The 50 Greatest Unrequited Love Stories Ever

The quest for love makes a great story. The question of will they or won’t they has fueled countless narratives, high and low. It’s Shakespeare. It’s Edith Wharton. It’s Gossip Girl. The happy endings – relieved embraces, engagements, sex made all the hotter by the building tension of various plot complications – give us a nice dose of literary oxytocin. In fiction as in the real world, though, mutual love won’t always happen. He’s just never going to be that into her, or she decides to stay with her spouse, or the cruel forces of society never let up to allow the aspiring lovers their due. Tales of relationship interruptus may not yield much oxytocin, but arguably they offer something much more profound: insights into how unreciprocated love forces us to reckon with ourselves. So here, as a counterweight to the smug rituals of Valentine’s Day, are the 50 greatest stories of unrequited love.

With apologies to Jane Austen, Gabriel Garcia Marquez, and the pre-Millennial Disney Industrial Complex, the rule for the list is simple: The unreciprocated yearning must come to naught. No eleventh hour unions, wedding bells, rides into the sunset, or necrophiliac kisses that end decades-long slumbers.


50. First Love by Ivan Turgenev

A Freudian nightmare: Your first big crush is having an affair with your dad, who beats your beloved with a riding crop.

Best line: “Each of us feels most deeply convinced that he has been too prodigal of his gifts – that he has a right to cry, ‘Oh, what could I not have done, if only I had not wasted my time.”


49. Last Night at the Blue Angel by Rebecca Rotert

Naomi Hill is an ambitious, self-destructive singer and single mother trying to make it in the 1960s Chicago jazz scene. Jim, a photographer documenting her life, is devoted to her and her daughter Sophia, even as Naomi careens through affairs with both men and women. His other unrequited love is for the crumbling historic buildings of Chicago. Both passions, as it turns out, are hazardous.

Best line: There’s a way adults smile at you when you want something you’re never going to get. That’s how I smile at Jim.”


48. The Throne of Saturn by Allen Drury

Gay astronaut unrequited love melodrama, written by a staunch anti-Communist! Balkis saves his straight guy crush from the evil Soviet cosmonauts, only to lose his own life just after declaring his love.

Best line: “It isn’t enough for me just to do my job. You-all won’t be satisfied with that. You’re asking me to respect you. You’re asking me to like you. You’re asking me to love you, because we’re all part of the same crew and people like you just can’t stand not being loved.”


47. Le Morte D’Arthur by Sir Thomas Mallory

Sir Lancelot and Guinevere have this hot forbidden love thing going on. But Lancelot is also the object of the attentions of Elaine of Astolat, who nurses him after he gets hurt in a jousting tournament. When she confessed her feelings to him, he tried to pay her off to go away and marry someone else. She dies of heartbreak, but not before she can plan a big show. She arranges for her funeral barge to greet him at Camelot and prepares a letter explaining how she died. In the era of courtly love, knights could wage wars in the name of their beloved ladies, but Elaine, it seemed, chose performative masochism as her outlet.

Best line: “Why should I leave such thoughts? Am I not an earthly woman? And all the while the breath is in my body I may complain me, for my belief is that I do none offence, though I love an earthly man, unto God, for He formed me therto, and all manner of good love cometh of God.”


46. The Well of Loneliness by Radclyffe Hall

The template for a rash of purple prose paperbacks depicting doomed lesbian love. The protagonist, Stephen, is actually transgender – in the terminology of the time, a “sexual invert.” His beloved Mary is by his side as a volunteer in World War I. But instead of partnering up à la Getrude Stein and Alice, Stephen pushes Mary into marriage with a man who can give Mary a respectable life, safe from persecution. The antidote to this major bummer of a novel is Patricia Highsmith’s The Price of Salt, a literary Stonewall in the history of lesbian fiction.

Best line: “The world hid its head in the sands of convention, so that by seeing nothing it might avoid Truth. ”



45. The Phantom of the Opera by Gaston Leroux

This novel (and the stage and screen adaptations it spawned) is proof positive of Bonnie Raitt’s anthem “I Can’t Make You Love Me.” Because Erik really, really tries.

Best line: “You must know that I am made of death, from head to foot, and it is a corpse who loves you and adores you and will never, never leave you!”


