[[quoteright:350:[[Fanfic/TouhouTonari http://static.tvtropes.org/pmwiki/pub/images/Touhou_Tonari_Yuyuko_2338.png]]]]

In addition to its many laughs, horrors and beautiful moments, Gensokyo also has quite a few stories of heartbreak.

[[folder: Official and Semi-official Lore]]
* [[http://www.youtube.com/watch?v=auYma2tRjz8 Mokou's]] backstory is tragic enough, especially when paired with her [[CrowningMusicOfAwesome theme song]].
** ''[[http://safebooru.donmai.us/pools/2493 Nitori Gets Caught In The Flow]]'' has its own soulcrushingly painful take on the story of Kaguya and Mokou's feud. [[spoiler:Mokou's Father secretly never loved her and tried to make use of her bond to Kaguya to marry the Moon Princess, so Kaguya decided to humiliate him and let Mokou hate her. This fanfic goes even further with the sadness, as a time-displaced Nitori [[YouCantFightFate futilely tries to change her destiny]] after making friends with her. To ''twist'' the knife even more, when Nitori returns to present-day Gensokyo, Mokou has somewhat forgotten her after the thousand-or-so intervening years.]] Luckily, they at least get a happy ending.
* [[http://www.youtube.com/watch?v=majdtmwRWfU Yuyuko's]] backstory is just as bawl-worthy. Her ability was, at first, to manipulate spirits of the dead. As time went on, it grew stronger and stronger, to the point of being able to will death onto mortals. Terrified of her ability, she committed suicide, and her body was used to seal off a misfortune-bringing tree, which later led to the events of ''Perfect Cherry Blossom''.
** The fan manga Fanfic/TouhouTonari focuses on her and Yukari's back story and as one might expect, it is heartwrenching.
** The fan PV [[https://www.youtube.com/watch?v=ShIocRk7Tcc Loitering Darkness]] focuses on her HeroicSacrifice to seal off the tree, it is both heroic and heartwrenching.
* Parsee Mizuhashi. Jealousy is a very strong emotion, as anyone who has felt it can attest to. Feeling it for a just a short time can bring great pain to the person, and Parsee has to feel it for thousands of years as part of her curse. Imagine how much pain she is in now, and how many times have a person crossing her bridge felt pity for her just for her to shrug it off again and again, out of, [[{{Fanon}} well, being jealous of all of them for even showing pity]], even if she doesn't even need or have to. [[FateWorseThanDeath And she's stuck with it, forever]].
* Koishi Komeiji's backstory is also pretty saddening. Like her sister Satori, she was born with the power to read minds, however she hated the fear it caused people towards her, so she closed her third eye to prevent herself from reading other people's minds. Sadly this included herself, denying her the ability to think, leaving her as an EmptyShell who can only communicate to people through her subconscious. Even worse, unlike her sister, she [[WalkingTheEarth travels around Gensokyo]] and whoever looks away from her after seeing her will forget they ever saw her, meaning that she practically doesn't exist except to the people who have prior knowledge of her. And if that wasn't enough, her dialogue after her fight with Reimu and Marisa implies that she is starting to feel [[HopeIsScary regretful]].
** Hopeless Masquerade has her actually expressing some emotions and thoughts; [[YankTheDogsChain however]], [[spoiler:this is due to her having the Mask of Hope, and when she gives it to Kokoro, it's implied that she will go back to her EmptyShell state]]. If there is any consolation, Byakuren does mention that by being an EmptyShell, Koishi is close to Enlightenment.
* Junko's backstory, what with possibly having lost her husband to another woman, and then learning that her [[OutlivingOnesOffspring son was killed]] by the same man, causing her to become mad with grief and resentment to the point she became a spirit representing her own feelings of anger and sorrow, with no other purpose to existence than to feel an everlasting hatred.
** Looking at Hecatia and who she's based on reveals that she suffered a loss almost as painful and equally scarring from Apollo's death - Hecate is often depicted as an aspect of the moon goddess Artemis. Hecatia lost ''her twin brother''.
* Some music from the series can be sad, too. See "Legend of Hourai", "Soul's Resting Place", and "The Purest Sky and Sea".

[[folder: Fanworks]]
* While this is a fanwork, Cool&Create's ''[[http://www.youtube.com/watch?v=40fwAWEiE3M&feature=response_watch S Complex]]'' puts a really tragic spin on the less memorable Aki sister, Shizuha. [[spoiler:She loves her sister dearly, but feels left out and lonely because Minoriko is constantly being invited to feasts. Harsh words are said, and Shizuha's heart is broken.]]
