Read update
- The romance genre is a widely popular one when it comes to the film industry. Given how intense and enthralling they can be, it isn't hard to feel connected with the characters and consequently, root for a happy ending, even if the relationship was doomed from the start. Barbie, for one, just hit the movie theatres and reflects on the importance of finding happiness on our own before sharing it with someone else. On Reddit, many users share their takes on memorable movies where love does not work out.
Through the course of a romantic film, it is expectable for viewers to believe that the main characters will eventually find their way to each other despite conflict, marking the beginning of a loving and passionate journey with a few ups and downs along the way, but ultimately a prosperous love story regardless. However, this is not always the case.
While some of these films depict every aspect of love perfectly (the falling; the longing; the honeymoon phase; the breaking point; the reeling; the ending), there are a few on-screen couples that were simply not meant to be or fell into the category of "right person, wrong time." Though we all love happy endings, these bittersweet movies emphasize that not every couple is meant to be together – and sometimes that is okay.
Updated on July 29, 2023, by Daniela Gama:
The romance genre is a widely popular one when it comes to the film industry. Given how intense and enthralling they can be, it isn't hard to feel connected with the characters and consequently, root for a happy ending, even if the relationship was doomed from the start. Barbie, for one, just hit the movie theatres and reflects on the importance of finding happiness on our own before sharing it with someone else. On Reddit, many users share their takes on memorable movies where love does not work out.
14 'Call Me by Your Name' (2017)
While it is hardly a stranger to anyone, Luca Guadagnino's film (James Ivory won an Oscar for Best Adapted Screenplay) based on the novel by André Aciman follows Elio (Timothée Chalamet), a 17-year-old student, and Oliver's (Armie Hammer) – an older man hired as a research assistant by Elio's father (Michael Stuhlbarg) – romantic affair set in 1980s Italy.
Call Me by Your Name is also a heavily mentioned film on the website, with a Redditor describing it as having a "nostalgic, bittersweet feeling." It portrays what it feels like to come to terms with yourself and others. Although a visually stunning film that almost feels like a poem unveiling a blossoming relationship, some viewers may argue that the characters' involvement triggers discomfort since Elio is not yet of legal age.
13 'My Best Friend's Wedding' (1997)
Directed by P.J. Hogan, My Best Friend's Wedding follows Julia Roberts' Julianne Potter as she — as in many other great films about weddings — attempts to stop one from happening only a few days before it takes place after realizing that she has fallen head over heels for her long-time best friend (Dermot Mulroney).
While the best friend-to-lover trope is quite beloved, lots of Redditors argue that it is actually a good thing that these two did not end up together, including rebecca-bunch: "I think it wouldn’t have worked out as well as it did if that were the ending. I quite liked the ending as it is." What makes the film's final moments even more poignant is the message they send about taking things for granted.
12 'Annie Hall' (1977)
Centering around a Jewish New York City stand-up comic, Alvy Singer (Allen), as he reflects on his relationship with ex-lover Annie Hall (Diane Keaton), an aspiring nightclub singer, Annie Hall stands the test of time as one of the most treasured romantic comedies even today.
"I can't believe nobody has mentioned best picture winner Annie Hall yet," nick22tamu wrote on the platform. Depicting the search for the secret to successful relationships by re-examining one's own life and behavior, the 1977 movie focuses on the importance of fully embracing and accepting happiness when you find it.
11 'Her' (2013)
Spike Jonze's Her is an incredibly refreshing and innovative romantic movie surrounding a lonely writer, played by Joaquin Phoenix, who has recently undergone severe heartbreak. When he feels the most alone and vulnerable in the world, Theodore ends up forging an unlikely connection with an operating system designed to meet his needs.
The perfect pick for those who'd enjoy a Black Mirror-esque romance, Her is also a popular pick on the website. "I was not expecting the emotions I felt while watching Her," joker_75 admitted. "I went in thinking it was going to be a story of a sad lonely dude who falls in love with a primitive version of Siri (no personality or anything, just her voice), not an actual emotional journey about society and interpersonal relationships."
10 'Lost in Translation' (2003)
Directed by Sofia Coppola, Lost in Translation stars Scarlett Johansson, the girlfriend of a famous workaholic photographer who has traveled to Tokyo for work, and Bill Murray's fading movie star, who is in the middle of a midlife crisis and promoting Suntory whisky. Throughout the thought-provoking film, an unlikely, intimate connection between the two characters flourishes as they find escapism and understanding in each other.
According to mawkword, "Lost in Translation would kind of fit into this category." A beautifully made and brilliantly written film that is equal parts heartbreaking and heartwarming, Coppola's feature analyzes the feelings of aloneness and alienation through two three-dimensional characters. Although it features a simplistic storyline, Lost in Translation beautifully explores the intimacy of human connection and the equally human need to bond with other people, even if for a short period of time.
9 'Atonement' (2007)
Ian McEwan's Atonement was the basis for a film in 2007, the picture delivering a heart-wrenching romantic tale that tore viewers apart with its unpredictability and intelligent story. It follows the slow-burn beginning and gloomy ending of Cecilia Tallis (Keira Knightley) and Robbie Turner's (James McAvoy) passionate relationship as it is torn apart by a fabricated lie with serious consequences.
With an enthralling pace and twists that nobody saw coming, Joe Wright's film is exquisitely haunting and heartbreaking. While it depicts a tragic romance, it also reflects on jealousy, misunderstandings that can ultimately cause great damage, and the terrible irreversibility of certain actions. On the platform, a Reddit user could not help mentioning the film in a thread about the best movies "where the couple doesn’t end up together in the end."
