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* ''Literature/ACourtOfThornsAndRoses'': Azriel has carried a torch for Mor for ''five hundred years''. Unfortunately for him, they're an IncompatibleOrientation.
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edited to correct misinformation
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* In Creator/VictorHugo's ''Literature/TheHunchbackOfNotreDame'', deformed bellringer Quasimodo, [[VillainousBreakdown increasingly unstable priest]] Claude Frollo, and lazy poet Pierre Gringoire are all in love with La Esmeralda (Gringoire even ends up ''married'' to her, though that doesn't mean [[SexlessMarriage he gets to touch her]]), who loves the soldier Phoebus, who's engaged to another woman but fine with boning Esmeralda on the side so long as it doesn't inconvenience him in any way and he doesn't have to acknowledge her in public.
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* In Creator/VictorHugo's ''Literature/TheHunchbackOfNotreDame'', deformed bellringer Quasimodo, [[VillainousBreakdown increasingly unstable priest]] archdeacon]] Claude Frollo, and lazy poet Pierre Gringoire are all in love with La Esmeralda (Gringoire even ends up ''married'' to her, though that doesn't mean [[SexlessMarriage he gets to touch her]]), who loves the soldier Phoebus, who's engaged to another woman but fine with boning Esmeralda on the side so long as it doesn't inconvenience him in any way and he doesn't have to acknowledge her in public.
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* In the ''Franchise/{{Disgaea}}'' [[LightNovel/DisgaeaNovels novels]], [[Characters/DisgaeaHourOfDarkness Laharl]] is given a [[UnwantedHarem harem]] of girls, none of them will even get what they want, because our “hero” is AllergicToLove and a CelibateHero.
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* In the ''Franchise/{{Disgaea}}'' [[LightNovel/DisgaeaNovels [[Literature/DisgaeaNovels novels]], [[Characters/DisgaeaHourOfDarkness Laharl]] is given a [[UnwantedHarem harem]] of girls, none of them will even get what they want, because our “hero” is AllergicToLove and a CelibateHero.
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** Per WordOfGay, Dumbledore once had a crush on [[spoiler: Grindelwald]]. It was unrequited, but that didn't keep the latter from exploiting it for their own gain.
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* ''Literature/ItsNotTheEndOfTheWorld'': Karen has a crush on Gary, a boy in her class, and is devastated when he moves away. Her best friend Debbie has a crush on Karen's big brother Jeff, who is openly rude to Debbie, calling her "fat and ugly" to her face, which doesn't dissuade Debbie at all.
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* A running theme in the town of ''Literature/EmpireFalls''. Rich girl Cindy Whiting has loved protagonist Miles Roby, proprietor of the local GreasySpoon, since they were teens. Miles is aware of this but simply doesn't love her back, instead being infatuated with Charlene, the curvaceous waitress at his restaurant. Unfortunately Charlene put Miles in the friend zone some 25 years ago--which is why he married Janice, despite the fact that he doesn't love her. She eventually divorces him when she realizes this.
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** Merope Gaunt fell in love with Tom Riddle to the point of brewing a love potion and spiking his drink with it. After a while, she stopped giving it to him, hoping that if he won't stay for her, he'll at least stay for their unborn son. He did nothing of the sort and instead he ran away for his life. Unbeknownst to Riddle, the boy that he abandoned would grow up to become the dark wizard Lord Voldemort.
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* ''Tons'' of unrequited love exists in ''Literature/ASongOfIceAndFire'', most of it spoiled by {{Arranged Marriage}}s. The most notable case is probably [[UnluckyChildhoodFriend Lysa Tully → Littlefinger → Catelyn Tully]] → Brandon Stark ← Barbrey Ryswell. The [[spoiler:Littlefinger → Catelyn part may have been the root cause of The War of the Five Kings]]. After a while, Catelyn [[PerfectlyArrangedMarriage learned to]] [[SettleForSibling settle for Brandon's brother]] Ned.
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* ''Tons'' of unrequited love exists in ''Literature/ASongOfIceAndFire'', most of it spoiled by {{Arranged Marriage}}s. Marriage}}s.
** The most notable case is probably [[UnluckyChildhoodFriend Lysa Tully → Littlefinger → Catelyn Tully]] → Brandon Stark ← Barbrey Ryswell. The [[spoiler:Littlefinger → Catelyn part may have been the root cause of The War of the Five Kings]]. After a while, Catelyn [[PerfectlyArrangedMarriage learned to]] [[SettleForSibling settle for Brandon's brother]] Ned.
** The most notable case is probably [[UnluckyChildhoodFriend Lysa Tully → Littlefinger → Catelyn Tully]] → Brandon Stark ← Barbrey Ryswell. The [[spoiler:Littlefinger → Catelyn part may have been the root cause of The War of the Five Kings]]. After a while, Catelyn [[PerfectlyArrangedMarriage learned to]] [[SettleForSibling settle for Brandon's brother]] Ned.
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** The Mad King, Aerys, would have rather wed [[spoiler:Joanna Lannister]] than his sister, which combined with his increasing madness as he grew older made him come to hate his childhood friend, [[spoiler:Joanna's husband Tywin Lannister]] out of jealousy and regularly abused his wife horrifically.
