The Best Movies About Strange Relationships

Cinema saves its sharpest love stories for its strangest couples. A boy and a woman sixty years older. A man and the voice inside his computer. These pairings should not work on paper, yet they hold up better than most conventional romances, because the oddness forces the writing to earn every feeling the audience gives back.

Harold and Maude (1971)

Hal Ashby’s black comedy pairs Harold, a young man who stages fake suicides to unsettle his mother, with Maude, a 79-year-old who steals cars and treats every day as her last. The sixty-year age gap is the joke and the point. What begins as a morbid friendship turns into a genuine romance, and the film treats it without a wink or an apology. Panned on release, it became a cult classic and now appears on film-school syllabuses as a study in tone. Cat Stevens wrote the soundtrack. It remains one of the few films that can hold death and joy in the same frame without cheapening either.

Her (2013)

Spike Jonze imagines a lonely writer, Theodore, who falls in love with an artificial-intelligence operating system named Samantha, voiced by Scarlett Johansson. The relationship is tender and real even though one half of it has no body. Jonze uses the setup to ask what intimacy needs and how much of it can survive without flesh. The film won the Academy Award for best original screenplay. Its warmth keeps it from feeling like a gimmick, and the ending lands harder than most human breakups on screen, because Samantha outgrows Theodore in a way no person could.

The Shape of Water (2017)

Guillermo del Toro builds a fairy tale around Elisa, a mute cleaner in a 1960s government lab, and the amphibious creature held captive there. She teaches it sign language, feeds it eggs, and falls for it, all without a word of dialogue between them. Del Toro plays the romance straight and refuses to treat the creature as a monster. The film won best picture and best director at the Oscars. It works because Elisa’s silence makes her an outsider too, so the pairing looks like two overlooked beings finding each other.

Lars and the Real Girl (2007)

Craig Gillespie’s film follows Lars, a shy man in a small town who orders a lifelike doll and introduces her to everyone as his girlfriend, Bianca. The premise sounds like a crude joke, and the film refuses to make it one. The town, on advice from a doctor, plays along, and the delusion becomes a slow route back to real human contact for a man who cannot manage it directly. Ryan Gosling plays Lars with total sincerity. The result is gentle and sad, a story about grief and isolation told as an odd comedy.

Sugar Daddy (2020)

Wendy Morgan’s Canadian drama follows Darren, a broke and talented young musician played by Kelly McCormack, who signs up to a paid-dating service to buy herself time to write. She steps into life as a sugar baby, and the film follows how that world reshapes her music and her sense of who she is. Morgan keeps the tone observational and unforced, letting Darren make her own choices and live with them. The film premiered at the Whistler Film Festival and won two Canadian Screen Awards. It belongs on this list because it takes an unusual modern relationship seriously as its subject.

Secretary (2002)

Steven Shainberg’s Secretary puts a dominant lawyer, played by James Spader, and his submissive assistant, played by Maggie Gyllenhaal, into a relationship built on rules most offices would fire people over. The film treats their dynamic as a form of care, tracking how each one finds something they need in it. Gyllenhaal’s performance turns what could have been lurid into something oddly warm. It divided audiences on release and has aged into a landmark for putting an unconventional relationship on screen without moralising about it.

Phantom Thread (2017)

Paul Thomas Anderson sets his film in 1950s London couture, where Reynolds Woodcock, a controlling dressmaker played by Daniel Day-Lewis, meets Alma, a waitress who becomes his muse and then his match. The power in the relationship shifts in ways neither expects, and the film turns a story about control into something close to a strange marriage of equals. Day-Lewis called Phantom Thread his final acting role. The tension comes from how far each will go to hold the upper hand.

The Lobster (2015)

The Lobster, from Yorgos Lanthimos, builds a deadpan dystopia where single people are sent to a hotel and given 45 days to find a partner or be turned into an animal of their choosing. Colin Farrell plays a man who flees into the woods, where a rebel group bans romance entirely. The film uses its absurd rules to satirise how society pressures people to couple up and punishes those who stay single. Its flat, affectless tone makes the cruelty funny and unsettling at once. Few films this strange are also this pointed about ordinary dating.

Eternal Sunshine of the Spotless Mind (2004)

Eternal Sunshine of the Spotless Mind, directed by Michel Gondry and written by Charlie Kaufman, follows Joel and Clementine, a couple who each pay a clinic to erase all memory of the other after a bad breakup. Most of the film happens inside Joel’s head as the procedure runs and he changes his mind, fighting to keep the memories he asked to lose. Jim Carrey and Kate Winslet play against type. The relationship is ordinary in its faults, and the science-fiction frame is what makes it strange, asking if you would still choose someone when you could delete the pain they caused.

Odd Couples on Film

These films last because oddness raises the stakes. A normal couple can coast on familiarity, while a boy and an old woman, a man and a machine, or a dressmaker and his muse have to make the case for the relationship scene by scene. That pressure is what produces the best writing. Familiar love may be easier to root for, but it is the strange pairings that stay with you long after the credits.