8 'Blue Valentine' (2010)
Dean Pereira (Ryan Gosling) and Cindy Heller Pereira (Michelle Williams) are a young married couple who live a quiet life in a modest neighborhood. Though the couple seems to lead a happy and fulfilled love life at the beginning, Dean's lack of ambition and Cindy's self-absorption are potential causes of irreversible cracks in their marriage.
Blue Valentine is the type of film to make audiences wonder if loving someone is temporary; the perfect watch for those who enjoy sad yet realistic romantic movies (with some of the best performances, too). It explicitly exhibits real circumstances in love and marriage in a soul-shattering and mature way — nothing is wrong with either person involved, it's just that both aim to achieve different things. On the platform, ashtundercrow considers it one of their "favorite [films] of all time."
7 '500 Days of Summer' (2009)
With a marvelous soundtrack, 500 Days of Summer follows the story of Tom Hansen (Joseph Gordon-Levitt) after being dumped by the girl he loves and wants to spend the rest of his life with, Summer Finn (Zooey Deschanel). The young man reflects on the past relationship and tries to figure out where things went wrong to win her back.
Though there's still debate on whether this is a love story or not, it almost feels like a satire that exposes the disadvantages of dating the overly nice guy: A relationship that is seemingly harmless at first but turns out to be unhealthy and obsessive. It helps the audience realize that a person's expectations of someone are not their responsibility and that two people having very similar tastes doesn't necessarily mean they're soulmates. "The movie is heartbreaking but in the end, it comes all together to explain why this was for the best," WhatabeezyBoy said.
6 'In the Mood For Love' (2000)
Wong Kar-wai's iconic love tale is guaranteed to sweep audiences off their feet and break their hearts simultaneously. The visually stunning movie follows two neighbors who suspect that their partners are practicing extramarital activities and find themselves increasingly and inexplicably drawn to each other.
Examining love, loss, separation, and suppressed desire, In the Mood for Love is undoubtedly an enchanting film throughout, featuring amazing chemistry and a very believable relationship between the two characters. "This comment made me happy," a Redditor wrote when someone mentioned the romance feature. "What a movie!"
5 'Brokeback Mountain' (2005)
Starring Jake Gyllenhaal and Heath Ledger, Brokeback Mountain is based on a book of the same name by American author Annie Proulx. The treasured romance film centers on two shepherds who develop a sexual and emotional relationship while working together through the summer on grazing pastures. However, their secret relationship gets a bit complicated when both get married to their girlfriends.
"One of the more heartbreaking movies to watch," herewego199209 said, adding that Ledger "deserved an Oscar for that movie." Indeed, the Ang Lee film features incredible acting performances from those involved and is far from an easy watch as it tackles repression, regret, and the traditional notions of masculinity.
4 'Moulin Rouge' (2001)
The beloved musical ≈ features Natalie Kidman and Ewan McGregor as a pair of lovers from different walks of life. Luxuriously directed by Baz Luhrmann, the film takes place in 1890s Paris and centers around a poet who is drawn to a stunning nightclub performer. However, their romance is threatened by the jealousy of a powerful duke.
"The greatest thing you will ever learn is just to love and be loved in return," Mocavius quoted one of the movie's best lines. The visually staggering Moulin Rouge explores loyalty, different societal backgrounds, and celebrates the idea of love conquering all.
3 'Roman Holiday' (1953)
Roman Holiday is yet another memorable and iconic romantic comedy. The 1953 film stars Audrey Hepburn and Gregory Peck and tells the story of a beautiful, bored princess who struggles to keep up with her suffocating schedule and manages to escape her guardians, falling in love with a reporter for the American news in the stunning city of Rome in the meantime.
William Wyler's bewitching and fairytale-like film delivers a very charming storyline while focusing on the two protagonist's relationship, and one of its biggest surprises – perhaps what makes it so memorable – is its unpredictable ending that viewers would not expect in a rom-com. "A truly great movie that fits your requirements is Roman Holiday," Kerry56 wrote. "From the 1950's and Audrey Hepburn won the Oscar for her first starring role."
2 'La La Land' (2016)
Starring Emma Stone as Mia and Ryan Gosling as Sebastian, La La Land is the critically acclaimed Damien Chazelle movie that earned the director an Oscar and tells the story of an aspiring actress and a jazz musician. While the love affair between the characters blossoms beautifully, both are faced with difficult, impactful decisions that affect their relationship when success mounts.
Chazelle's brilliant work of cinema inspires the question: must we choose between love and success? Mia and Sebastian's story, although incredibly touching and engaging, is faced with a couple of challenges mostly related to the incompatibility of the characters' working lives. Sadly, the couple ends up going separate ways while visibly still very much in love, breaking the audience's hearts and making viewers wonder if there really wasn't a way that their bond could have been saved. "It was more about wondering what might have been if different choices were made," TeamStark31 reflects on the platform.
1 'Casablanca' (1942)
Cinematically powerful and filled with exhilarating and touching moments, Casablanca tells the story of Rick Blaine (Humphrey Bogart), a mysterious and complicated ex-patriate who runs a nightclub in Casablanca, Morocco. Rick is faced with a challenge when former lover Ilsa (Ingrid Bergman) and her husband Victor (Paul Henreid) show up at his café one day.
"Casablanca, hombre," weak_read remarked. There's a reason why Michael Curtiz's movie is considered one of the all-time greats even today: It truly is the kind of film you can not help but immerse your entire being in while watching its beautiful, sentimental, and melodramatic scenes. Brimming with arising feelings of love and loss that are not easily forgotten, Michael Curtiz's movie is perfect from beginning to end – it gracefully reflects on letting the past go and making sacrifices.