This article was originally published February 14, 2019. It has been updated to include more movies.
It’s time to accept a truth we’ve known for a very, very long time: Valentine’s Day isn’t for everyone. Only people in relatively fresh, loving relationships who are still absolutely obsessed with each other are able to put on their blinders and fully indulge in cuddles, candies, and cards. They can watch romantic comedies and laugh and enjoy themselves. They are able to not feel a vague stabbing pain every time they pass the red-and-pink aisle in the supermarket each February.
But what of … literally everyone else? When you’re terminally single, have gone through a painful breakup, or are just not feeling it, any reminder of other people’s cute, soppy love can be a little too much to bear. So how can you celebrate February 14 while acknowledging the painful truth most of us know: that love is fleeting, devastating, and sometimes just really mundane?
With anti-Valentine’s films, naturally. The following movies, each in their own way, deal with the darker side of love and relationships and will comfort you with the knowledge that, if you’re less than thrilled about love and romance, you are absolutely not alone.
Past Lives (2023)
Are you still thinking about your seventh-grade crush, wondering what could have been if you’d just followed up on those heart-shaped doodles? Probably not. Still, it’s hard not to feel heartache for Na Young (Greta Lee) and Hae Sung (Teo Yoo) in Celine Song’s Past Lives. Na Young and Hae Sung are classmates in Seoul who go on a parent-chaperoned date shortly before Na Young’s family moves to Toronto. The pair lose contact, but 12 years later, Hae Sung and Na Young, who now goes by Nora and lives in New York, reconnect over Facebook. They emotionally become close again, but the distance between South Korea and America is too far, and they put a pause on their frequent video calls. Which brings us to the heart of the movie, when, after another 12 years goes by, they finally see each other again; this time, they’re in their 30s and in New York. The chemistry between them is palpable, but the timing is still not right. It’s a pretty heartbreaking glimpse into all the could-have-beens. Maybe things will be different for them in the next life?
Gone Girl (2014)
Picture a couple leaving the cinema in 2014 after having seen Gone Girl on a mediocre date night. Are they holding hands? Giggling in the back of a taxi? Or are they staring out of the window, lamenting ever getting together in the first place and fearing that the other has some Amy–esque plans in their future? Gillian Flynn’s tale of marital tedium — and then revenge — is every couple’s worst nightmare. Told in David Fincher’s distinctive style, Amy Dunne fakes her own death in an attempt to frame her husband for her murder after he cheats on her. But that isn’t the worst of it: After all of that, after Amy’s monologues about how terrible he is and after leading him on a dark treasure hunt, after murdering a man and showing up covered in blood on Nick’s doorstep — the ending hints at the chilling prospect of their staying together.
Eternal Sunshine of the Spotless Mind (2004)
No matter how your last relationship went, there’ll be a few memories burned into your brain. A pleasant walk on the beach, a Sunday morning in bed, a screaming fight in Ikea. These memories will come back to haunt you long after the relationship has reached its bitter end, long past the point where they’re pleasant to recount — and on Valentine’s Day, you’ll probably be more haunted by them than ever! But what if you could … not be? In Michel Gondry’s sci-fi romance film, Jim Carrey and Kate Winslet have the option to just erase their memories of each other entirely. Watching their relationship fall apart is depressing as all hell, but watching them find each other again is … kinda heartwarming? Either way, the technology sadly just isn’t there yet.
Her (2013)
In Spike Jonze’s 2013 film, Theodore (Joaquin Phoenix), a man who writes personal letters for strangers for a living, finds himself falling for an artificially intelligent personal assistant (Scarlett Johansson) that he believes loves him right back. It’s a haunting rumination on how far we will delude ourselves for love. Is your Alexa, chirping in the background right now to remind you to buy toilet paper, actually your wife? She isn’t. But what if she was? Theodore falls into a thrilling romance only to discover in one heartbreaking moment that Samantha also loves hundreds of other users. Her delves into the reality of intimacy — what do we want? Who do we want it from? Can we be truly intimate if all of our interactions are mediated by technology?
La La Land (2016)
What could be better than watching a couple’s relationship grow and then break down through the medium of song? Ryan Gosling and Emma Stone have been comedic gold together (see: Crazy, Stupid Love) but in La La Land, things take a pretty depressing turn as they fall in love, attempt to follow their dreams, and then achieve them — but lose one another in the process. In a particularly heartbreaking scene, Mia and Sebastian run into one another years after the fact … and, if somehow you haven’t seen the film yet, we’ll let you find out what happens for yourself.
Lost in Translation (2003)
It’s rumored that Her is a response to Lost in Translation, the 2003 movie written and directed by Spike Jonze’s ex-wife Sofia Coppola that was reportedly inspired by their marriage (with Jonze represented by Giovanni Ribisi). If it’s true, it’s pretty cutting. In the film, Charlotte (Scarlett Johansson) and Bob (Bill Murray) befriend one another in Tokyo while both suffering from insomnia in the same hotel. They share personal details with each other before fighting when Charlotte hears another woman in his room. When Bob departs, he shares a kiss with Charlotte in the street and, in a somewhat iconic ending, whispers something in her ear — something that the audience doesn’t hear. Lost in Translation is depressing, but if you’re sad this Valentine’s Day, just be grateful your ex isn’t in a position to make scathing art about you.