*** This gets worse when we learn that Rhaella Targaryen and Ser Bonifer Hasty had [[CourtlyLove a thing]] going on that both probably wanted to upgrade (well, most likely). Until, that was, Rhaella was informed that she was marrying Aerys, no ifs or buts. Ser Bonifer wound up joining the Faith Militant rather than getting over it and/or taking another woman to wife. He's... gone a little extreme in his piety over time since Rhaella's death in the Rebellion.
*** This gets worse when we learn that Rhaella Targaryen and Ser Bonifer Hasty had [[CourtlyLove a thing]] going on that both probably wanted to upgrade (well, most likely). Until, that was, Rhaella was informed that she was marrying Aerys, no ifs or buts. Ser Bonifer wound up joining the Faith Militant rather than getting over it and/or taking another woman to wife. He's... gone a little extreme in his piety over time since Rhaella's death in the Rebellion.
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** The Mad King, Aerys, would have rather wed [[spoiler:Joanna Lannister]] than his sister, which combined with his increasing madness as he grew older made him come to hate his childhood friend, [[spoiler:Joanna's husband Tywin Lannister]] out of jealousy and regularly abused his wife horrifically. \n*** This gets worse when we learn that Rhaella Targaryen and Ser Bonifer Hasty had [[CourtlyLove a thing]] going on that both probably wanted to upgrade (well, most likely). Until, that was, Rhaella was informed that she was marrying Aerys, no ifs or buts. Ser Bonifer wound up joining the Faith Militant rather than getting over it and/or taking another woman to wife. He's... gone a little extreme in his piety over time since Rhaella's death in the Rebellion.Rebellion.
** [[WifeHusbandry Jorah Mormont → Daenerys Targaryen]] ↔ Daario Naharis. While Jorah's love for Daenerys is undisputable, it's left to be seen if Daenerys's relationship with Daario is just a fling or not.
** [[WifeHusbandry Jorah Mormont → Daenerys Targaryen]] ↔ Daario Naharis. While Jorah's love for Daenerys is undisputable, it's left to be seen if Daenerys's relationship with Daario is just a fling or not.
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* In the book ''Literature/DeathStar'', twenty years after the events of the [[Franchise/StarWarsExpandedUniverse Medstar Duology,]] the one character to feature in all three books is a surgeon who went from a teenaged prodigy to a cynical middle-aged man who's been [[ResignationsNotAccepted permanently drafted]]. In ''Death Star'' he reflects that he still doesn't know if he loved Bariss Offee, a Jedi he'd known during the Clone Wars. Whether he did or didn't, her death hit him hard, and he thinks of her often. As the Medstar Duology featured Bariss as one of the viewpoint characters, the readers know that she was totally unaware--she'd known about another character who [[LovingAShadow thought he loved her]], and she'd spent a lot of time with the prodigy, but she never knew.
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* Franchise/StarWarsLegends:
** In the book ''Literature/DeathStar'', twenty years after the events of the[[Franchise/StarWarsExpandedUniverse Medstar Duology,]] Duology, the one character to feature in all three books is a surgeon who went from a teenaged prodigy to a cynical middle-aged man who's been [[ResignationsNotAccepted permanently drafted]]. In ''Death Star'' he reflects that he still doesn't know if he loved Bariss Offee, a Jedi he'd known during the Clone Wars. Whether he did or didn't, her death hit him hard, and he thinks of her often. As the Medstar Duology featured Bariss as one of the viewpoint characters, the readers know that she was totally unaware--she'd known about another character who [[LovingAShadow thought he loved her]], and she'd spent a lot of time with the prodigy, but she never knew.knew.
** ''[[Literature/StarWarsKenobi Kenobi]]'': Orrin is implied to be holding a torch for Annileen that nothing came of because he was married when they met and by the time his marriage ended she had already married Dannar. Annileen in turn develops feelings for Ben, who both doesn't reciprocate them and isn't available for a relationship anyway.
** In the book ''Literature/DeathStar'', twenty years after the events of the
** ''[[Literature/StarWarsKenobi Kenobi]]'': Orrin is implied to be holding a torch for Annileen that nothing came of because he was married when they met and by the time his marriage ended she had already married Dannar. Annileen in turn develops feelings for Ben, who both doesn't reciprocate them and isn't available for a relationship anyway.
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* ''Literature/MrsSmithsSpySchoolForGirls'': [[TheProtagonist Abigail Hunter]] has a crush on Quinn Gardener, who has a crush on Charlotte Cavendish, who has a crush on a kid named Xavier, who Abigail says doesn't even know Charlotte exists.
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* A text story in a 1980s UK girls' comic [[TheChristmasAnnual Christmas Annual]] entitled "I Love Him, He Loves Her" had the main character complaining to the narrator about loving a boy who was dating someone else, and saying the TitleDrop sounded like bad song lyrics. At the end, the narrator reflected that she'd got the lyrics wrong.
-->"It should go 'I love you, you love him, he loves her'."
-->"It should go 'I love you, you love him, he loves her'."
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** Vanilla has a crush Grisam Burdock, who actually likes her twin sister.
** Tommy Rye is in love with Vanilla, who only sees him as a friend.
** Tommy Rye is in love with Vanilla, who only sees him as a friend.
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** Vanilla has a crush Grisam Burdock, who actually likes Burdock since she was nine years old. The young wizard is attracted to her twin sister.
sister, Lavender, who has a harsher personality and shares some of his more macabre interest.
** Tommy Rye is in love withVanilla, who only sees Vanilla since they were children. She thought of him as a friend. sweet guy, but had not romantic interest in him, and instead focused on Grisam and, later, Jim.
