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Tear Jerker / Pony POV Series

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    Reharmonized Ponies 
  • Derpy Hooves' fate in Discord's universe. Dinky has been turned into a foal-shaped muffin, and Discord has promised to turn her back when Derpy has walked enough laps around his palace. Every day Derpy marches around the castle, starting in the morning as a foal and continuing until she's pratically undead, carrying Dinky on her back. All the while she defends her daughter-turned-muffin from hungry birds, screaming, "Not my baby," assuring Dinky she'll have enough laps soon. She's done over a trillion now...
  • Rainbow Dash in her first Reharmonizing sounds genuinely remorseful for her leaving her friends, and is clearly holding onto a lot of guilt through it all.
  • The background ponies dealing with the mental trauma of Discord's "fun", as seen in Applejack's Healed chapter. They may be back to normal, but they aren't "better".
    Derpy Hooves: [to Dinky] Mama loves you. Mama's sorry. Mama won't hurt you. Mama didn't mean it...
  • Applejack's heartbreak over her realization that the children she had in the "Orangejack" universe don't exist because of her choice.
  • One of the things Applejack sees when she looks into the Truth is an Alternate Ending to Story of the Blanks. Alternate!Applejack practically tears Everfree Forest apart trying to find Apple Bloom, and when she finally does, the poor girl is a traumatized zombie pony. Alternate!Applejack's reaction is perfectly understandable…
    • And then, after Princess Gaia creates her false paradise, Applejack meets with her children from the vision. She takes the time to give them hugs and say goodbye before allowing that entire fantasy to fall apart.
    • And unlike the others, she doesn't have the comfort of not knowing it's an illusion. She knows it's fake, but really wishes it wasn't. And then there's this line:
    Applejack: Mama loves you. Dontcha ever forget that, ya hear?…And Ah wish this could be real.
  • Trixie still being in a broken, catatonic state even after Discord was beaten. What's worse, her family is taking care of her and clearly distraught over this, hence why Twilight was summoned to help.
  • Pretty much everything about Diamond Tiara and her mother Golden Tiara aka Screwball. Especially Discord's Mind Rape of Diamond Tiara.
    • And then in "Mind Games Part 7" when we find out just why poor Screwball was sent away. To protect Diamond Tiara from her. You will shed more tears for poor Diamond Tiara then you ever thought possible.
  • Trixie explaining how she is afraid of dying into obscurity.
  • The Reveal about Scootaloo's Parental Abandonment
    • Speaking of Scootaloo, when Rainbow Dash accidentally snaps at her and makes her cry. The poor girl asks if Rainbow Dash is going to throw her in the Pegasus Machine (a Shout-Out to Rainbow Factory where said machine is used to melt down Pegasi fillies into rainbow goop, here it's just a story old Pegasi tell the fillies to get them to behave). Thankfully, it's followed by a Heartwarming Moment.
  • Applejack reading about Mimic's horrific death is sad enough, but then she realizes there are tear stains on the paper from where Luna cried while writing the account...


  • Fluttercruel being prepared to fade away into nothingness, fully prepared to die and leave Fluttershy alone... Then realizing her well-intentioned last lesson has turned Fluttershy to evil and made her into a Knight Templar. She ends the chapter sinking into darkness as she tries as hard as she can to undo it to no avail.
  • Applejack snapping herself out of Princess Gaia's fantasy and seeing all of her friends under the effect of Gaia's mind control — then realizing how hard it must have been for Twilight to go through the same thing when they were under Discord's influence.
    Applejack: Twi', is this what it felt like for you?
  • When they are forced to break Cheerilee's class out of the Lotus-Eater Machine, especially when Silver Spoon bursts into tears and begs to be returned to it.
  • Princess Gaia's POV in the beginning of "Teacher Teacher". She just sounds so unwell, practically as if she knows there something wrong with her. And what's more, it's quite genuine-it's her insanity that turns her intentions into something so horrific.
  • When entering Princess Gaia's lair, the group comes across the residents of Sunny Town, who have been made to forget their past actions and happily working for Gaia... Until Applejack looks them in the eye. Their reaction to remembering how much they'd cared for Ruby and then killed her will make you feel sorry for them despite of what they did. Especially Mitta, who was already wracked with guilt in the game itself and even moreso here.