Never Let Me Go (2010)
Several of these films are science fiction, partly because there is nothing scarier than when filmmakers take the anxieties that already plague our lives daily and imagine how much more terrifying things would be if there were the technology to make them even worse. In Never Let Me Go, Carey Mulligan, Keira Knightley, and Andrew Garfield play clones who are destined to die in early adulthood, once their organs are ripe to be harvested for medical purposes. Tommy (Garfield) and Ruth (Knightley) are in a relationship, partly because clones have been told that couples who are in love get to “defer” their donations. But years later, Ruth admits that she never loved Tommy at all. At one point, in a voice-over, Carey Mulligan reminds us that “we all complete” — clone parlance for dying. What’s better on Valentine’s Day than a reminder that we never get what we want, all love is doomed, and we’re all gonna die?
Blue Valentine (2010)
As we learned from the end of Gone Girl, there is nothing more terrifying than the concept of two people who should absolutely split up being bound together by a helpless child. In Blue Valentine, Cindy (Michelle Williams) and Dean’s (Ryan Gosling) relationship breaks down over the course of a narrative that dips into different eras of their relationship. We see them meeting, falling in love, and raising a child that isn’t Dean’s. Dean struggles with alcohol abuse, their dog dies, they have a really bleak “romantic getaway” at a motel. As if all of that isn’t depressing enough, the film ends with a reminder of their love: photos from their romance, illuminated by fireworks.
An Education (2009)
Numerous films on this list feature Carey Mulligan or Ryan Gosling, in part because they are both very good at conveying the saddest of emotions with little more than their eyes. An Education sees a young Mulligan falling in love and embarking on a journey with an older man who drives her home one day after school. They travel together in a grim nod to Lolita, arguing in hotel rooms until she loses her virginity to him — leaving her ultimately believing that she is special to him. What ends up happening is an emotional gut-punch that is devastating and sadly all too real. It’s a lot to bear on Valentine’s Day, but we think you can handle it.
Landline (2017)
Some of these films deal with alternate realities, and that, to some degree, can make stomaching the horrible relationships they depict, and their horrible outcomes, easier. But Landline, Gillian Robespierre and Jenny Slate’s first film together since 2014’s perfect Obvious Child, deals with the blood-and-guts realities that we already have to live in. Jenny Slate’s character, Dana, begins sleeping with an ex because, quite simply, her husband is boring and Nate is not. Simultaneously, she discovers that her father has been having an affair with someone who isn’t her mother. Things escalate, and although she reconciles with her husband, it’s a scary tale that’s as old as time but no less terrifying for it: What if the person next to you, snoozing safely in bed, is actually really dull? What if you aren’t actually content with someone sweet and kind who makes you happy? What if they’re thinking the same thing? Anyway, sleep tight.
The Kids Are All Right (2010)
Something a lot of these films get at is that marriage can be tough and boring. Boredom drives you to do crazy things: In The Kids Are All Right, Jules (Julianne Moore), after tracking down her and her wife Nic’s (Annette Bening) sperm donor, begins an affair with him (Mark Ruffalo). They have the bleakest midday sex of all time, pale bodies slapping together in a mid-shot that stays burned into your brain. While the realities of a marital breakdown and disagreements in parenting are pretty miserable in themselves, in The Kids Are All Right that misery is only compounded by the implication that if you date a bisexual woman, she’s going to cheat on you eventually!
Brokeback Mountain (2005)
Forbidden or restricted love, on top of a “right person, wrong time” plot, can be the saddest thing of all. In Ang Lee’s Brokeback Mountain, Ennis (Heath Ledger) and Jack (Jake Gyllenhaal) begin a romance while they’re working together herding sheep in the mountains. But it’s the 1960s, and their love is taboo — they both end up marrying women but, over time, become miserable in their respective marriages and meet up regularly to reignite their love. Things get tragic from there, and the line “I wish I knew how to quit you” can still bring a tear to the eye — as can a closet full of an ex-lover’s shirts.
Cabaret (1972)
Set against the backdrop of rising Nazism in 1930s Berlin, Bob Fosse’s Cabaret is about as depressing as any story gets. An adaptation of the stage musical based on Christopher Isherwood’s Goodbye to Berlin, Cabaret follows singer Sally Bowles (Liza Minnelli) as she performs at the Kit Kat Club and tries to find love in a cruel world. All the while, fascism encroaches on the promiscuous, homoerotic fun of the club. Sally and Brian (Michael York) enjoy a sweet but very doomed romance, and Minnelli’s number “Maybe This Time,” in which she laments her repeated heartbreaks, is a Valentine’s Day mood all in itself.
Carol (2015)
Doubling up as a devastating Christmas movie, Todd Haynes’s 2015 drama, Carol, is a great way to get deep into your feelings on the most depressing day of the year. In 1952, Therese (Rooney Mara) is working in a department store when she meets Carol (Cate Blanchett). As Carol fights out a divorce, in which her ex-husband tries to hit her with a “morality clause” based on her former relationship with a woman, things heat up between her and Therese. Tension and longing build between the two of them, shattering both. While it’s pretty heartbreaking, the ending offers some respite with a glimmer of hope that these two crazy gals might work things out even in such a cruel era for LGBTQ+ people.