** Tommy Rye is in love with
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* In the ''Fairy/Oak'' series:
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* In the ''Fairy/Oak'' ''Literature/FairyOak'' series:
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* In the ''Fairy/Oak'' series:
** Vanilla has a crush Grisam Burdock, who actually likes her twin sister.
** Tommy Rye is in love with Vanilla, who only sees him as a friend.
** Vanilla has a crush Grisam Burdock, who actually likes her twin sister.
** Tommy Rye is in love with Vanilla, who only sees him as a friend.
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** The Mad King, Aerys, would have rather wed [[spoiler:Joanna Lannister]] than his sister, which combined with his increasing madness as he grew older made him come to hate his childhood friend, [[spoiler:Joanna's husband Tywin Lannister]] out of jealousy.
*** This gets worse when we learn that Rhaella Targaryen and Bonifer Hasty had [[CourtlyLive a thing]] going on that both probably wanted to upgrade. Until Rhaella was informed she was marrying Aerys, no ifs or buts. Ser Bonifer wound up joining the Faith Militant rather than taking another woman to wife. He's... gone a little extreme over time since her death.
*** This gets worse when we learn that Rhaella Targaryen and Bonifer Hasty had [[CourtlyLive a thing]] going on that both probably wanted to upgrade. Until Rhaella was informed she was marrying Aerys, no ifs or buts. Ser Bonifer wound up joining the Faith Militant rather than taking another woman to wife. He's... gone a little extreme over time since her death.
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** The Mad King, Aerys, would have rather wed [[spoiler:Joanna Lannister]] than his sister, which combined with his increasing madness as he grew older made him come to hate his childhood friend, [[spoiler:Joanna's husband Tywin Lannister]] out of jealousy.jealousy and regularly abused his wife horrifically.
*** This gets worse when we learn that Rhaella Targaryen and Ser Bonifer Hasty had[[CourtlyLive [[CourtlyLove a thing]] going on that both probably wanted to upgrade. Until upgrade (well, most likely). Until, that was, Rhaella was informed that she was marrying Aerys, no ifs or buts. Ser Bonifer wound up joining the Faith Militant rather than getting over it and/or taking another woman to wife. He's... gone a little extreme in his piety over time since her death.Rhaella's death in the Rebellion.
*** This gets worse when we learn that Rhaella Targaryen and Ser Bonifer Hasty had
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*** This gets worse when we learn that Rhaella Targaryen and Bonifer Hasty had [[CourtlyLive a thing]] going on that both probably wanted to upgrade. Until Rhaella was informed she was marrying Aerys, no ifs or buts. Ser Bonifer wound up joining the Faith Militant rather than taking another woman to wife. He's... gone a little extreme over time since her death.
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* In Sarah Gailey's ''Literature/RiverOfTeeth'', the keen-eyed but impulsive cardsharp Cal is in love with the resident EmotionlessGirl contract killer Adelia. Adelia does not care for men, in general or in his specific case.
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** Hiroki Sugimura turns out to be in love with Kayoko Kotohiki, who in turn is in love with an older boy at her tea ceremony training school.
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** Hiroki Sugimura turns out to be in love with Kayoko Kotohiki, who in turn is in love with an older boy at her tea ceremony training school. Meanwhile, Hiroki's childhood friend Chigusa Takako seems to be in love with him.
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** By the end, the only aversions are [[spoiler:Shuya seeming to reciprocate Noriko's feelings]], and Sakura Ogawa and Kazuhiko Yamamoto, who are dating, but [[spoiler:[[kill themselves]] when the Program starts]]. Everyone else's love remains unrequited.
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** By the end, the only aversions are [[spoiler:Shuya seeming to reciprocate Noriko's feelings]], and Sakura Ogawa and Kazuhiko Yamamoto, who are dating, but [[spoiler:[[kill themselves]] [[spoiler:kill themselves when the Program starts]]. Everyone else's love remains unrequited.
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** By the end, the only aversions are [[spoiler:Shuya seeming to reciprocate Noriko's feelings]], and Sakura Ogawa and Kazuhiko Yamamoto, who are dating, but [[spoiler:[[TogetherInDeath kill themselves]] when the Program starts]]. Everyone else's love remains unrequited.
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** By the end, the only aversions are [[spoiler:Shuya seeming to reciprocate Noriko's feelings]], and Sakura Ogawa and Kazuhiko Yamamoto, who are dating, but [[spoiler:[[TogetherInDeath kill [[spoiler:[[kill themselves]] when the Program starts]]. Everyone else's love remains unrequited.
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* For the most part in ''Literature/BattleRoyale''. At the beginning of the novel, Yoshitoki has a crush on Noriko, who likes Shuya, who likes his upperclassman Kazumi Shinitani, who has a boyfriend. Then there's all the other girls who are in love with [[ChickMagnet Shuya]], while Chisato Matsui turns out to have a crush on Shinji Mimura, and Hiroki Sugimura turns out to be in love with Kayoko Kotohiki, who in turn is in love with an older boy at her tea ceremony training school. By the end, only [[spoiler:Shuya appears to reciprocate Noriko's feelings]], while everyone else's love remains unrequited.
** The only other aversion is Sakura Ogawa and Kazuhiko Yamamoto, who are dating are the start, but [[spoiler:kill themselves at the beginning of the Program, to avoid having to kill their classmates]].
