25 Painfully Unrequited Love Stories From Literature

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Great unrequited and unconsummated love affairs in literature act so powerfully on readers that we think we can change the story’s ending. Some of us will devour a book over and over again, knowing that two characters with great romantic chemistry won’t — and maybe shouldn’t — end up together but wishing against all reason that they will. Each time, we hope that the page might turn, and this time instead of a missed moment or a gaze or a goodbye, we will happen upon a kiss, or a reconciliation.

Even if there’s a sensible marriage or two with less combustive energy at these books’ conclusions, we tend to forget those pedestrian matches while the unrealized love lives on in our minds. These are the stories that we remember not because they ended with the altar or a fat smiling baby, but because they ended with a feeling of burning loss and enduring passion.

For your Valentine’s Day pleasure, here’s a selection of literature’s most painfully unrequited, star-crossed and thwarted romances. Read them and try not to weep. (My own heart broke a few times while composing this list.)

Lily Bart and Lawrence Selden, The House of Mirth

These two stars of the New York social scene are attracted to each other, they care for each other, maybe even deeply, but their own egos and snobbish hang-ups prevent them from committing and connecting in the one way that could save them both. “Well — you did love me for a moment; and it helped me. It has always helped me,” Lily says to Lawrence, before the downward spiral that sunders them forever. I have never read the last page of this book, which finds Selden running to Lily’s apartment a few hours too late, without hoping it would turn out another way this time.

Severus Snape and Lily Evans/Lily Potter, Harry Potter series

Once upon a time before they went to Hogwarts, Severus Snape fell hard for his friend and neighbor, Lily Evans. From their first schooldays to her late-teenage relationship with the charming bully James Potter to their shifting allegiances during various Dark Lord epochs to her death — and his years of mixed anger and protectiveness towards her son Harry — one thing about Snape’s feelings remained consistent: his absolute love for her.

Eowyn and Aragorn, The Lord of the Rings

“Thus Aragorn for the first time in the full light of day beheld Éowyn, Lady of Rohan, and thought her fair, fair and cold, like a morning of pale spring that is not yet come to womanhood. And she was now suddenly aware of him: tall heir of kings, wise with many winters, greycloaked, hiding a power that yet she felt. For a moment still as stone she stood, then turning swiftly she was gone.”

This is pretty much as sexy as Tolkien got, and he had even planned for these two to marry, but then decided to pair them off with less fiery sorts.

Milly Theale and Merton Densher, The Wings of the Dove

You know that your love interest is currently scheming to marry you because you’re terminally ill. He wants to take your inheritance and use it to marry his penniless friend, who is also pretending to be your friend. Maybe they care for you a little, but they care for themselves more. Yet you leave him your money anyway, because you love him so much. You’re Milly Theale, you’re a Henry James character, and your heart is far stronger than your constitution.

Laurie and Jo, Little Women

The laughter, the scrapes, and the hijinks of a youthful alliance bring them together as chums. One day in an alternate universe, the spirited loyalty and genuine love between two children who are perfect pals will blossom into a mature love on both sides, not just his.

Eponine and Marius, Les Miserables

She’s a girl of the streets and he’s a dashing student revolutionary. In both Victor’s Hugo’s novel and the beloved Broadway musical, Eponine’s moral ambiguity and one-sided love for Marius make her more multidimensional and, thus, treasured by fans. She loves him, but only on her own. At least she gets to die in his arms.

Healthcliff and Cathy, Wuthering Heights

From a childhood of perfect communion to an adulthood in which society’s patriarchal rules drive them apart, their love won’t die. They chase each other over the moors and exact vengeance nonstop, breaking each other’s hearts to pieces and upending others’ lives too. Even Cathy’s ghost won’t let him rest, but bangs on his window, haunting him. They at last find peace in a shared grave.

Gwendolyn Harleth and Daniel Deronda, Daniel Deronda

One of them is in the worst marriage of all time, abused and scorned. The other is an adopted nobleman who discovers he’s a Jew and struggles with his newfound identity. They help each other, maybe even love each other, but they can never be together. George Eliot was the champion of writing characters who touch each other’s lives too late.

Neil and Brenda, Goodbye, Columbus

Sometimes the gap that love cannot leap across is fate; sometimes it’s between noble and peasant, sometimes it’s master and servant, and sometimes it’s just between middle-class urban Jew and richer, more assimilated suburban Jew. That doesn’t make the angst of early Philip Roth any less poignant.

Stevens and Miss Kenton, The Remains of the Day

Throughout decades of service, these two servants do their duty, while concealing their feelings for each other. This is Kazuo Ishiguro’s masterpiece of polite, surface-level repression, with emotion running like a river beneath it, much of which only spills out (in the form of tears for both reader and characters) on the final pages.

Rhett Butler, Scarlett O’Hara, and Ashley Wilkes, Gone With the Wind

Scarlett pines for weak, romantic, and married Ashley Wilkes, while daring, pragmatic Rhett Butler will do anything to get Scarlett to turn her eyes to him instead, including marry her. Meanwhile, both Scarlett and Ashley have a bigger unrequited love problem: they’re obsessed with the white supremacist past of their evil plantations.