    • It gets even worse if you pay attention to the blink-and-you'll-miss-it comment in the chapter centered on Luna, where we discover that it was Nightmare Moon who originally cursed and destroyed Sunny Town and its inhabitants. And the town itself? Was created by Celestia to try to give ponies a perfectly happy life. Now think about what Princess Gaia is doing…
    • Even worse? Discord planned to Yank the Dog's Chain with them during Luna's side-story by breaking the curse for a day or two, allowing them to think their curse was over, only to have it return so he can see the looks on their faces.
    • And now that Princess Gaia/Nightmare Whisper has been 'dealt with', the ponies of Sunny Town returned to their normal condition…with each and every one of them screaming and begging to be saved by Princess Gaia as they go. "No! Not this again! Please, Princess, we'll do ANYTHING if you save us!"
    Generation Transitions/Origins 
    Mind Games 
    Dark World 
    Shining Armor Arc 
    Not the Wedding You Remember 
     7 Dreams/Nightmares 
    Side Stories/Recursive Fanfiction 


  • The audio adaptation of Applejack's Discording. The original was sad enough, but just how broken the voice actor manages to make her sound makes it much sadder.
    • Same goes for the adaptation of Pinkie Pie's Discording. It gets especially heart-rending when she reaches the the lines, "I hate laughter! I HATE IT!", and we realize just how utterly shattered Pinkie is by Discord's actions. Especially the "NO ONE TAKES ME SERIOUSLY UNLESS THEY HAVE TO!" due to the delivery.
    • The adaptation of Fluttershy's Discording is equally as heartwrenching. The voice actor and the music just put such a feeling into the point when Discord does his Mind Rape that, even though Fluttershy's voice doesn't change that much, it changes with just enough subtleness to make it absolutely chilling and heartwrenching.
    • Rarity's Discordification is both this and Nightmare Fuel, as you can practically hear her going totally insane throughout.
  • StarSong's Heroic Sacrifice followed by Pinkie Pie desperately pleading Anarchy to restore her and erase her instead.
    • StarSong's willingness to sacrifice herself for her friend counts doubly, as she knows that Pinkie probably won't even remember her after she's gone (it turns out Pinkie was allowed to remember her friends, but StarSong didn't know that would happen).
    • The entire side story. Generation 3.5 gets a lot of hate from fans, but as the author points out, it did have its good points.
  • Nightmare Whisper. She's a horrifying monster, to be sure, but from the context of the event, it's also shown that she's ashamed of what she really looks like. It's almost as if there's enough Fluttershy left to be horrified at what she's become…
  • The Mane Cast having to fight their best friend turned Nightmare is just downright heartwrenching. As if that weren't enough, there's this line from Twilight when she thinks of what it was like for Celestia to be in the same position 1000 years prior:
    Twilight Sparkle: 'Princess…Is this what is was like for you?'
    • Also, Rainbow Dash and Rarity feeling like that they have no choice but to use lethal force against Nightmare Whisper, both of them believing that Fluttershy would rather be dead than seeing what she has become.
  • Fluttershy, no longer Nightmare Whisper, still holding on to the pain and suffering of all of Equestria, refusing to let go so that others won't have to feel it. In what is also a Heartwarming Moment, Pinkie Pie voluntarily taking up the burden as well, so that Fluttershy does not have to bear it alone. Just imagining what these two are going through is hard enough…
    • Also Twilight (along with Rarity, Applejack, Rainbow Dash, and Trixie) helplessly watching their two friends literally torture themselves and trying to find some argument, any argument that will convince them to let go before the suffering destroys them.
  • Twilight almost breaking down in tears in reaction to Celestia's plan to use a tabloid article to paint herself as the Big Bad of the Princess Gaia incident so that Fluttershy can simply move on. She just can't bear the idea of her mentor and mother figure taking such a burden on herself. It doesn't help that two scenes before, Twilight outright says Celestia is like a mother to her.
  • Pinkie Pie finding a toy version of Generation 3.5 Ponyville, and recognizing it, talking about how she misses her old friends. Poor filly.