** The only other aversion is Sakura Ogawa and Kazuhiko Yamamoto, who are dating are the start, but [[spoiler:kill themselves at the beginning of the Program, to avoid having to kill their classmates]].
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* For the most part in ''Literature/BattleRoyale''. Specifically:
** At the beginning of the novel, Yoshitoki has a crush on Noriko, who likes Shuya, who likes his upperclassman Kazumi Shinitani, who has a boyfriend.Then there's There's also all the other girls who are in love with [[ChickMagnet Shuya]], while Shuya]].
** Chisato Matsui turns out to have a crush on Shinji Mimura,and which is only revealed [[spoiler:after he's killed]].
** Hiroki Sugimura turns out to be in love with Kayoko Kotohiki, who in turn is in love with an older boy at her tea ceremony trainingschool. school.
** There's also the complicated situation between Yoshimi Yahagi and Yoji Kuramoto. They had been dating, and while Yoshimi was deeply in love with Yoji, [[spoiler:when they run into each other during the Program, Yoji claims he was only with her because he thought she was easy, and yells at her stay away from him while holding her at gunpoint. After Yoshimi stops fighting him, reaffirms her love for him, and allows him to shoot her, he stops and tears up, seemingly actually returning her affections. Yoji's feelings are left unclear, however, as [[FemmeFatale Mitsuko]] shows up and kills them both right after.]]
** By the end, the only aversions are [[spoiler:Shuyaappears seeming to reciprocate Noriko's feelings]], while everyone else's love remains unrequited.
** The only other aversion isand Sakura Ogawa and Kazuhiko Yamamoto, who are dating are the start, dating, but [[spoiler:kill themselves at the beginning of the Program, to avoid having to [[spoiler:[[TogetherInDeath kill their classmates]].themselves]] when the Program starts]]. Everyone else's love remains unrequited.
** At the beginning of the novel, Yoshitoki has a crush on Noriko, who likes Shuya, who likes his upperclassman Kazumi Shinitani, who has a boyfriend.
** Chisato Matsui turns out to have a crush on Shinji Mimura,
** Hiroki Sugimura turns out to be in love with Kayoko Kotohiki, who in turn is in love with an older boy at her tea ceremony training
** There's also the complicated situation between Yoshimi Yahagi and Yoji Kuramoto. They had been dating, and while Yoshimi was deeply in love with Yoji, [[spoiler:when they run into each other during the Program, Yoji claims he was only with her because he thought she was easy, and yells at her stay away from him while holding her at gunpoint. After Yoshimi stops fighting him, reaffirms her love for him, and allows him to shoot her, he stops and tears up, seemingly actually returning her affections. Yoji's feelings are left unclear, however, as [[FemmeFatale Mitsuko]] shows up and kills them both right after.]]
** By the end, the only aversions are [[spoiler:Shuya
** The only other aversion is
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** The only other aversion is Sakura Ogawa and Kazuhiko Yamamoto, who are dating are the start, but [[spoiler:kill themselves at the beginning of the Program, to avoid having to kill their classmates]].
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* For the most part in ''Literature/BattleRoyale''. At the beginning of the novel, Yoshitoki has a crush on Noriko, who likes Shuya, who likes his upperclassman Kazumi Shinitani, who has a boyfriend. Then there's all the other girls who are in love with [[ChickMagnet Shuya]], while Chisato Matsui turns out to have a crush on Shinji Mimura, and Hiroki Sugimura turns out to be in love with Kayoko Kotohiki, who in turn is in love with an older boy at her tea ceremony training school. By the end, only [[spoiler:Shuya appears to reciprocate Noriko's feelings]], while everyone else's love remains unrequited.
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* Happens in a few cases in ''Literature/BoneStreetRumba'':
** Kia is in love with Gio, who has eyes for Jeremy.
** Dr. Tijou has a crush on Baba Eddie, who has a steady boyfriend already.
* In ''Literature/FarFromTheMaddingCrowd'' by Thomas Hardy, three men propose marriage to Bathsheba Everdene. Both of the first two men love her, but she refuses them both. She marries the third, then discovers that he's in love with another woman.
* Steinbeck's entire ''Literature/EastOfEden'' revolves around this trope, but with love in the general sense: father/son and brother/brother in addition to romance.
* Bret Easton Ellis' ''Literature/TheRulesOfAttraction'' exaggerates this trope to the point of comedic ridiculousness, using a narrative which transfers constantly between ten or eleven promiscuous arts college students (though there are 3 central protagonists), all of whom have unrequited feelings for one another and/or more minor characters.
* In Creator/VictorHugo's ''Literature/TheHunchbackOfNotreDame'', deformed bellringer Quasimodo, [[VillainousBreakdown increasingly unstable priest]] Claude Frollo, and lazy poet Pierre Gringoire are all in love with La Esmeralda (Gringoire even ends up ''married'' to her, though that doesn't mean [[SexlessMarriage he gets to touch her]]), who loves the soldier Phoebus, who's engaged to another woman but fine with boning Esmeralda on the side so long as it doesn't inconvenience him in any way and he doesn't have to acknowledge her in public.
