[[caption-width-right:350:[[Music/BonJovi Shot through the heart, and you're to blame!]]]]

->''"Love hurts, love scars,\\
love wounds and marrs any heart\\
not tough or strong enough\\
to take a lot of pain, take a lot of pain..."''
-->-- "[[http://en.wikipedia.org/wiki/Love_Hurts Love Hurts]]'', written by '''Boudleaux Bryant''' and recorded by The Everly Brothers/[[CoveredUp Nazareth]]/Cher/[[http://en.wikipedia.org/wiki/Love_Hurts#List_of_covers etc.]] (possible {{Trope Namer|s}})
%% One quote is sufficient. Put additional quotes in the quotes tab.

Forget life-threatening superheroism, acting TooDumbToLive, and TemptingFate. The dumbest, most insane and dangerous thing any hero can do in any media is... falling in love. Dare to love someone else and you set up yourself and your beloved for a plethora of emotional griefs. Love in RealLife is responsible for vast quantities of anguished poetry and tragic literature; factor in all the crazy stuff that happens on TV, and drama and disaster are practically guaranteed.

About to commit permanently? Look for an AnyoneCanDie to put a permanent end to the WillTheyOrWontThey issue. Forget to [[NeverGotToSayGoodbye say goodbye to your beloved that one time]]? It'll haunt you for the rest of your life. And let's not forget that becoming emotionally attached to one person leaves you open to the stress caused by the [[IHaveYourWife villain abducting your beloved]] or [[StuffedIntoTheFridge them even being killed off senselessly]] just to shape you into the AntiHero out for Revenge, or at the very least a HeartbrokenBadAss. Your love is hurt but alive? DontYouDarePityMe -- they will shove you away. Or perhaps you'd be their SecondLove -- if only they and you didn't think SillyRabbitRomanceIsForKids. Love will make your heart go soft and pitter-pattering into the path to be crushed by the cruel forces of fate against StarCrossedLovers. Small wonder that [[ItsNotYouItsMyEnemies so many try to protect their loved ones by dumping them]].

If you've got more than one love interest, you've got a [[GreenEyedMonster headache-inducing]] LoveTriangle or even LoveDodecahedron on your hands. Tread these waters ''very'' carefully, lest you be on the receiving end of a {{Yandere}}'s poisonous affections or a {{Tsundere}}'s MegatonPunch. Pick one lover and you can look forward to either a ThunderingHerd of [[ClingyJealousGirl jilted rivals]] or the [[ObliviousToLove silent shattering]] of [[AllLoveIsUnrequited many other hearts]]. All in the name of comedy, you say? Comedy never became as twisted as it does when dealing with lovers [[LoveMakesYouCrazy crazy]] enough to beat down your door, commit trespassing, [[TheGlomp glomp]] you, and refuse to let go. And [[ColdTurkeysAreEverywhere remembering the love interest anywhere you go]] makes it worse. Could also result in the character being NotGoodWithRejection.

And heaven forbid if your love turns out to be [[AllLoveIsUnrequited one-]][[AllTakeAndNoGive sided]]. You'll become a [[CrazyJealousGuy crazy]] LoveHungry [[StalkerWithACrush psycho stalker]] if you don't choose [[IWantMyBelovedToBeHappy to nobly sacrifice your love]]. Sometimes you'll even go all the way [[LoveMakesYouEvil into a full-fledged villain]] with a grudge against humanity because humanity was not kind enough to let you have that one person. Sometimes it's even [[CreatorBreakdown your own creator]] who decides that you can't get them because [[SourGrapesTropes he couldn't get her in real life]]!

Such a fragile illusion... Isn't it?

In the right/wrong genre, [[DeathBySex even when you win, you lose.]] Little wonder why many a [[TheCynic pessimist]] believes that "SillyRabbitRomanceIsForKids" and LoveMakesYouDumb, and many a hero has chosen to be a GenreSavvy CelibateHero.

Compare DestructiveRomance, HopeIsScary, TheFirstCutIsTheDeepest. A consequence when LoveRedeems goes with RedemptionEqualsDeath.

However, if you ''do'' [[TrueLovesKiss manage to get it right]], love can be the [[ThePowerOfLove purest and most powerful thing in the world]]. Another way to resolve this is through CleaningUpRomanticLooseEnds.

Contrast HappilyMarried. Unrelated to LoverTugOfWar, even though that may also hurt.


