Every couple in a romance has a different journey. No two are the same, and no two are always truly destined to be together. Some stories explore the one-in-a-million chance and praise the narrative of a woman finding her prince charming or the stereotypical manic pixie dream girl completing a man’s vision of what he wants. However, some films choose to tell stories grounded in harsh realities. While both of these plot structures are vastly different, unconventional romances focus on what happens when love doesn’t win but also never fades.
The meat and bones of a traditional rom-com movie is the basis of two people meeting (referred to as a meet-cute), falling in love, having a conflict, and then resolving said conflict. Significantly, the rom-com always ends in the desired happily ever after. Unconventional romances tell a similar story. However, the conflict is much harder to fix with a mere apology or having someone show up at your door and perform a grand, romantic gesture. Couples in these films are faced with real-life questions and the essence of wondering what happens after the conflict is always present. Here are some unconventional romance movie couples that were not meant to be.
January 20, 2024: Valentine’s Day is around the corner, and if you are looking for a more tragic romance for your viewing pleasures, this article has been updated with even more unconventional couples that did not work out and where each title is streaming.
10 Annie Hall (1977)
Aside from being a film debuting fantastic hats worn by Diane Keaton, Annie Hall depicts two people who are involved with each other but on much different individual levels. Alvy (Woody Allen), an overly anxious stand-up comedian who is absolutely in love with New York City, meets Annie (Diane Keaton), a go-with-the-flow free spirit who is from the Midwest. Alvy believes that he has worked out all of his problems in therapy, prefaced through his consistent self-defacing humor. Annie, struggling to find her place in the city and who she is, is constantly put down by Alvy as he tries to mold her into whom he wants her to be.
After the couple inevitably breaks up, it is revealed that Alvy has written a play based on their time together. Breaking the fourth wall, he addresses the audience by monologue while a montage of their greatest moments plays. Although it doesn’t work out for them, the fact that they end up as friends makes it hopeful, as they have, in a way, saved their love by transforming it. Annie Hall redefined the romantic comedy, showing that sometimes it could have a sad ending. Stream on Max
9 The Way We Were (1973)
The Way We Were is set in the late 40s and explores another plight in romantic relationships, which are political differences. Starring Barbra Streisand and Robert Redford, it follows their characters Katie and Hubbell’s complicated love story. Katie’s a committed anti-war activist, while Hubbell is a rich young man with no particular political inclinations. While they are initially madly attracted to each other the way opposites are, their fundamental differences become more and more evident as their relationship progresses, and they begin to resent each other as they build their lives together.
Eventually, Hubbell sabotages their relationship by having an affair, and Katie’s rose-tinted glasses are off for good. Their parting is bittersweet but ultimately inevitable, as they have diametrically opposing life projects, and not even the deepest love can surpass that. While Love Story is arguably the more popular 70’s romance of two young people from very different cultural backgrounds, those two remain in love until the very end whereas The Way We Were is a more tragic romance, and both the characters and the audience are left to think lovingly on how they used to be as opposed to what their love became. Rent on Apple TV
8 One Day (2011)
Love, tragedy, and the essence of timing are a few of the most relevant themes in One Day. The film follows Emma and Dexter — played by Anne Hathaway and Jim Sturgess, respectively — two college classmates who attempt to sleep together on their graduation day, but remain friends instead, vowing to reunite on the 15th of July each year. The two embark on a journey of trouble and triumph over the course of the years. Dexter’s need for validation through fame, a budding drug problem, and the death of his mother send him spiraling into a realm of disaster, eventually causing a brief rift between Emma and him. Emma, meanwhile, struggles to find a job that she is passionate about and works as a waitress before eventually breaking into teaching and writing her own children’s book.
The protagonists share an undeniable chemistry throughout the film, and just because people experience love differently doesn’t mean it’s not real. When they finally get together, the relationship isn’t without flaws, but they make it work because, underneath it all, they are best friends. When Emma is killed in a tragic biking accident, Dexter spirals yet again. Although the couple only ends up together for a brief time, their friendship throughout the movie is what makes this story connect with the audience, making One Day a certified tearjerker.
Stream on Starz Apple TV
7 A Star Is Born (2018)
This remake of a 1937 classic movie broke everyone’s hearts. A Star Is Born, starring Lady Gaga and Bradley Cooper, tells the story of Jackson, Maine, a rockstar battling his life-long addiction, and Ally, a very talented up-and-coming singer. Jackson meets Ally while she’s singing at a drag bar and is immediately taken by her. Their love story blooms alongside their musical collaboration, but when it seems both of them are at their highest point, it’s when the cracks in the foundation become evident.
For all his good intentions, Jackson can’t handle his success in a healthy way, and for all her love for him, it’s not fair for Ally to carry the responsibility of his recovery. Their ultimate end is as heartbreaking as it is, sadly, a realistic ending for people who are battling an addiction. Rent on Apple TV
6 Like Crazy (2011)
Like Crazy follows the turbulent long-distance relationship between British exchange student Anna (Felicity Jones) and American student Jacob (Anton Yelchin). They quickly fall head over heels for one another, but Anna is detained and denied access back into the United States after she visited her family due to not returning to the UK after graduating right away to spend more time with Jacob, violating her student visa. The two try a long-distance relationship while navigating how to continue their relationship, including a brief time apart and a marriage to speed up the visa process.