** Hugo likes this one. In 1400 pages, ''Literature/LesMiserables'' features ''one'' reciprocated romance with Cosette and Marius. The rest all end horribly. Fantine is ditched for a laugh by her feckless bourgeois lover Tholomyes--she becomes a prostitute to support their illegitimate daughter Cosette, [[IncurableCoughOfDeath gets sick]] and dies. Eponine develops a huge crush on Marius, but he doesn't even notice until she takes a bullet for him at the barricade and bleeds out in his arms. And in the ([[HoYay sort of]]) platonic sense, Grantaire [[NotInThisForYourRevolution doesn't care about the revolution]] but is deeply devoted to Enjolras, while Enjolras is too devoted to his glorious cause to put up with Grantaire's cynicism--until the National Guard comes to shoot Enjolras, and Grantaire is allowed to die at his side. Madame Thenardier is also stated to be deeply devoted to her husband while he is quite content to let her rot in jail and is completely unmoved when he hears she is dead. She hadn't ever done anything to earn his scorn, he simply never cared for his family in the first place. Their two youngest children would also count in a familial sense, being abandoned as children, forced to walk the street looking for parents they know nothing about.
* In the book ''Literature/DeathStar'', twenty years after the events of the [[Franchise/StarWarsExpandedUniverse Medstar Duology,]] the one character to feature in all three books is a surgeon who went from a teenaged prodigy to a cynical middle-aged man who's been [[ResignationsNotAccepted permanently drafted]]. In ''Death Star'' he reflects that he still doesn't know if he loved Bariss Offee, a Jedi he'd known during the Clone Wars. Whether he did or didn't, her death hit him hard, and he thinks of her often. As the Medstar Duology featured Bariss as one of the viewpoint characters, the readers know that she was totally unaware--she'd known about another character who [[LovingAShadow thought he loved her]], and she'd spent a lot of time with the prodigy, but she never knew.
* The ''Literature/{{Indigo}}'' series. Phereniq loves Augon. Augon is [[spoiler:[[ObliviousToLove oblivious to her feelings]]]]. Luk loves Jessamin. Jessamin is [[spoiler:apparently infatuated with Augon… but, as she turns out to be a [[OurDemonsAreDifferent demon's avatar]], it's academic]]. Forthright loves Indigo. Indigo thinks Forthright is a silly boy. Rimmi loves Veness. Veness [[spoiler:loves Indigo… and she ''returns'' his feelings, meaning [[DeathOfTheHypotenuse Veness is doomed]]]]. Lord Bray loves Moia. Moia loves [[spoiler:Gordo, and it [[TogetherInDeath gets them both killed]]]]. Ryen loves Brythere—despite [[ArrangedMarriage their marriage being an arranged one]]—and is worried that she doesn't reciprocate [[spoiler:(she does)]]. Vinar loves Indigo… [[spoiler:but, when that doesn't work out, [[PairTheSpares he eventually hooks up with Niahrin]]]]. Indigo loves Fenran [[spoiler:(or [[LovingAShadow at least her memories of him]]. Fenran, in the end, loves only his own ambitions.]]
* ''Literature/GreatExpectations''. The protagonist Pip has unrequited feelings on Estella, who was raised by her mistress to be an [[EmotionlessGirl unfeeling]] IceQueen who breaks boys' hearts. [[GoneHorriblyRight When so many men fall in love with her,]] Estella elects to marry the absolute ''worst'' of all her suitors, just to spite and hurt the others (including Pip). She suffers in an abusive marriage for years. Pip, after realizing his feelings for his [[ChildhoodFriendRomance childhood friend Biddy]], tries to start a relationship with her, only to learn that she was already in relationship with his ParentalSubstitute.
* In the ''Franchise/{{Disgaea}}'' [[LightNovel/DisgaeaNovels novels]], [[Characters/DisgaeaHourOfDarkness Laharl]] is given a [[UnwantedHarem harem]] of girls, none of them will even get what they want, because our “hero” is AllergicToLove and a CelibateHero.
* ''Tons'' of unrequited love exists in ''Literature/ASongOfIceAndFire'', most of it spoiled by {{Arranged Marriage}}s. The most notable case is probably [[UnluckyChildhoodFriend Lysa Tully → Littlefinger → Catelyn Tully]] → Brandon Stark ← Barbrey Ryswell. The [[spoiler:Littlefinger → Catelyn part may have been the root cause of The War of the Five Kings]]. After a while, Catelyn [[PerfectlyArrangedMarriage learned to]] [[SettleForSibling settle for Brandon's brother]] Ned.
** [[spoiler:Cersei Lannister]] → Rhaegar Targaryen → Lyanna Stark ← Robert Baratheon. This ''definitely'' caused the previous war, Robert's Rebellion.
** [[IncompatibleOrientation Brienne → Renly Baratheon]] ↔ Ser Loras Tyrell.
** The Mad King, Aerys, would have rather wed [[spoiler:Joanna Lannister]] than his sister, which combined with his increasing madness as he grew older made him come to hate his childhood friend, [[spoiler:Joanna's husband Tywin Lannister]] out of jealousy.
* ''Literature/ICaptureTheCastle'': Stephen is in love with Cassandra, who's in love with Simon, who's in love with Rose, [[spoiler:who's in love with Neil]].
* ''Literature/HarryPotter'':
** [[VictoriousChildhoodFriend Ginny]] likes [[TheHero Harry]], who has a crush on Cho Chang, who is dating Cedric Diggory. After [[spoiler: Cedric dies]], Harry and Cho try to date. It fails miserably. By this point in time, Ginny has moved onto Dean Thomas… just in time for Harry to realize [[spoiler: [[UnrequitedLoveSwitcheroo that he likes Ginny after all]]]]. Romilda Vane also tries to feed Harry a love potion.