* [[http://www.youtube.com/watch?v=oMPQWjb0rZo Double Scarlet]] tells a story about the Scarlet Sisters. [[spoiler:At the beginning, Flandre and Remilia are lonely, so, with the help of Patchouli Knowledge, they go conquering lands and make friends with Sakuya Izayoi and Hong Meiling after [[DefeatMeansFriendship besting them in battle]]. Over time, though, Flandre becomes more distant from Remilia, and is locked up in the basement. Patchouli shows Remilia a picture depicting the sisters holding hands that Flandre drew. Overcome with guilt, Remilia runs into the basement [[CrowningMomentOfHeartwarming and shares a tearful and apologetic hug with the sister she's been ignoring for some time]].]]
* The [[{{Doujinshi}} fancomic]] ''Red Sky of Japonesia'', where Shikeiki passes judgement on Remilia for her crimes against her sister, has a massive double whammy in its second half: [[spoiler:first, Shikeiki defeats Remilia in danmaku combat ''[[CurbStompBattle very]]'' [[CurbStompBattle thoroughly]], [[BreakTheHaughty completely shattering Remilia's facade of being an arrogant, in-control vampiress]] and causing her to scream for help in ''exactly the same way her sister did'' while locked in the basement, and [[MyGodWhatHaveIDone making her realise the weight of what she did to her own sister]]; the second whammy comes when Flandre interrupts Shikeiki's judgement to ''forgive'' her sister of the crime of locking her away out of fear of her power to destroy, [[TakingTheBullet absorbing Shikeiki's danmaku barrage]] and giving her sister a tearful hug.]] It's difficult to hold the tears in after that.
* [[http://safebooru.donmai.us/post/show/919702/airplane-alternate_wings-animal-apple-ascot-bear-b This]] image provides a good clue to how Flandre really feels mixed with a small dose of NightmareFuel. It really makes one start to question her insanity.
* A [[http://www.youtube.com/watch?v=MHRpwZeJ7xk remix]] of the [[http://www.youtube.com/watch?v=XdqV14_q6-s&NR=1 ever-popular Cirno's Perfect Math Class]] song turns something cute, playful, and cheerful into a depressing scenario of a grown-up Cirno being PutOnABus and sent into the big city, getting a job, and parting from her childhood friends. Fed up with work, she wishes for her old life and her friends to come back to her. [[GrowingUpSucks Growing up really sucks, doesn't it?]]
* [[http://www.youtube.com/watch?v=2CRLDxNEV1g A yukkuri's]] story has never been more heart wrenching.
* The final stage of the fangame ''VideoGame/ConcealedTheConclusion'', where it is revealed that [[spoiler:Reimu is dying, and when she dies, [[DreamApocalypse all of Gensokyo will go with her]]. After battling through countless foes, Marisa, perhaps Reimu's greatest friend, has to face her down in one final danmaku duel]].
* Gensokyo being home to many races, there are naturally countless fan works dealing with [[WeAreAsMayflies the inevitable regarding the characters' lifespans]].
** [[http://safebooru.donmai.us/pool/show/778 The End of the Maiden's Illusion]]. [[spoiler: The mood is then ruined at the end when it's revealed [[MoodWhiplash it's all a script Nitori's presenting to a very much alive (and quite annoyed) Reimu]].]]
** The [[http://safebooru.donmai.us/pool/show/1626 "Tragedy of Long Life"]] pool is 99% Sakuya, Marisa, and Keine dying, and Remilia/Meiling, Alice, and Mokou (respectively) grieving.
** Quite a few doujins and pics exist of [[http://safebooru.donmai.us/post/show/354627 Sakuya]] [[http://safebooru.donmai.us/post/show/455234 passing]] [[http://safebooru.donmai.us/post/show/622323 on]] and Remilia and the rest of the Scarlet Devil Mansion having to move on without her.
*** Speaking of which, [[http://safebooru.donmai.us/posts/322446?pool_id=439 this image.]]
*** For those of you who are tired of a Sakuya dying, and like their tear jerker with a side of nightmare fuel; [[http://safebooru.donmai.us/post/show/1007524/ try this]].
** Yuri couplings get them, too. [[http://www.youtube.com/watch?v=nCN3iJ_Mvzs A video]] of one with Alice.
*** Patchouli and others do not seem to try very hard to get their stuff back from Marisa. Leave it to fans to make Marisa's own rationalization that [[spoiler:she won't live long enough for them to miss anything]] [[FunnyAneurysmMoment that much more depressing]].
** Amida Kuzu's long line of Mokou doujins includes one where she inevitably outlives Keine.
*** Speaking of Mokou and Keine, [[http://www.youtube.com/watch?v=cF6PaxzmaRg Chiisana Koi no Uta]] more or less shows how much an immortal can grieve when they lose a mortal loved one.
