Big-Screen Romances That Will Rip Your Heart Out

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We were warned about Miranda July’s The Future — that it’s darker than her debut feature, Me and You and Everyone We Know, and that we’d leave the theater questioning our own life and choices. All this is true, but it didn’t prepare us for just how devastated we would be by the film’s central couple, Sophie and Jason. We don’t want to spoil the ending for you, so we’ll only say that what becomes of the relationship isn’t simple but absolutely destroyed us. Ten more on-screen romances that left us shaken (and sometimes teary-eyed) are after the jump.

Blue Valentine

Michelle Williams and Ryan Gosling sound like they’d make the perfect movie couple — and, in fact, we fall in love with their relationship as they fall in love with each other in Blue Valentine. Gosling’s Dean loves Williams’s Cindy so much that he takes a beating on her behalf and raises another man’s child as his own; she abandons her dream of becoming a doctor to support the family and puts up with the many excesses of Dean’s personality. What makes Blue Valentine so painful is its close-up view of how even the most touching, sympathetic love may, over the years, become so twisted as to become irreparable.

Who’s Afraid of Virginia Woolf?

This classic was adapted from an Edward Albee play and directed by Mike Nichols — two guys who are experts at devastating us. The film’s central relationship, between a professor named George and his wife, Martha, is built on abuse and delusion, and yet we get the impression that they’re doomed to keep reliving their epic fights until one of them drops dead. Of course, the fact that married stars Elizabeth Taylor and Richard Burton would go on to divorce, remarry, and then split up again only adds to the realism.

Eternal Sunshine of the Spotless Mind

Michel Gondry’s most artistically successful film to date, Eternal Sunshine is a movie about a couple who are so disturbed by the break-up of their two-year relationship that they both feel the need to forget they ever knew met — and are successful thanks to a mysterious company called Lacuna, Inc. that specializes in selectively erasing clients’ memories. When Clementine (Kate Winslet) and Joel (Jim Carrey) meet again and eventually discover that they dated in the past, they resolve that this time will be different. Us? Unfortunately, we know better.

Brokeback Mountain

Heath Ledger and Jake Gyllenhaal broke our hearts in this film, directed by Ang Lee and adapted from an Annie Proulx story, about two cowboys who loved each other for decades, beginning in 1963, but were pulled apart by a society that never would have accepted their relationship. While one meets a tragic end, the other is left with his memories and regrets.

Candy

Less famous than Brokeback Mountain (at least in the US) but equally heartbreaking is Ledger’s next film, Candy, which tells the story of a bohemian couple who fall hard for heroin and devolve into desperate junkies. Tormented by his guilt over having introduced Candy (Abbie Cornish) to the drug — which caused her to become a prostitute and deliver a stillborn baby — Dan (Ledger) realizes that their relationship needs to end if either of them is ever to get clean.

Annie Hall

Yes, Woody Allen’s masterpiece is technically a comedy. But there is something so charming about the impossible love between Allen’s Alvy and Diane Keaton’s Annie that it always tears us up to see that, despite their continued efforts, they aren’t meant to be. That final scene, where they get together as friends and Alvy muses on why we keep offering ourselves up to hurt, gets to us every time.

Casablanca

This may be an obvious pick, but omitting Casablanca from this type of list would surely be an oversight. Reunited with his former lover, Ilsa (Ingrid Bergman), in the titular city, Rick (Humphrey Bogart) orchestrates a brilliant escape to Lisbon for her imperiled husband, Laszlo — and then sacrifices his happiness for the greater good, persuading Ilsa to go with Laszlo instead of staying with him. If you can get all the way through “Maybe not today, maybe not tomorrow, but soon and for the rest of your life” without getting choked up, you might just be dead inside.

Heavenly Creatures

Heath Ledger isn’t the only actor with two films on this list: Kate Winslet earns her second slot with 1994’s Heavenly Creatures. In this early role, she plays Juliet, a teenager in New Zealand who quickly forms an intense and co-dependent friendship-turned-love affair with her classmate, Pauline (Melanie Lynskey). The relationship eventually blossoms into a full-out, twisted mutual obsession, with achingly tragic results.

Love Story

We’ve tried to steer clear of cheesy tearjerkers with this list, largely because pure romantic melodrama rarely gets to us. But we have to admit to having a soft spot for 1970’s Love Story, which tells the tale of Oliver (Ryan O’Neal) and Jennifer (Ali MacGraw), a photogenic couple from two very different background who fall for each other, marry young, and struggle to make it on their own after Oliver’s wealthy father cuts him off. The movie turns weepy when, at the age of 24, Jenny is diagnosed with a terminal illness and young love turns to untimely death.

Romeo and Juliet

While Baz Luhrmann’s ’90s update of Shakespeare’s immortal love story was an impressive spectacle, only a Leonardo DiCaprio-crazed tween would argue that it hits harder than Franco Zeffirelli’s 1968 version, starring Leonard Whiting and Olivia Hussey in the title roles. The relatively unknown actors played the parts beautifully — partially because they were actually as young as the Romeo and Juliet Shakespeare intended, they were utterly believable as two teenagers doomed by forbidden love.