44. The Perks of Being a Wallflower by Stephen Chbosky

High school freshman Charlie is quiet and shy but smart and funny enough to be adopted by a group of seniors. He quickly grows fond of Sam, a girl so appealingly nice and clever that I got a crush on her right along with him.

Best line: “You can’t just sit there and put everyone’s lives ahead of yours and think that counts as love. You just can’t. You have to do things.”


43. The Magician’s Assistant by Ann Patchett

Sabine is the alluring magician’s assistant to Parsifal, a gay man who has AIDS. She has been in love with him for more than two decades, even though he had a long-term partner. After the partner dies of the disease, Parsifal marries Sabine. There’s no sudden shift in his sexual orientation; he just wants Sabine, his closest friend, to be his widow. Once he’s gone, she sets out to uncover Parsifal’s past. While I read The Magician’s Assistant, I did experience suspension of disbelief. In retrospect it’s hard to believe how.

Best line: “Don’t pursue dead men. I don’t think I have any advice clearer than that.”


42. Middlemarch by George Eliot

Mr. Farebrother is an unrequited love martyr. Instead of wooing Mary, the woman he loves, he helps the man she adores clean up his act and marry her. This reminds me of Watt in Some Kind of Wonderful, playing chauffeur to the boy she adores as he romances his crush. The self-sacrifice ends well for Watt, but Mr. Farebrother has no such luck.

Best line: “What we call our despair is often only the painful eagerness of unfed hope.”


41. Wuthering Heights by Emily Bronte

The Romantic era’s best known and most celebrated novel of unrequited love. But I’d argue that the story isn’t really a romance. The novel is more about passion as rebellion against the strictures of class, gender, and race in nineteenth century English society. A worthwhile theme, but I could never root for these two narcissists as a couple. Cathy and Heathcliff may have bonded closely in childhood, but once the hormones kick in, they get into some pretty twisted sadomasochistic behavior. The kink is foreshadowed by the young Cathy’s request that her father bring home a whip for her. Instead, he brings home Heathcliff, a homeless orphan gypsy.

Best line: “Cathy, when she learned the master had lost her whip in attending on the stranger, showed her humour by grinning and spitting at the stupid little thing; earning for her pains a sound blow from her father, to teach her cleaner manners.”


40. The Peanuts by Charles Schultz

The Peanuts links its characters in chains of unreciprocated adoration: Peppermint Patty loves Charlie Brown, Charlie Brown loves the Little Red-Haired Girl, Sally loves Linus, who loves his teacher, Miss Othmar. Lucy loves Schroeder, who wants nothing more than to play Beethoven on his toy piano. While most of these pre-sexual crushes are funny and sweet, in one strip Lucy goes bunny boiler. She flings Schroeder’s piano into the “dreaded kite-eating tree,” which chomps the instrument to dust.

Best line: “Nothing takes the taste out of peanut butter quite like unrequited love.”


39. Medea by Euripides

Speaking of bunny boilers: This myth suggests that you probably don’t want to diss the woman who kills her own brother and scatters his limbs as a ploy to distract her father so she can run away with you.

Best line: “Who can stop grief’s avalanche once it starts to roll.”



38. The Little Mermaid by Hans Christian Andersen

In the Disney version, Ariel gets her man. But in the original fairy tale, the Little Mermaid gives up her voice and exchanges her tail for a pair of legs and feet that make her feel like she’s walking on knives, all in an effort to win a guy who couldn’t even recognize her as his rescuer. She’s turned into sea foam for her troubles, evaporates into the heavens, and gains an immortal soul. In Hans Christian Andersen’s worldview, this is the ultimate spiritual reward. But from another vantage point, her end looks a lot more like suicide by unrequited love. I presented this one to my daughter as the ultimate cautionary tale: Don’t change yourself for a guy.

Best line: “Nothing gave her so much pleasure as to hear about the world above the sea. She made her old grandmother tell her all she knew of the ships and of the towns, the people and the animals.”


37. Days of Abandonment by Elena Ferrante

This is a book that underscores the tremendous risk marriage and parenthood are to the partner we now politely call the “primary caregiver” – the one in charge of child-rearing and housekeeping. Usually it’s the mother. When Olga’s husband calmly tells her he wants to leave her for another woman, Olga explodes in a tirade of sexual jealousy. But as her reactions unspool, it’s clear her obsession with her abandonment is less about sexual fidelity than it is about reckoning with how much of her identity has been lost to being a wife. A merciless portrayal of despair.