** [[spoiler: [[ChildhoodFriendRomance Severus Snape]] has always loved Lily Evans. Lily eventually marries [[JerkJock James Potter]]]], who also has an unrequited crush on her for awhile.
** Bellatrix quite clearly loves Voldemort, who isn't really capable of feeling or comprehending love.
** [[BelligerentSexualTension Hermione and Ron]] love one another, but each has a few throw-away [[LoveInterest Love Interests]]; Hermione (along with the rest of the girls at school) has a crush on Gilderoy Lockhart, goes to the Yule Ball with Viktor Krum (who retains feelings for her after the fact, as well as expresses interest in Ginny at the wedding), and takes Cormac [=McLaggen=] as her date to the Slug Club party ''specifically'' to annoy Ron. Ron, on the other hand, has a thing for Fleur Delacour (who marries his older brother, Bill) and Madame Rosmerta, and dates the thoroughly obnoxious Lavender Brown to get back at Hermione for dating Krum. He also hilariously becomes infatuated with Romilda Vane after accidentally ingesting the love potions she put in Harry's chocolates.
** Per WordOfGay, Dumbledore once had a crush on [[spoiler: Grindelwald]]. It was unrequited, but that didn't keep the latter from exploiting it for their own gain.
* ''Literature/{{Wicked}}'': Boq has a long-time crush on Glinda, who seems to be in love with Elphaba, who may or may not return those feelings. Later on, Elphaba is in love with Fiyero, who is altogether confused about the concept of love (he was betrothed ''at the age of seven'', so that's understandable), but seems pretty convinced that he feels the same way. His [[spoiler: widow]], Sarima, doesn't care about him too much, but seems to be furious when confronted with the fact that he was cheating on her (but she thinks it was with Glinda).
* ''Literature/SadCypress'': Peter loves Elinor, who loves Roddy, who loves Mary, who [[AntiClimax finds him annoying and tells him to go back to Elinor]].
* ''Literature/TalesOfKolmar'' has the Will → Aral → Vilkas situation.
* ''Literature/{{Twilight}}'': Jessica likes Mike, Lauren likes Tyler but both boys (along with Eric and all the male population of Forks) are interested in Bella. Bella couldn't care less about them and falls for Edward, the only one who seemed to hate her at first.
** And of course Jacob also counts, as he also falls in love with Bella, but she only considers him a friend.
** Leah was engaged to Sam, until he imprinted on Emily. Losing her fiancé and best friend at once has naturally left Leah kind of bitter.
* If there is any love in ''Literature/GreekNinja'' it's unrequited.
* ''Literature/SongAtDawn'': Arnaud is in love with Estela who is in love with Dragonetz who is in a relationship with Emerganda [[spoiler: who is in love with him after he falls for Estela.]]
* ''Literature/WingsOfFire'': Fatespeaker loves [[TheSmartGuy Starflight,]] who loves Sunny, who only thinks of him as a brother. The second arc is much worse; Turtle may or may not have a crush on Kinkajou, who has a crush on Winter, who is in love with [[spoiler:Moonwatcher.]] Qibli is also shown to like [[spoiler:Moon,]] and it's unclear whether she likes either of them back. Qilbi also has some HoYay with Winter. [[ClosetGay Umber]] has a crush on Qilbi.
* ''Literature/TheSilmarillion'':
** Nellas, Finduilas and at least one unnamed woman all love Túrin. Túrin falls in love with and marries Níniel, [[spoiler: who turns out to be his sister]]. [[DownerEnding It doesn't end well for anyone involved]].
** Celebrimbor loves Galadriel. Galadriel loves Celeborn. This is one of the few cases of unrequited love in ''Silmarillion'' that doesn't result in the death of at least one person involved. Well, sort of - Celebrimbor dies, but because Sauron deceived him, not because of his love for Galadriel.
** Maeglin loves [[KissingCousins his cousin]] Idril, who loves Tuor. [[LoveMakesYouEvil It ends with Maeglin trying to kill Eärendil, Idril and Tuor's son]], before Tuor kills him.
** Daeron loves Lúthien, who loves Beren. Later Celegorm falls in "[[LoveMakesYouEvil love]]" with Lúthien. The results: [[LoveMakesYouCrazy Daeron reveals Lúthien's plan to rescue Beren to her father Elu Thingol]], who imprisons her in a tree-house, and Celegorm tries to force Lúthien to marry him.
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** Kia is in love with Gio, who has eyes for Jeremy.
** Dr. Tijou has a crush on Baba Eddie, who has a steady boyfriend already.
* In ''Literature/FarFromTheMaddingCrowd'' by Thomas Hardy, three men propose marriage to Bathsheba Everdene. Both of the first two men love her, but she refuses them both. She marries the third, then discovers that he's in love with another woman.
* Steinbeck's entire ''Literature/EastOfEden'' revolves around this trope, but with love in the general sense: father/son and brother/brother in addition to romance.
* Bret Easton Ellis' ''Literature/TheRulesOfAttraction'' exaggerates this trope to the point of comedic ridiculousness, using a narrative which transfers constantly between ten or eleven promiscuous arts college students (though there are 3 central protagonists), all of whom have unrequited feelings for one another and/or more minor characters.
