Top 20 Movie Couples That Didn't Live Happily Ever After
#20: Tom Hansen & Summer Finn “500 Days of Summer” (2009)
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It’s your typical romance – boy meets girl, girl tells boy she’s not looking for something serious, boy doesn’t listen and falls for her anyway, girl leaves boy … Ok, maybe not so typical. “(500) Days of Summer” follows the relationship between Tom and Summer. Summer insists on keeping things casual, but Tom doesn’t take her word for it and ends up falling – hard. The two eventually break up, and later, Tom finds out Summer is engaged to someone else. This one is interesting because even though the two main characters don’t end up together, it was probably for the best – they both learned something important, and moved on – and in Tom’s case, to another girl with a season for a name.
#19: Sam Wheat & Molly Jensen “Ghost” (1990)
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When one of you is a spirit, chances are your story isn’t going to end well. But at least we’ll always have the memory of the time we made “sweet pottery,” right? In “Ghost,” Sam is killed by a mugger right at the beginning of the movie, leaving his girlfriend, Molly, alone. But, as the film’s title would suggest, Sam sticks around as a ghost – Molly can’t see him, but he’s there. Turns out, Sam has some unfinished business to attend to, and he spends the film trying to show Molly he’s there while attending to said business. But when he finishes it, he has to move on. The two share one last kiss, and he’s gone. Maybe Heaven isn’t a place on earth.
#18: Oliver Barrett IV & Jennifer "Jenny" Cavilleri “Love Story” (1970)
Love means never having to say you’re sorry, but we might never forgive “Love Story” for making us cry like this. The classic 1970 film follows the story of Oliver and Jenny, two young people from opposite sides of the tracks who fall in love. Everything seems to be going alright for the lovebirds – they get married, Oliver graduates from law school, gets a job – but then, Oliver finds out Jenny is terminally ill. It’s a heartbreaking tale, but as Jenny says before she dies, it was worth it to see the love these two shared.
#17: Chow Mo-wan & Su Li-zhen [aka Mrs. Chan] “In the Mood for Love” (2000)
This beautiful film is all about longing and the secrets we keep – and the longing between Mr. Chow and Mrs. Chan is palpable. At first, the two come together as friends when they discover their spouses are cheating on them with each other. The relationship starts off friendly enough, but as time goes on, they can’t deny their attraction to each other. Do they act on their feelings? No – neither one wants to reduce themselves to the same behaviour that their spouses did. The tension and desire lead to heartbreak, with an ending that will have you softly weeping in your seat.
#16: Cecilia Tallis & Robbie Turner “Atonement” (2007)
Sometimes, movies like to trick you into thinking there will be a happy ending. So is the case with 2007’s “Atonement,” a story about a young girl, Briony, who witnesses an intimate encounter between her sister Cecilia and their housekeeper’s son, Robbie, and assumes – wrongly – the worst. The film moves through the lives of these three characters and the effect this event has on them. Robbie fights in World War II, and is reunited with Cecilia afterwards. But – and big plot twist here – he wasn’t. Turns out, Robbie and Cecilia both died during the war, and we’re hearing this story from a grown-up Briony, who became an author and wrote a happy ending for her sister. Not cool.
#15: Tony Stark & Pepper Potts “Avengers: Endgame” (2019)
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Buckle up, folks – this one hurts. Iron Man was the first superhero introduced into the MCU back in 2008, so we had a lot of time to buy into the Tony Stark/Pepper Potts relationship – and boy, did we! Pepper and Tony went through plenty of ups and downs – Anthony Edward Stark is not an easy man to be with – but by the time we made it to “Endgame,” the two were married, settled down, and even had a kid – all things we weren’t sure Tony was capable of doing. So, that made it hurt all the worse when he sacrificed himself for the entire planet, leaving Pepper and his daughter behind. We miss you Tony, and we love you 3000.
#14: Katie Morosky & Hubbell Gardiner “The Way We Were” (1973)
Highly considered one of the greatest romances of all time, “The Way We Were” deals in memory and longing for a time long past. Partially using flashbacks, the story follows Katie and Hubbell, who despite their vast political and personal differences, fall in love with each other and end up getting married. But trouble in paradise quickly arises when the two move to Hollywood – Katie can’t understand Hubbell’s lack of ambition and ambivalence towards politics, and Hubbell can’t stand being a disappointment to Katie. Despite having a daughter together, the two part ways – at least they’ll always have the memories.