Best line: “`What a mistake it had been to close off the meaning of my existence in the rites that Mario offered with cautious conjugal rapture,’ she reflects. `What a mistake it had been to entrust the sense of myself to his gratifications, his enthusiasms, to the ever more productive course of his life.’”


36. Don Quixote by Miguel de Cervantes

Don Quixote devotes his chivalric quests to a neighboring farm girl he calls Dulcinea. Even though he never exchanges a word with her and has seen her only in glimpses, his adoration allows him to have a great time playing the wandering knight-hero. He’s actually kind of a bumbling idiot, albeit a well-meaning one. He attacks windmills, believing them to be giants, and insists on rescuing a lady from a band of what he perceives as malevolent wizards, when they’re really a group of innocent friars.

Best line: “There were no embraces, because where there is great love there is often little display of it.”


35. Good Kids by Benjamin Nugent

High school classmates Josh and Khadijah catch Josh’s dad and Khadijah’s mom kissing at the health food store. They bond over the upsetting sight. As their parents’ marriages fall apart, the kids vow never to cheat on anyone for the rest of their lives. The only problem is, they have a thing for each other – a thing they can’t act on because Khadijah moves away. Then they meet again, at 28, both engaged to other people.

Best line: “Khadijah was always pretty, but crying, she was so beautiful my face was going to burn off. I found the discovery that tears enhanced beauty nearly as disorienting as everything else that was going on.”


34. The Sun Also Rises by Ernest Hemingway

Jake’s war wounds mean he can’t fully have his beloved Lady Brett, and he drowns his pain at Parisian bars. His yearning for Brett is a literary stand in for the castrated Lost Generation, longing for ideals lost in the horror of war: justice, love, masculinity, morality. What’s rough is Brett wants him back, but the impossibility of consummating their love keeps her at bay.

Best line: “You’re getting damned romantic.” (Brett)
“No, bored.” (Jake)


33. Cyrano de Bergerac by Edmond Rostand

Cyrano’s biggest problem is his huge nose, and his selflessness. He’s in love with Roxane, but ends up ghostwriting love letters to her for the hunky but inexpressive Christian. The letters work their magic, but then Christian is killed. Roxane checks herself into a convent. She doesn’t realize Cyrano’s love until years later, when he’s on his deathbed.

Best line: “A great nose may be an index of a great soul.”


32. Of Human Bondage by W. Somerset Maugham

Philip Carey is a character defined by longings: for his dead mother, his lost privilege, an able body (he has a deformed foot), and real artistic talent. Then there’s Mildred, a vulgar waitress who seems to be a stand in for all this other stuff. His love for her is utterly nonsensical, because she treats him poorly and has no class or taste, guffawing all the way through the tacky musicals Philip agrees to take her to. But wait! W. Somerset Maugham was gay, and he wrote Of Human Bondage in the repressive era after Oscar Wilde was tried and thrown into prison for “gross indecency” with other men. Hence Mildred’s distinctly transgendered air: “She was tall and thin, with narrow hips and the chest of a boy.”

Best quote: “The fact remained that he was helpless. He felt just as he had felt sometimes in the hands of a bigger boy at school. He had struggled against the superior strength till his own strength was gone, and he was rendered quite powerless – he remembered the peculiar languor he had felt in his limbs, almost as though he were paralysed – so that he could not help himself at all. He might have been dead. He felt just that same weakness now.”



31. “Bien Pretty” from Woman Hollering Creek by Sandra Cisneros

Lupe falls for Flavio, her pest exterminator, for his strong sense of Mexican identity. After he rejects her, she goes for a multicultural array of consolations: gringa-style New Age crystals and positive visualizations, Tibetan gongs, Amazon flute music, voodoo, and Aztec ocarinas. But ultimately it is her resolution not to live life like a telenovela victim that helps her move on.

Best line: “Be women who make things happen, not women things happen to.”


30. Written on the Body by Jeanette Winterson

The genderless narrator, who has a reputation as a love ’em and leave ’em cavorter, has a steaming affair with the married Louise. Louise gets leukemia and needs the cutting edge medical care that her husband, a famous cancer researcher, can provide. So the narrator slinks away, even though this time, it’s the last thing s/he wants to do. In fact the narrator remains obsessed with Louise and is consumed by studying the details of her anatomy and her illness. The result is a sort of manic lustful prose so forceful it seems as if it could push back the invading metastasis.