* In Creator/VictorHugo's ''Literature/TheHunchbackOfNotreDame'', deformed bellringer Quasimodo, [[VillainousBreakdown increasingly unstable priest]] Claude Frollo, and lazy poet Pierre Gringoire are all in love with La Esmeralda (Gringoire even ends up ''married'' to her, though that doesn't mean [[SexlessMarriage he gets to touch her]]), who loves the soldier Phoebus, who's engaged to another woman but fine with boning Esmeralda on the side so long as it doesn't inconvenience him in any way and he doesn't have to acknowledge her in public.
** Hugo likes this one. In 1400 pages, ''Literature/LesMiserables'' features ''one'' reciprocated romance with Cosette and Marius. The rest all end horribly. Fantine is ditched for a laugh by her feckless bourgeois lover Tholomyes--she becomes a prostitute to support their illegitimate daughter Cosette, [[IncurableCoughOfDeath gets sick]] and dies. Eponine develops a huge crush on Marius, but he doesn't even notice until she takes a bullet for him at the barricade and bleeds out in his arms. And in the ([[HoYay sort of]]) platonic sense, Grantaire [[NotInThisForYourRevolution doesn't care about the revolution]] but is deeply devoted to Enjolras, while Enjolras is too devoted to his glorious cause to put up with Grantaire's cynicism--until the National Guard comes to shoot Enjolras, and Grantaire is allowed to die at his side. Madame Thenardier is also stated to be deeply devoted to her husband while he is quite content to let her rot in jail and is completely unmoved when he hears she is dead. She hadn't ever done anything to earn his scorn, he simply never cared for his family in the first place. Their two youngest children would also count in a familial sense, being abandoned as children, forced to walk the street looking for parents they know nothing about.
* In the book ''Literature/DeathStar'', twenty years after the events of the [[Franchise/StarWarsExpandedUniverse Medstar Duology,]] the one character to feature in all three books is a surgeon who went from a teenaged prodigy to a cynical middle-aged man who's been [[ResignationsNotAccepted permanently drafted]]. In ''Death Star'' he reflects that he still doesn't know if he loved Bariss Offee, a Jedi he'd known during the Clone Wars. Whether he did or didn't, her death hit him hard, and he thinks of her often. As the Medstar Duology featured Bariss as one of the viewpoint characters, the readers know that she was totally unaware--she'd known about another character who [[LovingAShadow thought he loved her]], and she'd spent a lot of time with the prodigy, but she never knew.
* The ''Literature/{{Indigo}}'' series. Phereniq loves Augon. Augon is [[spoiler:[[ObliviousToLove oblivious to her feelings]]]]. Luk loves Jessamin. Jessamin is [[spoiler:apparently infatuated with Augon… but, as she turns out to be a [[OurDemonsAreDifferent demon's avatar]], it's academic]]. Forthright loves Indigo. Indigo thinks Forthright is a silly boy. Rimmi loves Veness. Veness [[spoiler:loves Indigo… and she ''returns'' his feelings, meaning [[DeathOfTheHypotenuse Veness is doomed]]]]. Lord Bray loves Moia. Moia loves [[spoiler:Gordo, and it [[TogetherInDeath gets them both killed]]]]. Ryen loves Brythere—despite [[ArrangedMarriage their marriage being an arranged one]]—and is worried that she doesn't reciprocate [[spoiler:(she does)]]. Vinar loves Indigo… [[spoiler:but, when that doesn't work out, [[PairTheSpares he eventually hooks up with Niahrin]]]]. Indigo loves Fenran [[spoiler:(or [[LovingAShadow at least her memories of him]]. Fenran, in the end, loves only his own ambitions.]]
* ''Literature/GreatExpectations''. The protagonist Pip has unrequited feelings on Estella, who was raised by her mistress to be an [[EmotionlessGirl unfeeling]] IceQueen who breaks boys' hearts. [[GoneHorriblyRight When so many men fall in love with her,]] Estella elects to marry the absolute ''worst'' of all her suitors, just to spite and hurt the others (including Pip). She suffers in an abusive marriage for years. Pip, after realizing his feelings for his [[ChildhoodFriendRomance childhood friend Biddy]], tries to start a relationship with her, only to learn that she was already in relationship with his ParentalSubstitute.
* In the ''Franchise/{{Disgaea}}'' [[LightNovel/DisgaeaNovels novels]], [[Characters/DisgaeaHourOfDarkness Laharl]] is given a [[UnwantedHarem harem]] of girls, none of them will even get what they want, because our “hero” is AllergicToLove and a CelibateHero.
* ''Tons'' of unrequited love exists in ''Literature/ASongOfIceAndFire'', most of it spoiled by {{Arranged Marriage}}s. The most notable case is probably [[UnluckyChildhoodFriend Lysa Tully → Littlefinger → Catelyn Tully]] → Brandon Stark ← Barbrey Ryswell. The [[spoiler:Littlefinger → Catelyn part may have been the root cause of The War of the Five Kings]]. After a while, Catelyn [[PerfectlyArrangedMarriage learned to]] [[SettleForSibling settle for Brandon's brother]] Ned.
** [[spoiler:Cersei Lannister]] → Rhaegar Targaryen → Lyanna Stark ← Robert Baratheon. This ''definitely'' caused the previous war, Robert's Rebellion.