  • Subtle, but Trixie's reaction to Twilight calling her a "half-dirt unicorn" (for good reason, but still). Not so much what her reaction is but the fact she has that reaction. She takes it very hard, which rather heavily implies she's been a victim of Fantastic Racism for her race. Combined with the other things that she's gone through, it makes her quite the tragic character.
  • Spitfire revealing how Discord tortured her and the other Wonderbolts. She herself had visions of the other Wonderbolts, her parents, and her old flight teacher laughing at her and telling her she'd make a better flying clown than a performing Pony. On top of this, she also reveals that Fleetfoot got Discorded and broke down crying when telling her, feeling like Discord violated her.
  • Orangejack revealing how Discord Mind Raped her. He made her drag her children around like rag-dolls, treating them like toys and not even realizing she was hurting them. Orangejack even doubted if she was a good parent because of it.
    • In the same chapter, the Cutie Mark Crusaders in the universe where the Mane Cast have basically created Brave New Equestria. Sweetie Belle literally begging Rarity to let their parents out of the reeducation camps, Apple Bloom reading off the lists of all the 'problems' for them to fix while trying not to think about them, Scootaloo being utterly abused by Rainbow Dash; the last of which is made all the worse after all the chapters of Dash being the epitome of Cool Big Sis. She pretty much treats Scootaloo as the court jester.
  • Just before being turned back into an adult, Golden Tiara realizes what will happen to her. She tells Celestia that she doesn't want to go and desperately pleads that she doesn't want to stop understanding, that she wants to see her "little princess" Diamond Tiara and her "prince" husband. Celestia is badly tempted to let her stay a foal, but ultimately decides against it.
    Celestia: Everything won't be confusing forever. I promise you'll get better. I promise you'll find your way through the fog and find your family waiting for you. You'll become a stronger self. And hopefully, being reminded of the good times he had with you will help your prince guide you out of your fog…You're not dying, you're just becoming something new. I promise, what makes you 'you' will never disappear. You're not vanishing, you're growing.
  • It's not exactly "official" but this gives us a heartbreaking portrayal of how Princess Celestia was corrupted.
    Celestia: He's right…Even…Even Twilight is afraid of me… The pony I love like a daughter is afraid of me…Terrified of me…They're all…They're all terrified of me…
    • It is now Loose Canon. And The Reveal that Celestia and Discord used to be friends, possibly lovers makes aspects of it even more depressing (even to the author of the fic).
  • "Butterflies Celestia" has the reveal that Celestia is really the G3 Pony Star Catcher, or at least remembers being her. Not only does this mean she's probably been through what Pinkie was, it also explains that her mother broke the immortality spell on herself by given birth to her, Celestia having to watch her own mother grow old and die right in front of her with no idea why except it was her fault for being born. Ouch…
  • Onyx Tiara's entry in the "Butterflies" series, detailing how his wife was gradually broken down by high society snobs.
    • Even worse are the effects of his Discording: any pony he touched turned into a physical replica of her, allowing him to surround himself with a harem of mindless Replacement Goldfish…and when his real wife appeared, he rejected her.
    • The way his Fantastic Racism colors his commentary is heartbreaking in its own way. To see a stallion consumed by so much hatred — let alone one who canonically is a Good Parent and anything but a close-minded Jerkass — that he rejects whatever help presents itself, including from Applejack, who should have been a family friend…!
    • Diamond Tiara's POV in the same entry is even worse, and Screwball's drives the knife home.
  • The whole "Generation Transition" parts 2 and 3. Especially the song from the third part…
  • We also see how Discord was born into the current version of Equestria. He's a bit of jerk growing up, but he loved his mother, lacked his normal cruelty, and was able to be happy and kind…until he met his real parents or memories of them. He tells them,
    "Stay away from me! Go to Pony Hell!"
    And they gleefully tell him:
    "Child... You ARE the Gates of Hell!"
    • Good!Discord is promptly consumed by Evil!Discord and reverts back to his true, evil nature, those who were his friends before he returned to his true nature left at a complete loss at what to do about their Evil Former Friend. His earthly mother? He exploits her Mama Bear nature to turn her into his loyal The Dragon. 1000 years later, she finally realizes it has to end, sheds a Single Tear and, in her mind, helps Celestia and Luna Shoot the Dog.