Best line: “Why is the measure of love loss?”


29. Layla and Majnun Ancient Arabian story adapted by Nizami Ganjavi

A suitor writes lots of love poems to his beloved Layla, so many that he becomes known among the locals as “Majnun,” which means madman. They might have had a point. He gets so preoccupied with writing love poems that he doesn’t even want to be around Layla. Because, you know, she distracts him from his craft.

Best line: “Be gone from me! Love for you so engages me that I have no time for you.”


28. The Remains of the Day by Kazuo Ishiguro

Mr. Moseley’s longing for Baxter on Downton Abbey ain’t got nothing on Stevens, a deeply repressed butler who has the hots for Miss Kenton, who is only slightly less repressed. Next to nothing happens between the two. But their unrealized relationship becomes a lens through which we watch the world change, exposing the moral failings of the British aristocracy in the ramp up to World War II. A “motoring trip” may form the narrative spine of the novel, but Stevens, tragically, gets nowhere.

Best line: “There was surely nothing to indicate at the time that such evidently small incidents would render whole dreams forever irredeemable.”


27. The Marriage Plot by Jeffrey Eugenides

At Brown University, Mitchell loves Madeleine, his close friend, but she’s unattainable because she’s gorgeous, entitled, and into Leonard, her sometimes-boyfriend who is exciting, brilliant, and frustrating in turns. He wards off his feelings with righteousness indignation and spiritual seeking. But she haunts his thoughts beyond graduation, even as he tries to immerse himself in the altruism of volunteering in Mother Theresa’s wretched missionary hospital wards.

Best line: “He remained heartbroken, which meant one of two things: either his love was pure and true and earth-shakingly significant; or he was addicted to feeling forlorn, he liked being heartbroken.”


26. The Story of Potiphar’s Wife In the Bible and Judaic commentaries

Joseph’s jealous brothers sell him into slavery to Potipahr. He’s hot (“comely of form,” as the Good Book puts it), and Potiphar’s wife has a thing for him. When he refuses to bed her, she accuses him of rape, landing him in jail. A medieval era commentary gives a truly bizarre elaboration on Potiphar’s wife’s obsession: She paraded Joseph in front of the ladies of the court. They were so smitten by the sight of him they sliced their hands with a knife while gripping a citrus fruit. Ow.

Best line: “She said to them: If you do thus after one moment, I who see him at every moment, am I not the more so?”


25. Little Women by Louisa May Alcott

As a teen, Louisa May Alcott had major crushes on Emerson, who home schooled her in literature, and Thoreau, who took her on his famous nature walks. So that might explain why Jo chose an older professor over neighbor boy and best buddy Laurie. Our hearts may break for the devoted Laurie, but his consolation prize – Amy – may very well have been Alcott’s giveaway about his true nature: an entitled preppy easily contented with a more traditional sort of woman.

Best line: “Love Jo all your days, if you choose, but don’t let it spoil you, for it’s wicked to throw away so many good gifts because you can’t have the one you want.”


24. The Game by A.S. Byatt

There’s no sibling rivalry like the rivalry over a lover. Cassandra, a celibate scholar of medieval literature, and Julia, an author of bestselling domestic novels, reconnect with the object of their mutual adolescent longing, now the host of a popular “Animal Kingdom”-type television show. But this time, he’s not the point. He’s just a catalyst for major emotional warfare between the women. The yearning for a remote, unknowable sibling may be one of the harshest forms of unrequited love. Blood never really lets you move on.

Best line: “You could say curiosity was the beginning of love. And most of us would do best to stop there since we aren’t capable of anything better.”



23. Gone With the Wind by Margaret Mitchell

So what if Scarlett has a 17-inch waist and a thing for velvets and lace? There’s an unmistakable butch-femme vibe going on in her spoiled-brat crush on Ashley, who is so girly I’m surprised she never catches him trying on her hoop skirts. Though I’m a fan of Scarlett’s chutzpah, my sympathies tend go to Rhett (a little guiltily, I admit, given the feminist debates over his rape culture behavior). He wins Scarlett without really winning her. It’s unrequited love in a marriage. Until, of course, he no longer gives a damn.

