However, it doesn’t always happen that way. What about those romantic comedy couples that don’t make it? The ones held apart by fate, by deep character flaws, by insurmountable differences? It’s a bold move to end a romantic comedy without “success.” If it isn’t done well, audiences will be disappointed after having sat through the film in hopes that the primary couple will come together in the end. When a romantic comedy couple can’t make it work, the film can come across as cruel or pessimistic or cynical. There needs to be a good reason why they stay apart—a reason that we can empathize with—and it needs to be executed with care and craft. Here are our picks for romantic comedy couples who didn’t make it in the end, leaving us heartbroken but not disappointed.
8. Alyssa and Holden (Chasing Amy)
From the mind of Kevin Smith comes Chasing Amy, which showcases the story of a group of comic book creators trying to bring their work to the masses. However, when Ben Affleck’s Holden meets Joey Lauren Adams’ Alyssa, sparks begin to fly between the pair. Their relationship rises and falls throughout the film as Holden and Alyssa’s bond becomes strained to a breaking point due to the parts of one another that they can’t get past. It leaves them heartbroken when their relationship falls apart entirely. The film’s ending sees them reunited for an emotionally devastating conversation—one where two people who still love one another realize that there’s little left to say.
7. Bob Harris and Charlotte (Lost in Translation)
Lost in Translation follows Bill Murray’s Bob Harris (a faded movie star arriving in Tokyo for a whiskey commercial) and Scarlett Johansson’s Charlotte (a recent graduate). The pair slowly become friends as they repeatedly encounter one another throughout the hotel. Director Sofia Coppola expertly provides a strong romantic bond between the leading duo—despite their stark age difference—and does so without ever promoting any level of sexual tension. It leaves us with a Bob and Charlotte who have only an emotional and intellectual connection. After their adventure together, Bob has to leave Tokyo to go home. But as he drives by a busy road, he sees Charlotte and stops to see her. They share a kiss and some unheard words, then part ways.
6. Jessica Stein and Helen Cooper (Kissing Jessica Stein)
Here we have an indie movie that made it despite odds. Kissing Jessica Stein was made with a tiny budget yet earned ten times that at the box office upon release, mostly because of the sharply written script and forward-thinking representation. Jessica Stein is a repressed woman in her early-30s who falls in love with quirky artist Helen Cooper. After struggling with the rigidity she faces in being a lesbian couple, Jessica sees that she truly loves Helen. However, while Helen knows that Jessica loves her, she also knows that Jessica isn’t sexually attracted enough to Helen to warrant a relationship. She knows it’s going to end in heartbreak. So, Helen breaks it off with Jessica. It’s a choice that proves itself right as Jessica and Helen remain close friends—ones who know that they love each other but also know it won’t ever work completely between them.
5. Jim and Amanda (Blue Jay)
The small indie film Blue Jay tells the tale of a man named Jim who returns to his hometown to pack up his deceased mother’s house, only to run into his high school ex-girlfriend Amanda. Blue Jay makes the point that their relationship had ended despite them having an unusually strong bond for a high school couple. As they spend more time together, the pair discuss their lives—and eventually discuss the reason why they broke up, leaving them both emotionally scarred. The pair’s realization that they could have had a life together becomes the heart of the film, with the regrets of decades passed mounting on them. However, when the credits roll, we don’t know what the future holds for them. Will they get back together or call their evening a one-off?
4. Laura and Alec (Brief Encounter)
There’s a lot of fun to be had in Laura and Alec’s tryst in Brief Encounter. The couple first meet at the train station and find themselves attracted to one another, despite both being married. Although it was an unusual choice to make the audience root for an affair in 1945, Brief Encounter smartly made it work. Laura and Alec aren’t two people looking to fall in love with one another—they’re two people who have fallen out of love with their spouses. When Alec reveals that he’s moving to South Africa, his last encounter with Laura becomes a tender goodbye. However, as they sit in the cafe and wait for his train to arrive, Laura’s blabbermouth friend sits down next to them and ruins their final moments. In the end, Alec stands up and gently touches Laura’s shoulder before saying goodbye for the last time.
3. Princess Anne and Joe Bradley (Roman Holiday)
Roman Holiday features the journey of Audrey Hepburn’s Princess Anne from young woman who doesn’t know the world outside her life as a princess to grown woman who understands the simple delights of life. Anne’s time spent in the presence of Gregory Peck’s Joe Bradley forms the heart of the film, who both spend the day together enjoying life around Rome, all the while quietly falling in love. In the end, Anne must return to her role as Princess and Joe must return to his life as a journalist. When they meet for the last time during a press conference, Anne is taken away by her aids and Joe is left alone to walk out of the embassy, each as heartbroken as the other.
2. Seb and Mia (La La Land)
La La Land is a wondrous dance through Los Angeles from the perspective of a struggling musician and a struggling actress who fall in love—and their struggles keep us hooked until the final scenes. After supporting each other up throughout the failures, disappointments, and dead-ends of their respective careers, Seb and Mia come to the end of their relationship and move on. Five years after their breakup, Mia (who is now a famous actress and married) enters Seb’s Jazz Bar to find that he has also made his dream a reality. Their eyes meet across the room as he plays their theme, and they know what they had was special—before Mia and her husband leave.
1. Vader and Thomas J. (My Girl)
Yes, they’re children. Yes, it’s unlikely that any relationship between them would sustain through adolescence and into adulthood. But what Vader and Thomas J. have in My Girl is more than mere friendship. It’s easy to imagine the pair having grown up, meeting again as adults, and falling helplessly in love with each other before getting married and living happily ever after. However, it isn’t to be—because Thomas J. dies while trying to retrieve Vader’s mood ring. His funeral scene is utterly devastating as Vader—who has barely left her room since Thomas J.’s death—breaks down when she sees him in his casket. The sequence leaves us in bits, knowing that these two had a special bond that’s been cruelly taken from them. Read next: Heavy, heartbreaking, and emotionally devastating movies worth watching