[[folder:Anime and Manga]]
* [[AntiVillain Anemone and Dominic]] of ''Anime/EurekaSeven''. The dangerous drugs she uses to pilot her mech take her DomesticAbuse {{Tsundere}} type behavior way beyond the usual fare. Sure, it can be funny at first to watch her beat the stuffing out of him, but as you gradually realize the depths of his devotion, her cruel indifference or abject violence becomes incredibly painful to watch. On Anemone's side, [[spoiler: when she finally realizes how much he means to her, but believes it's all too late,]] she delivers a gut-wrenching soliloquy, convinced that she doesn't deserve to live. [[spoiler: Amazingly, it all manages to end well.]]
* Dokuro-chan from ''LightNovel/BludgeoningAngelDokuroChan'' is an ''extremely'' brutal and literal version of this. The Opening probably puts this best:
-->''"I'll cut you, punch you, toy with you''\\
'' Kick you, be a cocktease, drip stuff on you''\\
''But that's just how I express my love."''
** Dokuro may not even be in love with Sakura. Read the [=WMGs=] for that series.
** Apparently, the main reason for [[SmugSnake Erika's]] obsession with the truth and her WhatKindOfLamePowerIsHeartAnyway tendencies is because of a failed relationship with her boyfriend.
* Roy/Riza in ''Manga/FullmetalAlchemist''. Even aside from the whole [[spoiler: burning her back]] thing, they have been a massive source of pain for one another. Most of the [[DarkAndTroubledPast traumatic events]] they have gone through would most likely never have taken place if they hadn't met each other (Roy wouldn't even [[spoiler: be a [[PersonOfMassDestruction State Alchemist]]]], she wouldn't have [[spoiler: joined the army and been sent to Ishval]] and he wouldn't have [[spoiler: [[MyGreatestFailure annihilated so many people]]]]; she has made it clear she doesn't like being in the army or killing people, but she won't quit as long as he needs her). They're practically the direct (albeit non-intentional) cause of everything in the other's life that makes them suffer, and still [[LivingEmotionalCrutch they're the very thing that makes the other want to go on living]] [[spoiler: as stated outright in chapter 95]].
** [[spoiler: Riza has her throat cut to force Roy to open the gate. Riza signals with a glare that not only would she beat him to death if he committed human transmutation, but help was on the way so it was pointless.]] It was nice of Arakawa to not force Roy to choose between the two options, though when you think about the fact that he was seriously considering [[spoiler: damning Amestris (and, possibly-eventually the whole world) for saving Riza, and couldn't even come to the decision to not do human transmutation till it seemed she would be saved]] you get a little worried at the lengths Roy would go to to keep his Lieutenant by his side.
* Pick practically ANY hero in ANY ''Franchise/{{Gundam}}'' series. If you don't believe me...
** ''Anime/MobileSuitGundam'': Amuro Ray [[spoiler: accidentally killed Lalah, his first love, when she [[TakingTheBullet took an attack meant for the man she loved]], Char Aznable]].
** ''[[Anime/MobileSuitZetaGundam Zeta Gundam]]'': Kamille Bidan [[spoiler: had his star crossed soulmate Four Murasame [[HeroicSacrifice sacrificing herself for him]] ''twice'']]. Oh, and his sworn rival Jerid Messa [[spoiler: losing both of his love interests ({{Dark Action Girl}}s Lyla Mira Lyla and Muar Pharaoh) to Kamille, so they can call it even]].
** ''[[Anime/MobileSuitGundamZZ Gundam ZZ]]'': Judau Ashta [[spoiler: loses Chara Soon, a {{broken|Bird}} young woman he didn't romantically love but still quite cared about, mere seconds after making her promise that she wouldn't die. He then proceeds to have to kill [[LadyOfWar Haman]] [[BigBad Karn]], one of his principle love interests, in the final battle]].
** ''[[Anime/MobileSuitVictoryGundam Victory Gundam]]'' : Even though nearly every couple in this series [[KillThemAll doesn't end well]], the main character's crush on [[spoiler: Katejina]] ends up very badly since she becomes an enemy AND in love with the resident CharClone too!
** [[SpellMyNameWithAnS Roybea]] Roy, the resident ChivalrousPervert of ''[[Anime/AfterWarGundamX Gundam X]]'' fame is well aware of this, its the reason why he chases away most of his lovers before he aligns with the Freeden crew. [[spoiler: This doesn't stop him from falling in with a female member of a LaResistance, who then ''dies in his arms''.]]
*** Ennil El happens to fall for TheHero Garrod, who, wanting nothing to do with her, aims a gun in her face; she becomes a StalkerWithACrush who follows the Freeden wanting revenge.
** ''[[Anime/MobileSuitGundamSEED Gundam SEED]]'': Kira Yamato [[spoiler: was manipulated by his first girlfriend, Flay, and later saw her die in front of him]]. Also Murrue Ramius, whose [[HerHeartWillGoOn heart goes on]]. ''Twice''. [[spoiler: At least one of them returned in the following series.]]
** ''[[Anime/MobileSuitGundamSEEDDestiny Gundam SEED Destiny]]'': Shinn Asuka [[spoiler: fell in love with [[{{Tykebomb}} Stellar]], who ''also'' died in front of him, despite his promise to protect her]].
** Not content to ruin just one couple, ''[[Anime/MobileSuitGundam00 Gundam 00]]'' has destroyed several of them. [[spoiler:Feldt lost her first crush before she even had the chance of admitting anything to him, and ditto for Tieria who was in love [[EvenTheGuysWantHim with the same man]] that Feldt loved; Christina and Lichty were already dying when they conceded that they had feelings for each other; Saji's relationship with Louise is to put it very nicely "on the rocks"; Allelujah and Soma's has also hit some rough ground with the death of Sergei Smirnov; Lyle, the twin brother of the guy loved by Feldt and Tieria, just saw his lover Anew get blown to pieces by Setsuna before his very eyes; Sumeragi's lover Emilio was already dead prior to the series beginning and then what relation she may have had with Billy got torn up when Setsuna opened his mouth about her being part of CB]]
** Flit Asuno from ''[[Anime/MobileSuitGundamAge Gundam AGE]]'' fell for [[spoiler:Yurin L'Ciel, only to see her get manipulated and later brutally killed by [[EnfantTerrible Desil.]] He becomes so [[UnstoppableRage enraged]] and psychologically broken that he not only refuses to acknowledge the UE as fellow human beings, but also starts to see himself as a savior... for the corrupt and genocidal Earth Federal Forces]].
** ''[[Anime/MobileSuitGundamIronBloodedOrphans Gundam Iron-Blooded Orphans]]'': On Gjallarhorn's side, Carta had unrequited feelings for [[=McGillis=]] [[spoiler:except the latter just sent her to her death]]. On Tekkadan-Turbines' side, Lafter slowly had feelings for Akihiro who is completely oblivious about it. [[spoiler:Unfortunately, she got shot to death by an assassin under Jasley who just want to get even with Tekkadan]]. Even the happy couple, Naze and Amida, are not spared from this particularly in Episode 40 [[spoiler:where after Amida's Mobile Suit got shot down, Naze pulls a kamikaze run on the enemy's ship so he can be with her in death]].
** ''[[Anime/MobileSuitGundamThunderbolt Gundam Thunderbolt]]'': On the Feddies' side, Io's girlfriend and commanding officer, Claudia, got too stressed out when she sends her men to die in the battlefield that she took up drugs to forget everything. [[spoiler:Then, her XO shoots her for being a horrible leader]]. On Zeon's side, Dr. Karla lost her boyfriend after he got killed by Io but she slowly moved on and became close to Daryl. She even stood by his side when he lost his remaining limbs. They didn't die in the end but [[spoiler:Karla went insane after she just watched her friends getting vaporized and got grabbed by a RX-77-2 Guncannon. Poor Daryl can't do anything about it as he hold her in his arms, watching laugh like a child]].
** Among those who got off (relatively) easy are:
*** ''[[Anime/MobileSuitGundamThe08thMSTeam The 08th MS Team]]'': [[spoiler:Shiro Amada only loses a leg, but he keeps Aina and they live in peace.]]
*** ''[[Anime/MobileSuitGundam0080WarInThePocket Gundam 0080]]'': [[spoiler: Christina Mackenzie is completely unaware that she killed Bernie.]]
*** ''[[Anime/MobileFighterGGundam G Gundam]]'': Domon Kasshu [[spoiler: almost lost [[HotScientist Rain]] to the same Devil Gundam that caused the deaths of many others, including his beloved older brother. But he managed to save her and get her back... [[AnguishedDeclarationOfLove in the most awesome]] [[IKnowYoureInThereSomewhereFight way ]] '''''[[CrowningMomentOfAwesome EVER]]''''']]. Also, [[spoiler:Allenby escapes the fate of most BrainwashedAndCrazy women because the person who fights her is Rain, who has a Gundam equipped for precision ''and'' is a doctor. Rain brings her down without deadly force and defuses her, leaving her with just a brief hospital stay]].
*** In ''[[Anime/AfterWarGundamX Gundam X]]'' losing [[MysteriousWaif Tiffa Adil]] causes Garrod a HeroicBSOD; [[GetAholdOfYourselfMan it]] [[HostageForMcGuffin didn't]] [[CrowningMomentofAwesome last]] [[CrowningMomentofHeartwarming long.]]
*** ''[[Anime/MobileSuitGundam00 Gundam 00]]'' (again) [[spoiler: Saji and Louise got back together; Alle and Soma survived their BattleCouple stint and went WalkingTheEarth; Sumeragi talked Billy outta his funk and they kinda reconciled; Patrick survived too and he and Kati got ''married'']].
*** ''Anime/GundamBuildFighters'': As expected of the most [[LighterAndSofter light-hearted]] Gundam series yet, the romance (confined mostly to ShipTease) results in far more comedy than angst. Reiji and [[spoiler:[[TykeBomb Aila]]]] face the most obstacles, but like almost everyone in the series, they get a happy ending.
* Then, pick any hero in any Gundam-''inspired'' series.
* ''Anime/SpaceRunawayIdeon'': Cosmo suffers a HeroicBSOD discovering that [[spoiler:a girl he grew fond of, Kitty Kitten, was killed almost accidentally. Later, Kasha Imhof dies in the movie... and then [[KillEmAll EVERYONE dies]].]].
* ''Anime/NeonGenesisEvangelion'':
** Gendo behaves like he does because [[spoiler:his wife's death broke him. He was afraid of other people and Yui was the only person reached out to him. Without her he did not know how to love other people, and he sent Shinji away because he was afraid of him]].
** Shinji and Asuka loved other but hurt each other a lot. When [[spoiler:Shinji cancelled Third Impact and returned to the real world Asuka returned with him because they needed each other and he did not want a world with no Asuka, the person he had hurt and the one who had hurt him]].
** One of the main messages of the series (with the addendum "...but you need it.")
* ''Anime/CodeGeass'': Suzaku [[spoiler:witnesses his big love Princess Euphemia fatally shot by his arch-nemesis, after which she effectively dies in his arms (PietaPlagiarism galore)]], then some fifteen episodes later Lelouch[[spoiler:, the said "arch-nemesis", experiences Shirley, a girl he always cared for (well, perhaps not romantically but it was definitely headed that way) dying on him in a very similar fashion... at the hands of his GayOption of sorts, a {{Yandere}} boy who later commits suicide to save Lelouch's own life.]].
* Ayumi from ''Manga/HoneyAndClover'' has a bad case of unrequited love for Takumi, who sees her more like his sister. A lot of the first season of the anime is devoted to Ayumi's suffering because of this. Takumi in turn has a hard time with his feelings for (older) Rika.
* In ''Manga/OnePiece'', "Pirate Empress" Boa Hancock of the Seven Warlords of the Sea has the power to turn anyone who's so much as ''attracted'' to her to [[TakenForGranite stone]]. And then when she herself falls in love, she might die by it.
** This is actually subverted when Hancock falls in love, given that she has decided to help [[ChasteHero Luffy]] rather than bottle her feelings within her, as ''that'' was the cause of death for two empresses before her, and almost killed the elder/ex-ex-ex empress herself. Except that even though her feelings are sincere and intense [[spoiler: and based on how he once defeated the Tenryuubito aka those who enslaved and tortured Hancock and her sisters as young girls,]] it's [[NoHuggingNoKissing almost depressingly]] [[ShipSinking apparent]] that she doesn't really have a chance with Luffy. Though, in all fairness, she has as much chance as any other woman with Luffy, the ultimate IdiotHero with a degree in ObliviousToLove.
** It's also painfully obvious Camie the mermaid has a pretty serious thing for Hatchan, but...well...same reasons as above.
** Sanji literally rides this trope like a horse, not only are the bruises Nami leaves on him heart shaped, but tanking brutal beatings so a woman will be unharmed or a wedding dress won't get his blood on it, is all pain Sanji will accept. Even just glancing at Boa Hancock will turn Sanji to stone even when she wasn't even using her powers. [[spoiler: Sanji has more tragic examples of this in Whole Cake Island as he must give up on his crew, so that they and his [[ParentalSubstitute Father figure Zeff]] will survive. Even being forced to beat down Luffy and letting a heart broken Nami [[ArmourPiercingSlap slap him]] in the face and farewell him... further heart brake ensured Sanji when [[FaceOfAnAngelMindOfADemon Pudding]] the girl he was in a ArrangedMarriage with, had planned to kill him during the ceremony]].
** Depending on how you interpret the relationship, Zoro towards [[HowDareYouDieOnMe Kuina.]] When you put the possibility in context with [[CelibateHero his present lack of interest in sex]], it makes his back story even more depressing.
* Lithuania in ''Webcomic/AxisPowersHetalia'' gets all his fingers broken by his crush, the eccentric {{Yandere}} Belarus. [[HorribleJudgeOfCharacter He doesn't seem to mind]]. Russia, who is both Lithuania's boss and Bela's older brother (and ''more'' of a {{Yandere}} than her), has a ''very'' twisted, rather one-sided relationship with Lithuania himself, showing his affections through [[StalkerWithACrush stalking]] and [[MadLove abuse]].
** It's implied that Allied Forces' TeamDad England has a one-sided crush on someone that has brought him at least 100 years of pain, and widely speculated that it's his former colony, America. Despite usually being harsh and drunk, he actually gets moments of being TheWoobie when America [[{{Tsundere}} shoots him down and sometimes looks like he has fun doing it]]. And then there's [[UsefulNotes/TheAmericanRevolution *how* they grew apart]]...
** Also, [[HotBlooded Prussia]] might have feelings for either [[TheDitz North Italy]] or [[ActionGirl Hungary]]. Either way, he's screwed because of their respective romantic ties to [[PerpetualFrowner Germany]] (Prussia's younger brother, who is also heavily implied to have feelings for Italy ''and'' [[spoiler: to be the Holy Roman Empire, Italy's childhood love interest.]]) and [[{{Meganekko}} Austria]] (Hungary's ex-husband).
*** And if there's the [[TakeAThirdOption other option]] of him possibly having feelings for [[FoeYay Austria]]... yup, still a loss either way.
** Turkey's strongly implied in canon to have a crush on [[YamatoNadeshiko Japan]] who's just as strongly implied to [[BirdsOfAFeather prefer his long-time rival Greece]] [[HopelessSuitor over him]]. And if the Hetalia Wikis are to be believed, he might have also been in love with Ancient Greece a long time ago and ended up ''killing'' her, according to the beta version of the drama CD. ''And'' if certain parts of the fandom are to be believed, he's [[FoeYay actually in love with either Hungary or Greece]], who he has combative relations with and [[TheMasochismTango spends 90% of his time fighting with the otherwise easygoing and kind nations]]. Either way you look at it, he sure gets the short end of the stick when it comes to romance. (Unless he goes for [[MayDecemberRomance the much younger Iceland]], that is.)
* Good God, Franz from ''Anime/{{Gankutsuou}}''. [[HoYay His unrequited love for Albert]] caused him a whole world of pain (and [[spoiler: his death]]). Seriously, he had a lot going for him - being rich, having good looks, and having no shortage of beautiful and kind women after him (including his fiance, who loved him initially). But instead, he ends up constantly angsting and [[LoveMartyr sacrificing everything]] for Albert (who [[ObliviousGuiltSlinging doesn't appreciate any of it]] until the very last moment).
** Albert doesn't have it any easier, though. He develops a crush at first sight on the Count, who at first leads him on and then proceeds to [[spoiler:[[BreakTheCutie break his heart and ruin his life]]]]. And while we're at it, there's the Count himself: Mercedes' "betrayal" aside, [[spoiler:his [[BecomingTheMask unplanned for and unwanted feelings for Albert]] cause him a lot of angst and heartbreak, although [[LoveRedeems they save him in the end]]]].
* In ''Manga/{{Chobits}}'', [[spoiler:Freya [[DrivenToSuicide essentially kills herself]] because of this trope]].
* All over the place in ''Anime/DanganRonpa3'':
** Hajime and Chiaki: Despite her best efforts, Chiaki is unable to convince Hajime that he ''is'' worthy of her, contributing to him disappearing to [[spoiler:sign up for the [[DeathOfPersonality Kamukura Project]]]]. She then spends an entire year waiting for him until [[spoiler:she finally meets him as Izuru, who personally states he doesn't remember her. He then watches her die, triggering some level of too-late recollection as he cries, and holds onto her hairpin in grief and memory.]]
** Kyosuke and Chisa: [[spoiler:Kyosuke losing Chisa drives him insane]]. Then for added fun it's shown [[spoiler:she was [[BeingTorturedMakesYouEvil tortured into Despair]] during ''Side:Despair'' and has been spending the time between ''Side:Despair'' and ''Side:Future'' corrupting him into the man he is currently.]]
** Makoto and Kyoko: [[spoiler:Kyoko willingly sacrifices herself, refusing to betray Makoto again, and leaving him heartbroken.]]
** Ruruka and Izayoi: Despite Izayoi's loyalty, [[spoiler: Ruruka murders him so he can't betray her in the future. Izayoi still responds that he loves her, leaving Ruruka full of regret and self-loathing.]]
** Adding insult to injury, unrequited and platonic love are also used to the most hurtful degrees, such as [[spoiler:Junko using Juzo's unrequited love for Kyosuke as a way to manipulate him and using the fact that Chiaki is the most loved person in the 77th Class to throw the rest of the class into despair.]]
* In ''Manga/{{Gantz}}'', Kei goes through severe depression multiple times due to his loves dying on him. The first time is when Kishimoto dies (although she never did return his feelings), and subsequent times of him becoming really depressed are caused by his girlfriend Tae (who died but got revived). And since the series is still going on, there's ''still'' no guarantee that they'll be able to be together. A DownerEnding is quite possible...
* Ako Izumi of ''Manga/MahouSenseiNegima''. She has a ton of self-esteem issues, and is described as something of a doormat. Then she meets Nagi, he reassures her of her importance, and she falls in love with him. Even after getting TrappedInAnotherWorld and sold into slavery, she's able to hang on because she knows that he's there for her. Too bad that [[spoiler:"Nagi" is her ten-year-old teacher Negi magically aged-up]]. Naturally, she's utterly crushed when she finds out. And then, she gets better, sort of; she still has a thing for 'Nagi'. Which may be transferring to Negi now.
* Sagara Sousuke from ''Lightnovel/FullMetalPanic'' towards Kaname. His whole HeroicBSOD in TSR was caused by being torn away from her after he developed an attachment and feelings for her. As [[spoiler: Gauron]] angrily notices, ever since falling in love, he seems to have a lot more conflicting feelings and doubts.
** And speaking of [[spoiler: Gauron]], ''he'' seems to have lost some of ''his'' edge and become even more messed up since falling for Sousuke... after all, if he didn't ''care'' about Sousuke, he wouldn't have been so very angry in the first place...
*** In regards to Gauron, this is actually brought up and symbolically implied in the novels (though apparently parts of it were lost in the fan translation). Members of Amalgam actually covertly bring up to Sousuke how Gauron was overtaken by "cancer," all while mentioning that he [[StalkerWithACrush "really really liked Sousuke"]]... and according to the original wording, a parallel is implied of Kaname being Sousuke's "Gan" (cancer), and Sousuke being ''Gauron's'' "Gan". Any possible double meaning was [[ObliviousToLove lost to Sousuke]]. In addition, reading about the overall attitude of Gauron's colleagues when they talk to Sousuke, it seems like it's a well known fact to them that Gauron was ''way'' too obsessed with Sousuke.
* ''Anime/RahXephon'': Hey Megumi. What's that, your crush already has a girlfriend who is your best friend? Ouch. Now what about that other guy? Sorry, [[spoiler:your sister Haruka already had the key to his heart long ago]]. Oh, and the ''other'' other guy? [[spoiler:Turned evil because of the death of the girl ''he'' loves.]]
* Jigen from ''Franchise/LupinIII''. His luck with women runs from bad to worse, with them either betraying him, dying, or both.
* Simon from ''Anime/TengenToppaGurrenLagann''. His first love, CoolBigSis Yoko, was in love with [[HotBlooded Kamina]], and he had a rather painful experience seeing her kiss him. [[spoiler:Seeing said kiss would lead to Simon suffering a HeroicBSOD, that resulted in [[BloodBrothers Kam]][[BashBrothers ina's]] death]]. His SecondLove, Nia, [[spoiler: ends up dying ''right'' when they get married]]. And whether you interpret the relationship between him and [[EvenTheGuysWantHim Kamina]] as HoYay or as HeterosexualLifePartners, it ''is'' undeniable that [[spoiler: Kamina's death hit him ''[[HeroicBSOD very]]'' hard]].
** Yoko had it pretty hard too: the event that changed her from a {{Tsundere}} to a CoolBigSis was [[spoiler: [[DecoyProtagonist Kamina]]'s death]]. [[TearJerker Which happened on the very morning of their first kiss]] right after he promised to [[spoiler: give her something ten times better when the battle is over ...damn {{Retirony}}]].
** Must have also hurt Kittan badly [[spoiler: when he only had the confidence (and partly because of it) to confess to Yoko before performing an [[DyingMomentOfAwesome EPIC]] HeroicSacrifice to spare her from doing the same... ]]
** And there's Viral, who is immortal and can't reproduce... [[spoiler: and whose greatest dream is to have a wife and child]]. [[TearJerker *sniff*]]
* Kenshin Himura and Tomoe Yukishiro from ''Manga/RurouniKenshin''. When he was in his ExtremeDoormat phase, she was the one that made him start feeling ''anything at all'' again. Apparently it was first caring, then love, and finally awful grief. He has his fair share of Love Hurts moments with his second girlfriend Kaoru too, but his story with Tomoe steals the show.
** It's also a whole deal for Tomoe herself. She lost her [[ChildhoodFriendRomance Victorious Childhood Friend]] Akira to Kenshin's sword, went to Kyoto to find him and have revenge, but once she knew Kenshin better she fell for him. [[spoiler: And she died. ''Horribly and tragically''.]]
* ''Manga/{{Basilisk}}'', has poor Oboro and Gennosuke. They were [[ArrangedMarriage engaged to bring peace]] between their two rival ninja clans but [[PerfectlyArrangedMarriage genuinely fell in love]], only for the truce to be broken and forcing them to choose between [[StarCrossedLovers their love or the honor of their clans]]. [[spoiler:In the end they are the only two left alive, and Oboro commits suicide rather than kill Gennosuke. Gennosuke declares Oboro's clan as victorious and commits suicide with her body in his arms.]]
* In ''Manga/MagicKnightRayearth'' Hikaru and Lantis had it pretty bad. She killed [[AntiVillain his brother]] without knowing the true story behind his actions, then spent the entire second season caught between falling in love with Lantis and feeling heartbroken because he probably hated her for killing his only family. Lantis didn't have it any easier. Though he didn't hold her accountable and wasn't averse to loving her after she unknowingly revealed her feelings for him, it all went downhill when she was chosen as a candidate for the Pillar...[[spoiler: thus threatening to repeat the tragic romance of his elder brother and the former Pillar Emeraude. Hikaru managed to destroy the Pillar system later on but still was forced to go back to her world after saving Cephiro in the end]].
* (Almost) everybody in Itoshiki-sensei's class loves their [[Manga/SayonaraZetsubouSensei Zetsubou-sensei]]. Too bad every single one of them is in some way severely unhinged.
* Tails and Cosmo from ''Anime/SonicX'' were the cutest and sweetest couple ever, but just at the series ends, [[spoiler: Cosmo must fuse herself with the BigBad, Dark Oak Planet to weaken it, so Tails (of all people, to boot) could fire his ship's supercharged cannon to destroy it and save the universe, killing Cosmo and crushing his heart in the process. To make it even worse, Sonic and Shadow's attempts to revive Cosmo are unsuccessful, leaving a completely broken Tails lying on the floor, crying his soul out. Not a total failure though; they managed to get a seed that they imply will grow back into Cosmo with all her memories intact]].
* ''Manga/{{Naruto}}''. The titular character's love for Sasuke (whether romantic or not) has torn his heart apart ever since he defected. His one-sided shallow crush on Sakura at the beginning didn't give him anything nicer until the end either. Poor guy can't even be relaxed in a mutual romance when he confesses to [[spoiler: Hinata in ''Anime/TheLastNarutoTheMovie'', he gets rejected over a BreakHisHeartToSaveHim, finds out she's getting married to the movie's BigBad which leads him to HeroicBSOD until his friends snaps him out. Fortunately he gets to [[EarnYourHappyEnding Earn His Happy Ending]] with all of the listed above]].
** And Sakura herself hasn't had it easy either because of Sasuke ([[spoiler:whom she has decided to kill ''with her own hands'' to spare him from more grief and betrayal.)]] At the end of manga [[spoiler: she finally [[EarnYourHappyEnding Earns Her Happy Ending]] by getting married to him]].
** ''Manga/{{Naruto}}'' is RIFE with this, whether romantic or not. There's Hinata, who [[spoiler: takes a suicidal attack to protect Naruto, whom she loves because he gave her the will [[PluckyGirl to be strong]]]]; Gaara, who [[spoiler:only wanted to be loved, but was hated by everyone until he befriended Naruto, and later cries when facing Sasuke]]; Konan, whose love interest is [[spoiler:none other than Pain]]; [[spoiler:Jiraiya, who was Tsunade's [[ChildhoodFriendRomance Unlucky Childhood Friend]]]]; Kakashi, who learned what friendship and love were when [[spoiler:he lost his best friend Obito and then rejected Rin's love for him.]]; etc.
* ''Anime/CowboyBebop'': The tragic love between Spike and Julia.
* Many all the clients or people they know in ''Manga/NightmareInspector'' are in love with someone, and if they aren't [[LoveMakesYouEvil evil]], [[LoveMakesYouCrazy mad]], or [[{{Yandere}} downright psychopathic]] from it, they're suffering a good deal.
* Akuyuki and Haru (especially ''Haru'') suffer through so much of this ''Anime/XamdLostMemories.''
* This is the lesson learned in ''Manga/ApollosSong'', where a young sociopath with a pathological hatred of love is condemned by the goddess Athena to live through a series of tragic love stories.
* In ''Manga/MaidenRose'', the main characters' relationship is the reason their lives are so miserable and screwed up. Their relationship is also exactly why they're both willing to put up with all the misery as they couldn't stand living without each other.
* One of Hinagiku's fears in ''Manga/HayateTheCombatButler'' is based on this, and it's implied that her fear of heights extends from this. She's afraid of loving someone because her parents left and her older sister has turned to drinking after making sure that Hina doesn't have to deal with the debt and has foster parents, thus she's afraid of loving anyone again, in an effort to keep from getting hurt by them. She may have even turned to her {{Tsundere}} personality because of it. Her admitting ([[CannotSpitItOut to Ayumu]]) that she does love Hayate has been shown as an effort because of these fears.
* ''Anime/PuellaMagiMadokaMagica''. Sayaka Miki, who becomes a magical girl so that her crush's permanent injuries heal (despite being warned that it won't work the way she wants to), [[spoiler:loses said crush to her friend because she is essentially a zombie as result of being a magical girl [[InsecureLoveInterest leading her to feel that she's unlovable]] (and thus when said friend ''does'' give her the chance to confess first to the boy, she cannot take it.) She becomes increasingly self-destructive ending with her turning into a witch, the creatures that magical girls are tasked to fight. In the end when the [[EndOfTheWorldSpecial universe is reset]] to give all magical girls a happier life Sayaka ''still'' ends up dying. WordOfGod says that, in any continuity where she becomes a MagicalGirl, she'll be damned to this and can't be saved]].
** And that's not even counting the YuriGenre pairings... Kyoko's care for Sayaka accomplishes nothing except angsting [[spoiler:and Kyoko's unnecessary HeroicSacrifice to destroy Witch!Sakaya]]. Homura's attempts to save Madoka only end up making both of their lives worse, [[spoiler:and even after Madoka hits the ResetButton, they end up indefinitely locked in separate dimensions]].
** In ''Anime/PuellaMagiMadokaMagicaTheMovieRebellion'' [[spoiler: Homura's [[ThePowerOfLove love for Madoka]] actually drives her to become ''[[SatanicArchetype the devil]]'' [[LoveMakesYouEvil and she steals Madoka's powers]] in order to create [[WellIntentionedExtremist a world where]] [[IWantMyBelovedToBeHappy Madoka can be happy]]. At the very end, Homura accepts that this makes her and Madoka enemies...[[IDidWhatIHadToDo but as long as Madoka is happy she doesn't care.]] As if to reflect this, Demon Homura's outfit has a broken heart]].
* ''Manga/RanmaOneHalf'': While many of the romantic hi-jinks are PlayedForComedy, it is obvious that all the girls in Ranma's harem are in love with him. Shampoo is probably the most blatant and forward with her feelings for Ranma, concocting multiple schemes to win his heart while brushing off the similarly strong if not stronger affections that Mousse has for her. Ukyo strives to actually be seen as a "woman" by Ranma, while Konatsu probably wishes for Ukyo to see him as an actual man. Kodachi is difficult to place as she is crazy but she does seem to generally have honest feelings for Ranma. She claims that she knows that he doesn't feel the same way but is determined to keep trying. And that brings us to the Akane. Akane is in love with Ranma. There are just a couple of things that stand in the way of their romance actually going anywhere.
** Akane also goes through this for years by having a crush on [[FirstLove Dr. Tofu]], a man who's in love with her sister, Kasumi. It isn't until she's 16 that she finally moves on and develops a crush on [[SecondLove Ranma]].
--->'''Akane:''' You can stop your feeble attempts to cheer me up now. I've got a broken heart, remember?\\
'''Ranma:''' Well, then...\\
'''Akane:''' Then what?\\
'''Ranma:''' Then you gotta realize that these things happen.
* The plot, point, story and character motivation of Minami Ozaki's ''Manga/{{Zetsuai 1989}}''. Period. Even the bystanders get traumatized by the events.
* In chapter 40 of ''Manga/RosarioToVampire'', it is revealed that [[spoiler:succubi can die from heartbreak, which seems to be happening to poor Kurumu]].
* ''Manga/GEGoodEnding'' has this all over the place with all the girls, but specially [[DoggedNiceGuy Ut]][[NiceGuy su]][[UnluckyEverydude mi]], the main protagonist.
* Akise Aru of ''Manga/FutureDiary'' has an unreturned [[HoYay crush on Yukiteru]] and all his actions of love towards Yukiteru get him is [[spoiler: a beheading by [[{{Yandere}} Yuno]]]].
* Rune from ''Manga/KarakuridoujiUltimo'' has an unreturned [[HoYay crush on Yamato]] and he [[AttemptedRape doesn't take rejection well]]. His love for Yamato causes him a lot of heartache.
%%* Kagetora and Naoe's relationship in ''LightNovel/MirageOfBlaze''.
* There's loads of this in ''Manga/DNAngel''. For example, there's Daisuke's unreturned feelings for Risa who has a crush on Dark who he sees kissing Risa at one point breaking his heart.
* Harry [=MacDoogal=] from ''Manga/OutlawStar''. You've got to feel for him because he has feelings for Melfina and she doesn't share the same feelings for him and he does everything he can to make her love him only to fail and get curb stomped by a massive douchebag with the ability to break his body parts like a bendy straw.
%%* ''Manga/RevolutionaryGirlUtena'' is rife with this.
* The Guts, Griffith, Casca LoveTriangle in ''Manga/{{Berserk}}''.
* In ''Manga/KatekyoHitmanReborn'' Tsuna has an unreturned crush on Kyouko and Gokudera is implied to have [[HoYay feelings for Tsuna]]. His soft spot for Tsuna results in many, many touching woobie moments for him. The fact that he's willing to (and many times does) go through hell and high water for Tsuna who just thinks of him as a friend makes many people just want to give him a big hug.
* Chaos from ''Manga/HeavensLostProperty'' is an unusual spin on this. She believes that pain is love and as a severe LoveFreak she seeks to spread her "love" to everyone.
* Jeremy in ''Manga/ACruelGodReigns''. His girlfriend Vivi breaks up with him after she suspects that he cheated on her (although he was forced into having sex with Greg so he wouldn't break off his engagement with Jeremy's mother) and he spends the next several books not only reeling at Greg's abuse, but mourning the loss of his beloved girlfriend. Poor guy.
** This trope also applies to Ian and Nadia in later books; Ian, because of his confusion about falling in love with Jeremy despite the latter's slight case of BeingTorturedMakesYouEvil and Nadia [[spoiler: because of her heartbreak over losing Ian to Jeremy]].
** Can also be applied to Sandra when Greg breaks off their engagement because Jeremy refuses him. Also tied in with Sandra's DrivenToSuicide and BungledSuicide.
* Happens to Bird's Nest a couple of times in ''Manga/CopernicusBreathing'', once after he thinks [[spoiler: Leo has died in his juggling accident]] (which then leads to a FreakOut ) and then again when [[spoiler: he confuses Michel Bohringer with his dead little brother Michel (twice)]] (again, IncestSubtext. )
* When [[PatientChildhoodLoveInterest Misaki]] sees [[TheCasanova Jin]] and [[IdiotSavant Mashiro]] on their date in episode 3 of ''LightNovel/ThePetGirlOfSakurasou'', it really breaks her heart. Later when the two are seen outside a {{Love Hotel|s}}, she decides to go home rather than interrupt them.
** Sorata also feels this way after seeing those two together. Unlike Misaki, he does interrupt them, [[spoiler: but fortunately for him Jin had no intentions of entering the hotel with Mashiro, and set this up knowing both he and Mashiro were being followed by him]].
* Happens to Nanami in ''Manga/KamisamaKiss'' when she confesses her love to Tomoe. See Tomoe is Nanami's familiar and a LittleBitBeastly {{Kitsune}} while Nanami is a teenage human girl and Tomoe does not approve of InterspeciesRomance. So he immediately tries to force her to take back her confession which works out about well as you can expect.
* Rick Hunter/Hikaru Ichijyo has it pretty bad in ''{{Anime/Robotech}}'' and the original ''Anime/SuperDimensionFortressMacross.'' For most of the series, he's in love with [[{{Kawaiiko}} Lynn]] [[IdolSinger Minmei]]/Minmay. She, on the other hand, has her own issues with her IdolSinger career ''and'' is very ObliviousToLove. Of course, Rick/Hikaru himself isn't blameless, as he pretty much ignores the feelings of the much more mature CO Lisa Hayes/Misa Hayase until it's almost too late. And Lisa/Misa has her own DarkAndTroubledPast that includes a lost fiancé among other very complicated issues.
* Jellal Fernandez and Erza Scarlet of ''Manga/FairyTail'' have this hard. They were slaves together as children in the Tower of Heaven and were deadset on one day escaping and living their lives together. Then, their plan was discovered, and Erza was dragged away to be punished. Jellal manages to save her, but is punished with unimaginably cruel torture that, coupled with [[ManipulativeBastard Ultear's]] brainwashing, drove him completely insane. Erza rescues him only to have him drive her out of the Tower when she refuses to join him in his madness, and she spends the next eight years dreading the day they'll meet again. Eventually they do, and she's forced to leave him to die after their confrontation. A bit of time after that, he's revived with no memories and completely back to his real personality, but is arrested by the authorities for his previous actions right after they reconcile. Shortly afterward, she is put into a coma for seven years, and when they ''finally'' meet again, he pushes her away because he feels he does not deserve her love any longer, though he can't quite keep himself from following her around. Their whole relationship is built on this trope.
** Zeref. [[spoiler:His love for his little brother Natsu and his desire to bring him back to life resulted in him getting cursed to kill those around him the more he values life. That same curse killed the girl he loved, Mavis.]] In short: love ''kills'', at least for him.
* In ''VisualNovel/{{Clannad}}'' [[spoiler: when Tomoya's wife dies tragically in [[DeathByChildbirth childbirth]], Tomoya feels that he should never have met Nagisa in the first place, because of the horrible pain her death is causing him.]]
* ''Anime/{{K}}'''s Fushimi Saruhiko has an [[AllLoveIsUnrequited Unrequited Love]] for [[spoiler: Yata Misaki]] that is apparently so strong that it drove him [[AxCrazy insane]]. Because [[spoiler: Misaki]] had found new friends and a new family with [[spoiler: HOMRA]] and started to drift away from him he lost himself in [[GreenEyedMonster jealousy]] and heartbreak, believing that making [[spoiler: Misaki]] hate him was the only way to get his attention. The Manga Days of Blue shows very clearly that he still suffers badly over being away.
* In ''Anime/UmiMonogatari'', this is Oshima and Kanon's situation in a nutshell.
** Kanon realizes that it was her own insecurity that made her feel like Kojima was going to dump her, when in fact he had liked her all along and never intended to dump her. At the same time, Kojima confesses to Marin that he had liked Kanon from the start, but felt she was purposely separating herself from him, and so they grew distant. Kanon realizes that she never told ''anyone'' she liked them out loud even once.
** Oshima initially seems to be your classic AlphaBitch, but she has heartbreaking hidden depths. She tells Kanon that even when she was going out with Kojima, all he ever talked about was Kanon. She feels she'll never measure up to Kanon in his eyes, and that it ''hurts'' to like someone that much knowing they'll never feel the same way about you.
* Tsukiyama from ''Manga/TokyoGhoul'' has an obsession towards Kaneki and is said to "love Kaneki above all other things". This is to the point where he breaks down into a sobbing mess when he tries to keep Kaneki from going on a suicide mission who rejects him and ends up in an AngstComa continuing into the sequel.
** Further complicating things is how Tsukiyama comes out of his AngstComa after he learns from Kanae that Kaneki is still alive but is now Sasaki and doesn't remember his past life as Kaneki and the time he spent with Tsukiyama.
** In Chapter 43, Eto confronts Kanae and gives him a Breaking Speech centered around his conflicted feelings about Tsukiyama and Sasaki. She tells him that he's actually afraid of being alone, and his "loyalty" is actually possessiveness over his master. According to her, he enjoyed Tsukiyama being helpless and dependent on him, and found true joy not in helping Tsukiyama reunite with Sasaki......but in tormenting Sasaki and making him suffer. She goes even further, stating that Tsukiyama will never return his feelings. Having broken Kanae down, she suggests that they should break the ones that won't return their love.
*** In the above encounter, the word Eto uses to describe Kanae's feelings is "Aishiteu", the strongest possible word for "love" often reserved for married couples. As such, his feelings are explicitly romantic love.
*** The cover of Chapter 45 shows Kanae vomiting and choking on rose petals. This is called "Hanahaki Byou", a sort of fictional disease/artistic symbolism where a person vomits flower petals as a result of Unrequited Love.
* ''Literature/TheSecretGarden'': In the anime, and how. Not only did Archibald cross the DespairEventHorizon when his dear Lillias died, but [[spoiler: Camilla and Max Hawkins become StarCrossedLovers as well]].
* In ''Manga/AssassinationClassroom'', Akari is hit with this trope both [[TheFourLoves platonic and romantically]]. While undercover as a normal teenage girl, she came to truly care about her classmates (especially Nagisa) and their BadassTeacher. After a year of '[[BecomingTheMask being]]' [[spoiler:Kayano]] (and being defeated and depowered by her would-be target), the two personae start to clash, and [[HeroicBSOD it ain't pretty]]. Cue angsty screaming... well, she ''is'' a teenager.
* The first intro to ''Manga/NurseAngelRirikaSOS'' is about how love can hurt you.
* ''Manga/SeraphOfTheEnd'':
** In the light novels Guren recalls the love story 500 years ago that led the Hiragi Clan to scorn the Ichinose Clan. Apparently, two Hiragi brothers were in love with a beautiful Ichinose girl. They both competed for her love with the younger brother winning her affections. The older brother responded by raping and impregnating the girl and castrating his younger brother. He then banished them from the clan which led to them having to create the Order Of Imperial Moon for themselves. The scorned brother could have defeated them but chose to let them live so they, their children, and their children's children would forever be looked down upon and humiliated by others as the lowly Ichinose clan. Also, since the younger brother was castrated by the older brother he couldn't even impregnate his wife and she would end up giving birth to the older brother's child.
** Mahiru and Guren fit the StarCrossedLovers scenario, in that since Mahiru is becoming a demon and is dangerous Guren has been ordered to kill her unless he can get her to stay with him. Given how far gone she is though...
** The fact that Mika has been with vampires for FOUR years all alone, with the same vampire who killed his beloved family in front of him, AND with an undeniable thirst for blood shows just how sad his circumstances are...not to mention learning that his entire family were experimented on and that his remaining family Yuu (whom he [[HoYay is implied to have feelings for]]) is exposed to the organization currently leading the experiment. There's also the StarCrossedLovers implications with circumstances threatening to keep them apart. Also, if Yuu becomes a complete demon imagine how Mika who cares greatly for Yuu would feel. Vampires can only retain humanity so long as they have human connections after all. If, for argument’s sake, Mika had his way right now and the two of them managed to run away, he would be able to save his precious Yuu-chan and maintain what’s left of his humanity for the time being, but at the same time, Yuu wouldn’t be able to retain his, knowing that he had betrayed and abandoned his comrades. They’re pulling in the opposite directions, so first they need to find a compromise. Luckily, Yuu is charismatic enough to possess a potent power of persuasion, and Mika is sensible enough to be willing to believe in Yuu and compromise, so they quickly found the common ground in the beginning of the chapter. But if, say, Yuu becomes a full demon, Mika might be be even worse off than Crowley, because not only would he lose his precious person, he would probably have to kill demon!Yuu-chan with his own hands, and it’s obvious that it would destroy him emotionally.

