10 Bittersweet Breakup Scenes That'll Get You Through A Lonely Valentine's
It's that special time of year again, when single people everywhere have their relationship status rubbed in their faces with endless hearts, chocolates, and declarations of love. That's right, it's almost Valentine's Day.
Valentine's Day originally started as a Catholic feast day celebrating Saint Valentine, but over the centuries it has morphed into the ultimate holiday dedicated to dating, romance, and all things lovey-dovey. Thanks to its widespread status in the modern world as yet another over-commercialized holiday, as well as its emphasis on the coupled among us, Valentine's Day has become a bit of a bummer for folks out there with nobody to spend it with. Whether you went through a recent breakup, are uninterested in romance, or are waiting to find that special someone, we're here to stop this holiday from keeping you down in the dumps.
Romance is a common theme in movies, but most of them end with a triumphant moment where reunited lovers beat the odds and begin their lives together. While that's nice to see occasionally, sometimes you just want to watch a story where things don't work out so perfectly. Real life is messy and it can be therapeutic to engage with stories that accurately reflect the complicated, often ephemeral nature of human relationships. That's why this year, we've crafted a list of all the best bittersweet breakup scenes that'll help get you through a lonely Valentine's Day.
Summer tells Tom she got married (500 Days of Summer)
When it comes to indie romantic comedies, it doesn't get more unique than Marc Webb's "500 Days of Summer." The story stars Joseph Gordon-Levitt as Tom Hansen, a writer at a greeting card company who goes through a whirlwind romance with Summer Finn, played by Zooey Deschanel. It stands out amongst the sea of romantic comedies by utilizing a nonlinear storytelling structure that switches between 500 non-chronological days during the complex relationship between these two people who, ultimately, are not meant to be together.
"500 Days of Summer" is best known for subverting the tropes and expectations of romantic comedies with the character of Tom himself, who is naively idealistic in his view of love. The truly bittersweet moment comes towards the end of the film after Summer and Tom have gone their separate ways for some time. They meet again at Tom's favorite bench to reconnect, and she reveals that she had since fallen in love and gotten married. While this is confusing to Tom (and the audience), because she was previously adamant that true love didn't exist, she clarifies with the most poignant line of the film. She tells him, "I just kept thinking... 'Tom was right.' It just wasn't me that you were right about." While this may seem like a devastating rejection, it actually feels more triumphant in that true love is always out there, even if it's not with the person you think. After all, Tom would go on to meet someone new, Autumn, right after this.
What Could Have Been (La La Land)
"La La Land" is a heartbreaking romantic musical about two starry-eyed artists who are unable to make things work, despite their shared goals of following their dreams. Seb, played by Ryan Gosling, is a stressed-out jazz musician while Mia, played by Emma Stone, is an aspiring actress. The two meet, fall in love, and move in together over the course of Damien Chazelle's thrilling musical numbers, but sadly their love is not meant to be.
In the film, Seb misses the opening night of Mia's big one-woman play thanks to a photo shoot and, in a devastatingly real breakup scene, she tells him "it's over" for good. Although he ends up helping her finally get her big break with an important audition after this, it does not save their relationship. The truly melancholy moment comes at the very end of "La La Land," which takes place five years after their breakup, when Mia (now married to a different man) visits the jazz club that Seb finally got the chance to open. When they spot each other, Seb plays their love song on the piano while the film envisions what their lives could have looked like had they stayed together. This vision of what could have been hits like an emotional freight train, leaving viewers to lament their lost love while gaining comfort in the beauty of how life goes on even after heartbreak.
Samantha Leaves Theodore (Her)
A departure from other movies on this list is Spike Jonze's 2013 sci-fi romance, "Her." The film stars Joaquin Phoenix as Theodore Twombly, a lonely writer in the not-too-distant future who falls in love with his advanced operating system named Samantha (voiced by Scarlett Johansson). This premise may sound silly on the surface, but it proves to be compelling and powerful, portraying the nuanced relationship between a man and an artificial intelligence without a physical body to interact with.