Best line: “I loved something I made up, something that’s just as dead as Melly is. I made a pretty suit of clothes and fell in love with it. And when Ashley came riding along, so handsome, so different, I put that suit on him and made him wear it whether it fitted him or not. And I wouldn’t see what he really was. I kept on loving the pretty clothes—and not him at all.”


22. Sputnik Sweetheart by Haruki Murakami

K., an elementary school teacher, loves Sumire, a writer who relies on his creative input but is just not that into him. Sumire falls for an older Korean woman. The two women go on an extended business trip. Sumire vanishes. After going abroad to search for her, K. comes to believe she’s literally vanished into another world. Which is, in a way, what happens when we lose someone we love to someone else.

Best line: “So that’s how we live our lives. No matter how deep and fatal the loss, no matter how important the thing that’s stolen from us – that’s snatched right out of our hands – even if we are left completely changed, with only the outer layer of skin from before, we continue to play out our lives this way, in silence.”


21. Twelfth Night by William Shakespeare

Cross-dressing and faux (or not so faux?) homoerotic attraction shake Orsino out of his unrequited love for Lady Olivia. And the same forces lead her to her proper match.

Best line: “If music be the food of love, play on; Give me excess of it, that, surfeiting, The appetite may sicken, and so die.”


20. Great Expectations by Charles Dickens

Bitchy, brainwashed Estella beguiles Pip until the end, after she’s been wisened and gentled by a rough. But there are no second chances for Estella’s adopted mother, Miss Havisham, who was jilted at the altar and spent the rest of her life in her bride’s dress, the wedding cake rotted to dust before her, the clocks stopped at the precise time of she was notified of her abandonment. Psychologists now call the condition that besets people who become addicted to grief over a lost love the “Miss Havisham Effect.”

Best line: “Love her, love her, love her! If she favours you, love her. If she wounds you, love her. If she tears your heart to pieces – and as it gets older and stronger, it will tear deeper – love her, love her, love her!”


19. Madame Butterfly by John Luther Long

Don’t do it, Cho-Cho-San! Pinkerton is not worth it, no matter how opera ready his betrayal. The story and all its spin-offs remind us that the spoils of war and imperialist paternalism have a beating, suffering heart.

Best line: “It was, too, exactly in Pinkerton’s line to take this dainty, vivid, eager, formless material, and mold it to his most wantonly whimsical wish. It was perhaps fortunate for her that his country had had need of him so soon after his marriage.”


18. Song of Solomon by Toni Morrison

Manic unrequited love crossbred with TLC’s “A Makeover Story.” Hagar is so crazed over Milkman that she spends money from Reba’s pawned diamond ring on cosmetics, clothes, a garter belt, pantyhose and underwear. Her purchases get soaked in a rainstorm, but she tries to adorn herself anyway. She rips the hose, stains her dress, and smears on lumpy face powder. Then she falls ill and dies.

Best line: “The lengths to which lost love drove men and women never surprised them. They had seen women pull their dresses over their heads and howl like dogs for lost love. And men who sat in doorways with pennies in their mouths for lost love. ‘Thank God,’ they whispered to themselves, ‘thank God I ain’t never had one of them graveyard loves.’”


17. Death of the Heart by Elizabeth Bowen

Portia, a recently orphaned teen, falls under the care of her older brother and his coolly ambivalent wife in manners and class-obsessed 1930s London. She’s easy bait for the Eddie, who is a shout-at-the-page frustrating combination of alluring and noncommittal (the kind of chap who “lashes himself to his bedroom chair so as not to have to go and cope with the burglar”). Portia’s innocence goes the slaughterhouse – along with the bogus façade of her brother and sister-in-law’s drawing room marriage.

Best line: “In the first great phase of love, which with very young people lasts a long time, the beloved is not outside one, so neither comes nor goes. In this dumb, exalted and exalting confusion, what actually happens plays very little part.”


16. White Teeth by Zadie Smith

Irie tries to improve and Westernize her Anglo-Jamaican appearance so Millat, her crush, will notice her. She dyes and straightens her hair and schemes to whittle down her “substantial Jamaican frame, loaded with pineapples, mangos and guavas.” Her unrequited love comes to a strange end: She goes to bed with Millat and his twin brother.

