8 Epically Doomed Relationships in Literature

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Some relationships are doomed before they even begin. While it stinks to experience dramatic breakups in real life, it’s often exhilarating to read about these roller coaster romances from the safety of our bedrooms. From star-crossed teenagers to mythical Greeks, here are some of literature’s most tragic couples.

Orpheus and Eurydice from Greek Mythology

Romeo and Juliet from Romeo and Juliet by William Shakespeare

Heathcliff and Catherine from Wuthering Heights by Emily Brontë

Vronsky and Anna from Anna Karenina by Leo Tolstoy

Gatsby and Daisy from The Great Gatsby by F. Scott Fitzgerald

Winston and Julia from 1984 by George Orwell

Frank and April from Revolutionary Road by Richard Yates

Augustus and Hazel from The Fault in Our Stars by John Green


When Orpheus’ wife dies from a snake bite on their wedding night, he does what any doting husband would do: he dives down to the depths of the Underworld to rescue her. After hashing things out with Hades, Eurydice is freed on the condition that Orpheus will not look at her until they return to Greece. Given that this is a list of doomed lovers, it shouldn’t come as a surprise that Orpheus fails. His beloved is sent back to the Underworld, leaving Orpheus to wander the countryside singing the most lovelorn songs this side of a Bright Eyes concert.


These teens set the template for star-crossed lovers everywhere (the phrase didn’t even exist until Shakespeare made it up). While we know they’re doomed from the start, the most frustrating part isn’t their warring families forbidding their love but rather their ridiculous lack of communication skills. If Juliet had told Romeo she was just pretending to be dead, they’d have never gotten into this mess. But hey, at least they inspired a great Dire Straits song.


Heathcliff, an orphaned gypsy raised by the Earnshaw family, falls in love with their daughter Catherine. Despite their seemingly all-encompassing romance, Catherine opts to marry for status instead of love, leaving a raging Heathcliff to lash out via acts of vengeance. Set among the gothic moors of England, this is selfish and self-destructive love at it’s best.


Sure, sacrifices are made in any relationships, but the countless losses Anna and Vronsky endure are depressingly unbearable — especially for her. When the two leave their respective lovers to be with each other, Vronsky’s career slightly suffers, but it’s Anna who really loses everything (her son, her social standing… her sanity). You can’t really fault her for the fatal train incident that ensues, can you?


Fitzgerald’s searing critique of the roaring twenties and the American dream also gave readers one of literature’s most doomed romances. Mysterious millionaires, self-absorbed flapper girls and jealous, murderous husbands are just some of the elements working against Daisy and Gatsby’s affair. But lucky for us, the tragedy is so beautifully and symbolically told that we keep coming back to it decades after its initial publication.


There is no way for love to bloom in a totalitarian state, but that doesn’t stop Winston and Julia from trying. The couple surreptitiously engage in a passionate affair, one that leads them to conspire to overthrow their dystopian dictatorship. As the novel’s bleak ending proves, however, the tortuous tyranny of Big Brother is ultimately stronger than any emotional bond the lovers might share.


Suburban ennui can be a relationship killer; no couple knows this more than Frank and April Wheeler. The Connecticut suburbs of the 1960s breed marital angst, boredom and adultery. Despite the couple’s best attempts to escape their white picket fence cage, they remain eternally dysfunctional and ultimately doomed. Once April becomes pregnant with their third child, circumstances are so dire there is no way these two can be redeemed.


A book about teenagers with terminal cancer can’t possibly end with dry eyes. When Augustus and Hazel embark on a romantic relationship, they are just as aware as the reader of their limited time together, and boy do they make the most of it. An exotic trip to Amsterdam in search of their favorite author finds them making out in the Anne Frank house and living life beyond anything they’d ever imagined.

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