13 Of The Worst Heartbreaks In Literary History

20th Century Fox

Anyone who loves books as much as I do knows that sometimes the attachments you form with characters on the page are as strong — or sometimes (maybe embarrassingly) stronger — than the attachments you form with people in your real life. And once you’re on that roller coaster of narrative arcs and plot twists, there’s usually no getting off until the book’s end — which means when your favorite characters are overwhelmed with joy, you’re overwhelmed with joy too; and when they’re heartbroken, you’re sobbing between the covers right along with them. (Something that can make for some seriously soggy literature. This would be the time for that waterproof cover for your Kindle.)

But while some of the greatest heartbreaks in literature can be found in the romance section of the bookstore — tales of unrequited love, or love lost — that’s hardly always the case. While I’ve cried my fair share of tears over literary romances that just didn’t make it, I’ve also been known to grow a tad verklempt over everything from epic literary deaths and beloved fictional dogs to the egregious acts of injustice some of my favorite book characters have had to face. Though it all, I’m just sniffling away.

If you’re in the mood to indulge in some totally tear-worthy tales, check out these 13 literary heartbreaks that still make us cry.

Hazel Lancaster and Augustus Waters in ‘The Fault in Our Stars’ by John Green

Of course John Green starts this list (and appears again later) because everything he writes makes practically everyone who reads it cry. And cry. And cry and cry. I can appreciate that this doomed couple started to fall in love by exchanging their favorite novels, though.

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Louisa Clark and Will Traynor in ‘Me Before You' by Jojo Moyes

There’s nothing like falling in love with someone who you know, at least theoretically, has six months left to live. (Why is it always “six months left to live”, by the way? Does anyone know? Is there something especially sad about six, as opposed to say, five or seven?) Quite frankly, if I were Louisa, I think I would have been more pissed off at Will than heartbroken.

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Fred Weasley in ‘Harry Potter and the Deathly Hallows’ by J.K. Rowling

I will always be salty about this. Because honestly, like, why? Why did Fred have to die? And, perhaps even more heartbreaking, why did George have to spend the rest of his life without his twin? It's just wrong. I’M LOOKING AT YOU, J.K. ROWLING.

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Tom Robinson in ‘To Kill a Mockingbird’ by Harper Lee

Every time I pick up Harper Lee’s To Kill a Mockingbird — maybe once every few years — I always find myself wishing that Tom Robinson’s life ended differently (as in: not at all.) This is one of those heartbreaking literary deaths, filled with injustice, that readers will just never get over.

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Miles Halter and Alaska Young in ‘Looking for Alaska’ by John Green

When it comes to romantic heartbreak, there’s unrequited love and there’s love found and then lost, but there’s also something especially sharp about the experience of a love never-realized, that never WILL be realized because of a life cut short. And John Green just keeps breaking our YA-lovin’ hearts over and over again.

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Matthew Cuthbert in ‘Anne of Green Gables’ by L.M. Montgomery

The death of one of the sweetest old men to ever grace the pages of literature is something I will never get over, no matter how many times I venture back into Green Gables. It’s unbelievably devastating for Anne, sure — but there’s also something totally tear-worthy about the fact that Matthew never got to see everything she became.

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Theodore Finch and Violet Markey in ‘All the Bright Places' by Jennifer Niven

There’s nothing like a near double-suicide to bring a couple together. But while Finch helps Violet learn how to save herself, nobody in Finch’s life — including the teen himself — is able to save him. (But it really wasn’t Violet’s fault. If anything you could maybe blame her parents.)

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Anney and Ruth Anne "Bone" Boatwright in ‘Bastard Out of Caroline’ by Dorothy Allison

Sometimes the heartbreaks we face courtesy of our parents — the people in the world who should want to break our hearts least — are some of the hardest, and what little Bone Boatwright endures from her mother, Anney, is no exception. Even Anney’s last gesture to Bone, though it saved her daughter, was so utterly sad and final.

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Jack Twist and Ennis Del Mar in ‘Brokeback Mountain’ by Annie Proulx

Honestly, if these two could have just gotten off of that mountain and out of Wyoming, I don’t think any of us would have been left crying nearly as much.

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Noah Calhoun and Allie Nelson in ‘The Notebook’ by Nicholas Sparks

Anyone who loves a good literary romance knows that Nicholas Sparks’s The Notebook is a tear-jerking classic (and not just because you’re wishing YOU could make-out with Ryan Gosling in the rain.) While it’s heartbreaking to lose the one you love young, there’s almost something even more devastating about losing them after a lifetime. And Noah, technically, lost Allie twice.

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Susie Salmon in ‘The Lovely Bones’ by Alice Sebold

What clobbers me most about this one is that Susie Salmon, the young rape and murder victim at the heart of Alice Sebold’s The Lovely Bones, so very desperately wanted to live. I think she was more heartbroken by her death than anybody (except, maybe, me.)

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Carrie Bell in ‘The Dive From Clausen’s Pier’ by Ann Packer

I know plenty of readers who totally disagree with me on this one, but here’s the thing: there are the heartbreaks that are inflicted upon you by others, and then there are those rare moments when you break your own heart. And sometimes those can hurt the worst. Carrie should have stayed in New York, that’s all I’m saying.

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David and Giovanni in ‘Giovanni’s Room’ by James Baldwin

This entire novel is written by Giovanni’s lover, David, on the night before Giovanni is about to be executed (I mean, for committing murder, but still.) If that’s not painful enough, practically every character in Giovanni’s Room is living a double life that is slowly killing them, if not literally, then in spirit.

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