These Are The Biggest Heartbreakers In Literature

17 Book Characters Who Are Total Heartbreakers
Actor Clark Gable, as Rhett Butler, and Vivien Leigh, as Scarlett O'Hara, passionately look at each other in a scene from the movie Gone with the Wind by Victor Fleming. United States, 1939. (Photo by Mondadori Portfolio via Getty Images)
Actor Clark Gable, as Rhett Butler, and Vivien Leigh, as Scarlett O'Hara, passionately look at each other in a scene from the movie Gone with the Wind by Victor Fleming. United States, 1939. (Photo by Mondadori Portfolio via Getty Images)

There's nothing quite like the feeling of having your heart metaphorically ripped out of your chest. Whether it be unrequited love or a messy breakup, heartbreak can be absolutely unbearable.

Book characters fare no better than we do (in fact, they probably fare much worse). Though "Great Expectations"'s Pip pines after Estella for about 15 years, he never ends up with her (Dickens was pressured into changing the ending of the book to make it appear SLIGHTLY more hopeful for the pair). Several of literature's heartbreak victims are even driven to suicide. The cads and temptresses that seduce unwitting victims tend to feel little repentance for their actions, either. (Authors aren't much better than their characters. We also have a list of author heartbreakers).

Without further ado, here are the biggest heartbreakers in literature:

estella havisham

Estella Havisham from Charles Dickens's "Great Expectations"

Well, Estella is actually RAISED to be a heartbreaker (by her crazy guardian who never takes off the wedding dress she was jilted in), so what did you expect? Pip is in love with her from the moment he sees her, but she is always cruel to him. Despite this, he never falls out of love. As Estella grows older, she is courted by many men. Estella goes on to marry a total scumbag, even after Pip confesses his love for her. After the scumbag dies, Estella and Pip meet again, promising to remain friends (though we'd like to imagine there is no romantic hope for this pair...Pip is way too good for her).

Brett Ashley from Ernest Hemingway's "The Sun Also Rises"

When stunning divorcée Brett Ashley enters Jake Barnes's life, the first thing he can think of her is that she is “damned good-looking." Not only that, but she's pretty much one of the boys. She dresses masculinely, wearing a man's hat and refusing to wear stockings. Her hair is cut androgynously. She also behaves like a stereotypical man: She sleeps around and not only has extreme sexual confidence but openly admits to enjoying sex. Jack Barnes adores her, but his impotence renders Ashley uninterested in anything but friendship. While in Spain, she takes up with a bullfighter, leaving Barnes brokenhearted. The closing scene is one of the BEST heartbreaking scenes in literature. Brett says, “Oh, Jake...we could have had such a damned good time together" and he responds, "Yes...isn't it pretty to think so?" SIGH.

rhett butler

Scarlett O'Hara AND Rhett Butler from Margaret Mitchell's "Gone With the Wind"

Scarlett and Rhett are kind of tied for this one. Scarlett is known for being a flirt, and many men adore her. When we meet Rhett, we know he has the reputation of being a rogue. Of course they are going to have a tumultuous hot-cold relationship. They eventually get married, and say a ton of horribly mean things to each other, Rhett is a drunk, Scarlett has an emotional affair, and one of their fights ends in Scarlett falling down the stairs and losing her unborn child. Rhett leaves at the end, and Scarlett is still convinced that she can make him love her. He's also known for one of the most cavalierly douch-y lines in literature: "My dear, I don't give a damn" (slightly different from the film).

Yunior from Junot Diaz's "This Is How You Lose Her"

This whole book is basically about how Yunior screws up every single relationship he has ever been in because he is such a cheater. He goes from woman to woman, screwing each and every one of them over. I admit, he does learn a lot, and he begins to see how to become a better romantic partner. But he definitely starts off as a total heartbreaking jerk.

Steerforth in Charles Dickens's "David Copperfield"

David Copperfield introduces Steerforth, an old college friend, to an acquaintance of his, Little Em'ly, and they end up running off together and "living in sin." Eventually, Steerforth leaves her and she is socially ruined. She has to move all the way to Australia to escape the vicious gossip. What a guy!

Richard Katz from Jonathan Franzen's "Freedom"

Richard Katz is a classic heartbreaker. He's in a band. He sleeps with all the girls. He's one of those guys about whom every pretty girl thinks, I bet I can tame him, before getting her heart ripped out of her chest. Patty thinks she can date him as well, but ends up settling for the safe, boring, obnoxious Walter and living unhappily ever after.

daisy buchanan

Daisy Buchanan from F. Scott Fitzgerald's "The Great Gatsby"

Daisy is kind of the worst. Even though I personally find Gatsby super annoying in his going on and on about Daisy (this whole book is essentially about Gatsby showing off for Daisy), I still felt sorry for the guy. Daisy strings Gatsby along, giving him the impression that she'll eventually leave her cheating, kind of scary husband. She never really intends to. Gatsby wastes his whole life just to impress ONE girl, and she ends up blowing him off in the end. Sad.