** [[IncompatibleOrientation Brienne → Renly Baratheon]] ↔ Ser Loras Tyrell.
** The Mad King, Aerys, would have rather wed [[spoiler:Joanna Lannister]] than his sister, which combined with his increasing madness as he grew older made him come to hate his childhood friend, [[spoiler:Joanna's husband Tywin Lannister]] out of jealousy.
* ''Literature/ICaptureTheCastle'': Stephen is in love with Cassandra, who's in love with Simon, who's in love with Rose, [[spoiler:who's in love with Neil]].
* ''Literature/HarryPotter'':
** [[VictoriousChildhoodFriend Ginny]] likes [[TheHero Harry]], who has a crush on Cho Chang, who is dating Cedric Diggory. After [[spoiler: Cedric dies]], Harry and Cho try to date. It fails miserably. By this point in time, Ginny has moved onto Dean Thomas… just in time for Harry to realize [[spoiler: [[UnrequitedLoveSwitcheroo that he likes Ginny after all]]]]. Romilda Vane also tries to feed Harry a love potion.
** [[spoiler: [[ChildhoodFriendRomance Severus Snape]] has always loved Lily Evans. Lily eventually marries [[JerkJock James Potter]]]], who also has an unrequited crush on her for awhile.
** Bellatrix quite clearly loves Voldemort, who isn't really capable of feeling or comprehending love.
** [[BelligerentSexualTension Hermione and Ron]] love one another, but each has a few throw-away [[LoveInterest Love Interests]]; Hermione (along with the rest of the girls at school) has a crush on Gilderoy Lockhart, goes to the Yule Ball with Viktor Krum (who retains feelings for her after the fact, as well as expresses interest in Ginny at the wedding), and takes Cormac [=McLaggen=] as her date to the Slug Club party ''specifically'' to annoy Ron. Ron, on the other hand, has a thing for Fleur Delacour (who marries his older brother, Bill) and Madame Rosmerta, and dates the thoroughly obnoxious Lavender Brown to get back at Hermione for dating Krum. He also hilariously becomes infatuated with Romilda Vane after accidentally ingesting the love potions she put in Harry's chocolates.
** Per WordOfGay, Dumbledore once had a crush on [[spoiler: Grindelwald]]. It was unrequited, but that didn't keep the latter from exploiting it for their own gain.
* ''Literature/{{Wicked}}'': Boq has a long-time crush on Glinda, who seems to be in love with Elphaba, who may or may not return those feelings. Later on, Elphaba is in love with Fiyero, who is altogether confused about the concept of love (he was betrothed ''at the age of seven'', so that's understandable), but seems pretty convinced that he feels the same way. His [[spoiler: widow]], Sarima, doesn't care about him too much, but seems to be furious when confronted with the fact that he was cheating on her (but she thinks it was with Glinda).
* ''Literature/SadCypress'': Peter loves Elinor, who loves Roddy, who loves Mary, who [[AntiClimax finds him annoying and tells him to go back to Elinor]].
* ''Literature/TalesOfKolmar'' has the Will → Aral → Vilkas situation.
* ''Literature/{{Twilight}}'': Jessica likes Mike, Lauren likes Tyler but both boys (along with Eric and all the male population of Forks) are interested in Bella. Bella couldn't care less about them and falls for Edward, the only one who seemed to hate her at first.
** And of course Jacob also counts, as he also falls in love with Bella, but she only considers him a friend.
** Leah was engaged to Sam, until he imprinted on Emily. Losing her fiancé and best friend at once has naturally left Leah kind of bitter.
* If there is any love in ''Literature/GreekNinja'' it's unrequited.
* ''Literature/SongAtDawn'': Arnaud is in love with Estela who is in love with Dragonetz who is in a relationship with Emerganda [[spoiler: who is in love with him after he falls for Estela.]]
* ''Literature/WingsOfFire'': Fatespeaker loves [[TheSmartGuy Starflight,]] who loves Sunny, who only thinks of him as a brother. The second arc is much worse; Turtle may or may not have a crush on Kinkajou, who has a crush on Winter, who is in love with [[spoiler:Moonwatcher.]] Qibli is also shown to like [[spoiler:Moon,]] and it's unclear whether she likes either of them back. Qilbi also has some HoYay with Winter. [[ClosetGay Umber]] has a crush on Qilbi.
* ''Literature/TheSilmarillion'':
** Nellas, Finduilas and at least one unnamed woman all love Túrin. Túrin falls in love with and marries Níniel, [[spoiler: who turns out to be his sister]]. [[DownerEnding It doesn't end well for anyone involved]].
** Celebrimbor loves Galadriel. Galadriel loves Celeborn. This is one of the few cases of unrequited love in ''Silmarillion'' that doesn't result in the death of at least one person involved. Well, sort of - Celebrimbor dies, but because Sauron deceived him, not because of his love for Galadriel.
** Maeglin loves [[KissingCousins his cousin]] Idril, who loves Tuor. [[LoveMakesYouEvil It ends with Maeglin trying to kill Eärendil, Idril and Tuor's son]], before Tuor kills him.
** Daeron loves Lúthien, who loves Beren. Later Celegorm falls in "[[LoveMakesYouEvil love]]" with Lúthien. The results: [[LoveMakesYouCrazy Daeron reveals Lúthien's plan to rescue Beren to her father Elu Thingol]], who imprisons her in a tree-house, and Celegorm tries to force Lúthien to marry him.
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