#13: Jackson "Jack" Maine & Ally Maine “A Star Is Born” (2018)
The “A Star is Born” tale is almost as old as Hollywood itself – each rendition has its charms, but for this list we’re doing to focus on the early 21st century iteration starring Bradley Cooper as country rock star Jackson Maine and Lady Gaga as Ally. Throughout the story, Jackson struggles with addiction along with his feelings about Ally’s rising fame as well as his own stardom, which is deteriorating. But what hurts so much about this lost romance is that for a time, it feels like things are getting better: Jackson goes to rehab, Ally’s singing career is going well. But, Jackson simply can’t get over his own insecurities and failings, and the film ends as all the other iterations do, with him losing his life.
#12: Gwen Stacy & Peter Parker “The Amazing Spider-Man 2” (2014)
Fans of the Spidey comics knew this one was coming, but that doesn’t make it hurt any less. In this movie rendition of the Spider-Man story, Gwen Stacy and Peter Parker fight against Electro and the Green Goblin himself – and they almost make it out. When the Green Goblin kidnaps Gwen, Peter is able to fend him off, but not before Gwen falls to her death. This one is particularly hard because Peter and Gwen are played by Andrew Garfield and Emma Stone, who were actually dating at the time. So watching Peter cry over Gwen’s body, you got the feeling Andrew Garfield was really in that moment.
#11: Dean Pereira & Cindy Heller “Blue Valentine” (2010)
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Don’t be fooled by the holiday in the name of this one. “Blue Valentine” follows the course of a single relationship – from its sweet start to its ultimate downfall. And folks, this couple falls HARD. Ryan Gosling and Michelle Williams star in this romantic drama, playing Dean and Cindy, a couple who meet, get married, and eventually end things – but not before engaging in brutal arguments, crippling depression, and everything else under the sun along the way. It’s far from a sunny story, but what makes it harder is just how lovely the couple is at the beginning of their relationship. After they end things and the credits roll, you’re reminded of their happier times through old pictures - but there’s no going back.
#10: Elio Perlman & Oliver “Call Me by Your Name” (2017)
We couldn’t get through this list without the obligatory coming-of-age heartbreak. Teenaged Elio meets grad student Oliver when he works for Elio’s father at their Italian villa over the summer. They both stave off their initial attraction to each other for almost the entirety of the summer, but eventually give in and spend the last few days in a romantic haze. Oliver eventually leaves, and Elio hangs onto the summer they had – until Oliver calls him over the winter to tell him he’s getting married. It’s a bittersweet phone call, and Timothee Chalamet’s excellent performance during the closing credits has us sobbing every time.
#9: Hazel Grace Lancaster & Augustus "Gus" Waters “The Fault in Our Stars” (2014)
We never thought we’d tear up from hearing the words, “Okay? Okay,” but here we are! The star-crossed lovers at the center of “The Fault in Our Stars” already have enough going on in their lives without failed romance getting in the way – Hazel Grace has cancer, and Augustus, while in remission, had to have a leg removed. The two fall in love, and the entire time, the audience is primed for Hazel Grace’s death. But – in a terrible turn of events – Augustus’ cancer returns, and he passes away. Before Augustus dies, Hazel Grace reads her eulogy to him in a scene that still makes us weep to this day.
#8: Christian & Satine “Moulin Rouge!” (2001)
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Our gift is our lists! And viewers, this one’s for you. “Moulin Rouge” is full of bright colors, popular songs, romance – sounds like a fun time, right? Unfortunately, this musical ends in heartbreak for everyone. Christian and Satine fall in love, but multiple obstacles work against them and keep them apart – including the fact that Satine has tuberculosis. Christian and Satine fight against all odds, but at the end of the movie, Satine ends up dying from her illness. Christian is left heartbroken, but he remembers her through song – honoring their love that will live forever.