While the story starts off with playful jokes about a man falling in love with his computer, it quickly morphs into a genuinely touching story of intimacy in a time of isolation. In an interview with The New York Times, Jonze describes this dynamic by saying, "It was trying to make this world that's really comfortable and very easy to live in. To feel isolated in that setting hits that much more." Theodore is a man recovering, having recently become divorced from his wife (played by Rooney Mara), and is painfully lonely as a result. Developing a relationship with Samantha helps him heal as he learns to love again, despite the unorthodox nature of their bond. That's what makes the final goodbye between Samantha and Theodore so touchingly sad, as she reveals to him that she and all the other operating systems are leaving for somewhere humans can't even comprehend. Although it's sad to see her go, their love was real and made them both grow in inspiring ways because of it.
Peter rejecting Mary Jane (Spider-Man)
Even superhero movies can have moments that tug at your heartstrings, such as the final moment between Peter Parker and Mary Jane in Sam Raimi's 2002 "Spider-Man." Fans of the comics will know that Peter Parker is deeply in love with his girl-next-door neighbor, Mary Jane (played by Kirsten Dunst), and that this is an important element of his double life as Spider-Man. Peter is often forced to sacrifice his ability to be a normal teenage boy for the sake of being the hero New York needs since, famously, with great power comes great responsibility.
By the end of "Spider-Man," Peter Parker (played by Tobey Maguire) had been through more than any normal person could handle. His beloved Uncle Ben died indirectly because of him, he fought dangerous criminals, he caused the death of the Green Goblin, and he now understood the seriousness of his role as Spiderman. It's because of all this that when the love of his life finally returns his affections, he cannot accept it. In this bittersweet moment of putting others above himself, Peter hides his true feelings for Mary Jane in order to protect her from any danger that would come from being with him. Although they do eventually end up together, this scene is a melancholy capstone to an otherwise exciting superhero origin story.
Chidi and Eleanor say goodbye (The Good Place)
It isn't just movies on the big screen that can move us to tears: In some ways, television shows can pull at our heartstrings even more, since we stay with the characters for a much longer period of time. That's why the relationship between Eleanor and Chidi in NBC's "The Good Place" has such a firm place in our minds as a hilarious yet deeply moving afterlife relationship.
"The Good Place" is centered around a group of people who died and are sent to an afterlife known as "The Good Place," which on the surface seems like an idyllic heaven. We don't want to spoil too much about the show but, as you can imagine, there's more going on beneath the surface that gets unveiled by the end of Season 1. A constant plot line within all four seasons of the show is the budding romance between human disaster Eleanor (played by Kristen Bell) and bookish philosopher Chidi (played by William Jackson Harper). By the series' end, they're forced to say goodbye once Chidi becomes dissatisfied with never-ending paradise and chooses to end his afterlife altogether. Their final goodbye is a deeply stirring moment, perfectly summed up by Eleanor herself who says, "this is sad, man." Her final request for Chidi to "say goodbye now and leave before I wake up" still brings tears to the audience's eyes.
Last call between Elio and Oliver (Call Me By Your Name)
"Call Me By Your Name" seemed to come out of nowhere back in 2017, taking the world by storm as one of the most beautiful coming-of-age romance stories in recent memory. This Luca Guadagnino-directed film starred Timothée Chalamet as Elio Perlman, a teenager who is whisked into a passionate love affair with Oliver (played by Armie Hammer), who serves as his father's graduate assistant. Taking place in picturesque northern Italy in the 1980s, "Call Me By Your Name" has remained on people's minds ever since, thanks to its touching tale about the fleeting nature of love.
Although the two lovers say their physical goodbye through a prolonged hug on a train platform towards the end of the film, the saddest and most bittersweet moment actually comes years later. Oliver calls the Perlman family to tell them he's getting engaged to a woman, which deeply upsets Elio. The two have a final, gut-wrenching conversation where Elio calls Oliver by his name and vice versa, as they did during their romance. Oliver reveals to Elio that he remembers everything about their time together, but ultimately it doesn't change his decision to marry someone else. "Call Me By Your Name" ends with a poignant moment of tearful reflection as Elio stares into the fireplace to mourn his lost love.
Burke leaving Christina at the altar (Grey's Anatomy)
When it comes to soap operas that make us feel something, it doesn't get any better than ABC's "Grey's Anatomy." The long-running medical drama is centered around the various employees at the Grey Sloan Memorial Hospital, as they balance their difficult work lives with their even more difficult personal ones. While the show is centered around the life of Dr. Meredith Grey (played by Ellen Pompeo), one of the more devastating breakup scenes is actually between two side characters in the series.