[[folder:Comic Books]]
* ''ComicStrip/{{Peanuts}}''
** One of the many reasons Charlie Brown is TheWoobie is his inability to get the Little Red Haired Girl to notice him. A minor case of CreatorBreakdown; Schulz admitted that he had his own "Little Red Haired Girl," whom he lost.
** If this wasn't so funny, it would be depressing: Charlie Brown is to Peppermint Patty as the Little Red Haired Girl is to Charlie Brown, making it an unrequited LoveTriangle. ''Good Grief!''
** Love Rectangle. Marcie also loves Charlie Brown. Too bad her loyalty to Peppermint Patty requires her to aid and abet her "Sir's" plans.
** Indeed, unrequited love is a running theme throughout the comic's run: Linus towards Miss Othmar, Sally towards Linus ("[[SheIsNotMyGirlfriend I'm not your sweet baboo!]]"), Lucy towards Schroeder... the list goes on.
* Dr Allison Mann in ''ComicBook/YTheLastMan'' angrily denies that love is anything other than a label stuck on a biological process. We later find this apparently cynical attitude comes from Allison being dumped by her first girlfriend (and her parents' miserable marriage). Despite this it is clear she still craves love herself.
* Any romance in any Creator/{{Marvel|Comics}}, Creator/{{DC|Comics}}, or other company you care to name wherein the relationship lasted more than 3 years real-time/10 months in-universe and the characters, to this day, are not together. Don't even go into the ones that -are- together... Examples are just too numerous to list. Averted with Ralph (Comicbook/ElongatedMan) & Sue Dibny, who were happily married in his second appearance back in the 1960s and in death [[TogetherInDeath were still together]].
* Explored (somewhat) in ''Comicbook/JohnnyTheHomicidalManiac'', where the main character is very much under the impression that this trope is in full effect (and that is only the tip of the iceberg where his intimacy issues are concerned). He attempts to murder the only person he cares for in an attempt at 'immortalizing the moment' and prevent the relationship going bad (because...somehow murder doesn't count as going bad) and later attempts to apologize for the faux pas with a rather bizarre pre-recorded phone message in which he states his intention to forget about her, lest he attempt to hurt her again.
-->'''Johnny:''' I like you immensely, Devi. And to prove it, I shall obliterate all of my affection and interest for you. Just like before, but different. I cannot hurt what I do not acknowledge. I don't know of anyone that I love, or of anyone that loves me, but I give you what I can. I give my nothing.
* Rose Walker's great "love hurts" speech to ''Desire'' in ''ComicBook/TheSandman''. This exchange sums up Desire's approach to most things but ''especially'' love:
--> '''Rose''': Are you going to hurt me? Kill me? Mess me up?\\
'''Desire''': No more than usually; no; and perhaps a little. But only with love.
* ''ComicBook/ScottPilgrim''. No one is safe from that in that comic. Gets to its extremes with Ramona and Knives though. A chapter is even named 'Love Hurts'.
* Comicbook/{{Supergirl}}:
** Kara doesn't seem to have much luck in the romance department. Most of guys she dates turn out to be jerks, creeps, cheaters, or super-villains. When she dates a guy who is actually nice and well-meaning, she often has to break up with him. This is true of all her incarnations.
** Pre-Crisis Supergirl dated Dick Malverne when they were teenagers. Many years later Dick sought her out to confess that he always loved her... because he was dying from cancer. They kissed the night he died, leaving Kara heart-broken.
--->That was the last time I saw Richard. Tonight I know what it is to be human. Tonight my super skin is still invulnerable, but my Richard is never coming back, and my heart is broken into a million pieces.


[[folder:Fairy Tales]]
* The original version of ''Literature/TheLittleMermaid:'' The mermaid loves the prince and gives up her voice and family to be with him, but he ends up marrying someone else and she turns into sea foam. But a tacked-on [[AnAesop Aesop]]-fuelled ending gives her an immortal (i.e. human) [[OurSoulsAreDifferent soul]] anyway. Reputedly fueled by CreatorBreakdown. Technically, in the Creator/HansChristianAndersen version, she doesn't get a soul - yet. She get's turned into an air spirit that, after a preset amount of time, will get an immortal soul. As an extra twist, whenever she passes through a house with a well behaved child, she gets a few years knocked off her sentence. Ill behaved children add years. That's right, kids. If you don't eat your vegetables... you're preventing mermaids from going to heaven.

