This site contains affiliate links to products. We may receive a commission for purchases made through these links. Learn more

25 literary girls who'll break your heart

25 literary girls who'll break your heart

25 literary girls who'll break your heart

Literature is rife with villains. Just check out our malicious list of the most evil lines to ever grace the page. But there's nothing quite as dastardly as a woman with the ability to crush a heart with her words, actions and, yes sometimes, actual weapons.

We've already listed the movie girls who will break your heart but here are 25 literary heartbreakers. Steer clear okay?

Beware of spoilers...

Nana Coupeau (Nana)

Author: Emile Zola

Year: 1880

How would she do it? Plain and simple manipulation. She might start off lowly, but Zola’s eponymous anti-heroine has her eyes set on a higher prize. In an eerie foretaste of modern day celebrity culture, Nana has no recognisable talent, other than controlling men with her captivating beauty. She ruins every man that is bewitched by her – one gouges himself to death with a pair of scissors. Just imagine what fate will befall you. Actually, best not bother. Thankfully, she meets a suitably messy end. Just don’t fall under her spell before then.


Lori (Skippy Dies)

Author: Paul Murray

Year: 2010

How would she do it? In archetypal teenage style, this Frisbee-throwing temptress will use you to make another boy (a drug dealing psychopath no less) jealous. And while your geeky innocence will charm her (she’s not that evil really), she’s still engineering your ‘relationship’ for other means. Avoid doughnut eating competitions while nursing your broken heart.


Becky Sharp (Vanity Fair)

Author: William Makepeace Thackeray

Year: 1847-48

How would she do it? By using her copious feminine wiles. Unlike, say, Zola’s Nana, Becky is talented. She’s also ruthless, destructive and amoral. She’ll shamelessly flirt with you if she thinks you can assist her in her quest for financial betterment. She will lie (in fact she’s already secretly married), cheat and forget about you once you have fulfilled your purpose. Plus point being that unless you’re supremely loaded she won’t bother you.


Lady Susan Vernon (Lady Susan)

Author: Jane Austen

Year: 1871 (published)

How would she do it? Sex, stupid. Ok, maybe not actual sex – this is the 19th Century after all – but a wicked suggestion of it. She’ll seduce you, and even allow you to seduce her daughter (Lady Susan might be in her late 30s, but she looks devilishly younger), but behind this obvious attraction, she will selfishly manipulate you into marriage.


Rain Turner (Imperial Bedrooms)

Author: Bret Easton Ellis

Year: 2010

How would she do it? How would she do it? By appealing to your vainglorious ego. Like many of her deceitful kindred spirits, Rain possesses many of the traits commonly applied to femme fatales. You might think that you’re controlling her – she’s needy, young and ambitious; you’re mature, successful and charming – but, in reality, we all know who’s pulling the strings. Clue: it’s not you. Kleenex at the ready.


Catherine Earnshaw (Wuthering Heights)

Author: Emily Bronte

Year:1847

How would she do it? By ignoring her heart, shunning your advances (and her palpable love for you) and marrying your rather priggish rival for status. A complex web of deceit will follow and eventually cause havoc between her daughter and your son. You will always love her. She will always love you. But, too bad, she’s dead.


Bathsheba Everdene (Far From The Madding Crowd)

Author: Thomas Hardy

Year: 1874

How would she do it? The impossibly beautiful Bathsheba will befriend you, save your life, reject you, employ you, fire you, prance about with other men – eventually marrying one of them. Your heart will be broken, and then placed back together repeatedly. But, wait, what’s this? One day she will be yours. Just a bit of patience needed then. And a shedload of plasters for all those fractured hearts.


Moll Flanders (Moll Flanders)

Author: Daniel Defoe

Year: 1721

How would she do it? In a messy and convoluted manner: she will marry countless times (one colourful union will be to her half-brother), cheat, rob, seduce, spend time in Newgate Prison – all from a desire to find security. If you find yourself in the middle of this dense web, start praying.


Estella Havisham (Great Expectations)

Author: Charles Dickens

Year: 1860-1861

How would she do it? In a brazenly callous fashion. Having been raised by the notoriously cold-hearted Miss Havisham, Estella delights in breaking men’s hearts. She might see you in a sympathetic light (she might even secretly love you), but have no fear, that ticking muscle in your chest will splinter.


Margaret Pollitt (Cat On A Hot Tin Roof)

Author: Tennessee Williams

Year: 1955

How would she do it? The scheming Maggie (or Maggie the Cat as she’s otherwise referred to) will constantly nag you to step up and be a man. She will lie about being pregnant with your child. Oh, didn’t we say? You’re married to her. Them’s the breaks – at least Paul Newman will play you in the cinematic adaptation.


Nicole Diver (Tender Is The Night)

Author: F Scott Fitzgerald

Year: 1934

How would she do it? By slowly grinding you down. Originally, you will have the upper hand as Nicole – sweet Nicole – will be your patient. You’re a psychoanalyst; she’s a screwed up kid that’s had an incestuous relationship with her dad. Slowly, and surely, your life will become a mess. She will have an affair with your friend, and eventually divorce you to marry him.