** [[http://www.youtube.com/watch?v=e4p1kkuM2Hg COOL&CREATE]] puts a tragic twist on the shy kappa Nitori, when she falls in love with a human.
** [[http://www.youtube.com/watch?v=mmG5Sk5dyaI You may know "DREAM"]] shows that the Prismriver Sisters must have grieved when Layla reached the end of her mortal life.
* And of course the [[http://www.youtube.com/watch?v=5Sj5kN7sdlY Maze]] animation.
* Gensou Koumuten. Perhaps the most tear jerking ones is Flandre breaking apart and Rumia's imperfect metamorphosis.
* From the doujinshi ''[[http://safebooru.donmai.us/pools/2777 Lovely Dream]]'':
** The story is as follows: Reimu, as part of her duties as the Shrine Maiden of Hakurei, must [[spoiler:marry an unknown man and bear a child in order to maintain the Hakurei bloodline]]. What makes this feels-inducing is that the story is told from the point of view of Marisa, who considers Reimu a best friend in this story, and must deal with Reimu [[GrowingUpSucks growing up]] and having less time to spend with her.
** Very early into the series, Reimu's mother passes away. The look on Reimu's face is heartbreaking.
** Not only that, the story hints that the shrine maiden's life is very short and needs to have a child early in order to ensure the bloodline and the safety of Gensokyou continues.
* From the 1.5 hours or so of fanvid of doujinshi ''[[http://youtube.com/watch?v=DxtTNsn6C2w Touhou Little Reimu]]'' is one of the most tearjerking, heartfelt stories ever encountered.
** In the author's own words, "This is a story of when Hakurei Reimu was still young and the man-eating youkai (Rumia) was big." It can be split up into two parts: the heartwarming story of a newly formed family and the emotional [[spoiler:spiral out of control as Rumia's man-eating instincts take over, leading to the death of the elder Hakurei miko, memory wipes, and a load of]] DAMN YOU YUKARI!!
** Luckily, there is the sequel, that ends up with a BittersweetEnding: [[spoiler:Rumia regaining her memories and adult-like appearnace and fighting against Reimu. After Rumia is defeated, she begs Reimu for forgiveness for having killed her mother years ago before she fades away. And all the while Marisa and the others are bawling their eyes out.]] Ouch.
*** Mercifully, the final episode ends on a much happier, albeit still slightly bittersweet note: [[spoiler:Reimu shatters reality with Fantasy Heaven to resurrect Rumia, and they and Yukari all get to say goodbye to Reimu's Mother. In the end, Reimu and Rumia are holding hands.]]
** Now has [[FanFic/OsanaReimu its own page]], for the interested.
* The fanmade arrangement of Flandre's theme U.N. Owen Was Her [[https://www.youtube.com/watch?v=vL7-uxTFWf8 "495 GO! Little Sister Emotion"]] sounds chirpy and has a TastesLikeDiabetes video, but then you read the [[http://lyricstranslate.com/en/495-go-little-sister-emotion-495-go-little-sisters-emotion-emotion-little-sister.html lyrics.]]
* The fangame VideoGame/TouhouALive [[spoiler:Fantasy Chapter: Lots of people die, and that's BEFORE the end of the scenario. Also some in the earlier chapters. Everyone save Shang, Alice, and Reisen die aboard the Momento Mori. Kaguya is assimilated by liquified humans at the end of Mokou's chapter, anyone fed the Slave Drug is turned into a zombie that requires specialized air tanks to live, and to power Patchouli Robo; the Marisa Yukkuri sacrifices itself using its' filling to make fuel. Also the humans whose flesh makes Yagokoro Rapid Drugs (Fully heals party). And the humans who are hooked up and drained of their life force.]]
** [[spoiler:Also in the Fantasy Chapter, Mima experiences what Oersted did, and just like him, she snapped.]]
* Some fans make Junko's situation even worse by showing her as [[http://safebooru.donmai.us/posts/2333489 never having gotten over]] [[http://safebooru.donmai.us/posts/2474956 her son's death.]]
* The music video for the SOUND HOLIC song [[https://www.youtube.com/watch?v=lWMBnFoSrWU Priere]] frames Remilia's implied past and her deepest fears in a nightmare: She and Flandre were victims of child abuse as vampire children, until the scarlet moon gave her the strength to bloodily free themselves from imprisonment. It then depicts her having accidentally killed Sakuya during a bloody rampage, and her sorrow and regret at having killed someone dear to her in anger. The music video also implies that Flandre bears severe emotional scars from that dark past, and still stays in the Scarlet Mansion basement anyway because she loves her sister that much.