      • Let's be honest; EVERYTHING about Origins belongs here.
  • The period between the post Cosmic Retcon of G2 and G3. Dear Celestia…
    • Rather then the wish spell to make everyone's dreams come true coming about, Destruction blows up the entire civilization, killing millions including Starlight and Misty. Racism is abound and everyone is barely surviving.
      • Worse? Keep in mind Destruction didn't want to do this and was in his 'Omega State' at the time, and after he regains his senses seems to have felt the scope of destruction was too much.
    • Poor Patch goes on a quest to find the pieces of the Rainbow of Light, all the while denying that Starlight ever died. She ends up living far beyond the deaths of all of her friends, and in the end dies herself just as she completes her goal, meeting her friends in the afterlife.
    • What Film Critique did to Patch for that matter was horrible and heartbreak. Especially when it's shown later Patch was traumatized by it.
    • Music loving Melody losing her voice during the apocalypse and her family assuming she was brain damaged. And eventually having her daughter taken from her.
    • Bright Eyes losing her memory and how effects her and Lancer. And her ultimately having to fight the vengeful Shadow of D___t for her very existence as he tries to break her will to make absorbing her easier.
  • The Moochick, one of the iconic characters of G1, passing away after giving Patch the mission to find the scattered pieces of the Rainbow.
  • "New Game Plus" manages to pull this off. Did you know that New Fluttershy's "The Reason You Suck" Speech in "Putting Your Hoof Down" could've been worse? Welllllll…
    • And then there's the fact that Rainbow Dash doesn't even try to fight back against Shy's vicious rift on her abandoning her years ago. She just quietly admits she has no excuse, and that she was "a selfish nag" back then. Just the sheer humility of this snaps Shy out of her meanness streak, and she flees in utter despair.
  • "Mind Games 7" has a series of flashbacks to when Diamond Tiara's mother went insane. Remembering it is enough to more or less finish breaking Diamond's mind.
  • And then in "Mind Games 8" Screwball finally recovers her sanity…and remembers everything she did or tried to do to Diamond Tiara. And she is reduced to sobbing hysterically as she begs for somepony, anypony, to tell her that it isn't true. And oh yes, just in case that didn't tear your heart out enough in that chapter, Discord shows Diamond Tiara what would have happened if she hadn't rummaged around in her mother's jewelry case. Basically, her mom got the help she needed; her father never became a racist conspiracy nut; she and Silver Spoon never became bullies and ended up friends with the Cutie Mark Crusaders; and DT was just plain happy. But no, she made the choice she made, so everyone's life became a total hell and it's ALL. HER. FAULT. Or at least that's how Discord set it up to look like from her POV. And the best part? This little revelation turned Diamond Tiara into a Nightmare!
  • Dark World in general is this given the premise that the heroes failed to stop him and the world has suffered for a thousand years with the corrupted Mane Six now as his enforcers.
  • The entire scene between Liarjack and Epilogue!Apple Bloom. Apple Bloom has the same curse Sunnytown did, but remains alive during the day and had children. It's been almost 500 years, her family has died right in front of her from old age or Fauna Luster knows what, and she succeeded in freeing all the Sunnytown Ponies from their curse. She breaks down and begs Liarjack to break her curse and let her pass on…she does, and Apple Bloom ages to dust right in front of her.
  • The death of epilogue Cadence. No further words can be said beyond the tragedy of that.
    • Really? How about the fact that Twilight Sparkle regained her sanity when confronting her just long enough to remember her foal-sitter before she saw her die?
    • And now, someone drew it! Warning, VERY disturbing!
  • Rarity's reharmonizing chapter, Irreplaceable, pretty much takes every heartbreaking moment of that story Up to Eleven.
  • One of the worlds glimpsed by Liarjack in the Truth is one where rather than taking her in, Rainbow Dash tried to hand Scootaloo over to the foster care system. This caused her to run away and become Discord's servant the way Diamond Tiara did in the POV universe. Considering how close those two become in the main story, it's impossible not to cry at this possibility.