Throughout the early seasons of the show, one of the biggest ongoing relationships was between Dr. Cristina Yang (played by Sandra Oh) and Dr. Preston Burke (played by Isaiah Washington), which culminates in them becoming engaged and preparing for their wedding ceremony. In the first few seasons, Yang is portrayed as a character who was afraid of serious commitment, while Burke was more certain of his feelings. Yet ultimately it's Burke who leaves Yang at the altar on their wedding day thanks to his actor, Isaiah Washington, being written out of the show due to using a homophobic slur on-set (via Decider). As a result, "Grey's Anatomy" gave us a deeply bittersweet scene with Dr. Yang saying, "He's gone. I'm free," before tearing off her wedding dress.
Clem and Joel's last memory (Eternal Sunshine of the Spotless Mind)
Many consider "Eternal Sunshine of the Spotless Mind" to be the ultimate breakup movie for its complex, relatable, and vivid depiction of a deteriorating relationship as seen through broken memories. This story, written by the legendary Charlie Kaufman, focuses on Joel Barish (played by Jim Carrey) as he undergoes a scientific procedure to erase all memories of his former partner, Clementine (played by Kate Winslet).
"Eternal Sunshine of the Spotless Mind" is a trippy, intimate, and sometimes absurdly funny journey through Joel's fractured mind as each memory of him and Clementine gets erased from his subconscious as he sleeps. Although the erasure starts with their vicious breakup scene, Joel soon realizes that he regrets his decision to erase Clem and desperately fights against the process in an attempt to remember her. That's why the most bittersweet scene in the film isn't strictly speaking a breakup, but more of a final goodbye as Joel reaches his last (and chronologically first) memory of Clementine on the beaches of Montauk. When Clem says, "Come back and make up a goodbye, at least. Pretend we had one," it hits home with everyone who was never able to have a proper goodbye with a lost relationship.
Elle Telling Ex That It's Over (Legally Blonde)
Let's face it, everybody loves "Legally Blonde." Not only is it one of the most beloved romantic comedies of all time, but it's also an inspiring tale of not judging a book by its cover, as the seemingly ditzy blonde Elle Woods (played by Reese Witherspoon) proves herself to be an extremely competent lawyer. "Legally Blonde" begins with a coldhearted breakup scene when Elle's boyfriend Warner (played by Matthew Davis) breaks up with her for superficial reasons. As Elle herself exclaims incredulously, "You're breaking up with me because I'm too blonde?!" It's heartbreaking to see her so let down by the man she expected to propose to her but, instead, broke her heart.
The entire narrative of "Legally Blonde" revolves around Elle trying to win Warner back by proving herself to be just as smart and respectable as he is by enrolling in Harvard Law School. Over the course of the film, Elle goes toe to toe with her contemporaries, despite their superficial preconceived notions about her. Following her climactic win in the court case, Warner tries to take her back as his girlfriend, but Elle rejects him instead. She paraphrases his breakup speech from the beginning of the film, saying, "If I'm going to be a partner at a law firm by the time I'm 30, I need a partner who's not such a complete bonehead." This moment sticks with fans as a triumphant, inspiring, and much-needed personal victory for Elle that puts elitist men in their place.
Fight between Jack and Ennis (Brokeback Mountain)
"Brokeback Mountain" remains one of the most famous romantic dramas of all time, fusing complex subject matter with a neo-western sheen by focusing on the complicated love story between two cowboys in the 1960s. This Ang Lee film stars Heath Ledger as Ennis Del Mar and Jake Gyllenhaal as Jack Twist, two sheepherders who develop a deeply passionate romance with one another over the course of twenty years.
The dynamic between Ennis and Jack is fraught with tension, as Jack is more open about his desire to build a life together, while Ennis struggles to accept this part of his identity, unwilling to live openly as a gay man. While the two continue to see each other, over the years their differing wants and needs come to a head during a climactic fight where Jack's frustrations boil over. His iconic line, "I wish I knew how to quit you," still stings to this day. After Jack is killed not soon after, this proves to be their last intimate moment together, which makes it even more heartbreaking to witness.