20 Dark Movies for an Unhappy Valentine’s Day

Moviegoers love love. We love love so much that not only does Hollywood make movies all about love, but studios also put love into movies that don’t require love. So if you’ve got a hot date this Valentine’s weekend, or if you’re just going to spend it on the sofa with someone you adore, you’ll find a multitude of movies to compliment the mood.

But what about everyone else? What about the people who are sick to death of all this crap? Are they forced to swear off cinema this weekend?

Not at all. We’ve compiled a list of 20 films all about the unpleasant parts of romance, movies that will make you happy that you’re so unhappy and alone.

Tillie’s Punctured Romance (1914)

In the early silent era, few studios were as successful as Keystone Pictures. Founded by Mack Sennett, Keystone built its reputation with ludicrous slapstick shorts, launching the film careers of Mabel Normand, Roscoe “Fatty” Arbuckle, and Charlie Chaplin. Keystone’s sole feature-length film captured everything great about the studio and its anarchic vision of the world, turning its eye specifically toward love and romance. Tillie’s Punctured Romance stars Marie Dressler as a lonely woman who gets swept away by promises of love from a swindler (Chaplin), who plans to bilk her of her fortune and run away with his own girlfriend (Normand). Not only does Tille’s Punctured Romance turn a dispeptic eye toward all things lovey-dovey, it punctuates its cynicism with lots of people getting kicked in the rear and an epic pie fight.

Casablanca (1942)

Many a couple have turned on Casablanca for Valentine’s Day only to find very little of the love and affirmation they hoped for. Sure, a flame still burns between Rick (Humphrey Bogart), the nightclub owner who swears he’s an uncaring and amoral mercenary, and Ilsa (Ingrid Bergman), the woman who broke his heart. But the film recognizes that the two cannot be together, even if her presence is enough to spark some sort of passion in him again. As the movie’s famous final lines point out, Casablanca is about the beginning of a beautiful friendship… and about the death of a long-past romance.

Vertigo (1958)

Alfred Hitchcock made great use of Jimmy Stewart’s affable persona in his thrillers, none better than 1958’s Vertigo, precisely because it could be confused as a romance. Stewart plays Scottie, a police detective stricken with the titular malady and hired to investigate a woman named Madeline (Kim Novak). No sooner does Scottie fall for Madeline than she commits suicide. However, he later meets a woman named Judy Barton, who looks just like Madeline (also Novak). As the twisty plot unfolds, Jimmy and Madeline become less doomed lovers and more obsessives who want to control the people around them.

Contempt (1963)

Just the title of Contempt is enough to tell you how director Jean-Luc Godard is going to approach the petite bourgeoisie couple at the center of his film. On a plot level, Contempt deals with playwright Paul Javal’s (Michel Piccoli) attempt to work on a screenplay adapting The Odyssey. However, Godard is more interested in the banal and dying marriage between Paul and his wife Camille (Brigitte Bardot). The rich colors and warm cinemotopgraphy belie the film’s frank depiction of an uncoupling that occurs because neither person has the capacity to care.

Who’s Afraid of Virginia Woolf? (1966)

Who’s Afraid of Virginia Woolf? is the loud, angry American cousin to Contempt. Both movies chronicle the end of middle-class marriages, but Virginia Woolf, based on the play by Edward Albee and directed by Mike Nichols, does so with plenty of shouting and grandstanding. The film seems simple enough, capturing a dinner shared between professor and his wife (Richard Burton and Elizabeth Taylor) and a young new professor and his partner (George Segal and Sandy Dennis). However, the party is enough to open up all manner of festering wounds, which leads everyone involved to shout about how much they hate their relationships.

A Woman Under the Influence (1974)

Nobody takes a hard look at relationships like actor-turned-filmmaker John Cassavetes, especially in films that starred his real-life wife Gena Rowlands. That is particularly clear in Cassavettes’s best film, A Woman Under the Influence. The movie lives up to its title, a raw look at a nondescript working-class woman (Rowlands) who has a nervous breakdown. Although her husband (Peter Falk) stands by his wife throughout it all (imperfectly, to be sure), and the film ends on a tender note, A Woman Under the Influence reminds viewers that it being in relationship work can be hard work.