* ''Fanfic/ACrownOfStars'': Shinji and Asuka have hurt each other… and still love each other.
** Asuka does not want to love anyone because she is deadly frightened of getting hurt again. [[BigGood Daniel]] tells her that’s tantamount to refusing eating because you are frightened of getting poisoned.
* ''Fanfic/AdviceAndTrust'':
** Gendo is a bastard because he had always been frightened of other people. Yui was the only person he ever opened up to. When he lost her he became a broken, pathetic shell of a man, too afraid to love and relate to other people and utterly obsessed with saving her. All of it is explored in chapter 8.
** When Shinji and Asuka got together they were happy because they were not alone anymore... so that when [[spoiler:one of them was in danger or they were forcibly separated]] they were terrified of being alone again.
** Shinji and Asuka helped Rei to stop being a puppet and connect with other people. She bonded with them to the point [[spoiler:she loves them both]] and it hurts her being unable to be with them because they don't love her that way and she does not want to disrupt their bond either.
** Shinji and Asuka helped Touji and Hikari to get together. When [[spoiler:Hikari got absorbed into Unit 03]] spent several days depressed, lonely, afraid and worried, not knowing what had happened to her.
* In ''FanFic/APikachuInLove'', [[spoiler: Pikachu gets hit ''hard'' with this in the ending, having to say goodbye to Pichi when he finally made his choice to stay with Ash. Misty's comment when she sees it pretty much sums it up]].
--> [[spoiler: '''Misty''':''"I’m sorry Pikachu... It must have been hard, saying goodbye to someone you love."'']]
* ''Fanfic/TheChildOfLove'':
** Shinji fell in with Asuka. When she treated him rudely to push him away or claimed wanting nothing with him, not even after getting pregnant with his child, or got hurt, it hurt him. Especially if she got hurt.
** Asuka did not want love anyone because she had been hurt by people she loved. She did not want to admit she loved Shinji because she was afraid of getting hurt again. Later [[spoiler:she opened up to him. However he broke up with her for a while because he thought he was not strong enough to protect her and their child. As a result she got hurt and furious because she had trusted her and he left her]].
** Both of them argued the subject here:
--->'''Asuka''':''"I-I mean...you're speaking with confidence...you're so shy, usually. I think I'm like this because I trust you and I feel that I can put my trust in you. You're like a confidante."''\\
'''Shinji''':''"I...it's the same for me. We've got a lot in common, don't we?"''\\
'''Asuka''':''"You try to avoid pain by running away from people. I try to avoid pain by driving them away. But in the end, we just hurt ourselves more. Aren't we pathetic, Shin-chan?"''\\
''It sounds more like a statement than a question. Shinji can't help but be surprised by this sudden truth coming from the mouth of the girl he normally knew to try to avoid it. Somehow, the suicide attempt, as bad as it was, seemed to have turned Asuka into a more mature person.''\\
'''Shinji''':''"You're right, Asuka-chan. It's kind of like...we're hiding ourselves from the pain behind a shield."''\\
'''Asuka''':''"But we just feel more and more pain."''\\
'''Shinji''' (nodding):''"Yeah...you're right, we are pathetic."''
** And later Misato offered her input:
--->'''Misato''':''"You're not alone, Asuka...I'm here, we're all here for you. You know that...and, yes, this is love. With all the happiness and sadness it can bring to you. Love is like a double-edged sword. One day it can make you the happiest person on earth, and the next day, it can make you cry like you never did before."''
* ''Manga/{{Evangelion 303}}'': Asuka was the first and only woman Shinji had loved. Before meeting her he had no drive to live on. Then they got together, were happy for a while... and [[spoiler:Asuka's experimental jet fighter crashed down. She was in a coma for several months. Shinji refused leaving her side during that whole time. When she woke up]] she was a nearly completely different, ever-angry person. For several months Shinji had to see her self-destroying gradually as he put up with her abuse, having no idea of how helping her. Later she got better [[spoiler:after trying to kill herself and then running away]] and she admitted it hurt her remembering how she treated him during that time.
* In ''Fanfic/GhostsOfEvangelion'' Shinji and Asuka hurt each other many times but they stay together and keep trying to make their relationship working because they care for each other.
* ''Fanfic/{{HERZ}}'': Shinji and Asuka truly love each other but they have hurt a lot throughout the years. Shinji's obliviousness deepened Asuka's emotional and psychological scars, his actions in “End of Evangelion” cost her life -albeit temporarily- and made her feeling defiled and an ugly, unlovable monster. On the other hand her posterior abuse, fuelled by her resentment and self-loathing, drove Shinji to the edge.
* ''Fanfic/OnceMoreWithFeeling'':
** Shinji fell in love with Asuka. When [[spoiler:he saw that she had gotten killed by the MP-Evas]] it shattered his sanity to pieces. Even though he returned to the past to SetRightWhatOnceWentWrong it haunts him knowing he did nothing as she was getting chopped into pieces and eaten alive.
** After meeting Shinji Asuka starts to connect with him deeply, and it scares her because she is afraid that she will get hurt if she falls in love with him.
* ''Fanfic/TheOneILoveIs'':
** Shinji had been alone since he was a kid and he was resigned to it. Then he met Asuka and Rei and he fell for them. However [[spoiler:Rei blew herself up to stop Armisael and Asuka ran away and slit her wrists because she thought she had lost him]]. Shinji was alone again [[spoiler:for a while]] and he felt loneliness was unbearable now.
** Asuka fell for Shinji and it hurt her knowing he had feelings not only for her but also for Rei. After her MindRape she felt he was the only thing she had left. Thinking she had lost him too was the final blow to her mental stability. She [[spoiler:ran away and attempted to kill herself]].
* ''Fanfic/ScarTissue'': Shinji and Asuka loved each other but had hurt each other badly. After Third Impact Asuka's mind was broken and her temper out of control, and Shinji blamed himself for his actions and inactions. He put up with Asuka's abuse for several months because he loved her, he could not live without her and he thought he deserved her punishment. On ther other hand Asuka beat him and she always felt sick with herself afterwards. After a while she managed to stop abusing him but she still hated herself for hurting the only person she loved.
* ''Fanfic/TheSecondTry'': In chapter 4 "Love" Shinji told Asuka that Instrumentality had taught him that you can not to experience love and happines without taking the risk to feel pain and loneliness too. Both of them choose taking a chance and get together [[spoiler:and later have a child.]] Later they got flung back to the past [[spoiler:without Aki]] where they had to cope with [[spoiler:their daughter's disappearance]] and the fear to lose each other again during the Angel War. When Shinji [[spoiler:got swallowed by Leliel and later absorbed into Unit 01]] Asuka was freaking out, feeling alone and frightened of losing him again. Later Shinji [[spoiler:believed the MP-Evas had killed Asuka again and he could not stand the pain. He very nearly set Third Impact again]].
* The ''FanFic/TamersForeverSeries'' uses love as a surgical scalpel to subject the characters to unimaginable suffering.
* ''Fanfic/ThousandShinji'':
** When Shinji arrived on Tokyo-3 he slowly got granted that he had always wished: a family -Misato and Rei-, a lover -Asuka-, friends... When they got hurt he got hurt. And then he ''made'' someone else hurt. Later [[spoiler:Misato and Asuka got killed and their deaths broke him down completely]].
** Shinji taught Rei a new world of emotions and feelings. However he loved her like a sister. His brotherly love was insufficient to her, and it hurt her seeing him with Asuka and resented Asuka for making him happy. Her inability to deal with her unrequited feelings and her accumulated jealousy and resentment led him to make very stupid things she ended up regretting.
** When they got together Asuka became fully dependent on Shinji. He made him happy took the pain way only for being there. She loved him but she was frightened of losing him and getting hurt again. When he [[spoiler:got absorbed into Unit 01]] she fell completely apart. She was hurt, lonely, depressed, snappy... and homicidally furious at everyone.
* In ''Fanfic/NeonGenesisEvangelionGenocide'':
** Shinji and Asuka love each other, and they've hurt each other a lot.
** Yui's actions also hurt and traumatized her son Shinji, but even so he loves his mother.
--->Shinji thought about that, and about what Asuka said regarding them never losing their mothers, and how when she made him talk about her he had felt so dejected until she took his hand and shared her own pain with him. And then he realized that even though he badly missed her, he was also glad he could remember her. Her memory remained strong in him because he loved her, and the day he stopped missing her was the day he stopped loving her.
* ''Fanfic/ChildrenOfAnElderGod'':
** Rei fell for Shinji as soon as she met him, but Shinji was deeply in love with Asuka and he regarded Rei as a good friend. Worse still, one of the Eldritch Abominations absorbed by Rei forced her to hurt Asuka physically and mentally. Rei had no chance to talk Asuka into sharing Shinji or having a three-ways relationship after that, so she resigned to having an unrequited love.
** In the FinalBattle, [[spoiler:Rei sacrificed herself]] to save everyone. Even though they won and survived the war, her teammates couldn't fully celebrate their victory because they loved her and missed her.
* ''FanFic/HuntingTheUnicorn'': Blaine is a LoveMartyr who's head over heels for [[TheWoobie his boyfriend Kurt]]. Why does love hurt so much? Because Kurt is Blaine's ''SecondLove.''
** Also because Kurt [[ForegoneConclusion leaves Dalton]], but this time we get to see it break Blaine's heart into tiny little pieces because "No-one ever comes back to [him]."
** It's not just limited to romantic love, since he's vehemently loyal to his estranged, neglectful father.
* Minako and Shinjiro in ''FanFic/DeathAndKer'' get to face just how much love can hurt. Bad enough that Minako died without warning two years prior as a result of a HeroicSacrifice - worse that she's come ''back'', but only temporarily, and must return to death when her mission is complete, the knowledge of which keeps both of them from feeling able to act on their feelings the way they'd like to. Aigis in the same work has it just as bad; she also loves Minako and blames herself for not being able to protect her two years previously, and since she's a RidiculouslyHumanRobot she's struggling with the concept of being able to feel human emotions at all.
* ''FanFic/StarsAbove'': Hoo boy. Quoth one of the villains: "Your love [[TheEndOfTheWorldAsWeKnowIt destroyed your world,]] over and over again until even magic couldn't fix it..." [[spoiler:To make matters worse, said villain is technically ''right.'']]
* [[http://www.fanfiction.net/s/2756948/1/ ''The Taste of Pomegranates'']]. A ''[[WesternAnimation/TheGrimAdventuresOfBillyAndMandy Billy and Mandy]]'' fanfic.
--> '''[[spoiler: Mandy:]]''' "It doesn't matter either way, none of it really matters because I could not live without this feeling no matter how much it hurts. No matter how much I love it or hate it, I am in love with him and I cannot do anything about it."
* ''Fanfic/ForGood'' is ''made'' of this trope, be it in regards to family or romantic interests (or very good friends). The Ships 50 one-shots are especially {{Egregious}}.
-->'''Erin:''' "Doggone it, why is this so hard? I don't want to be [[AllGirlsWantBadBoys in love with the galaxy's Most Wanted]]!"\\
'''Mira:''' "Hey, kiddo, nobody ever said love was easy. Like I said before, look at me and you think ''you've'' got issues?"\\
'''Erin:''' "Yeah, I guess I wouldn't want to be [[LoveTriangle in love with two guys at the same time]]."
* Three Franchise/SherlockHolmes FanFic examples:
** The ''Fanfic/DeliverUsFromEvilSeries''. ThePowerOfFriendship and ThePowerOfLove are the two powerful motifs of the stories, but this series is all about the canonical struggle between Holmes (along with Scotland Yard) and Professor Moriarty's [[TheSyndicate criminal empire]]. The first book, ''Mortality'', is one long TraumaCongaLine for the Great Detective, and dealing with it is ''not'' an easy thing for the people closest to him.
** A similar example (TraumaCongaLine and all) is ''Fanfic/AStudyInRegret'', in which Watson is KilledOffForReal, leaving his wife and InspectorLestrade as Holmes's only hope for freedom, as well as physical and spiritual healing.
*** Holmes deals with ''massive'' SurvivorGuilt as a result of watching Watson die and blaming himself for it. This underscored by his saying, several times in almost as many words, "MyGodWhatHaveIDone"
** ''Fanfic/TheGhostMap'' kills Holmes's protege Wiggins Off For Real, then leaves Watson to deal with the fallout of Holmes's desperate gambits. Much heartbreak and ManlyTears ensue.
* The ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' fanfic ''Fanfic/ADelicateBalance'' is largely about the stress that romantic relationships can put on people, even when everyone involved is trying their hardest to make things work, even extending to characters who aren't directly involved in the romance.
* ''[[Fanfic/WeightlessMassEffect Weightless]]'' has this trope as one of its main themes. God knows whether there will be more but currently, we have some of the following examples of how much love can hurt:
** Loving someone but afraid to do so because you afraid that person will die like everyone who cared for you before (Shepard's case with Garrus and she had to break his heart once before managed to get over that to be with him).
** Being coldly rejected by the person you love after you had given up everything for her. Have a fight with her only for her to die and you know that she did love you after all. Even worse if you get to know about her past and thought you scared her for trying to rush things physically as she was a raped victim. (Garrus's case with Shepard, resulted in 2 sleepless years drowning in guilt).
** Unrequited love (Mierin to Garrus and, in the past, Shepard to [[spoiler: Nihlus]]).
** Your loved one was dead and you can't move on (Thane to his wife and Garrus to Shepard, though lucky for the latter that she came back).
* ''FanFic/WhiteRain'': Lucia van Alstyne realizes that she loved the father of her children, Itachi Uchiha, after a therapy session/interrogation with Ibiki. It hurts, because by the time of this realization, Itachi has been dead for ''years'', and is not coming back. The fact that her son is the spitting image of his father most definitely does not help at all.
* ''Fanfic/OneYear'' [[VideoGame/{{Persona 4}} Rise]] takes the relationship between Yu and Yukiko the hardest, particularly considering that Yu, who'd hooked up with Yukiko in early July 2011 (after Rise was rescued but before she joined), had been taken ''the entire time'' Rise had been flirting with him. It also doesn't help that her being an IdolSinger essentially precludes her chances of getting together with Yu. Thankfully, Chie, who also had a crush on Yu and struggled with being jealous of Yukiko, helps Rise work through her feelings.

* Davey Jones and Calypso's relationship in the ''Franchise/PiratesOfTheCaribbean'' movies. Yeah, that ended well.
* From the ''Film/{{Hellboy}}'' movie art book: "When, in 1988, Liz Sherman joined the B.P.R.D., Hellboy fell in love. From then on, he knew the meaning of pain."
* "Film/TheHitchhikersGuideToTheGalaxy has this to say on the subject of love: 'avoid, if at all possible.'"
* The only woman Film/{{James|Bond}} [[TheCasanova Bond]] ever married ([[Film/OnHerMajestysSecretService Teresa "Tracy" Di Vincezo]]) was killed moments afterwards in a botched attempt to assassinate him. In later movies, it shows that even with all his flirting and skirt-chasing that he ''still'' mourns her.
* ''Film/MenInBlack'':
--> '''J''': You know what they say, it's better to have loved and lost than never to have loved at all.
--> '''K''': (looking horribly cold and restrained) Try it.
* ''Film/LoveActually''. Daniel knows something has been bothering his stepson for a long time now, and he finally gets it out of him: he's in love with a classmate.
-->'''Daniel:''' ''[laughing]'' Aren't you a bit young to be in love?\\
'''Sam:''' No.\\
'''Daniel:''' Oh. Right. Well, I'm a little relieved!\\
'''Sam:''' Why?\\
'''Daniel:''' Well, you know, I thought it might be something worse!\\
'''Sam:''' Worse than the total agony of being in love?\\
'''Daniel:''' ...No, you're right. Yeah, total agony.
* Any of Creator/WongKarWai 's films, especially ''Film/InTheMoodForLove'' and ''2046.''
%%* Just use "Love Hurts" as a sub-title for ''WesternAnimation/ToyStory2'' and ''[[WesternAnimation/ToyStory3 3]]''. - ZCE
* The hero of ''Film/FiveHundredDaysOfSummer'' suffers a lot when his love to Summer remains unrequited.
* Stefan, from the film ''Film/LetterFromAnUnknownWoman'' never remembers Lisa, the woman who has loved him her whole life, and once he does find out about her, it's too late. Lisa dies.
* ''Disney/TheSwordInTheStone''. Three words: heartbroken girl squirrel.
* The whole point of ''Film/ScottPilgrimVsTheWorld'' ... in this case love multiplies itself by seven and storms into town on a homicidal rampage.
** Poor Scott. As one tagline approximately reads: ''Scott Pilgrim has no trouble finding a girlfriend. It's getting rid of them that proves difficult.''
** But it turns out alright.
* ''Disney/BeautyAndTheBeast'': Goodness, the Beast's heartbreak after the uplifting ballroom scene is palpable. As he lets Belle go to her father at the risk of breaking the curse and spending his life with Belle he starts sobbing and finally breaks into a primal scream of despair as Belle gallops away. This is essentially the entire message of the VillainSong in the midquel ''[[Disney/BeautyAndTheBeastTheEnchantedChristmas Enchanted Christmas]]''.
* The central theme of the Mexican film ''Film/AmarTeDuele'', which is about a rich girl and a poor boy who fall in love with each other, but society tries to keep them apart. It's even in the meaning of the title!
* ''WesternAnimation/StrangeMagic'': Marianne catches her fiancee cheating on her right before her marriage, causing her to swear off love. [[spoiler: Turns out the supposed BigBad is similarly bitter and [[CommonalityConnection they bond over it]].]]
* One of the major themes of the musical ''{{Theatre/Camelot}}''. Love a woman? She's either married to your best friend or having an affair with your best friend. Love a man? He's either married to your girlfriend or having an affair with your wife. Love two men? You've made one of them a cuckold and the other a traitor. And you just can't seem to stop.
* ''Film/TheHungerGames'': One of the two main reasons why Katniss Everdeen is so reluctant to admit to herself that she's falling in love.