Best line: “She wanted to find out whoever had damaged him like this, damaged him so terribly; she wanted to find whoever had made him unable to love her.”


15. “The Cheater’s Guide to Love” in This is How You Lose Her by Junot Diaz

Boy cheats on girl. 50 times. Girl leaves boy. Boy tries everything he can think of to get over her: the gym, drinking, other relationships, one-night stands, yoga. Five years later, he figures out what he has to do: write a book about it. This is the author’s version of how fifth graders like to end their short stories: with the protagonist realizing everything was all a dream. “And then he woke up and it was all material.”

Best line: “I’m okay, you tell them, but with each passing week the depression darkens. You try to describe it. Like someone flew a plane into your soul. Like someone flew two planes into your soul.”


14. Les Misérables by Victor Hugo

Every teen girl alto wants to play the sexy and daring Eponine in “Les Miz.” She’s the street urchin who is so smitten with student revolutionary Marius that she delivers mash notes to his beloved Cosette, dresses as a man so she can join him at the barricades, and takes a fatal bullet for him. But Hugo’s novel portrays her as “pale, puny, meagre creature” with the look of “a corrupted old woman.” The real story of unrequited love in Victor Hugo’s life happened to his daughter Adele, whose 15-year obsession with a British soldier eventually landed her in an insane asylum.  Perhaps taking her cues from daddy’s novel, Adele often dressed as a man so she could go out at night in pursuit of her beloved.

Best line: “All at once, at the very moment when Marius fancied her asleep forever, she slowly opened her eyes in which appeared the sombre profundity of death, and said to him in a tone whose sweetness seemed already to proceed from another world:–‘And by the way, Monsieur Marius, I believe that I was a little bit in love with you.’ She tried to smile once more and expired.”


13. Echo and Narcissus Greek Mythology

What this story captures is so much of how a stupid crush feels: The guy’s only thinking about himself, while you’re so awkward that all you can do, essentially, is echo what he says, in hopes he’ll be pleased at how much you have in common. Then there’s a deeper moral: Unrequited love can waste you away (Eros eventually becomes nothing but a voice), but so can unbridled narcissism. And sometimes they’re pretty much the same thing.

Best line: “While he is drinking he beholds himself reflected in the mirrored pool—and loves; loves an imagined body which contains no substance, for he deems the mirrored shade a thing of life to love.”


12. The Sorrows of Young Werther by Johann Wolfgang Von Goethe

The story of Werther’s self-destructive yearning for the black-eyed, über-nurturing Lotte led to a series of bizarre copycat suicides across Europe. Young men, dressed in Werther’s trademark blue waistcoat and yellow vest, shot themselves at their desks with the novel opened in front of them. The Sorrows of Young Werther is one of the defining novels of the Romantic era, with its veneration of monomaniacal obsessiveness and death-as-transcendence. Yet the characters have a strangely familiar feel, like early prototypes for John Hughes films: Werther the emo-Goth angry youth, Lotte the popular yet kind beauty, her fiancé Albert the honorable and dull high-value mate.

Best line: “They tell of a noble race of horses that, when they are terribly driven and overheated, instinctively bite open a vein to help themselves breathe. I often feel that way.”



11. The Great Gatsby by F. Scott Fitzgerald

I never thought Daisy was worth it (does anyone?). But if Gatsby hadn’t loved her so much there would have never been those stacks of shirts, those parties, and that single green light across the bay.

Best line: “There are only the pursued, the pursuing, the busy, and the tired.”


10. I Love Dick by Chris Kraus

Chris Kraus, a struggling filmmaker/academic wife, falls in love with the eponymous Dick, a British cultural critic teaching at a university in California. She writes him lots of letters, occasionally with contributions by her husband, who’s intrigued, in a postmodern spouse kind of way, by the whole thing. Dick responds to these outpourings with mainly evasion and silence, though he does consent to her request for sex with the distinctly dickish line: “I’m not uncomfortable with the idea.” I Love Dick is an in-your-face extravaganza of abjection and literary revenge. Kraus is Alex Forrest, Glenn Close’s vengeful Fatal Attraction villainess, with a pen instead of a pot of boiling water.

Best line: “So in a sense love is just like writing: living in such a heightened state that accuracy and awareness are vital.”


