Lily Bart, The House of Mirth
Poor Lily. She has every chance in the world to become the wealthy, well-regarded woman she wanted to be, but she sabotages them all, rejecting various socially advantageous marriage proposals, innocently (but indecently!) visiting bachelors in their private rooms, accepting money from a friend’s husband. Ultimately, the vicious gossip and better played hands of the other women in her social circle ruins her, and in the end, she dies from an overdose of the sleeping potion that had been her last refuge, just as the only man she truly loved was on his way to tell her he felt the same.
Patty Berglund, Freedom
You know it’s going to be a rough road for Patty when, 150 pages into Franzen’s much-lauded novel, a new section begins, titled “Mistakes Were Made: Autobiography of Patty Berglund by Patty Berglund (Composed at Her Therapist’s Suggestion).” True enough, Patty’s trajectory seems to be built from almost nothing but mistakes, despite her usually-good intentions. Her marriage deteriorates due to her own confusion and selfishness (and her affair with her husband’s best friend), she becomes estranged from the son she loves to the point of distraction, and though she ultimately faces her mistakes and convinces Walter to take her back, the reunion is bittersweet, and nearly too late.
Bridget Jones, Bridget Jones’s Diary
Is there any contemporary heroine as charmingly hopeless as Helen Fielding’s Bridget Jones? A Singleton in a sea of Smug Marrieds, Bridget frets about her weight, her smoking, and her dying alone in her apartment. She beds her handsome boss to disastrous results, constantly embarrasses herself at work and in social settings, and nearly ruins her chances with, ahem, Mr. Darcy, responding to each setback by drowning herself in alcohol, cigarettes, and sugar-based foods. Unlike some of the others on this list, Bridget’s fuck-up status is more funny than tragic, perhaps it’s because we know it will all work out in the end. Or because she slides down a fireman’s pole and shows her panties to all of Britain. Either one.
Emma Bovary, Madame Bovary
In Flaubert’s masterpiece, hopeless romantic Emma Bovary is dissatisfied with her provincial life, considering it dull and passionless. To amuse herself, she engages in multiple affairs and spends as much money as she can manage, building an enormous amount of debt. Her devoted husband sees nothing of her faults and loves her unconditionally, but she hates him for what she sees as him commonness. Easily influenced by anything or anyone she deems romantic or high class, when she sees the opera “Lucia di Lammermoor,” she becomes obsessed with Lucy Ashton as the example of how to be a woman, and decides to follow in her footsteps and kill herself. She did get one thing right, however: self-styled as a tragic heroine, she succeeds in becoming truly tragic indeed.
Anna Karenina, Anna Karenina
Aptly, this novel begins with one of the most quoted lines about unhappiness: “Happy families are all alike; every unhappy family is unhappy in its own way.” Like Lily Bart, Anna Karenina starts off with everything. She is highly born and well-married to an affluent senior statesman, yet she falls in love with the young Count Vronsky and begins an affair that will lead to her downfall. Vronsky is willing to marry her should she leave her husband, but Anna cannot cope with the concept of disgracing herself socially and leaving the safety of her marriage, and so waffles in the middle space, paralyzed by her fear and confusion. Eventually, Vronsky and Anna move to Europe, but still Anna is not happy, becoming more and more paranoid that he will betray her as she betrayed her first husband, and ultimately kills herself.
The Lisbon Sisters, The Virgin Suicides
Whatever is going on with Lux Lisbon and her sisters isn’t quite as evident as the problems plaguing most of the other women on this list. Nor do they systematically sabotage their own lives in quite the same way, unless you count deliberately missing curfew. However, they make the list for being blessed with the best of circumstances — loving family, comfortable life, youth, beauty — yet managing to turn their teen angst into what seems like a deadly game of one-upmanship for no reason anyone can tell.