The film was based on director Drake Doremus’s own long-distance relationship with a woman living in London, and as opposed to a traditional screenplay. The film had a 50-page outline, and the actors were encouraged to improve and ad-lib most of their dialog. The result was a very real, intimate, and heartbreaking romance that shows how sometimes, no matter how much you love someone, life gets in the way and can be the ultimate strain on a couple. The movie ends on the note that while the two appear together briefly, it is clear it will not last as time has made a riff too great to overcome. Stream on Hoopla.
5 Celeste and Jesse Forever (2012)
Celeste and Jesse Forever stars Andy Samberg and Rashida Jones, two actors known for their roles in successful sitcoms, and it is hands down one of the saddest movies made to date. Celeste and Jesse have been together since high school and are best friends. The two know each other better than anyone and have called the other home for many years. However, Celeste begins to grow tired of Jesse’s slacker mentality as she starts to progress in her career. Jesse moves out into the guest room, and the two hang out as friends, both appearing seemingly cool about their divorce. Jesse eventually gets into a new relationship, and Celeste realizes that moving on from Jesse is much more difficult than she thought it would be.
Throughout the film, it is impossible not to want these two to get back together. There is no outside tragedy that impacts the couple in Celeste and Jesse Forever. It is all from within. And that makes it all the more devastating because it makes painfully clear that love is not always enough. Stream on Max
4 My Best Friend’s Wedding (1997)
My Best Friend’s Wedding is a classic movie that is both about romance and about the fear of being alone. The premise is simple but relatable. Jules (Julia Roberts) and Michael (Dermot Mulroney) are best friends, and years before, they had made a pact that if they were both still single by the time they were 28, they would get married. Jules doesn’t think much of it until, days before Michael turns 28, he announces he’s engaged to a younger woman named Kimmy. She realizes she’s in love with him, and does everything she can to break up the couple, but comes to the shocking realization that life is not a fairy tale.
Michael is truly in love with Kimmy, and she doesn’t have a claim over him just because of their friendship. She does her best to undo the damage she caused and finally lets Michael go. While the cliché would have been for Michael to realize her true love was right in front of him the whole time, the truth is that, just because Jules had some fantasy about them being meant to be, people aren’t just collateral damage, and she can’t just ruin people’s relationships for her own benefit. Stream on Netflix
3 La La Land (2016)
La La Land depicts a love story that flickers as fast as a candle before it goes out. Sebastian (Ryan Gosling) and Mia (Emma Stone) are drawn to one another due to their desire and drive to achieve their dreams. Mia is an aspiring actress, and Sebastian is a remarkable jazz pianist who longs to open his own jazz club. The two encourage each other to grow and follow their dreams despite their vastness while living in a city full of similar talents. As their success heightens, their romance begins to fade, and although the two achieve their dreams, they must fall away from one another.
As the lovers go their separate ways, in the end, the two share a glance in a jazz club years after they break up. While their eyes meet, it is clear that there is a sense of pride, sadness, and love that still exists between the two as they acknowledge that they received everything that they ever dreamed of at the expense of sacrificing a future, beautifully shown in the movie’s epilogue, with the other. It teaches us that some loves aren’t meant to be forever; they exist to give us what we need at a moment in our lives before we find our true destiny. But they will always be meaningful. Stream on Netflix
2 Brokeback Mountain (2005)
A revolutionary movie set in the 1960s, Brokeback Mountain stars the late great Heath Ledger and Jake Gyllenhaal. The two of them play Ennis and Jack, respectively, two cowboys who work together and maintain a secret relationship for years before the societal pressure becomes too much for them to handle. They go their separate ways after a violent encounter, marry women, and have children. Life goes on, and eventually, they find their way back to each other, resuming their on-and-off relationship, which once again ends abruptly. Ennis’ marriage falls apart, but he’s still too scared to commit to a life with Jack, which is ultimately his biggest regret.
The painful ending of their relationship leaves the audience devastated and angry, but unfortunately, it was the bitter fate a lot of homosexual relationships met back then. Not only do Ennis and Jake have a tragic falling out, but so do their wives, who fall in love with men who cannot fully be themselves. Societal pressures and hatred ended up breaking many hearts. The flashbacks to Ennis’ childhood and what he was forcefully taught about homosexuality showcase the struggles non-straight people faced back then and why this particular love story was not written in the stars. Stream on Starz Apple TV
1 (500) Days of Summer (2009)
(500) Days of Summer is often considered the most misinterpreted romance of its time. More likely than not, Summer (Zooey Deschanel) is often characterized as the villain of this movie for breaking Tom’s (Joseph Gordon-Levitt) heart and then getting married. That couldn’t be any further from the truth. Summer might have caused some of the misinterpretations on Tom’s part. However, she does make it very clear to Tom that she doesn’t want a serious relationship or to be anyone’s girlfriend. Tom simply ignores this, and when he becomes too clingy for Summer, she breaks things off. Since the movie is told from Tom’s POV, it is easy for him to appear to be the good guy and Summer to be the story’s villain when the truth is far more complicated.
Although the two get one last conversation together on a park bench, there is more dialogue in what the movie chooses not to say. If the audience manages to separate themselves from the feelings of heartbreak and indignation that this ending naturally causes, there is actually a lot to learn from this love story, and that is to believe people when they tell you what they want. Summer was clear to him from the beginning, and Tom failed to listen. It is also important to remember that the great heartbreak, or losing what appears to be the love of your life, is pain that eventually does heal. (500) Days of Summer has become a go-to break-up movie for men, but one that certainly should feature a bit more examination. Stream on Max
This story originally appeared on Movieweb