* ''Literature/{{Animorphs}}'': However much Jake and Cassie loved each other - and it was a ''lot'' - being together after the war wouldn't have been good for either of them. Despite that, being apart hurt them as well because of how much they cared about each other. Also, Tobias loved Rachel so much that her death destroyed him.
* Medieval ChivalricRomance, anyone?
* This is far and away one of the oldest, most universally recognized tropes in existence. A perfect example of it is found in the 12th century Persian epic, Layla and Majnun. Boy meets girl, boy loses girl, boy loses mind. It's not a cheerful tale.
* Creator/EdgarAllanPoe was a ''very'' firm believer in this. He thought the best theme to write about was the death of a beautiful young woman, often leading to the protagonist's descent into madness.
** Given the things that happened to women in his life, this isn't really surprising.
** For those who don't know, tuberculosis killed every woman he loved[[note]] Except for his first girlfriend; She died of brain cancer.[[/note]]. It killed his mother when he was young, two women that he was courting, and his wife. It's often speculated that the disease, which involves a great deal of blood loss, was the titular "Red Death" in his short story, "Masque of the Red Death".
* Yuan, Lord of City Europe in David Wingrove's ''Literature/ChungKuo'' series, falls for the wrong woman. Although the stage is set for serious tragedy, he manages to pull out of it.
* ''Literature/TheHouseOfNight'':
** Zoey ends up falling for three guys simultaneously (ish). It ends badly when [[spoiler:she thinks her own-age vampyre boyfriend Erik is dead, flees to the hot-but-older Loren for comfort, and ends up losing her virginity to him. Proving that Creator/JossWhedon is not the only one who can be incredibly cruel to his characters, the following things happen in quick succession: it breaks her bond with her human boyfriend Heath, Erik walks in on her and Loren Kissing, and it turns out Loren was in cahoots with the villainess and only using Zoey. And then Loren is brutally murdered]]. Ouch. Poor Zoey. And it gets worse for her: the guy she displays a brief romantic interest in in the fourth book promptly [[spoiler:dies, only to be resurrected as a bizarre zombie-vamp hybird controlled by her archnemisis]]. Zoey has a bit of a CartwrightCurse, it seems...
** At the end of ''Burned'' between Stevie Rae and her consort [[spoiler:Rephaim. The returning of Zoey's and Kalona's souls to their respective bodies serves to keep the two apart.]]
* ''Literature/AndThenThereWereNone'' features two victims who [[LoveMakesYouEvil committed their crimes to keep their loved ones]] when it was those exact deeds that drove them away. [[spoiler: General [=McArthur=] manipulated his wife's lover/his right hand into going [[MurderTheHypotenuse in a suicide mission]]; Vera Claythorne caused the death of her pupil Cyril so his uncle/her lover could inherit the family fortune and drove said lover into alcoholism]]
* In the ''Literature/WarriorCats'' series, falling in love is likely to get you broken-hearted, insane, and/or killed. [[spoiler:Bluestar]] wound up with all three because of her relationship with [[spoiler:Oakheart]]. Some lucky couples just end up getting their kits killed off. Yes, you heard right, ''they are the lucky ones''.
* Though ''The Engineer Trilogy'' as a whole plays this trope catastrophically straight, there is a scene lampshading it in the second. Miel Ducas, a powerful noble wounded in battle, hallucinates that he is having a conversation with Death. When Death points out that Ducas is not very grateful for having everything a man could ever want, Ducas replies that he is the poorest man in the world because no woman he ever loved returned his affection. Death explains that love is nothing more than a trick meant to override humans' free will in order to reproduce, and that Ducas might as well be upset that he never contracted diphtheria.
* In Creator/EdgarRiceBurroughs's ''[[Literature/JohnCarterOfMars A Princess of Mars]]'', John Carter [[ObliviousToLove realizes]] he fell in LoveAtFirstSight with Dejah Thoris, but then [[CultureClash manages to offend her]].
-->''Yes, I was a fool, but I was in love, and though I was suffering the greatest misery I had ever known I would not have had it otherwise for all the riches of Barsoom. Such is love, and such are lovers wherever love is known.''
%%* Love doesn't hurt ''every'' character unlucky enough to experience it in the ''Literature/{{Indigo}}'' series...just ''most'' of them.
* The ''Literature/DuelOfSorcery'' series: [[spoiler:Serroi and Tayyan are a couple at the beginning; then Serroi freaks out and [[BetterToDieThanBeKilled effectively gets Tayyan killed]]. Rane and Merralis were a couple; Merralis contracted a terminal disease, and Rane is still mourning years later. Michael's boyfriend is beaten to death in front of him. Serroi and Hern have a thing for a while...but then, Serroi [[TakenForGranite gets turned into a tree]] [[EquivalentExchange in order to defeat Ser Noris]]. (She does get better in the follow-up trilogy, but Hern's long dead by then.)]]
* Richard and Alec in ''Literature/{{Swordspoint}} and ''The Privilege of the Sword'', to the point where their relationship is such a mess that neither they nor the reader can figure it out.
* A recurring theme in sonnets, especially those from the Renaissance.
* ''Literature/AnnaKarenina'' is 864 long, long pages of this trope.
* ''Literature/TheGreatGatsby'' could be argued to have love ''kills'', and causes killing. It's arguable because actually being "in love" strongly tends to make the lovers happier - it's the fallout on everyone and everything else around them that actually brings the pain.
* In L. Jagi Lamplighter's ''[[Literature/ProsperosDaughter Prospero Lost]]'', Ferdinard speaks eloquently of having suffered torments for the pure love of a chaste maiden.
* ''Literature/AnneOfGreenGables'': Poor Gilbert Blythe lives this trope for over ten years; he falls in love with classmate Anne Shirley the day she smashed his slate over his head, but the reason for the smashing -- Gilbert calling her "Carrots" and teasing her for her [[BerserkButton red hair]], causing her to resent him for many years. When they finally become friends, Gilbert bides his time. He proposes, she turns him down. He proposes again (a couple years later), and she shoots him down again. It takes a near-death experience with ''typhoid fever'' for Gil to get his girl.
* Many romantic relationships suffer from this in ''Literature/ASongOfIceAndFire'' as par its [[DeconstructedTrope Deconstructionalist nature]], but no other character can claim that they've been through the worst of the Love Meat-Grinder than Petyr "Littlefinger" Baelish, who dared to fall in love with a girl above his social status. For his romantic idealism he was almost killed, [[spoiler: possibly raped by the younger sister of the girl he loved, who then got pregnant and was tricked into aborting the child by her father,]] and sent packing from the home of his foster family, the place where he had grown up, back to his dreary homeland where no one knew him and he was mostly likely doomed to live out a lonely exile. The whole experience left him so severely [[{{Yandere}} unhinged]] that he became a MagnificentBastard and [[spoiler: started a continent-wide civil war to get back at his childhood crush]].
* [[Literature/TheDresdenFiles Harry Dresden's]] romance life is an exercise in pain. Of the women he's been involved with or who he has strong feelings for/who have strong feelings for him, one [[spoiler: gets turned into a vampire, has his child, and gets sacrificed]], another is [[spoiler: the copy of a FallenAngel living in his head that kills herself to save him]], and another is [[spoiler: only in love with him because TheMole was mind-controlling her]]. Murphy still cares for him, but [[spoiler: her reward for her affections is learning Harry is now dead]]. And then there's [[spoiler: Molly, who goes from teenage crush on Harry to honestly being in love with him, but carrying all the baggage of his death as well and going almost completely nuts thanks to BlackMagic and mental trauma]].
* ''Literature/ThePictureOfDorianGray'' features Basil who has to watch Dorian Gray, the [[HoYay love of his life]] and his greatest inspiration, descend deeper and deeper into corruption against his wishes and ultimately [[spoiler: gets murdered by him]]. And then there's [[spoiler: Sybill Vane]] who [[spoiler: takes a fatal dose of poison right after Dorian cruelly dumps her]].
* In Creator/CSLewis's ''Literature/TheFourLoves'', he makes a point that there really is no escape outside of {{Heaven}} itself from this -- except {{Hell}}.
* Charlotte Bronte's protagonist Lucy Snowe in Literature/{{Villette}} is dripping with this. She even utters the line "My heart will break!"
* ''Literature/HarryPotterAndTheDeathlyHallows'': Poor, poor [[spoiler:Snape. Spent the last years of his life trying to protect the son of the woman he loved -- the same woman who rejected him for going with the Death Eaters (which was his fault entirely), and the same woman he all but killed. To make it worse, the guy she married was his worst enemy (who was reformed by that point). What makes it so painful is that their son is the spitting image of his father, yet his most distinguishing feature is his mother's eyes, reminding Snape of his failures and the fact that he DidNotGetTheGirl]].
* In ''Literature/TheHungerGames'' Katniss isn't so much deciding between two boys (it's made clear halfway through the book that introduces the triangle which guy she's fallen in love with) as it is her deciding whether or not she dares to love. She's terrified of losing people close to her heart and her only real experience with genuine love is the love between her parents. They loved each other a lot but then her father died and left her mother a shell of a woman. Katniss is determined never to care that much about another person which is why she keeps resisting/ignoring her own feelings. Then comes the third book and [[spoiler:Peeta, the guy she's fallen in love with, gets captured by the Capitol and is tortured, mind raped and turned into a weapon against her]]. Cue all that emotional pain she was trying to protect herself from.
* ''Literature/TheHouseOfNight'': Does it ever. Oh, does it ever. The end of "Chosen," anyone? Or "Tempted?" Though, considering that [[spoiler: she was juggling three boyfriends at the time]], the impact may have been lessened.
** At the End of Burned between Stevie Rae and her consort [[spoiler: Rephaim. Zoey and Kalona's souls return to their bodies, thus keeping the two apart]].
* ''Literature/TheSilmarillion'': Beren and Lúthien go through absolute hell for one another. Beren is a mortal Man, and Lúthien is the daughter of the Elven king Thingol and the [[OurAngelsAreDifferent Maia]] Melian. After eventually losing his father and all his kin fighting Morgoth, Beren wanders into Thingol's kingdom, where he has the gall to fall deeply in love with Lúthien. Thingol does ''not'' take this well, and sets him an ImpossibleTask: retrieve a ''silmaril'' from Morgoth's crown. Along the way, Beren and his companions are captured, tortured, and killed one-by-one by Sauron until Lúthien shows up and humiliates him. Together, Beren and Lúthien succeed in recovering one of the gems, but then Beren loses his hand (with the ''silmaril'' clutched inside it to the wolf Carcharoth. And then Beren dies helping slay the wolf to get it back. Then ''Lúthien'' dies of grief, and is faced with an eternity of being separated from her love because Men are not allowed to remain in Valinor upon death, while Elves are denied to pass wherever it is the souls of Men go. Her grief is ''so'' profound that her song of her fate manages to move ''[[ThePowerOfLove the otherwise pitiless Mandos]]'', who asks Manwë to intercede on their behalf, and [[EarnYourHappyEnding the lovers are sent back to live again together]]. And this is pretty much the only ''happy'' story in ''The Silmarillion''.
* 19th century writer ''Higuchi Ichiyō'''s works are rife with this. Nearly all of her protagonists are young women, most are in love and none of them ever end up happy. If they aren't in love, they are married to a man they don't love and end up depressed, poor, and/or dead one way or another, [[YouCantFightFate with no way to escape their fate]]. She herself considered that in those times, women had very little power over their lives, so her writings are… not very optimistic overall. It doesn't help that she herself had been hurt by her unrequited love for her mentor in her first years of authorship.
* In Creator/EdgarRiceBurroughs's ''Literature/APrincessOfMars'', Sola tells John Carter that because of this, and HopeIsScary, she has wished to be like the other women of her race, without hope or love.