#7: Jamie Sullivan & Landon Carter “A Walk to Remember” (2002)
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[“You have to promise you won’t fall in love with me”]: the words that spawned a thousand tears. “A Walk to Remember” tells the story of Jamie and Landon, and starts out as your typical bad boy/good girl romance. The two become close when Landon is forced to be in the school play as punishment – who could forget the best song in the world, “Only Hope” – and Jamie makes him promise he won’t fall in love with her. Of course, he does, and then learns Jamie has leukemia. Instead of giving up on their love, Landon spends the rest of the movie making sure Jamie gets everything she wants before she dies – including the wedding of her dreams. Cue the tears.
#6: Sebastian “Seb” Wilder & Mia Dolan “La La Land” (2016)
Who doesn’t love a classic Hollywood musical? Well, this particular one doesn’t end as happily as you might expect. The story follows two struggling artists – Mia, an actress, and Sebasitan, a jazz pianist – as they begin dating while both trying to follow their dreams. Unfortunately, there comes a time when they start to believe they can’t have both each other and professional success, and follow separate paths. They meet five years later, both wildly successful, and a dream scene ensues, showing the life the two could have had if they decided to stay together. It’s a gorgeous montage, and it’s heartbreaking to watch the pair think about what could have been.
#5: Scarlett O'Hara & Rhett Butler “Gone with the Wind” (1939)
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Chalk this one up to timing, folks. Scarlett O’Hara spends pretty much the entirety of “Gone With the Wind” rebuffing Rhett Butler’s advances, and pining over her beloved Ashley – even when she and Rhett are literally married. She denies him over and over again, until towards the end of the movie, she realizes she’s been in love with Rhett the entire time – but by the time she figures it out, Rhett has had enough. He leaves her, uttering that famous line: [“Frankly, my dear, I don’t give a damn.”] And honestly, it’s probably for the best – these two are the definition of toxicity. But boy, do we love to watch them.
#4: Ennis Del Mar & Jack Twist “Brokeback Mountain” (2005)
We wish we knew how to quit this movie – because it makes us break down in tears every time. Ennis and Jack’s relationship starts off professional, but quickly becomes romantic. But, being two men in the 1960s, they can’t exactly shout their love from the rooftops. They both end up marrying women, but keep meeting up with each other over the years, until eventually it becomes too hard for Ennis to admit his feelings, and too hard for Jack to keep getting his hopes up. But, that’s not the saddest part – Jack ends up dying, leaving Ennis alone, wondering if things could have been different. The end of the movie is tragic, and like we said at the beginning of this entry, breaks us down every time.
#3: Rick Blaine & Ilsa Lund “Casablanca” (1942)
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Here’s looking at you, viewers. “Casablanca” is one of the most iconic films of all time, but it also has one of the most famous lost romances. Starring Humphrey Bogart and Ingrid Bergman, the movie follows Rick, an expat who owns a nightclub in Casablanca during World War II. His life is turned upside down when Ilsa, a woman he used to be involved with, shows up. Although Ilsa is now married, the two rekindle their relationship and almost run away together – but Rick changes his mind at the last minute, sure that Ilsa will regret leaving her husband for him. The two share a tearful goodbye – one that we won’t soon forget.
#2: Romeo Montague & Juliet Capulet “Romeo + Juliet” (1996)
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“For never was a story of more woe than this of Juliet and her Romeo”: truer words have never been spoken. We had to include the original star-crossed lovers in this list, and of course, had to go with the Leonardo DiCaprio and Claire Danes iteration – we mean, what teen girl didn’t swoon over the pool balcony scene? Everyone knows the story of Romeo and Juliet, but the tragic end of the 1996 movie hits a little harder than most. Right as Romeo poisons himself, Juliet wakes up – the two lock eyes right before Romeo starts to die, making their final fate even harder to accept. “Thus with a kiss, I die” has never hurt so much.
#1: Jack Dawson & Rose DeWitt Bukater “Titanic” (1997)
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Rose won’t ever let go, and we won’t either – we’re going down with this ship. Jack and Rose meet aboard the Titanic, and despite their differing backgrounds – Jack is poor, Rose is upper-class – they immediately fall in love. The name of the movie is “Titanic,” so audiences knew this couple didn’t have much of a shot to begin with. But, even in the terror of watching the ship go down, we hoped and prayed for the pair to make it out alive. Of course, Rose lives, but Jack dies, and the heartbreaking sequence of her trying to shake him awake when help arrives is burned into our brains. Couldn’t you make some room on the debris, Rose? Come on!