9. Prep by Curtis Sittenfeld

Crushes often have an element of Jungian aspiration. You want someone because you want to be like him – a phenomenon that psychologists call an identity crush. Prep is a novel that underscores how class can intersect with unreciprocated adolescent desire. Lee, the daughter of an Indiana mattress salesman, gets a scholarship to a prestigious Massachusetts boarding school. Her obsessive entanglement with a confident, entitled, and sexually attentive hyper-achiever exposes the frustrations of no-strings-attached hookups – and of social striving.

Best line: “The wrongness of what had happened between Cross and me – I could feel it now. Not a moral wrongness, but a screwup, a thing that needed explanation: a bird in the grocery store, a toilet that won’t stop running, that moment when your friend has come to pick you up and you open the door and realize it’s not your friend’s car at all; the person driving is a stranger, and now you must apologize.”


8. Enduring Love by Ian McEwen

Science writer and devoted husband Joe Rose and Jed Parry, a stranger, survive an attempt to rescue a boy caught in a renegade hot air balloon. The boy lives, but another would-be rescuer is killed. Rose tries to move on. But he can’t, because Parry becomes completely emotionally, erotically, and spiritually obsessed with him. The obsession, which is Single White Female-level wack, scalps Rose of his ultra-rational worldview and threatens his marriage. Erotomania as page-turner.

Best line: “See? Reading you all night has strengthened me. That’s what God’s love does. If you’re beginning to feel uncomfortable now, it’s because the changes in you are already beginning to happen and one day you’ll be glad to say, Deliver me from meaninglessness.”


7. Clearcut by Nina Shengold

Romantic obsession à trois, in the wild forests of the Pacific Northwest: a guy, a guy, and a girl. Sexual orientation and monogamy are notions that scatter away like wood chips out of a particularly voracious mill.

Best line: “If he’d fallen in love with a whole pack of lies, were his feelings lies too? No, he thought. They were as real as it gets.”


6. La Vita Nuova by Dante Alighieri

Dante spotted Beatrice Portinari at a flower festival in Florence. She was eight. He was nine. But he was smitten. He liked to look at her from afar. When he was 18, he had a psychedelic dream about her eating his flaming heart. La Vita Nuova is a testament to the fact that he was much more comfortable writing about her than seeing her, because he was a total mess in her presence. He plays the submissive courtly lover, looking up at his medieval gal on a pedestal, but the book comes across as totally egocentric – all about exalting himself through his feelings for a woman he barely knew.

Best line: “Thus pallid and void of all power, I come to behold you, thinking to be made whole.”

Anne-Louis Girodet-Trioson2


5. The Song is You by Arthur Phillips (no relation, though this is also my dad’s name)

On the surface, the plot is like a particularly overwrought episode of MTV’s Catfish: Instead of boy meets girl, boy, an advertising director, watches girl, an up-and-coming St. Vincent-esque singer, enthrall a tiny Brooklyn bar. Boy leaves behind career advice for the girl, cartooned on the back of eleven cardboard bar coasters. Then, as her career blooms, they exchange cryptic emails, texts, and videos. Boy, maddeningly, still does not meet girl. But what Phillips gets right is how unrequited obsession is often a way of confronting other, far more important yearnings. Julian, the protagonist, isn’t just a restless soon-to-be divorced man on the make. He’s a father trying to figure out how to move forward in the wake of unfathomable grief.


4. My Education by Susan Choi

Regina Gottlieb has an affair with her professor’s wife, the sex so steamy it strained the limits of prose (one passage made Slate’s Worst Sex Writing of the Year list). When her lover betrays her by sleeping with her best (male) friend, Regina is so epically sad she moves out of town. She eventually undergoes the typical pseudo-redemptive (and heteronormative) rites of finding a husband and starting a family. But there’s second, perhaps truer redemption when she re-encounters her ex-lover and plays matchmaker/muse of fate.

Best line: “I didn’t grasp that desire and duty could rival each other, least of all that they most often did.”


3. The Confessions of Noa Weber by Gail Haveren

An Israeli attorney turned detective novelist finds refuge from the “ancient human landscape” of her conflicted country in her obsession with a Russian immigrant wanderer. He is her dybbuk (evil spirit), yet her love for him arguably inspires everything she does, including the creation of the wildly popular feminist heroine of her books. So goes the warped privilege of unrequited love: the assertion of the self through the idea of the beloved.