[[folder:Live Action TV]]
* ''Radio/OurMissBrooks'': Miss Brooks is deeply in love with largely ObliviousToLove Mr. Boynton. Because FailureIsTheOnlyOption, Miss Brooks' schemes to get Mr. Boynton to marry her inevitable fail [[spoiler: until TheMovie GrandFinale when Mr. Boynton finally proposes and the two of them wed]].
* In ''Series/{{Smallville}}'', [[ChildhoodFriendRomance Chloe Sullivan]] puts it best, and mildly.
-->Clark, things always get messy when you start throwing around the Clark-Lana triangle, and I'm speaking from experience when I say the third point always hurts.
* The new ''Series/{{Battlestar Galactica|2003}}'' series ''loves'' this:
** Lee/Kara: [[spoiler: They meet and fall in LoveAtFirstSight - and nearly hook up]] - when she's already dating his baby brother, whose death she accidentally has a hand in. They become good friends and later survive the end of their homeworlds together, but the memory of the dead baby brother, and their guilt, keeps them apart and in JustFriends mode until [[spoiler: they get together with other people, rather than face their feelings for each other]]. When Lee ''finally'' admits his love to Kara and gets her to do the same, [[spoiler: she freaks out and marries someone else the next day, breaking his heart and leading to his own marriage to a woman he doesn't really love. After Kara survives a Cylon prison and some serious mind games, they later reconcile and have an affair, but Kara won't get a divorce because of her religious beliefs, and when she finally unbends and considers the possibility, Lee is reluctant to leave his wife]]. [[spoiler: And then Kara goes unhinged and dies, then returns and leads the Fleet to Earth. And just when it looks like it's all ok since they've found Earth, Lee doesn't care that Kara was really DeadAllAlong, and it looks like they'll finally get to be together, she tells him the fact that she was DeadAllAlong means she now has to disappear. As in, ''into thin air'']]. Suffice it to say, Ron Moore is one of the few people who knows how to inflict more pain on a couple than Creator/JossWhedon.
** Adama/Roslin: They [[spoiler: start out strongly disliking each other, move into a tenuous kind of peace with attraction, which gets shattered by the mutiny. Just as they fix that and get back to the tenuous attraction, she almost dies. Then, just as they fix ''that'', SURPRISE CYLONS. Then once they kick the Cylons out, Adama gets hit with an attack of conscience, and then she's dying again, and then Earth, and then she ''dies.'']]
** Chief/Boomer.
* John/Aeryn in ''Series/{{Farscape}}''. They make out. They fight alongside each other. They're tortured. They try to kill each other. They have sex. [[spoiler:They die. (They get better.)]] They murder people to get back to each other. They fight. They make out. They blow up a bunch of bad guys. [[spoiler:They have a kid]].
** D'Argo and Chiana are just as much fun!
* Falling in love [[DatingCatwoman with the bad guy/girl]] is always a bad idea. Just ask Series/AceLightning, who had to go and fall in love [[spoiler:with the bad guy?s main hench-lady, who ended up sacrificing herself for him]] at the end of the series.
* Every relationship in ''Series/{{Supernatural}}''. The Winchesters are crazy and clingy, Bobby had to kill his wife, Ellen lost her husband because John was an idiot, Sam's girlfriends tend to die horribly and Dean blurted out everything to his one-time girlfriend only to have her think that he was a lunatic and that she should break up with him.
* In ''Series/{{House}}'', House's hopeless love for his ex Stacy causes the pain in his leg to increase. When Wilson points out that this is the reason House is having more pain, House wacks him with his cane and replies: "''Awww, you miss Stacy too''?" when Wilson keels over.
** There is also a Season 1 episode titled "Love Hurts," in which Cameron blackmails House into going on a date with her and House responds by shooting her feelings for him down. Hard.
* ''Franchise/KamenRider'', at least in the new generation, is as fond of this trope as it's fond of AnyoneCanDie. On the rare occasions where a love interest to a major character is still alive by season's end, the relationship between them will likely have ended instead.
* ''Series/{{Highlander}}'': According to WordOfGod, Duncan [=MacLeod=] has had "four great loves" in his life. All four are dead, and not of natural causes. In one flashback, a gypsy curses him, saying that he will "bury many women but marry none" - but his bad luck seemed to have started even before that..
* Series/{{Oz}}'s Tobias Beecher loses his wife (she commits suicide), and later falls for Chris Keller, who it turns out was working for Schillinger, and they both subsequently break both his arms and legs. Busmalis even {{lampshade|Hanging}}s this after the incident. Though Keller arguably feels guilty afterwards, he spends the rest of the series trying to make it up to Beecher, both failing and succeeding at various points.
* ''Series/{{Friends}}'': Ross and Rachel continually break each other's hearts with their CantLiveWithThemCantLiveWithoutThem relationship, Phoebe and David were separated by his job, Monica and Richard split up over wanting children and Chandler was devastated after Janice and later Kathy cheated on him and left. Averted with Monica and Chandler who were extremely happy after falling in love and had a healthy, fulfilling relationship. Also Phoebe and Mike eventually.
* ''Series/TheVampireDiaries'': Primarily Stefan and Elena, but any couple who has been together fits.
** Damon and Elena could fit too, although not as much as Stefan and Elena.
* Love hurts quite a few people in ''Series/{{Torchwood}}'':
** Ianto's attempt to save Lisa after she was partially roboticized causes nothing but grief.
** Tosh is the show's poster child for CartwrightCurse.
** In "Out of Time", [[TokenEvilTeammate Owen]] falls for an aviatrix from the 1950s. She feels the same way, but loves adventure more and risks another flight through the Rift. Owen has no idea where she ended up or if she survived.
** "Children of Earth" - The only conceivable reason [[spoiler: Ianto would've been in that room with the 4-5-6 is his absolute faith in and love for Jack, and then everyone Jack loves causes him terrible terrible pain in the end]].
* ''Series/DoctorWho''. All of the Doctor's companions "break his hearts".
** And he broke Martha's. (And Jack's. And Sarah-Jane's.) That was exactly why she decided to stop traveling with him.
** The Doctor and Rose are depicted as StarcrossedLovers. Ultimately they are [[spoiler: separated permanently, although at least they got to share a short goodbye quite a while after the fact. Subsequently a human version of the Doctor is created. Ten takes his human self to Rose's parallel universe to spend the rest of his human life with her. While for Rose this is a somewhat happy ending, the real Doctor looks heartbroken and lonely as he watches the two kiss each other, knowing she will be happy but he will go on alone without her. Rose gets to be with Ten, technically, but he will never get to be with her]].
** And later, the Doctor and River Song, on both sides. The day he meets her is the day [[spoiler: she dies]]. And while he sees her again (their timelines running roughly in opposite directions), falls for her and [[spoiler: marries her]], it's all knowing how and when he's going to lose her. And from her perspective, she starts with a man who loves her enough to [[spoiler: sacrifice his life for her]], but with each consecutive meeting he knows - trusts, ''loves'' - her less and less, until their final meeting [[spoiler: (or [[BackForTheFinale so they think]])]] when he has no idea of who she is.
* Sadly, this was the course that ''Series/RobinHood'' decided to take. Only two couples get a happy ending: Will Scarlett/Djaq and John/Beatrice (who were only guest stars). All the other couples: Robin/Marian, Guy/Marian, Robin/Isabella, Robin/Kate, Much/Kate, Allan/Djaq, John/Alice, and any slash pairing you can think of, ended badly. VERY badly. Though Robin/Marian did get a [[spoiler: TogetherInDeath]] scene.
* Marcus over Ivanova in ''Series/BabylonFive'', going so far as to [[spoiler:sacrifice himself to save her life, transferring his life energy to her as she lay fatally injured. She is devastated that he would do such a thing, regretting she never returned his affection]].
* Naomi from ''Series/{{Skins}}'' lives in blind terror of this trope, constantly running away from her love of Emily until she can't handle it any more; and when they eventually get together, she's ''still'' so scared of getting her heart broken that [[spoiler:[[YourCheatingHeart she tries to break Emily's first.]] It all ends with a HappilyEverAfter, though, after an AnguishedDeclarationOfLove in the finale in which Naomi admits - and seemingly gets over - all her fears]].
* Creator/JossWhedon must HATE happiness. Pick anything written by Whedon. The only exception is [[Series/{{Firefly}} Simon and Kaylee]], and that's just because they didn't get together [[LastMinuteHookup until the end of]] [[Film/{{Serenity}} the movie.]]
** Series/{{Buffy|the Vampire Slayer}} sleeps with Series/{{Angel}}? He loses his soul and starts killing her friends, and then she has to send him to literal hell.
** Willow and Oz are actually happy together? Oh no! We better [[spoiler:make Oz go away to try and get rid of his wolf problem.]]
** Giles has a nice grown-up relationship that's started to go somewhere? [[spoiler:Guess who Angelus's next victim is?]]
** Xander and Anya about to tie the knot? [[spoiler:Xander gets a false vision of the future that destroys their relationship and sets Anya on the road to becoming a vengeance demon again.]]
** Willow and Tara get back together? [[spoiler:Oops, stray bullet on a physically impossible trajectory. Sorry, Tara.]]
** Xander and Anya rekindle their love in the final season? [[spoiler:Anya dies in the last episode.]]
** Spike and Buffy patch things up in the last few episodes of Season 7? [[spoiler:Time for some vampire flambé, everyone!]]
** Then there's Joyce. In five years she dates a [[spoiler:StepfordSmiler psycho robot]] and [[spoiler:becomes a hormonal sullen teen along with Giles, to their mutual embarrassment]] - then she starts dating and enjoying it and [[spoiler:BOOM, anyeurism.]]
** In Season 5, Spike is tormented by his unrequited FoeYay for the Slayer.
--> '''Spike:''' "What the bleeding hell is WRONG with you bloody women?! What the hell does it take?! Why do you bitches torture me?!"
--> '''Buffy:''' "Which question do you want me to answer first?"
** Hooray! Angel and Cordy are going to have DINNER! Oh, ok Angel, we need to[[spoiler: have your son lock you up underwater for the summer, and yeah, Cordelia, you're going up to watch over them for a while, and come back different]].
** Wesley and Fred couple up? [[spoiler:"Hey, Fred, you want to die and come back as an ancient pure demon living in your body?" "Sure." "Sorry, Wes..."]]
** The only happy marriage in the ''Series/{{Firefly}}'' 'verse? [[spoiler:"I am a leaf on the wind..."]]
** ''Series/{{Dollhouse}}''. Topher and Bennett. So freaking adorab[[spoiler: BOOM, HEADSHOT]]!
*** The worst part is that every single time it happens, he makes you forget that he has that habit and then it hits out of nowhere. Fresh wounds every time.
* This could be the theme for ''Series/GossipGirl''. If he's a nice guy, he'll sleep with someone else. If he's a redeemed jerk, turns out he's just a jerk. If he's your true love, he'll whore you out. If he seems perfect, he's sleeping with his stepmother or conning you out of your money or about to blackmail you into being his mistress. Love is pain, rich kids.
* The titular character in ''Series/{{Merlin 1998}}'' (played by Sam Neill) goes through this several times in his relationship with Nimue. After he meets her for the first time, [[spoiler: she is taken as a hostage by King Vortigern]]. When he gets around that, [[spoiler: she is severely scarred by a dragon and withdraws to Avalon]]. When there is finally a good king on the throne and he thinks he can spend time with her, [[spoiler: he learns of Mab's plot and has to rush back to Camelot to see Arthur]]. Then, years later, he thinks that they can finally, ''finally'' be together away from the rest of the world, but [[spoiler: he leaves the place where they are staying, and it seals behind him, trapping her away forever]]. Unsurprisingly, the aged Merlin in the present says almost these exact words when telling his story. [[spoiler: However, things turn out better at the very end.]] [[Series/{{Merlin2008}} His BBC counterpart]] wasn't much luckier. The only girl he ever loved, Freya, ended up [[spoiler: being a [[BalefulPolymorph monster]] who was killed by Arthur and [[DiedInYourArmsTonight died in Merlin's arms]]. Thanks to Merlin's love for her, she was able to come back as a spirit of the lake but they rarely get to see each other]].
* [[MyLittleTown Art Kanji-Daemon]] is probably the TropeCodifier at how much love hurts him through all his life.
* Bo and Lauren Any one who watches ''Series/LostGirl'' will know this couple is a good definition of this trope. Bo and Lauren want each other from the first time they meet, but they can't even kiss because if they do Bo will lose control and drain Lauren of her life force, Bo gains control and gets together with Lauren... but only for one night because Bo learns that Lauren was with her to distract long enough to stop Bo from killing someone (even though they would have gotten together on their own as Lauren explains) and Bo refuses to talk to Lauren for the next few episodes unless it is work related. Then in the season finale just before Bo goes to fight her mother Lauren gives her a kiss which Bo responds to.
** Season 2 Bo and Lauren get closer again eventually shacking up in the 6th episode only for Lauren to return to the Ashes compound and Bo finds out that Lauren has a girlfriend in a Coma, they move past this a few eps later and kiss its all going well then Laurens girlfriend wakes up. this season is not even finished yet and there will be at least a 3rd season.
* Oh, ''Series/CallTheMidwife''! Dr Turner and Sister Bernadette spend an entire series in agony over their feelings for each other. On her part, she's a ''nun'', and torn between her vows to God and the man she loves. On his part, he openly admits he would rather die than come between her and her God. As if that's not bad enough, [[spoiler:oh guess what, she comes down with tuberculosis]]! ''Finally'', in the last episode of the second series, [[spoiler:they [[EarnYourHappyEnding earn their happy ending]] when Bernadette, cured of her TB, decides that God is calling her to a different path. He asks her to marry him in ''very'' short order, and she says yes]] -- but [[spoiler:it is still bittersweet, as it means Bernadette has to leave the Order, which is all the family she has -- most notably her beloved ParentalSubstitute Sister Julienne]].
** This applies to Sister Julienne as well in this storyline. [[spoiler:When she finally no longer has to watch Bernadette going through her own personal hell]], it's because she [[spoiler:has to watch the young woman who is essentially her daughter leave the Order behind to marry the man she loves. The pain of letting her baby girl go is written all over Sister Julienne's face]], giving a whole new meaning to the word [[spoiler:bittersweet]].
* Like the book its based on, love in ''Series/GameOfThrones'' usually spells tragedy. By the end of season 3...
** Ned Stark [[spoiler: dies far away from his wife Catelyn, and she is left grieving]].
** Daenerys Targaryen [[spoiler: loses her husband Drogo, despite her best efforts to save him]]. Her knight Ser Jorah Mormont is also in love with her, but she doesn't reciprocate his feelings for her.
** Despite the homophobia of Westerosi society, Lord Renly Baratheon and Ser Loras Tyrell are in a loving, long-term relationship. [[spoiler:Loras is heartbroken after Renly is murdered and is consumed by a thirst for vengeance against the kinslaying Stannis Baratheon. Losing the love of his life is already incredibly painful enough as it is, but what makes Loras' suffering even worse is that he cannot openly express his grief, as Renly was a man and a traitor to the crown.]] Also, since Joffrey has expressed a desire to execute all homosexuals, Loras can't afford to reveal any of his true feelings for Renly.
** King Robb Stark and Talisa Maegyr have probably the happiest relationship on the show, [[spoiler:but the political problems surrounding their marriage eventually lead to the Red Wedding, where the Freys deliberately murder Talisa (who was pregnant) in front of a [[HeartbrokenBadass devastated Robb]], who has just enough time to crawl over to her corpse before being murdered as well]].
** [[HeroicBastard Jon Snow]] and the wildling Ygritte are also [[StarCrossedLovers quite happy together]], but the fact that Jon is a FakeDefector in the wildling ranks, and they both know it, grates on their relationship, until [[spoiler: Jon is forced to show his true loyalty to the Night's Watch when he refuses to kill an old man after [[IfYoureSoEvilEatThisKitten being ordered to do so to prove he is no longer loyal to the Watch]] but Jon can't bring himself to murder an innocent in cold blood. A battle between Jon and the wildlings ensues, he gets Ygritte out of the way so the wildlings don't turn on her and when the battle is done, he escapes back to the Watch, leaving Ygritte, despite her being willing to run with him. She then shoots him three times with a bow to try and stop him. They meet again during the Wilding siege on Castle Black, but Ygritte is shot by Olly and dies in Jon's arms, [[HeartbrokenBadass devastating Jon]]]].
** Tyrion Lannister and Shae both love each other but Tyrion can never let his father Tywin Lannister know their relationship since Tywin would kill her, and he's too scared of his father to run away with her at her suggestion.[[spoiler: His marriage to Sansa does not help matters.]] It gets worse later on when Tyrion tried to send Shae away, except it made her furious and she bites back [[spoiler:implicating Tyrion in Joffrey Baratheon's murder by lying to the court during Tyrion's trial that she overheard him and Sansa plotting to kill Joffrey and twisted one of the sweetest moment between her and Tyrion ("my lion") into a sickening abusive moment, causing Tyrion to snap and declare a TrialByCombat. When Tyrion escapes from his cell, he goes to his father's room and finds Shae naked on his bed, causing him to strangle her while apologizing to her with tears]].
** Oberyn Martel and Ellaria Sand are clearly in love [[spoiler:only to end with Oberyn's brutal death in the hands of Ser Gregor Clegane during Tyrion's TrialByCombat which she just watched. Unlike in the books where she tried to move on and doesn't want to be part of the revenge plot against the Lannisters because the people responsible of Oberyn's and Elia's deaths are already gone, she's the one instigating the revenge plot by trying to kill Myrcella Baratheon because of her Lannister blood and she succeeded by poisoning her which would likely worsen the feud between the Martells and the Lannisters]].
* ''Series/WhiteCollar'': Neal goes through a ''lot'' because of his love for Kate - to start with, the four years he spent in prison were because he was desperate to find her and tell her that he loved her.
* ''Series/HowIMetYourMother'' isn't immune to this where the five main characters experienced heart break at some point in the show:
** Ted loved Robin but certain issues showed that they're probably not meant to be together and he tried it again for the second time only to be rejected. He also got dumped in the altar by Stella and broke up with Zoey when she tried to sabotage his career. [[spoiler:And in the series finale, the titular Mother died of the SoapOperaDisease.]]
** Marshall and Lily are still going strong with their relationship and later, marriage. But they still experienced some problems like when Marshall was very depressed after Lily left him to go to San Francisco due to cold feet though they managed to work it out for a while. This issue is revisited again in the last season.
** The reason why Barney's such a suit-wearing womanizer? [[StartOfDarkness His girlfriend cheated on him with a suit-wearing womanizer]] which he became in the present.

* The probable {{Trope Namer|s}} is an old country standard the Everly Brothers played. Famously, Nazareth gave it an epic metal treatment. From the sound of the singer's voice, love ''really'' hurts.
* Music/{{Incubus}}' aptly titled song "Love Hurts", although it could be considered a subversion; the chorus is, "Love hurts, but sometimes it's a good hurt and it feels like I'm alive".
* Another subversion in "Hurt Me Bad (In a Real Good Way)" by Patty Loveless. The protagonist was hurt by love, but the pain set her free to find a better lover.
* Sing with me…[[Music/JoyDivision Love, love will tear us apart again]]...
* Music/{{Pink}}:
** "Please Don't Leave Me" by Music/{{Pink}}. WAY more so in the video of the song, where - when the guy tries to leave - [[{{Yandere}} she goes Stephen King on him]].
** Another P!nk song, "Try":
--->''"Where there is desire, their is gonna be a flame,\\
Where there is a flame, someone's bound to get burned."''
* "... that's the pain that cuts a straight line down through the heart, we call it love ..." - Theatre/HedwigAndTheAngryInch
* Music/{{Aerosmith}}, "Falling in Love (Is Hard On The Knees)".
* "Love Stinks" by Music/TheJGeilsBand.
* Baby, don't hurt me... no more... (Haddaway, best known as the theme song for the "Roxbury Guys" on ''Series/SaturdayNightLive''.)
* Music/LeonardCohen's famous "Hallelujah" is mostly about this, although the overall idea seems to be that it's worth it anyway as long as you know what to expect.
* "Running Water" by DJ Shog featuring Irma Derby: "Love's like hot running water, once it runs through your fingers, painful in every way..."
* "Love Bites" by Music/DefLeppard. Describes love as an addiction.
* Half the ''Rumours'' album by Music/FleetwoodMac are songs about how bitter falling out of love can be. "Never Going Back Again," "Go Your Own Way," and "Gold Dust Woman" in particular. The crowner is "The Chain," an anger-filled tune ("Damn your love, damn your lies") and is the only song on the album credited to all five members.
* Music/{{XTC}}'s "I'm the Man Who Murdered Love" depicts the title character as a highly SympatheticMurderer.
* "To Love Somebody", originally by Music/TheBeeGees.
* "It's a Heartache", originally by Music/BonnieTyler (and Music/JuiceNewton).
* "Too Much Love Will Kill You" by [[Music/{{Queen}} Brian May]].
* "Fool for Your Loving" by Music/{{Whitesnake}}.
* "Only Love Can Hurt Like This" by Paloma Faith.
* "Lollipop" by Music/{{Mika}}.
-->Mama told me what I should know:
-->''"Too much candy gonna rot your soul''
-->''If she loves you, let her go''
-->'' 'Cause love only gets you down"''
* [[http://www.youtube.com/watch?v=EfBwb4I8wWk "Adult Female: A Song"]] by [[WebVideo/VlogBrothers Hank Green]]
--> ''"Love is hard and love is messy and it can hurt worse than fire\\
and sometimes it makes you want to tear down a building with your bare hands!"''
* The song "You Always Hurt The One You Love".
-->"You always hurt the one you love/The one you shouldn't hurt at all"
** It was [[SuspiciouslyAproposMusic sung by the main character]] in the ''Film/BlueValentine'', which depicted a DestructiveRomance.
* "Terrible Thing" by Music/MaydayParade, which is song from the viewpoint of a father telling his son about how he met, fell in love with and married his mother. It then reveals the mother in fact died years ago and the father than tells his son that he should never fall in love and avoid anyone that tries to make him do so, because life can do [[TitleDrop terrible things]].
* "Breaking Us In Two" by Music/JoeJackson is about a couple who love each other but just can't make the relationship work long-term.
* Music/DanielJohnston lives this trope. He has been in love with many girls, but due to his mental illness all of it [[AllLoveIsUnrequited has remained Unrequited Love]], resulting in a lot of very tragic but heartfelt songs, including on his albums ''Music/YipJumpMusic'' and ''Music/HiHowAreYou''.
* Music/BillieHoliday had a tragic life where she was the victim of rape at age 11, teenage prostitution, abusive partners and severe alcohol, morfine and heroin addiction. All it culminated in ''Music/LadyInSatin'', where she sings about break-ups, unrequited love and all hardships of relationships in her drug ravaged voice. Only a year after recording this album she would die from liver cirrosis.
* Music/{{Garbage}}'s [[AntiLoveSong "I Hate Love"]], a long diatribe on the ways it hurts - specially [[AllLoveIsUnrequited not being loved back.]]
* "Everything We Had" by Music/TheAcademyIs... "Take the pain out of love, and then love won't exist..."