Quentin and Cady Compson, The Sound and the Fury

Smart, tortured, Harvard-bound Quentin Compson has a creepy obsession with his sister Cady and her impure sex life. But so, apparently, does everyone in Faulkner’s Gothic family masterpiece. In the end, Quentin’s ruminations about his sister’s reputation lead him to suicide.

Winnie Foster and Jesse Tuck, Tuck Everlasting

Natalie Babbit’s classic YA novel gets super-poignant when Jesse offers Winnie a bottle of water from the magical spring that will grant her immortality, like he has. Take it when you’re older and marry me, he offers her. Though she cares for Jessie, Winnie eschews living forever. Unlike Bella Swan, she elects to keep her love in her mortal heart, and gives the water to a toad, which the Tucks later find hanging around her grave.

Catherine Sloper and Morris Townsend, Washington Square

Henry James knew how to write a pathetic love story. Catherine is a plain, sheltered heiress, and Morris is the opportunistic suitor who sweeps her off her feet. Her father’s interference, and eventually her pride, keep them apart forever. We never know if she might have been happier living with an imperfect man than she was alone.

Romeo and Rosaline, Romeo and Juliet

“That same pale, hard-hearted wench, that Rosaline, torments him so that he will sure run mad.” Romeo’s first, unrequited love sends his heart into a tailspin. He goes to a Capulet party to try to get out of his funk, and there is Juliet. Is she an improvement over Rosaline or a replacement? Critics can’t agree.

Pip and Estella, Great Expectations

Miss Havisham engineers their childhood encounters so Pip will fall in love with Estella and Estella will be indifferent, and break his heart. It’s all a proxy revenge for her own abandonment at the altar, and the plan works to poor Pip’s detriment. But alas! Estella ends up broken, too, married to a brute.

Harriet Smith and Mr. Elton, Emma

Emma tries to make a match for her protegé Harriet Smith, and manages to influence her heart so much that Harriet falls for the pompous clergyman, Mr. Elton. Everyone’s folly is fully on display in these early scenes, as it turns out that he’s had his eye on Emma all along. The awkward comedy of manners that results from this triangle of love and misunderstanding is achingly amusing for the reader.

Ralph and Isabel, Portrait of A Lady

“You’ve been my best friend,” the married Isabel says to her dying (and very much besotted) cousin, the invalid Ralph. “It was for you that I wanted — that I wanted to live. But I’m of no use to you,” he replies.

And Henry James, never one to spare us, offers us the kicker: “Then it came over her more poignantly that she should not see him again.”

Dean Priest and Emily, Emily of New Moon

L.M. Montgomery’s darker, more Gothic companion to Anne of Green Gables has a memorably disturbing love plot. Artistic, mystic Emily is pursued by the older, disabled Dean Priest, with whom she has an intense spiritual connection. They prepare to get married and furnish a house together before she realizes she loves someone else, and thus his love remains unrequited.

Sarah and Charles, The French Lieutenant’s Woman

John Fowles’ meta-Victorian novel offers us multiple possible endings for its star-crossed lovers, but none is simple, and all exist without years of longing and separation.

Olivia and Orsino, Twelfth Night

In Shakespeare’s sexiest comedy, Orsino wants so much music to feed his love for Olivia that his appetite for love will sicken, and die. Why? Because as much as he adores her, she ignores him. His pining comes to an end, eventually, when a pair of twins arrive in Ilyria after a shipwreck and gender-bent romantic pratfalls ensue, culminating in a double wedding.

Florentino Ariza and Fermina Daza, Love in the Time of Cholera

Years of pure unrequited love (if not fidelity or chastity) spin out, until they come to a quiet, happy end at the conclusion of this romantic epic of thwarted passion and stunning patience.

Jacob and Bella, The Twilight Saga

Sorry, Team Jacob. Not only does your husky wolf-boy not get Bella in the end after years of trying, but he ends up “imprinting” on her infant child. This final twist turns a typical teen love triangle into one of the weirdest unrequited love stories ever to grace the page.

Everyone, I Capture the Castle

In this cult-classic novel, impressionable and spunky young girls in a castle purchased by their eccentric father join together with their neighbors and sundry household members for youthful adventures, and they begin to experience the pangs love. At times, it feels as though everyone has fallen for someone who doesn’t return the sentiment.

Ellen Olenska and Newland Archer,The Age of Innocence

His fiancée’s countess cousin, divorced and therefore dangerous, arrives on the scene in New York, and staid Newland Archer suddenly finds all kinds of things awakened within him, including — gasp! — an affinity for displeasing the leading ladies of society. In an Edith Wharton novel, that’s never a good sign. A few stolen kisses and an abortive room-key exchange have us rooting for this unlikely couple, but the aforementioned ladies band together and drum Ellen out of town.