  • In the second half of Chapter 9 of the Dark World arc, Applejack, Twilight Sparkle, a temporarily Taken for Granite Living Statue of Sweetie Belle, and Spike who's just been mind raped by Discord with the revelation that Discord was the one keeping Spike's violent draconic instincts under control just as he breaks that control all battle Rarigreed. Early on in the battle her 'boyfriend' Tom shatters to reveal a magnificent statue of a stallion named Tom. He battles for his fair Rarity like the Knight in Shining Armor she always wanted, and is in all ways heroic, noble, and brave, and with his own soul. And the girls have to kill him to save Rarity.
    • The saddest part? The girls didn't want to kill him because they realized he was nothing more than a child doing what his 'mother' told him to do. He simply didn't know any better, but they had no choice but to kill him to keep him from stopping them from saving Rarity.
  • The Imagine Spot (most likely Twilight's) in Chapter 14 of the Dark World arc. When Derpy is convinced to entrust her muffin-turned daughter to Apple Pie in order to strengthen The Power of Trust between the new Element bearers, we are abruptly treated to one of the worse possible scenarios: Apple Pie grabs Dinky with her mouth and tosses her on her back, whereupon Derpy goes absolutely ape-shit, bucks Apple Pie in the face, and snarls at the terrified filly to never touch her daughter again. Thankfully, this never comes to pass.
  • The effects Discord has on Mayor Mare are very sad; he had turned her into a statue that kept shouting into a megaphone that she doesn't care about any of the citizens of Ponyville and the only reason she's working there in the first place is because she had turned down an offer in Canterlot. When she realizes what she'd done under Discord's reign, she starts working herself ragged, even skipping meals and losing sleep, just to prove that…
    Mayor Mare: I do care about all of you. I promise.
  • Dark World 15. Scootaloo did come down to redeem Rainbow Dash just like Apple Bloom and Sweetie Belle did. But unlike Rarity and Applejack, Dash would not listen.
  • Bon Bon's chapter of the Gaiden. From looking at it, the entire Gaiden will probably be that way.
    Bon Bon: This wasn't supposed to happen…it just wasn't…The spell was supposed to make everyone's dreams come true! Instead, my parents, Misty, Rusty, and Misty's husband…they're all dead.
  • The Discordifications in Reharmonization and the psychological aftermath.
    Rarity: I'll admit I don't know Applejack's brother all that well, but seeing that mountain of strength and silent will so…damaged like that carries a whole new flavor of wrongness.
  • Ladies and gentlecolts, the sadness of the Duel of Tears:
    • Probably the first main hit was when you find out that Rainbow Dash in her younger days said that Derpy cheated on an exam, and because of this, her mother grew suspicious, and never looked at her the same again. It was probably after this incident that she tried to drown Derpy, and despite this being the catalyst for that to happen, after 1000+ years of thinking it over, the first thing Derpy says to her is, "I forgive you."
    • TD just sounds so crushed. She literally begs Twilight to let her kill her, desperately trying to convince her, the others, and herself that everything will go back to the way it used to be if she does.
    • Twilight demands that Rarigreed decides whether she wants the power to fight Discord easier, or to get another friend back. Rarigreed takes two deep breaths, and after her mad dash to get power, quietly admits,
    "I'd want my friend back."
    • What about, after her defeat, Traitor Dash begging them to kill her if she can't kill Twilight to end her suffering. Thankfully, they manage to pull her out of it and redeem her.
  • From the dark world 17, Pinkie Pie has fallen a long way. She goes into a Villainous Breakdown just because Apple Pie manages to "giggle at the ghosties" and kills zombies with it. It's just so sad to see that she now sees all of her pinkie quirks as nothing but nonsense now.
    • The Valeyard threatens to kill Sparkler in an attempt to force the group to surrender. Derpy tearfully apologizes and tells Sparkler she CAN'T give up saving the world to save her. Then Rarity shatters Sparkler. Yeah, it turns out it was a fake Sparkler the entire time and Rarity knew it, but that doesn't make Derpy's response any less heartbreaking.
    Derpy: Sparkler…Mommy's sorry…
  • Derpy's total despair about not been able to let the the Valeyard regenerate into the Doctor. She figures out how to do it later.