Lotte in Johann Wolfgang von Goethe's "Sorrows of Young Werther"

Essentially the SORROWS of Werther are all a direct result of Lotte. Lotte is already engaged to a man 11 years her senior, but even though Werther knows this, he falls in love with her. He becomes really close friends with both members of the engagement (maybe he's a masochist?). After she gets married, Lotte says it's probably not a good idea that Werther visits so much, and she cuts him off. Werther comes to the conclusion that someone in the love triangle has to die (I'm not really sure why he comes to this conclusion), and he knows he can't take another's life, so he decides to take his own. He shoots himself, but doesn't even die for 12 whole hours. Lotte doesn't come to his funeral. In a lot of ways, none of this is Lotte's fault, so she's kind of an INDIRECT heartbreaker.

Trip Fontaine from Jeffrey Eugenides's "The Virgin Suicides"

Everyone in school is obsessed with Trip! He ends up choosing Lux Lisbon. He even manages to charm her ridiculously uptight, strict parents into letting her go to the homecoming dance, where he has sex with Lux on a football field (probably taking her virginity). He disappears after that, and Lux starts having sex with strangers. Eventually, she commits suicide (although this is not directly related to Trip).

the picture of dorian gray

Dorian Gray in Oscar Wilde's "The Picture of Dorian Gray"

Dorian Gray is one of the biggest literary scumbags of all time. He causes a girl to KILL herself over him, for goodness' sake. Basil is also probably unrequitedly in love with him. First of all, Dorian is so good looking that absolutely everyone is in love with him. Secondly, he essentially has no soul, so he has no qualms over breaking hearts. Thirdly, he doesn't age, so he can just do it forever. However, he DOES end up punishing himself for all his cruelty at the very end by killing himself. Not a very happy ending.

Zenia from Margaret Atwood's "The Robber Bride"

Zenia is super beautiful and charismatic. She's really good at winning people over, both as friends and lovers. She uses these capabilities to seduce every single one of her close friends' love interests. Way harsh. We mean, that's not only breaking the hearts of all these men, but also leaving her good female friends devastated as well.


Edward Fairfax Rochester Rochester from "Jane Eyre"

Where to even begin with Rochester? We know some people like to think of "Jane Eyre" as a romantic story, but it certainly doesn't begin that way. I have always thought that Rochester KNOWS from the beginning that Jane has feelings for him, but that he toys with her intentionally. It honestly does appear that Rochester was courting Blanche Ingram, and not Jane. Who could blame Jane for thinking so? Also, when he proposes to Jane, he forgets to mention that he has his wife locked up in the attic. Yikes.

Rodolphe Boulanger from Gustave Flaubert's "Emma Bovary"

Emma herself is no saint, but Rodolphe is just mean. Poor Emma is so romantic at heart; she wants her life to be a romance novel. She really just wants to run away, and escape her boring marriage. She begins to have a heated, steamy affair with Rodolphe, who promises her they will run away together...then he just ups and runs away alone.

hamlet kenneth branagh

Hamlet in William Shakespeare's "Hamlet"

Hamlet becomes consumed with killing his uncle, and forgets about Ophelia, the poor girl he used to love and have sex with. Oh, also, Hamlet also accidentally kills her father. Ophelia totally loses it at that point, and drowns herself. When Hamlet goes to the graveyard and sees her grave, he doesn't even realize she is dead until her funeral starts and they bring her body out. We know he's a busy guy, but come on. He then gets in a fight with Ophelia's brother about how much he had loved Ophelia...but we think actions speak louder than words. The guy didn't even know she was dead, for crying out loud!

George Wickham from Jane Austen's "Pride and Prejudice"

Oh, Wickham. There are quite a few cads in Jane Austen's novels (hello, John Willoughby), but we think Wickham takes the cake. What a scoundrel. First, he gets Elizabeth to fall for him, and tells her a made up story of Darcy being a jerk (the truth is that Wickham had tried to elope with Darcy's very young sister in order to get all of her money). He then takes off with Elizabeth's young dumb sister, demanding money in exchange for his marriage to her. There really is no appropriate word for this guy.

Catherine Earnshaw from Emily Brontë's "Wuthering Heights"

Despite Catherine's love and adoration for her childhood best friend, Heathcliff, she decides that he's too low class for her and goes off and marries another. Heathcliff pines away for her, going so far as to leave in order to become a "gentleman." Catherine dies prematurely. Even after she DIES, she haunts him! How cruel is that?!

CORRECTION: An earlier version of this article stated that Little Em'ly from Charles Dickens's "David Copperfield" was his cousin. This has been corrected.

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