Best line: “Much of what I am today stems in a crooked way from this wish to be worthy in his eyes, equal in power to his imaginary power.”


2. The House of Mirth by Edith Wharton

I forced myself to pick just one Edith Wharton novel, and it was difficult. Much of Wharton’s work — and a good part of her life — was preoccupied with unrequited love. Lily Bart is an orphan without money of her own.  She is supposed to marry well, and not be picky about little things like whether she loves the guy. Yet, again and again, she is too choosy for her own good.  The deeper problem is that she can’t even acknowledge that her true love, however economically inappropriate, is right in front of her – until it’s Too Late. One reader got so upset by the lack of a happily ever after ending that she stopped Wharton on the street to reprimand her.

Best line: “As the pain that can be told is but half a pain, so the pity that questions has little healing in its touch. What Lily craved was the darkness made by enfolding arms, the silence which is not solitude, but compassion holding its breath.”


1. The Woman Upstairs by Claire Messud

Nora is 42 and single, a devoted elementary school teacher and sometimes artist whose life is upended when she begins to share studio space with the mother of one of her students. This is a novel of unrequited love for a family. She feels an erotic/intellectual/creative pull toward mother and father and maternal yearnings for their son. The feelings thrill her, exhaust her, inspire her — until she’s victim to one of the most brutal emotional betrayals in the already business of unrequited love. A barn-burning portrayal of spinsterhood.

Best line: “In our lives of quiet desperation, the woman upstairs is who we are, with or without a goddamn tabby or a pesky lolloping Labrador, and not a soul registers that we are furious. We’re completely invisible. I thought it wasn’t true, or not true of me, but I’ve learned I am no different at all. The question now is how to work it, how to use that invisibility, to make it burn.”




Lisa A. Phillips

About Lisa A. Phillips

Lisa A. Phillips, a recovered unrequited lover, is the author of Unrequited: Women and Romantic Obsession, published by HarperCollins.
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12 Responses to The 50 Greatest Unrequited Love Stories Ever

  1. Barbara Mansfield Babs Mansfield says:

    So much to read. LOVE the inclusion of Medea–utterly unique.

  2. Furrydice says:

    Have you not read “Harry Potter”?

    Did you just forget Snape and the immense power of his love?

  3. John C. Williams says:

    I could write a few volumes on this subject myself. I won’t go into any real detail, but I know I am not alone, so that gives me some semblance of solace. Amazingly enough, however, I am almost convinced that this is somehow oddly my lot in life, as it is part of my makeup and I have learned some great lessons about humanity, and the true meaning of love, love at all costs, love that asks nothing, expects nothing, but is willing to give all, because it knows no bounds.

  4. Rose says:

    You know you did a bad job when you left out love in the time of cholera in a list about unrequited love.

    • Cooperrr says:

      Well the author of this list did include a disclaimer that Gabriel Garcia Marquez would not feature… Though I do agree, it is an immense tale of exquisite, heart-aching unrequieted love.

      As an aside, funnily enough, the asexual community has constructed a branch of their movement to describe those who endlessly crush on/develop feelings of romantic love towards others but who don’t need the object of their affections to return said sentiment (or who actively prefer that those feelings are not reciprocated), the crush alone is enough for them (and ironically, in certain instances, if the crush is returned, the person’s feelings towards the object of affection may change and they may no longer feel romantic attraction). It’s called lithromantic – interesting stuff!

  5. Greg says:

    Scrolled the whole way down, expecting to find A Tale of Two Cities as no. 1, or close to it, but it isn’t included at all!?!?

  6. Sweston says:

    MY almost gratitude goes to Dr Emuan for bring back my husband dumped me for another woman but by the grace of God we are now back with the help of Dr Emuan .I contacted [email protected] com concerning my ex husband and he guaranteed me of 3 days to my greatest surprise my husband came back to me in the third day i want to say a very big thank you.if you are in any kind of problem about your relationship you can contact him on; [email protected] com he will put a smile on your face.

  7. Maria Hossain says:

    You totally forgot about White Nights by Fyodor Dostoyevsky. That was like the biggest classic story about unrequited love. Otherwise this list was awesome.

  8. Sarah says:

    “Forever Amber” check it out

  9. nadia says:

    Large collection of garcia marquez much drama in his novels but I just love

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