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10 Tragic Love Stories That Will Break Your Heart

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The 14th of February seems happy and harmless. Flowers and chocolates! Sappy notes and shameless rom-coms! Obligatory dinner dates. Candy hearts. Lots and lots of pink.

But V-Day’s contemporary style is as far removed from its origins as your family’s Thanksgiving dinner is from your syphilis-sharing Pilgrim predecessors. Valentine’s Day is rooted in violence and loss. Brutality. Death. The punishment of the innocent. V-Day’s always had love notes and flowers. It’s just that they were written moments before slaughter and placed carefully next to a cracked skull and a fresh grave.

So in the true spirit of Valentine’s Day, here are 10 Tragic Love Stories that Will Break Your Heart. Because as St. Valentine knew better than anyone, the best romances don’t end happily, and the greatest love stories are tragedies above all.


1. Lolita by Vladimir Nabokov

Yes, it’s creepy. But it’s also a tragic love story. Perhaps one of the greatest ever written. A pedophiliac road trip that turns into a suburban farce, it features an entirely unreliable, endlessly nauseating, yet inexplicably compelling narrator–a middle-aged lit professor in love with a 12 year old girl. After causing the death of her mother, then driving her across an American wilderness, Humbert Humbert is part Walter White, part Kevin Spacey in American Beauty. And he’s Nabokov’s most magical accomplishment: an at-once pathetic, frustratingly endearing, unquestionably disgusting figure. His final act–to kill a man who has taken advantage of his now-grown Lolita–is both satisfying and ironic. The story ends as you’d imagine: in complete ruination of everyone involved.


2. Never Let Me Go by Kazuo Ishiguro

Skip the movie–despite Carrie Mulligan and Kiera Knightley.  Read the book. Ishiguro’s sleight of hand will astonish you, and 100 pages in you’ll feel your stomach drop. Then you’ll fly to the end. Teenagers in England, growing up as friends in a strange kind of boarding school, are forced to confront the meaning of their short lives and imagine the possibility that love and friendship can make their years mean more than their commodotized bodies. This novel will crush you. And the pleasure of that pain will make you want to read it again.


3. Giovanni’s Room by James Baldwin

I read Giovanni’s Room for a literature class in college. It is the one novel that has stayed with me after all these years (there is no shortage of good quotes). No one gets closer to the essence of human emotion than Baldwin does—he claws at it, pokes and prods at it, fully exposes it. He understands pain, forces his reader to feel every last ounce of it along with the characters. It’s an intense, fearless love story involving three different people. You’ll fall in love with all of them.


4. The House of Mirth by Edith Wharton

Astonishingly contemporary for a book written 110 years ago, Wharton’s breakout novel features a young, hot Lily Bart, who might as well be a millennial in modern-day midtown Manhattan. Caught in a sticky social web of wealth and infidelity, Lily clumsily traverses a world of elite parties and stock market gamesmanship, engaging in an endless series of missed connections with the man she’s meant to be with. Scandals in New York lead to scandals in Europe. Millions are lost and gained. Yacht trips are taken. This is Gatsby before F Scott. The moral vacuum of the Manhattanite elite before Wolfe was born to write it. Eventually Lilly has her moral awakening. And the man of her dreams realizes he loves her as she him. But in a master-stroke of love eternally unrequited, he arrives to tell her so mere hours after she has expired from an overdose of sleeping pills. Ouch.


5. This is How You Lose Her by Junot Diaz

This novel, like Drown and The Brief Wondrous Life of Oscar Wao, features our favorite reckless bad boy, Yunior. While Diaz’s two other novels focus mainly on Yunior’s childhood and formidable years, in This is How You Lose Her, we zoom in on his tumultuous and confused love life. It’s a side of Diaz that isn’t quite exposed in his other books—we are witness to a different type of hurt, caused by Yunior’s careless/selfish decisions in his encounters with various women.  My favorite line: “And that’s when I know it’s over. As soon as you start thinking about the beginning, it’s the end.”


6. The Notebook by Nicholas Sparks

If you haven’t yet read or seen the movie, I suggest you do, either by yourself or with a loved one—it’s by far, Nicholas Sparks’ best novel. It’s a story filled with love and loss, and finding love again, and with characters that you find yourself becoming so completely attached to that you refuse to accept anything but a happy ending. You’ll cry—a lot. So keep that pile of tissues close.


7. The Woman Upstairs by Claire Messud

This is a book in which nothing happens. And that’s why it’s magic. For anyone who has ever felt like they are living on “the treadmill of the ordinary” in “a cage built of convention and consumerism and obligation and fear,” this book gives you a mirror. A broken woman, lost in her regrets and addicted to replaying the inequities of the past, offers a picture of the invisible, inconsequential person we all fear we’ll become. Reading it forces you to climb deep inside the castle of your own insecurities. Close it and you come back out again, broken and motivated, eyes open to the small tragedies of the lives that stride past you on the snowy sidewalk.


8. The Wings of the Dove by Henry James

If you thought House of Mirth harnessed melodrama to drive a dagger through your heart, just wait until Henry James introduces you to Milly Theale. Pristine in every way, wealthy beyond belief, Milly’s flaws number only one: she is dying. Tragic news on its own terms, but more tragic still when the news reaches Densher, the handsome Londoner that Milly has fallen in love with. But Densher, lacking in money or social standing, is in love with Kate, who is no better off than he. You can guess the plan: Densher will trick Milly into thinking he loves her. They’ll marry. She’ll die. And Voila! Densher will inherit her cash and then he’ll marry Kate. Happily ever after. The brilliant plan failed to account for one detail: Milly’s unshakeable kindness, her unflappable spirit. As the con plays out, Densher is won over by the dying woman’s moral brilliance, and after her death he presents Kate with a terrible choice: turn down all the money and marry him, or take all the money and lose him. Few novels ask the reader more directly to imagine which they’d choose: money or love.


9. The Bell Jar by Sylvia Plath

I know, The Bell Jar isn’t your typical lovey-dovey, romance novel–it’s way beyond that. This novel is the closest we’ll ever get to the true Sylvia Plath. But more than that, it’s a twisted coming of age story of a young girl trying to chase her dreams in the city known for its glamour, wealth, and fame. I view it as being about the importance of learning to love yourself, and I don’t think Sylvia Plath’s Esther Greenwood ever had that chance. Instead, she was locked away in a psych ward, essentially pushed into her insanity.


10. Under the Jeweled Sky by Alison McQueen

I had the privilege of reading Under the Jeweled Sky while it was still in draft form, and I hadn’t read such a brilliant and beautiful, emotionally-charged love story in so long. I followed the main character Sophie from her gardens in India to the gloom of London, and back again. It’s a deep exploration into forbidden love, scandal, and leaving a beloved and magical place behind. You’ll be teary-eyed at the end but you’ll have become attached to Sophie, and you’ll be better for it. TC mark

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    • Alexandria

      Reblogged this on The Chronicles of Me.

    • Deboleena Roy

      Reblogged this on A Summer Garden and commented:
      Found the reading list I was looking for

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