* Pick an {{Opera}}, ''any'' opera. ''Theatre/{{Aida}}'' by Giuseppe Verdi is a good example. Aida, an Ethiopian [[RagsToRiches princess in hiding]], falls in love with and is loved by Radames, the general of the Egyptian army. Her mistress, the Pharaoh's daughter is her canny rival. After Radames saves her father, the king of Ethiopia, from certain death after being captured in battle, he brow beats her into fulfilling her "duty" as an Ethiopian to get Radames to reveal the Egyptian's troops' positions, sentencing him to death and dooming them to live apart. It's a "HappilyEverAfter" ending though; Aida sneaks into the tomb where Radames has been buried alive so they can slowly die together. So yes, the DeusAngstMachina is as integral a part of Opera as humor is to Comedy.[[/folder]]

* ''Theatre/RomeoAndJuliet'' and every imitator. Entire dissertations could be written on how both would have lived longer, happier lives if Romeo had decided to stay in and mope, Juliet had told him she wanted at least [[FourthDateMarriage three dates before considering marriage]], or the friar's advice to Juliet had been to take up her father's offer of being kicked out of the house so she could run away with Romeo easily, rather than telling her to fake her death.
* ''Theatre/ThePhantomOfTheOpera'' is based around this trope with a StalkerWithACrush and MadArtist with a CompellingVoice and a TortureCellar (who often becomes the DracoInLeatherPants) proving that LoveMakesYouEvil and StalkingIsLove in a LoveTriangle with a DamselInDistress and her [[SheIsAllGrownUp childhood sweetheart]]. He chooses in the end [[IWantMyBelovedToBeHappy to let his beloved be happy]], giving us a BittersweetEnding.
* ''Theatre/CyranoDeBergerac'' centers around a LoveTriangle between three perfectly honorable, admirable people who all like and respect each other, two rivals who try as hard as they can to make the girl happy instead of fighting over her, and the original PlayingCyrano plot that isn't revealed until death has taken too many members out of the picture for anyone to be happy.
* A fact of life for Fiyero, Elphaba AND Glinda in ''Theatre/{{Wicked}}'' (and Boq and Nessarose for that matter). Elphaba even comments on it during Defying Gravity 'Well if that's love/it comes at much too high a cost'
* ''Theatre/CityOfAngels'':
-->'''Stone''': Whoever said 'Time heals all wounds' never knew anyone like Bobbi.
* ''Theatre/NextToNormal'':
-->The price of love is loss
-->But still we pay.
-->[[SomeAnvilsNeedToBeDropped We love anyway]].
* ''Theatre/{{Company}}'': The entire point of the song "Being Alive" and it's a ''good thing'', because otherwise you're not really living.
-->Somebody hold me too close, somebody hurt me too deep
-->Somebody sit in my chair and ruin my sleep
-->And make me aware of being alive, being alive
-->Somebody need me too much, somebody know me too well
-->Somebody pull me up short, and put me through hell
-->And give me support for being alive, make me alive!
-->Make me confused, mock me with praise
-->Let me be used, vary my days
-->But alone is alone, not alive!
-->Somebody crowd me with love, somebody force me to care
-->Somebody let me come through, I'll always be there
-->As frightened as you to help us survive being alive
-->Being alive, being alive, ''[[IncrediblyLongNote being alive]]!''

[[folder:Video Games]]
* ''VideoGame/MaxPayne2''
-->''This is love. When someone drags you from the wreckage when you have given in, ready to just lie there and die. This is love. When someone, no matter what the cost, shows you there is hope, a choice, that you can put down your gun. This is love. Love hurts.'' - Max's narration in a cutscene in ''MaxPayne2'', just before [[spoiler: his love interest is gunned down by the BigBad because she refused to kill him. Depending on the difficulty you play on she gets better.]]
** Max's first line in the game says it all: "They were all dead. Love kills."
* ''VideoGame/OdinSphere'': The plot is full of this. Only a few characters actually get happy endings, assuming you didn't muck it up and get the bad ending, in which case it turns into a KillEmAll.
** The plot isn't just full of it. The plot exists ''because'' of it. The only things that don't seem to be linked to love is a war over control of a MacGuffin, and ''that'' was originally caused by this.
* ''VideoGame/NeverwinterNights'': The unjustified execution of her fiancee led Aribeth de Tylmarande to insanity and an eventual FaceHeelTurn. The picture in the slideshow between chapters 1 and 2 with her crouched under the tree crying her eyes out sums this trope up very effectively.
* ''VideoGame/NeverwinterNights2'' has this for just about every relationship in the original campaign. Males who romanced Elanee [[spoiler:learn she was killed saving them from a falling boulder]]. Females who romanced Casavir [[spoiler:are told he was buried beneath tons of rock while helping everyone else escape]]. Females who did Bishop's [[TheNotLoveInterest semi-romance]] [[spoiler:are betrayed, then later have to watch him die on the Wall of the Faithless]]. Guys who liked Shandra [[spoiler:arrive just in time to watch her be killed by her grandfather]]. The only romance/potential romance that doesn't end in hurt is Neeshka's.
* ''[[Franchise/ShinMegamiTenseiPersona Persona]]''
** ''VideoGame/{{Persona 2}}: Eternal Punishment'' plot is started because Tatsuya, who was supposed to forget his memories of Maya from ''Innocent Sin'', couldn't let her go and creates a TemporalParadox because of it, allowing the BigBad from the previous game to [[HisStoryRepeatsItself repeat the events]]. [[spoiler: In the end, he gives up those memories and Maya [[StarCrossedLovers can't be with him]] for fear of Tatsuya regaining his memories and dooming the world.]]
** ''VideoGame/{{Persona 3}}'''s Yukari and Aigis. [[spoiler: After the Protagonist dies,]] Yukari tries to move on, but is inevitably brought back to the dormitory where fond memories of our hero visit her. She's also jealous of Aigis, who [[spoiler:inherited the Protagonist's power]]. Aigis is so saddened by the [[spoiler: Protagonist's death]], she wished she could return to being a mere machine, which [[spoiler: gave birth to Metis, causing the events of The Answer.]]
** ''VideoGame/{{Persona 4}}'' could also be considered as having an example of this. Even if you have a love interest ([[YourCheatingHeart or several]]) you will still [[spoiler: leave any and all of your love interests behind as you go back to your actual home via train]].
* ''Franchise/MetalGear''. There is maybe one successful romance in this series that does not put the characters and gamer through hell first. Meryl and Snake [[spoiler:don't make it. Meryl winds up in a successful romance with Johnny, the series ButtMonkey]]. Raiden and Rose [[spoiler:have so many issues that they deserve their own trope. They make it, which is more than most can claim, but they go through hell first]]. The Boss and The Sorrow [[spoiler:were damned before the series started, with The Boss being forced to shoot her own lover. And he let her]]. Naked Snake and EVA [[spoiler:failed. Fanon aside, EVA doesn't get Snake, even though she loves him and bore his sons (against his will)]]. And Otacon? [[spoiler:He might as well put a bullet in the head of every woman he shows affection for and save time]]. ''Ground Zeroes'' adds [[spoiler: Chico and Paz. Chico, who is in love with Paz, attempts to rescue her, only to be captured and tortured physically, emotionally, and psychologically. Once it finally looks like they might make it out alive, Paz reveals that she has a second bomb inside of her and sacrifices herself to save the MSF survivors, dying right before Chico's eyes]]. Yes, this game is [[SlidingScaleOfIdealismVersusCynicism very cynical]], whatever gave you that idea?
** Is it any wonder Kojima averted this hard in ''VideoGame/ZoneOfTheEnders?'' There, only one "pair" ends badly (in this world, at least).
** Kojima played this straight again in ''VideoGame/CastlevaniaLordsOfShadow'', damning Gabriel and Marie right before the beginning of the story.
%%* ''VideoGame/PlanescapeTorment'': It's not the only thing that hurts. But boy does it ''hurt''. See also: [[LoveMartyr Deionarra]].
* Good God, VideoGame/{{Utawarerumono}} with Hakuoro and... well, everyone. Eruruw is apparently physically unable to confess [[spoiler:until her contract with him is dissolved]]. He doesn't pick up on Karura's rather [[TheTease blatant]] overtures. Touka just weirds him out. [[GeniusDitz Which is understandable]]. Urtoriy can't be in a relationship with anyone apparently [[spoiler:and most certainly not the divinity of her religion]]. Oh, and the ill girl kind of gets what she wanted [[spoiler:except it was mostly out of pity/platonic love, and she died after giving birth anyway]]. For the hurting part on ''his'' side, [[spoiler:losing Mutsumi]] hurt so much that [[spoiler:his identity split into two godlike beings that cause chaos, wars and destruction every couple years]]. There's an implication at the end [[spoiler:that Hakuoro comes back, and he did essentially admit he loves Eruruw]]. Oh, and Kamua probably didn't love him so she's okay.
* ''VideoGame/FinalFantasyIV'' has Kain and his unrequited love for Rosa. AllLoveIsUnrequited hurts by itself, but then you factor in how he lost her to his [[AlwaysSomeoneBetter best friend]] Cecil, and it gets real painful, especially since he clearly ''wants'' them to be happy, but is still full of jealousy and sorrow.
* ''VideoGame/FinalFantasyVI'' has this with Locke and Rachel, where [[spoiler: Rachel accidentaly loses her memory and her parents blame Locke for the whole mess, he blames himself because Rachel in her memory stricken form tells Locke to leave because her parents are yelling at Locke, afterwards, he learned that at the time of the villages demise, she regained her memory, and called for him... Then, he asked a doctor to preserve her body, while he searches for a way to save her, while still blaming himself for everything..]]. Damn....
* In ''VideoGame/FinalFantasyIX'', Sir Fratley, the love of Freya's life leaves on a journey of epic training. When she doesn't hear of him for some time, she embarks on the world to find him. During the events of the game, she eventually runs into him but he is suffering from amnesia and doesn't remember her. Ouch.
** It's even on her quote in the game's manual. Quite a PlayerPunch when you find out what it means:
--->'''Despair.''' To be forgotten is worse than death.
** In the game's ending, his memory [[spoiler: never returns, but he [[EarnYourHappyEnding falls in love with Freya again]], anyway. [[CrowningMomentofHeartwarming Awww.]] ]]
* In ''VideoGame/SuperRobotWarsAlpha Gaiden'', resident badass {{Samurai}} Sanger Zonvolt gets this. The woman he deeply cared for (not to the point of open romance, but deep, deep loyalty and affection) was turned into a monster he and the [[Anime/MobileSuitGundamWing Preventers]] had to kill, and the poor bastard not only gets to watch her die, but his only comfort in the end of the game is cry over her grave. Alpha 2 gives him a RoaringRampageOfRevenge when Kukuru tries to off Sophia Nate (woman he cares for). He's a little better off in the OG Timeline, only now it's Wodan Ymir who gets screwed, which (long story) is the same thing.
* ''VideoGame/MegaManX4'' has finally included the option of playing as AscendedExtra and [[EnsembleDarkhorse major fan-favorite]] Zero, along with his own story. The bad part? In Zero's story, he has to fight ''and'' kill Iris, ''his own girlfriend'', who wants to seek revenge on Zero for killing her brother. The {{narm}} that came with the game's horrible voice acting ruined one of the truly [[TearJerker heartwrenching]] moments in the series. (The original Japanese voice acting did a much better job in powering the said TearJerker moment.)
** ''She doesn't even want to kill him'', instead attacking him because she can't forgive him for killing her brother, but can't bring herself to move on from his death. Essentially, the poor girl is so shattered that she's choosing SuicideByCop, and it ''breaks'' Zero as well as herself.
* Oichi in ''Videogame/SengokuBasara'' is this ''in spades''. Thanks to her love with Nagamasa and her care about her brother, who happens to be ObviouslyEvil, she's in for tons and tons of tragedy, starting from seeing her lover die in front of her, then delusionally thinking that Nagamasa wants everyone dead, then she kills off all her family and then gets herself killed.
** The fourth game introduces Shibata Katsuie, whose unrequited love for Oichi is why he's such a downer, though he shows tinges of EntitledToHaveYou as well. In one of Oichi's story routes, he goes so far as to [[MurderTheHypotenuse kills Nagamasa]], which simply drives Oichi into a murderous rage.
* In ''VideoGame/BreathOfFireIV'', this was essentially what fuels the Hex Cannon/Carronade. The closer the sacrifice was to the intended target, the stronger the hex will be. This was what [[spoiler:broke Fou-lu and cause him to go KillEmAll]] near the end.
** Cray spent much of the game searching for Princess Elina, Nina's sister and his love interest. [[spoiler:When they found her, Elina was turned into an artificial Endless, in order to exploits her love as an limitless fuel for the Carronade. Cray [[MercyKill ends her suffering]] with the Dragon Slayer.]]
* In ''VideoGame/BrutalLegend'', a female voice cites a sad poem about a girl whose heart is broken and is compelled to drown in the Sea of Black Tears. [[spoiler:It's actually talking about TheOphelia of the cast, who is named, well...Ophelia.]]
* Played straight and exaggerated in ''VideoGame/KingsQuestIVThePerilsOfRosella''. Edgar, Lolotte's homely [[spoiler:adopted-by-kidnapping]] "son" develops a fondness for Rosella, and pulls a HeelFaceTurn to free her from a prison. Rosella escapes, takes Cupid's love arrows and shoots Lolotte. The evil fairy is so overcome with sheer pain she shrieks "It HURTS!" before [[spoiler: falling over dead]]. Edgar is rewarded for his heroism by Genesta [[spoiler: returning him to what's later revealed to be his ''true'' form]], and he asks Rosella to stay with him. Rosella has to refuse his offer and get back to Daventry, presumably leaving him alone and somewhat heartbroken. At least, until the seventh game...
* ''VideoGame/FallenLondon''. Common parlance in the game is to never, ever fall in love. Particularly, it's important to never, ever ask the Bazaar for help in situations involving love. [[spoiler: Results tend towards horrific transformations, resulting in the Cantigaster and the current state of most of the Empress's children. Horrible things happen when beings that just don't get how humans work get involved to try and make a love story more interesting.]]
* The ''VideoGame/PretentiousGame'' series plays this ''painfully'' straight. The blue square suffers [[AllLoveIsUnrequited Unrequited Love]] for the bright pink square. The light pink square loves her husband, the gray square, only to get cheated on, and when she divorces him and gets into a relationship with the blue square, he gets killed by her drunken ex-husband. As for the gray square? He feels massive amounts of guilt for cheating on the light pink square, with whom it's implied that [[LadykillerInLove he was genuinely in love]], and turns to alcohol to deal with his feelings.
* ''[[Franchise/DragonAge Dragon Age]]'' loves this trope.
** In ''[[VideoGame/DragonAgeOrigins Origins]]'', you have [[LadyOfBlackMagic Morrigan]] who turns out to [[spoiler:have had a [[WasItAllALie secret agenda the whole game]] and leaves -- while possibly pregnant with your child -- despite having genuinely fallen in love with you]]. Alistair will also break up with you if he [[spoiler:becomes King and you're not a human noble, unless you become his mistress (at the cost of [[CorruptTheCutie hardening]] him)]]. He will also [[spoiler:[[AlwaysSaveTheGirl sacrifice himself to save you]] if you refused to do Morrigan's ritual]]. Leliana and the Warden will separate somewhere between the end of Origins and Inquisition. On top of all this, the Warden themselves [[spoiler:[[HeroicSacrifice can die]]]] at the end of game depending on your choices.
*** In Witch Hunt, after you find Morrigan, you can [[spoiler:convince her to let you go through the [[MagicMirror Eluvian]] with her, getting your happy ending after all.]]
** In ''VideoGame/DragonAgeII'', [[WellIntentionedExtremist Anders]] will [[spoiler:manipulate you into helping him blow up the Chantry]] at the end of the game. Hawke can choose to stay with him and [[spoiler:go on the run, but some players consider it a unforgivable betrayal. You can really take this trope to the extreme if you choose to kill him]]. All the other romance options except for Merrill will also [[SecondActBreakup break up with you at one point]], but will return to you later.
*** Hawke can possibly [[spoiler:die]] during their cameo in Inqusition, which inevitably [[spoiler:leaves behind their love interest]].
** In ''[[VideoGame/DragonAgeInquisition Inquisition]]'', Blackwall reveals that [[spoiler:he is a wanted murderer [[DeadPersonImpersonation pretending to be a Grey Warden]]. You can forgive him but he'll eventually leave on a {{Redemption Quest}}]]. Dorian will [[spoiler:return to Tevinter [[LovedINotHonorMore without you in his quest to change his homeland]]]] and Cassandra will (sort of) break it off if she [[spoiler:becomes [[HighPriest Divine]]]]. The real doozy is Solas, who [[ItsNotYouItsMe breaks up with you]] and leaves for mysterious reasons. In {{The Stinger}} you find out [[spoiler:he's an [[DidYouJustRomanceCthulhu ancient elven god]] who was the catalyst for the entire plot of the game. You finally see him two years later only for him to tell you his plan to [[UtopiaJustifiesTheMeans destroy the world]]. You can tell him that you'll change his mind, but he still [[ItMakesSenseInContext takes your arm]] and leaves, despite [[TearJerker still loving you]]]].
* Each antagonist in ''VideoGame/RuleOfRose'' has a different motivation for hurting people, but the worst antagonists are motivated by love. The BigBad's entire plan is "Hurt [[spoiler:Jennifer]] so much that she will become a broken, mindless shell and never hurt (read: [[WomanScorned reject]]) me again", and her [[TheDragon Dragon]]'s love for his dead son drives him [[spoiler:murderously]] insane. Fortunately, TheHero is motivated by everything ''good'' about love, so it all [[{{Foil}} sort of balances out]].

