intensely life affirming prism, an unexpected and powerful journey of love, laughter, and forgiveness unfolds.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisHarold and Maude (1971)
A deadpan young man obsessed with death meets an eccentric septuagenarian who teaches him to live life to the fullest.
Why it matches: Similar story and style · both drama & romance
Worth the HypeMovies like thisFire (1997)
In a barren, arranged marriage to an amateur swami who seeks enlightenment through celibacy, Radha's life takes an irresistible turn when her beautiful young sister-in-law seeks to free herself from the confines of her own loveless marriage.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisBaby Udon (2026)
Fanny Kondoh, a young Indonesian woman, falls in love with Hajime Kondoh, a Japanese man who comes to Indonesia for work. After getting married, Fanny and Hajime begin building a life together, embracing both its joys and challenges. As they struggle to fulfill their dream of having a child, they are faced with one heartbreaking trial after another, testing the strength of their love, especially when Hajime is diagnosed with cancer.
Why it matches: Similar story and style · both drama & romance
Revanche (2008)
Alex, an ex-con working as muscle in a Vienna brothel, dreams of escaping with his girlfriend Tamara, who also works there. Their attempt to break free sets off a chain of events that links their fate with a rural police officer and his troubled marriage. As their lives intersect, a quiet struggle unfolds between guilt, grief, and the desire for redemption.
Why it matches: Similar story and style · both drama & romance
Worth the HypeMovies like thisGriffin & Phoenix (2006)
A terminally ill man falls in love with a woman who has a secret that threatens their time spent together.
Why it matches: Similar story and style · both drama & romance
Worth the HypeMovies like thisHappy Endings (2005)
Filmmaker Nicky offers to track down the son that Mamie gave up for adoption nearly two decades before. Meanwhile, Mamie's stepbrother (and the father of her child), Charley, along with his boyfriend, Gil, try to find out what became of the sperm Gil donated to a lesbian couple. Finally, singer Jude becomes entangled in a love triangle with androgynous drummer Otis and his conservative father.
Why it matches: Similar story and style · both drama & romance
SnoozefestMovies like this20th Century Girl (2022)
In 1999, a teen girl keeps close tabs on a boy in school on behalf of her deeply smitten best friend – then she gets swept up in a love story of her own.
Why it matches: Similar story and style · both romance & drama
Absolute CinemaMovies like thisCléo from 5 to 7 (1962)
Agnès Varda eloquently captures Paris in the sixties with this real-time portrait of a singer set adrift in the city as she awaits test results of a biopsy. A chronicle of the minutes of one woman’s life, Cléo from 5 to 7 is a spirited mix of vivid vérité and melodrama, featuring a score by Michel Legrand and cameos by Jean-Luc Godard and Anna Karina.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisThe Pianist (2002)
The true story of pianist Władysław Szpilman's experiences in Warsaw during the Nazi occupation. When the Jews of the city find themselves forced into a ghetto, Szpilman finds work playing in a café; and when his family is deported in 1942, he stays behind, works for a while as a laborer, and eventually goes into hiding in the ruins of the war-torn city.
Why it matches: Similar story and style · both drama
Absolute CinemaMovies like thisThe Celebration (1998)
The family of a wealthy businessman gather to celebrate his 60th birthday. During the course of the party, his eldest son presents a speech that reveals a devastating secret that turns the night into a battle of truth and denial.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like When I Was The Prettiest?
The closest matches to When I Was The Prettiest are Christmas in August (1998), All My Life (2020) and Five Feet Apart (2019). Below are 27 more, each with the reason it matches.
What should I watch after When I Was The Prettiest?
Start with Christmas in August (1998), the closest match to When I Was The Prettiest.
What is the highest-rated movie like When I Was The Prettiest?
The Pianist (2002), rated 8.4/10 by 10,624 TMDB users.
What is the newest movie like When I Was The Prettiest?
Baby Udon (2026) is the most recent release on this list.
Are there Korean movies like When I Was The Prettiest?
Yes: Christmas in August (1998), April Snow (2005) and Man in Love (2014).
How are movies similar to When I Was The Prettiest chosen?
First come films that Trakt’s viewers watch alongside When I Was The Prettiest, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.