6 Movies We Shouldn't Watch on Valentine's Day (But Probably Will Anyway)
There’s something deliciously masochistic about choosing heartbreak for company on Valentine’s Day. Maybe it’s the comfort of shared pain, or the relief of knowing love doesn’t always look like a perfect rom-com montage. Either way, we all have that one film we press “play” on, knowing full well it’ll leave us emotionally wrecked but cathartically cleansed.
With Emerald Fennell’s “Wuthering Heights” adaptation starring Margot Robbie and Jacob Elordi already stirring up discourse—complete with stormy moors, doomed passion, and the promise of gothic misery—it feels right to revisit the cinematic heartbreak hall of fame. The following films scratch a peculiar Valentine’s itch and remind us that love, however fleeting or flawed, is the fundamental stuff of life. So if you’re craving something tender, tragic, and maybe even a little toxic, gather your tissues and a hefty box of chocolates, and settle in for an emotionally devastating February 14.
Michel Gondry’s Eternal Sunshine of the Spotless Mind has become something of a ‘softboi’ romance cult classic since its 2004 release. Featuring Jim Carrey in one of his most emotionally restrained roles as the moody Joel, and Kate Winslet as the chaotic, neon-haired Clementine, the film follows their strange, fragmented love story. After their breakup, Clementine undergoes a procedure to erase her memories of Joel—and he does the same, only to regret it mid-process.
This movie is an emotional rollercoaster, both tender and devastating. The heartbreak comes from watching their relationship unravel across time and memory, but also from the film’s quiet insistence that love is worth remembering—even when it hurts. In Alfred Lord Tennyson’s immortal words, “‘Tis better to have loved and lost than never to have loved at all”.
John Green’s adaptation of The Fault in Our Stars remains a masterclass in emotional demolition. Shailene Woodley and Ansel Elgort play Hazel and Gus, two teenagers with terminal cancer who meet in a support group and fall, unavoidably, in love. You know where it’s going, and yet every rewatch hurts more than the last.
Hazel and Gus’s connection through shared humour, exchanged books, and vulnerabilities brings the story forward, even as their mortal deadlines loom closer. Despite the devastation this film wreaks, it’s a powerful reminder to appreciate small, intimate moments, and to remember that although love can be cruelly brief, there is beauty in choosing to feel it anyway.
“You always hurt the ones you love”, that’s the little Mills Brothers ditty Dean sings to Cindy on his ukulele while they’re falling for each other—and it foreshadows everything that comes to pass in Derek Cianfrance’s Blue Valentine. Starring Ryan Gosling and Michelle Williams as Dean and Cindy, and told in a non-linear fashion, the film tracks the tender beginning and painful disintegration of their marriage.
Both Gosland and Williams give raw, heartbreaking performances that make Dean and Cindy feel tragically real. While their love for each other is palpably authentic and beautiful, their resentments, exhaustion, and lost dreams make it tragically impossible for them to find their way back to each other. I’d recommend this one only for those who can handle a particularly blue Valentine’s Day.
Every Nicholas Sparks adaptation should come stamped with the warning label “tears ahead”, and A Walk to Remember is a prime example of why. The film (which is set to be rebooted) stars Mandy Moore and Shane West as high schoolers Jamie and Landon. The popular Landon finally notices the quiet Jamie when they both participate in the school play, and their push-and-pull dynamic eventually leads to them falling in love. The catch? Jamie has terminal leukaemia.
Deeply moving and devastating in equal measure, A Walk to Remember is ultimately a story about choosing love, even when you know the ending. It’s a testament to the bravery of the heart—but boy, will it wreck you on Valentine’s Day (and any day, tbh). Don’t believe us? Just ask Sinners’ director, Ryan Coolger.
Ang Lee’s Brokeback Mountain remains one of cinema’s most aching portrayals of forbidden love. This tragic romance stars Heath Ledger and Jake Gyllenhaal as Ennis and Jack, two cowboys whose brief affair in 1960s Wyoming becomes an intense, impossible lifelong attachment.
Ledger and Gyllenhaal are magnetic on screen, and their portrayals convey the tenderness and tragedy of Ennis and Jack’s stolen moments together. The film is ultimately a study in repression and longing that refuses to simplify the cost of love. The ending may wreck you, but the beauty of Brokeback Mountain will stay with you far longer.
My personal favourite for whenever I fancy ripping my heart out of my chest is Berry Jenkins’s Best Picture winner Moonlight. It is the quietest—but perhaps most devastating—film on this list. Told in three acts, Moonlight centres around Chiron, from his childhood growing up Black and closeted in an impoverished neighbourhood in Miami, through his teenage years as an outsider bullied for his sexuality, and as an adult, where a chance phone call leads to the slow disintegration of his armour.
Moonlight is based on playwright Tarell Alvin McCraney’s unpublished autobiography, and you can tell it is based on lived experience from its specificity and raw emotion. From complex figures like the drug dealer Juan, who takes Chiron under his wing, to Kevin, whose tender reconnection with Chiron years later brings tears to my eyes just thinking about it, Moonlight is the rare film that both exposes and carefully heals the most painful wounds of the heart.