Brigid O’Shaughnessy (The Maltese Falcon)

Author: Dashiell Hammett

Year: 1930

How would she do it? By asking you and your partner to investigate a possible abduction, which turns out to be a complete sham. She’s actually behind a labyrinthine web of murder, betrayal, robbery. You might feel some stirring in the loins for her, but when you discover she killed your partner you have to do the right thing.


Cathy Ames (East of Eden)

Author: John Steinbeck

Year: 1952

How would she do it? Well, as someone described as a ‘psychic monster’ with a ‘malformed soul’ there are a number of ways she could fracture your heart. When you meet her she’s already driven one man to suicide and framed two teenagers for rape. So sleeping with your brother (and possibly falling pregnant in the act), fleeing after giving birth to twins and shooting you is no big thing for this grotesque lady.


Lady Macbeth (Macbeth)

Author: William Shakespeare

Year: 1606

How would she do it? By urging you to kill your King. No biggie. Power will corrupt you. She’ll go mad. You’ll have your head chopped off. She’ll kill herself. Word to the wise. Don’t listen to anyone who suggests regicide. That way trouble lies.


Delilah (The Old Testament)

Author: n/a

Year: n/a

How would she do it? By getting you to reveal the secret of your superhuman strength – your long, luxurious locks, funnily enough. She’s given oodles of cash in exchange for extracting your secret. Minus your hair, you are also shorn of your power. You are captured by your enemies and blinded.


Alison Poole (Story Of My Life)

Author: Jay McInerney

Year: 1988

How would she do it? Think of the most vapid upper middle class blonde imaginable – her life is seven-days-a-week whirl of cocaine, parties, sex and money. She isn’t going to stay faithful to you. She has issues. Daddy issues. You might know your Shakespeare, but she knows how to get laid. Pain is coming quickly.


Daisy Buchanan (The Great Gatsby)

Author: F Scott Fitzgerald

Year: 1925

How would she do it? An extravagant cheater among cheaters, the shallow and frivolous Daisy is great fun to be around, but girlfriend material? No. Not unless you’re a millionaire – and from old money too. She might inspire you to riches, but at what cost?


Annie Wilkes (Misery)

Author: Stephen King

Year: 1987

How would she do it? How would she do it? Torture most likely. Annie is a serial killer, whose victims include 11 children, her own father, a college roommate and a hitchhiker who was also briefly her boyfriend. If you’re an author thinking of having a car crash, do NOT, under any circumstances have this car crash in the vicinity of Wilkes. It will not be pretty.


Abigail Williams (The Crucible)

Author: Arthur Miller

Year: 1952

How would she do it? Aged 17, she might be a mere slip of a lass but Abigail knows what she wants. And she doesn’t care what she has to do – accuse people of witchcraft specifically – to achieve it. Oh, you silly man, you fell for her feminine charms didn’t you? Best hope your wife doesn’t find out. What’s that you say? She has? Ooops.


Holly Golightly (Breakfast At Tiffany’s)

Author: Truman Capote

Year: 1958

How would she do it? She would accept all your gifts, your expensive meals, your introductions to fancy friends, but you would never know the real Holly. The creation was charismatic, stylish and fun, but she was just that; a chimera. The real Holly Golightly was a call girl. And no one wants to get involved with those ladies. It would never last.


Charlie Nicholson (High Fidelity)

Author: Nick Hornby

Year: 1995

How would she do it? Maybe the question should be how will you do it? Charlie is your ideal woman – beautiful, sophisticated, cool, knowledgeable, garrulous, we could go on. She’s also out of your league. You know it. You spend two years waiting for her to break your heart. She breaks your heart. With someone from her design course called Marco. Were you paranoid? Did you push her towards Marco? We all know the answer to that.


Dolores Haze (Lolita)

Author: Vladimir Nabokov

Year: 1955

How would she do it? By being herself – which is, as most will know, a rather knowing 12-year-old girl. Feeling repulsed. Good. You will go slowly mad. You deserve it.


Emma Bovary (Madame Bovary)

Author: Gustave Flaubert

Year: 1856

How would she do it? By holding a mirror up to your boring provincial life and shattering it. Frustrated by her empty life, hating you and craving something visceral she will have two affairs. As a consequence of her infidelities she will rack up piles of debt.


Verna Ekelof (Roger’s Version)

Author: John Updike

Year: 1986

How would she do it? By not-so-suggestively lifting her dress above her waist, thus exposing her non-knicker-wearing state. She is too young for you. You are too old for her. But she awakens a desire in you. Those extracurricular lessons you give her are a pretense. You know why you’re tutoring her. But have you learned nothing? Nothing good will come of this.


Anaïs Nin (Incest, From A Journal Of Love)

Author: Anaïs Nin

Year: 1992

How would she do it? A non-fiction entry, but boy would you have to have been made of some serious stuff to get involved with the erotic adventurer Anaïs Nin. She shamelessly repudiated the traditional diktats of marriage sleeping with countless authors and other artistes. Rumours of orgies, threesomes and the like also stuck to the colourful Nin. Could you handle her free spirit? Or would that heart of your’s finally crack?