The Stepford Wives (1975)

Based on the novel by Ira Levin, The Stepford Wives a classic conspiracy thriller built around the American dream, as reimagined for the women’s lib generation. Katharine Ross stars as Joanna Eberhart, a free-spirited photographer who moves to the suburbs with her daughters and her apparently supported husband Walter (Peter Masterson). But as Walter becomes friendly with his male neighbors, Joanna begins to feel that he’s comparing her to his friends’ perfect wives. Probably everyone knows the twist of The Stepford Wives, but they may have forgotten that it paints such a dismal portrait of the marital couple.

Possession (1981)

Anyone just reading the synopsis of Possession may be forgiven for thinking it’s a sexy espionage movie in the vein of Mr. and Mrs. Smith. The dour tone that Polish director Andrzej Żuławski brings to Possession quickly disabuses anyone of that expectation, but it’s really the performance of Isabelle Adjani as Ana, wife of spy Mark (Sam Neill) that makes the film wholly unique. Adjani’s performance as a woman who becomes something different after asking her husband for a divorce remains one of the most powerful pieces of acting ever put on screen.

Modern Romance (1981)

The other 1981 pick on this list goes in the exact opposite direction of Possession. Modern Romance stars Albert Brooks, who also directs and co-writes the script with Monica Johnson, as film editor Robert Cole. When Robert lets his worries get the best of him, he breaks up with his long-suffering girlfriend Mary (Kathryn Harrold). Yet, as he goes through date after date, Robert shows the audience (though he doesn’t quite show himself) that he is the problem. Although it’s possible that some could read the end of Modern Romance as a statement about the hard, worthwhile work of a relationship, the prospect of ending up with a guy like Robert is enough to scare anyone into being single forever.

Heartburn (1986)

The name Nora Ephron is synonymous with When Harry Met Sally… and Sleepless in Seattle, as she wrote some of the best romance movies of all time. But her first movie about relationships took a decidedly more cynical approach to the topic. Heartburn, directed by Mike Nichols (this whole list could be made up of his movies), tells a fictionalized account of Ephron’s marriage to Carl Bernstein of All the President’s Men fame, with Meryl Streep and Jack Nicholson standing in as Rachel Samstat and Mark Forman. We won’t spoil the story for you here, but let’s just say that Rachel and Mark don’t end Heartburn on the observation deck of the Empire State Building.

She’s Gotta Have It (1986)

Spike Lee isn’t a name often associated with romance movies, so it may be surprising to some that his debut feature She’s Gotta Have It deals with relationship issues. The film follows Nola Darling (Tracy Camilla Johns) as she deals with three boyfriends (played by Tommy Redmond Hicks, John Canada Terrell, and Lee himself). Within comedic moments of Nola loving and loathing her suitors, She’s Gotta Have It becomes a celebration of non-monogamy and non-commitment—even through its surprising and potentially bleak final moments.

The War of the Roses (1989)

Modern viewers showed little interest in The Roses, the 2025 remake of The War of the Roses starring Olivia Colman and Benedict Cumberbatch. But that shouldn’t diminish the power of the 1989 original. Based on the novel by Warren Adler and directed by Danny DeVito, who also has a supporting role, The War of the Roses chronicles the increasingly ridiculous divorce battle between a rich couple played by Michael Douglas and Kathleen Turner. As mean-spirited as any movie on this list, The War of the Roses doesn’t have much to say about how we get together, but it has a lot to say about the depths to which we sink when we break up.

Wild at Heart (1990)

For as weird and off-putting as he could be, David Lynch was an unfailing optimist, which makes Wild at Heart a potentially strange pick for this list. After all, the movie ends with no less than Glinda the Good Witch from The Wizard of Oz arriving in her bubble to tell Sailor (Nicolas Cage) to go back to his beloved Lula (Laura Dern). Yet, Wild at Heart is also Lynch’s most off-putting movie, and not just because of the bizarre figures who try to break the couple apart. While Lynch himself probably believed in the purity of Lula and Sailor’s devotion to each other, everyone else might be wondering if their romance was worth the destruction left in its wake.

Three Colors: White (1994)

Technically, White is the comedic portion of Polish director Krzysztof Kieślowski’s Three Colors trilogy, coming after the heartbreaking Blue and the more affirming Red. But some may find it hard to laugh at the sad sack protagonist Karol Karol (Zbigniew Zamachowski) and the abuse he suffers at the hands of his French wife Dominique (Julie Delpy). Abandoned in Paris after Dominique demands divorce before they can consummate their relationship, Karol is forced to make his way through a foreign country while trying to win back his love. Even allowing for the fact that Dominique is played by the radiant Delpy, one has to wonder if it’s all worth it.

