Tired of the Valentine’s Day Frills and Fanfare? Here Are 11 Films That Explore the Satisfying Side of Romantic Pain

For an occasion that's sold as a celebration of love's warm and fuzzy sides, Valentine’s Day can have excruciating side effects. There's undue pressure to be in a relationship, a panoply of capitalist ploys to commodify romance, too much pink. Yet the holiday’s film offerings tend to avoid the holiday's underbelly. Romantic comedies and dramedies give in to satisfying coupling after just a little bit of yearning. Pain—with its charged and, at times, erotic aspects—is rarely explored. 

Jealousy, desperation, anger, resentment—these are where the more three-dimensional love stories lie. Happy couples come undone when another person enters the scene. Power imbalances reverse, then reverse again. Revenge delivers a satisfaction arguably sweeter than any storybook ending.

It’s only right that Valentine’s Day fanfare evolves to embrace this catharsis. To that end, from missed connections to intergalactic kinks, CULTURED recommends 11 films to watch when love hurts.

Image courtesy of New World Pictures.


When creating this 1987 horror juggernaut, Clive Barker pulled from his own experiences in the S&M and kink scenes of 1970s New York. The resulting cenobites—intergalactic priests devoted to the extremes of experience—are some of the most aesthetically recognizable monsters in horror, decked out in piercings, latex, and open wounds. Yet, Barker understood that this combination is what makes these monsters sexy as well as unsettling. They're emblematic of what the people he partied with sought out: pain and pleasure, indivisible. 

Image courtesy of New Yorker Films and Filmverlag der Autoren.

The Bitter Tears of Petra Von Kant

Rainer Werner Fassbinder situates the entirety of his play-turned-film in the titular fashion designer’s hybrid bedroom-atelier. In this tale of masochism and sartorial sublimation, the restricted set exacerbates a sense of entrapment and obsession as a downtrodden Petra (Margit Carstensen) finds her new muse in Karin (Hanna Schygulla), upsetting the dominant-submissive relationship Petra has with her silent assistant, Marlene (a devastating Irm Hermann). Against a backdrop of Renaissance murals and an iconic white shag carpet, Petra’s precarious relationships unravel as Carstensen creates one of the most desperate performances ever committed to film. 

Image courtesy of United Artists Releasing and Metro-Goldwyn-Mayer Pictures.

Bones and All 

Luca Guadagnino lends his cinematic sensuality to this cannibalistic coming-of-age romance, complete with unnerving foley artistry. Maren Yearly (Loewe muse Taylor Russell) meets drifter and fellow “eater” Lee (Timothée Chalamet), and together they set out on a journey across an American Midwest as rollicking and unpredictable as young love itself. With an achingly beautiful score by Nine Inch Nails’s Trent Reznor and producer Atticus Ross, Bones and All breaks your heart, then eats it whole. 

Image courtesy of Miramax.

Kill Bill (Volumes 1 and 2)

Taking the Tarantino position that it’s really one film and not two, Kill Bill drags its audience through a bombastic, highly stylized breakup. Beatrix Kiddo’s (Uma Thurman) quest to annihilate every last one of the assassins who wronged her, ending with titular ex-boyfriend Bill, has a shocking emotional punch that holds up 20 years after its initial release. A purging watch for those who prefer emotional explosions to implosions. 

Image courtesy of Gaumont.


Considered one of the most polarizing films of the past 50 years, Andrzej Żuławski’s Possession was nominated for a Palme d’Or at Cannes and branded a “video nasty” in the early 1980s, making it nearly impossible to find until 2021. Mark (Sam Neill) comes home to West Berlin only to find that his wife, Anna (Isabelle Adjani), wants a divorce. What ensues is a slow-burn body horror film that answers one the most painful questions of them all: What if your wife is dating someone (or something) cooler than you?

Image courtesy of Paramount Pictures.

Deep End

Well before his film EO was nominated at the 95th Academy Awards, Polish filmmaker Jerzy Skolimowski made his unsettling debut with this psychosexual romantic drama about the violence of entering adolescence. High school dropout Mike (John Moulder-Brown) starts working at a bathhouse and falls for his coworker Susan (It-girl Jane Asher), who is 10 years his senior. What begins as a crush quickly morphs into a study of overexposure, isolation, and obsession, with tension that does not break until a deeply disturbing end. 

Image courtesy of MUBI.


When filmmaker Tomas (Franz Rogowski) gets into an argument with his husband Martin (Ben Whishaw) at a wrap party, the mercurial artist begins an affair with young teacher Agathe (Adèle Exarchopoulos). The ensuing love triangle crackles with intensity and frustration, with Tomas ping-ponging between his husband and lover as regularly as there is a change of the wind. Bisexual chaos, though maddening, has never looked so stylish as it does with costumes by Khadija Zeggaï. 

Image courtesy of Lionsgate.


The “office siren” trend owes something to Maggie Gyllenhaal’s hard-won performance in this psychosexual melodrama. Lee (Gyllenhaal), a socially awkward young woman living at home, begins working for domineering attorney E. Edward Grey (James Spader) as his secretary. Before long, they descend into a submissive-dominant relationship. Based on a Mary Gaitskill story of the same name, the film delivers charm and pearl-clutching visuals as it explores power, consent, and carrying the mail on all fours. 

Image courtesy of Focus Features and Universal Pictures.

Phantom Thread

Paul Thomas Anderson’s romance between London fashion designer Reynolds Woodcock (Daniel Day-Lewis) and waitress-turned-muse Alma (Vicky Krieps) is as taut and gorgeous as a well-boned corset begging to come undone. Delving into what it means to know and love someone, and the unconventional ways to do so, Anderson’s beloved film produces scenes of jealousy and miscommunication that feel lived in, despite the stylized, high-fashion setting. It also has some of the most memorable crotchety dialogue in recent memory, with Day-Lewis delivering, with gorgeous exasperation: “Are you a special agent sent here to ruin my evening and possibly my entire life?”

Image courtesy of New World Pictures.

The Brood

Pulling from his own acrimonious divorce and subsequent custody battle, David Cronenberg transmutes a classic tale of marital fallout into skin-crawling body horror. Frank (Art Hindle) goes to see his institutionalized wife, Nola (a commanding Samantha Eggar), as she receives unconventional treatment, the results of which are more monstrous than either one of them realizes. Not one to shy away from the revolting corners of life, Cronenberg’s film physically manifests the pain of divorce with some of his more shocking creature design. 

Image courtesy of B-Plan Distribution, Pandora Film and Camera Film

Fallen Leaves

Finnish director Aki Kaurismäki’s working-class romantic comedy is an exercise in yearning (and a winner of the 2023 Palm Dog Grand Jury Prize). Set in Helsinki against the backdrop of Russia invading Ukraine, grocery store worker Ansa (Alma Pöysti) meets sandblaster Huotari (Jussi Vatanen) one night at karaoke before encountering obstacle after obstacle to meeting again. A tender, if more mild ache, Kaurismäki’s tale of shy crushes, missed connections, and drunken debauchery sweetly wraps up after 81 minutes. It can’t all be too painful.