[[folder:Visual Novels]]
* ''VisualNovel/FateStayNight'':
** The ending of the Fate route exhibits this to a certain extent. [[spoiler:Saber dies]], and although [[spoiler:Shirou manages to get over the loss remarkably well, he says that he will always remember that he loved her]].
** The Heaven's Feel [[TearJerker Normal End]], however, takes this trope UpToEleven. [[spoiler:[[HeroicSacrifice Shirou dies]] in order to protect Sakura, and she moves into his house and spends the rest of her life mourning him and waiting for him to return to her (he never does...).]]
* Love, be it platonic, familiar, or romantic, in the ''Franchise/WhenTheyCry'' franchise tends to end in tragedy.

[[folder:Web Comics]]
* ''Webcomic/{{MAGISA}}'' - The message is, [[http://mag-isa.thecomicseries.com/comics/pl/156004 "Love hurts...but you need it."]]
* In ''Webcomic/SluggyFreelance'': Torg's crush on Zoe earns him quite a bit of this as the series goes on, best summed up in the MindScrew arc [[http://www.sluggy.com/daily.php?date=060404 "Wayang Kulit"]].
** He gets off easy compared to Oasis, who has ''died'' multiple times because of her [[AllLoveIsUnrequited unrequited love]] for Torg.
* While Lia and Fiona, from ''Webcomic/YuMeDream'', don't have any easy time at first, this is nothing compared to when the major DramaBomb hits. This seems to be intentional, as the author/artist explains [[http://rosalarian.com/yume/?p=941 here]].
%%* [[http://djbogtrotter.co.uk/2009/02/06/love-is-the-answer/ "What can hurt more than a concrete enema?"]]
* ''Webcomic/{{Digger}}'': Ed's backstory. [[DomesticAbuse Dear God, Ed's backstory.]] And through it all he never, ever stopped loving. Oh, Ed.
* ''Webcomic/NoRestForTheWicked'':
** The Beast is crazily obsessed with Beauty and rages, insane with jealousy, when she's late returning.
** Prince Ricardo, being MinorFlawMajorBreakup embodied, goes around breaking hearts as quickly as he can rescue princesses -- and is none too happy himself.
** Claire and King Gareth appear to have been HappilyMarried, but he went to war. Now they are separated; Claire won't explain what happened to her child, and refuses to meet him because she feels too guilty; and Gareth signed a peace treaty because he was too heartbroken over the news of his wife.
* ''Webcomic/{{Zoophobia}}'': Damian's obsession with Kayla always leads to this.
* In ''Webcomic/{{Sinfest}}'',
** [[http://www.sinfest.net/view.php?date=2006-03-17 Slick gives a graphic demonstration of the principle.]]
** [[http://www.sinfest.net/view.php?date=2007-02-24 And Monique rejects honesty as a means for love because of this.]]
* In ''Webcomic/DocRat'', [[http://www.docrat.com.au/default.asp?thisItem=622 Doc observes that both love and martial arts hurt.]]
* In ''Webcomic/{{Homestuck}}'', due to the complicated social dynamics and age of the protagonists, this trope gets used a lot.
** In particular, with Karkat Vantas, who despite being adept at helping other people sort out their romantic issues, is constantly tortured by his inability to sort out his own, [[spoiler: in particular, with Terezi, his love interest.]] Being a self-loathing JerkassWoobie doesn't help this.
** Eridan Ampora also invokes this, as he desperately hits on everyone but ends up with nothing to show for it, usually to comedic effect. This is justified because he is a douchebag, but later becomes a lot less funny when it becomes a factor in [[spoiler: him murdering two of his friends]].
** Nepeta Leijon also qualifies. She wants nothing more than for Karkat to just notice her, but she doesn't think that anything will ever happen. And then [[spoiler: she gets horrifyingly butchered by an AxCrazy Gamzee]].
** Davesprite and Jade [[spoiler:breaking up]] is an interesting example of this; [[spoiler: Jade initially seems largely unaffected by the whole thing despite the fact that Davesprite's the one who broke up with her. It's Davesprite himself and, oddly enough, John who seem to be upset about the whole thing (Davesprite, being [[TheStoic Dave]], isn't exactly ''emotional'' about it but doesn't appear to be all too happy about it either; with John it's implied to be a BigBrotherInstinct scenario). When Jade is under mind control, her confrontation with Dave has her vent some of her feelings about the relationship, shouting that he broke her heart]].

[[folder:Web Original]]
* In ''Literature/TheAntithesis'', love is a perpetual curse on most characters, whose personalities and ideas of affection become tainted through life experiences pertaining to love. Alezair's love for Leid repeatedly condemns him to fits of rage, insanity and substance abuse, and at one point his devotion for her nearly ends his existence entirely.
* Comes up a lot in ''Roleplay/SurvivalOfTheFittest'' because AnyoneCanDie ([[KillEmAll and usually will]]), the most prominent examples include:
** Bryan Calvert goes through the death of [[spoiler:Tori Johnson]], whom he'd been protecting for almost the entire game.
** Adam Dodd's girlfriend Amanda Jones is killed in his absence, setting him off on a path of revenge going after her murderer.
** Ricky Callahan similarly safeguards his girlfriend Whitney Acosta for most of v2. [[spoiler: When Calvert accidentally kills her, Ricky commits suicide.]]
** Sean O'Cann, after recently coming out of the closet and engaging in a thoroughly romantic relationship, gets this treatment, with his boyfriend Andy Walker biting the dust not long after the game began. Cruelly, they'd ''met'' each other prior to this and become separated, leading to Andy's death.
* Billy (Doctor Horrible) spends the entirety of ''WebVideo/DoctorHorriblesSingAlongBlog'' painfully infatuated with Penny, only for [[spoiler: his Arch nemesis Captain Hammer to accidentally kill her while trying to kill Doctor Horrible with his own Death Ray. This was after Captain Hammer dated Penny just to screw with Billy]].
* In ''WebAnimation/HappyTreeFriends'', every single episode featuring a romantic relationship ends in tears (and often, blood as well). The only characters who have survived an episode unharmed and together are Cuddles and Giggles in ''I Nub You'', and [[BetaCouple they weren't the stars of that episode]].
* In ''Series/{{Noob}}'', Arthéon has a girlfriend during the entire fourth season. Long story short, ''Noob'' is a five-season webseries.
* Whether played for [[PlayedForLaughs laughs]] or [[PlayedForDrama drama]], being in love never works out well for the characters of ''Machinima/RedVsBlue''. Emphasized in the [[CerebusSyndrome later seasons]], when [[spoiler: Church]] spends an entire season learning to let go and move on from [[spoiler: Tex]], York and Carolina's relationship [[DidNotGetTheGirl ends before it ever really begins]], C.T. [[spoiler: dies in the arms of her Insurrectionist boyfriend]], and the implication that the events of the whole series happened because [[spoiler: [[TragicVillain the Director]]]] [[TheMourningAfter never got over]] [[TheLostLenore his lost love]].

[[folder:Western Animation]]
* ''WesternAnimation/TeenTitans'':
** Just when things were looking up for Beast Boy in the last season, culminating in him [[spoiler:successfully leading a team of C-list teen heroes against the arc's ''BigBad'', the series gave him a DownerEnding[=/=]NoEnding with the return of either a look-alike or an amnesiac Terra, his morally conflicted season 2 flame]]. According to the spin-off comic, [[spoiler:Terra is faking amnesia]].
** That whole thing with Malchior betraying Raven in "Spellbound" after she fell in love with him.
* True for both TheHero and WorthyOpponent on ''WesternAnimation/AvatarTheLastAirbender'': Aang is told he will have to let go of his love for Katara to ever master the Avatar State, and after becoming disillusioned with his life in the Fire Nation, the one thing Zuko has to leave behind that he still cares about is his NewOldFlame Mai. See, they're NotSoDifferent. [[spoiler:They get them in the end, though.]]
** And then there's Sokka who had [[spoiler:his first love perform a HeroicSacrifice and become the new moon spirit]].
* In its sequel ''WesternAnimation/TheLegendOfKorra'': The LoveDodecahedron in Book 1 is suitably messy for a teenage love triangle. Korra goes on a date with Bolin after being rejected by Mako whose dating Asami. Korra then kisses Mako the next day who kisses her back, only for Bolin to see, breaking his heart. Mako regrets the kiss but Korra getting kidnapped causes a {{love epiphany}} which makes Asami suspicious. After she finds out Mako has been hiding the kiss, she breaks up with him. Korra and Mako become an {{Official Couple}}.
** In Book 2 Korra and Mako breaks up over their jobs. Asami and Mako kiss in the heat of the moment so it seems like they might get back together. Korra lost her memories and therefore doesn't remember that they broke up. So Mako doesn't tell her and tries to act like it didn't happen, something that everyone and Asami disapprove. Eventually Korra regains her memories and they break up again. Bolin meanwhile gets into a relationship with a {{Yandere}} Eska and has to run away from it.
* At ''WesternAnimation/{{Chowder}}'' episode "At Your Service", Panini threw some tacks to the running tall-legged Chowder, and when he is trapped in the middle of the tacks, he states that "Love hurts".
* Taken to its logical extreme in an episode of ''WesternAnimation/TheGrimAdventuresOfBillyAndMandy''. When Pud'n wishes on a JackassGenie skull for a pet bunny that will love him, he gets a literal interpretation of this trope.
-->''"Sometimes love hurts, Pud'n, [[PreAssKickingOneLiner and I love you a lot]]."''\\
''"I forgive you, Pud'n. I forgive you because I ''love'' you! [[spoiler: And I love you... [[PreMortemOneLiner to death.]]]]"''
* The ''WesternAnimation/KaBlam'' episode "A Nut in Every Bite" had Henry falling for Mr. Stockdale's visiting granddaughter, Dawn, but he only seemed to be able to charm her [[AmusingInjuries by hurting himself]]. (It's probably also worth noting that [[ShipTease June wasn't exactly happy with this.]]) After Dawn leaves:
-->'''June:''' I'm sorry she had to leave, Henbud.\\
'''Henry:''' I'm not. She was ''killing'' me!
* ''WesternAnimation/TotalDrama''.
** Trent develops a relationship with Gwen, only for Heather to screw it over through a GambitRoulette and [[spoiler:send him packing]] after he and Gwen manage to patch things up. Come Total Drama Action, he gets jealous over her getting closer to [[AllGirlsWantBadBoys Duncan,]] which leads to his obsession with the number nine and [[spoiler:throwing challenges so that Gwen's team would win, which leads to her dumping him so the competition would be fairer]]. Ouch.
*** It doesn't help that [[spoiler:the nine obsession has nothing to do with their relationship, instead having to do with an incident involving one of the wheels of a ten-wheel toy train given to him by his late grandfather falling off]].
** Tyler and Lindsay fall in love, only for Lindsay to forget who Tyler is until Season 3. [[spoiler:And two episodes after that, she's eliminated.]]
** Alejandro confesses his love for Heather in the final episode of Season 3, [[spoiler:only for her to knee him in the kiwis, throw him down the volcano, and grab the million-dollar briefcase instead]].
** Courtney becomes an OfficialCouple with Duncan in Season 1. They dance a very painful MasochismTango throughout all of Season 2, [[spoiler:Duncan is the cause of her downfall close to the end,]] and the relationship [[spoiler:dissolves for good in Season 3 after Duncan cheats on her with Gwen and remains in a relationship with her. She then falls for Alejandro, who is just using her]].
** Cody really likes Gwen, [[AllLoveIsUnrequited but she doesn't like him back.]] And meanwhile, Sierra really, ''really'' likes him, but he doesn't like her back. Ow.
** Harold harbors yet more one-sided love for [=LeShawna.=]
** Owen [[spoiler:broke up with Izzy, but later regrets it deeply. [[BreakUpSong "Oh, my Izzy,]] [[TearJerker why'd I ever let you go?"]]]]
** Finally, Gwen. Poor, poor Gwen. [[spoiler:In Season 1, she sees Heather kissing Trent as part of the aforementioned GambitRoulette, [[HeroicBSOD with expected results.]] After she dumps Trent in Season 2, she loses all of her popularity in-universe due to some behind-the-scenes manipulation by Justin. It doesn't get any better in Season 3: [[TheyDo Duncan finally kisses her]]...[[YourCheatingHeart while he's still with Courtney.]] Cue [[WhatTheHellHero everyone being mad at them,]] but Gwen getting [[DoubleStandard the worse load of blame]] and finally being eliminated just two episodes after the incident.]] ''Jesus Christ.''
* ''WesternAnimation/{{Superjail}}'': The Warden's one-sided love for Alice is this.
* In ''WesternAnimation/GreenLanternTheAnimatedSeries'' Aya discovers this when [[spoiler:Razer claims he can never love her because she is JustAMachine]]. Most of her considerable processing power is spent replaying the moment over and over again. [[spoiler:It gets so bad that she shuts down her emotions. Things get worse from there.]]
* The main character's rejection drama in the first episode of ''WesternAnimation/CityHunters'' is symbolized multiple times, and causes the listless attitude that inspires Dr. Lynch to help him out.
* While more a PuppyLove example, on ''WesternAnimation/TheSimpsons'' there's the infamous crush Ralph Wiggum developed on Lisa when she was the only one to give him a Valentine.
-->'''Krusty''': Is this your ''girl''friend, Ralph?\\
'''Ralph''': Yes, she is. I love Lisa Simpson, and when I grow up I'm going to marry her.\\
'''Lisa''': [[BigNo Noooooooooooo]][[SkywardScream oooooooooooo]]! Now you listen to me! I don't like you, I never liked you, and the only reason I gave you that stupid valentine is because nobody else would!\\
(''Back at home'')\\
'''Bart''': Watch this, Lis. You can actually pinpoint the ''second'' when his heart rips in half. ''(Slo-Mos the video)'' Aaaand... ''now!''

[[folder:Real Life]]
* Linguistic examples:
** In Swedish, Norwegian and Danish the word "gift" (pronounced "yift") means both "married" and "poison", one wonders if this was made so on purpose...
** In Japanese, "Ai" means love but it can also mean "grief/sorrow" when written differently.
** The Japanese got it from Chinese, where the exact same thing happens: save for the tones, the words for the two concepts are homophones.
** In Russian, "брак" ("brak") means, among other things, both "marriage" and "spoilage/defect."
** In English:
*** Apparently, "to wed" (Or some form of marriage word) comes from the same roots as "gamble".
*** The word "passion" itself ultimately descends from the Greek ''pathos'', "suffering" (i.e. ''Film/ThePassionOfTheChrist'').
** In Spanish, "Cazar" is "to hunt" and "Casar" is "to wed." In Latin America and some parts of Spain, the pronunciation is identical. The word "esposa", which means wife, also means handcuff. Same goes for the plural "esposas".
** In Portuguese, "Caçar" is "to hunt" and "Casar" is "to wed."[[note]]'ç' and 's' are usually pronounced the same in Portuguese, although in this case the 's' is pronounced with a 'z' sound and the 'ç' with a 's' sound[[/note]], so it's as above.
** In Danish:
*** The words for heart (hjerte) and for pain (smerte) rhymes, which is sometimes used as a proverb.
*** Again with "lidenskab" meaning "passion" and "lide" meaning "to suffer", though unlike German, the connection is for some reason rarely made, possibly because the word "lidenskab" is barely being used among most people in everyday life. In an inversion, "(at kunne) lide" can also mean "to like".
** In German the word "Leidenschaft" which means "passion" belongs to the root word "leid" which means "suffering".
* As if we need to say it: TruthInTelevision.[[/folder]]