First Wives Club (1996)

Easily the most upbeat of the entries on this list, First Wives Club is the paradigmatic film about divorce leading to freedom. First Wives Club stars Bette Midler, Goldie Hawn, and Diane Keaton as women who were all left by their husbands for younger women. The trio team up to get revenge, a journey that involves both financial success and, in at least one case, a reconciliation. It’s not exactly realistic, but there is something refreshing about seeing a movie in which the key to happiness is not found in marriage.

Audition (1999)

Oh, to be one of the people who saw Takashi Miike’s Audition before the twist became common knowledge… The first half of Audition, based on the novel by Ryū Murakami, plays like a sweet, if odd, story about a widower searching for love. With the help of a friend in the movie business, the widower Shigeharu (Ryo Ishibashi) holds a series of auditions for a fake movie, where he is immediately enchanted by Asami Yamazaki (Eihi Shiina). Thinking that he’s found the love of his life, Shigeharu pursues Asami, especially after she disappears. Eventually, Shigeharu and Asami reunite and where it goes from there is, well—if you know where it goes, then you know nothing I could write can match it. If you don’t know, don’t let yourself be spoiled. Just go watch Audition now (if you have the stomach for it).

Blue Valentine (2010)

Ryan Gosling has long been a reliable leading man, but he’s always had a weird side. Director Derek Cianfrance, who also worked with Gosling in the crime drama The Place Beyond the Pines, taps into that energy for Blue Valentine, an incredible bummer of a love story. Cianfrance employs a bifurcated narrative structure to contrast the passionate beginning of the marriage between Dean and Cindy Pereira (Gosling and Michelle Williams) and their equally fiery but far less pleasant break-up. The two leads have constant chemistry through it all, making their dissolution all the sadder.

Gone Girl (2014)

Audition may be the ultimate relationship cautionary tale, but Gone Girl is the more famous one. David Fincher‘s icy adaptation of the hit novel by Gillian Flynn (who also pens the screenplay) features a couple at their worst. The film deftly plays with audience allegiances, inviting viewers to believe that Nick Dunne (Ben Affleck) killed his famous wife Amy (Rosamund Pike), and then revealing the true reason that Amy went missing, before finally settling on the fact that both Nick and Amy are terrible people. Gone Girl is a thrilling and unpleasant film, and perhaps be the worst date movie of all time.

It Follows (2014)

Horror movies have long drawn an implicit connection between sex and death, but It Follows made it explicit. So when teen Jay (Maika Monroe) has a dreamy romantic tryst with a new guy called Hugh (Jake Weary), we know that she’s in for a bad time. Maika doesn’t get to bask in the afterglow long, as she’s immediately drugged by Hugh and tied to a chair while he explains the rules to her. By having sex, Hugh has passed onto Jay an invisible entity that will slowly and constantly follow her to destroy her. The only way she can delay her fate is to have sex with someone else, making them the next target. The gauzy direction from David Robert Mitchell and Monroe’s fresh performance transform what could have been an obvious STD allegory into something moving and frighting, but definitely not romantic.

Marriage Story (2019)

Everyone on the internet knows the meme showing Adam Driver punching a wall while arguing with Scarlett Johansson. However, most of them probably don’t know how scary and sad that scene is in its original context, the Noah Baumbach film Marriage Story. Like many films on this list, Marriage Story shows a couple at the start and the end of their relationship, and includes the expected dramatic beats such as the discovery of an affair or sessions with cut-throat lawyers. However, Baumbach keeps the movie grounded in reality, which gives the movie a sense of earned melancholy.

Die My Love (2025)

Many movies of 2025 felt like they were trying to follow in Cassavettes’s footsteps. Movies like If I Had Legs I’d Kick You and Hamnet had big performances of women breaking down, but only Lynne Ramsay’s Die My Love put the protagnist’s marriage at the forefront. Jennifer Lawrence plays an absolutely feral woman who marries an unfaithful dimwit played by Robert Pattinson. That summary promises a broad comedy, but between Lawrence’s ferocious performance and Ramsay’s sensitive filmmaking, Die My Love is a rich movie about how some people should never be in a relationship.