  • In Pinkie's Reharmonizing chapter, she mentions the following:
    Like I was saying, the Cutie Mark Crusaders turned in that extra homework on Discord like they were supposed to…Miss Cheerilee was so glad to see them so diligent she broke down crying right there in front of the entire class and told the entire class to go home early! Wasn't that nice?
  • In the most recent chapter of Pony POV, we briefly see into the most cherished memories of that paragon of stability, Angry Pie. Are they memories of the ponies she's killed? Of her greatest victories? No, they're of the dead foals she adopted and raised. Discord promises her that he'll restore them all to life if she kills her former friends. Angry agrees, thinking that this way she'll finally be alone with her loved ones. And after she goes, Discord thinks with amusement about how he'll just warp her mind again so she forgets them all and becomes his 'Queen of Madness'.
  • There's Dark World!Spike's reaction to finding out Angry Pie seemingly killed Twilight while he chose to go help Rarity instead, who had already killed Fluttercruel.
    Spike: No...p-please no...not her...please...
  • While also a Heartwarming Moment, Apple Pie saying goodbye to Poison Apple and Pinkie to Morning Light are both this. Particularly Apple Pie, who was heartbroken that her sister has to go and breaks down crying. She recovers, but it's still sad.
  • In a moment that doubles as Nightmare Fuel in this chapter, Off Da Rails we see the horrible, horrible fate of Sparkler: she becomes Fluttercruel's new body. Yes, that means that Little Miss Psychopath isn't just immortal, she's UNKILLABLE.
    • Fluttercruel's reaction to Discord being mortally wounded by Rancor. Yes, she's a monster and Serial Killer, but it's heartrending to see her react like anyone else would react to seeing their father be die. Applejack even compares the loss of her own parents to Fluttercruel's reaction. To put this in perspective, the entire mane six can hardly bear to watch.
  • During the battle with Cruelty as a draconequus Pinkie becomes an old mare. She reveals that when she became Pinkie she knew her element was dying but kept it secret from the others except for Applejack. And even Rainbow Dash is in attendance so she finally gets to see her old friend after a thousand years only to see her rapidly aging. And the only thing that stops Rainbow Dash from killing Twilight is that Pinkie made her make a Pinkie Promise.
    • The group saying goodbye to her and Fluttershy's spirits.
  • After the defeat of Odyne!Cruelty, Rainbow Dash is overjoyed to see Pinkie seemingly ok and rushes to hug her...only to pass right through her. Pinkie's Rapid Aging killed her during the fight and her spirit remained behind to help finish the fight. Poor Rainbow Dash is heartbroken.
  • G3 Rainbow Dash's near breakdown when confronted with her conflicting and vanishing memories during the Cosmic Retcon.
  • Seeing the G2 Mane Cast having drifted apart before Patch finds Paradise Estate was always hard, but just Bright Eye's reaction to the whole thing, even mentally lashing out at her friends while thinking about them, is hard to read. Thankfully, they do rekindle their friendship...but we all know how that's going to turn out.
    • Even worse, there's some handy foreshadowing on how she realized that ponies needed to change their hearts for there to be real change. The moment you see that, you know that this will be the catalyst for the attempted spell.
    • Zipzee, Bright Eyes' G3 self, reacting to the G3 Apocalypse. Particularly when the newly formed G4 Rainbow Dash (who's yet to stabilize). How innocent the Breezies are just makes it harder to watch.
    • Bright Eyes' memory loss and the wedge it puts between her and Lancer. Made worse by the fact they still love each other, she simply can't remember their life together.
    • A moment when Bright Eyes founds her old journal from when she was a filly and experiences a rather crushing memory of being bullied as a filly.
    • As strange as it is, Havoc gets one when He actually cries when His son D__t's Shadow, the only thing left of him, is destroyed. When He appears to Bright Eyes' later, she actually feels sympathy for Him and offers her condolences, something Havoc outright admits no one has ever done before. Even more tragic is the implication that Havoc knows D___t succeeding in resurrecting himself would've been horrible for the universe and possibly even negated Pandora's Concept and thus, Bright Eyes winning was a good thing. Pandora and Strife even imply Havoc could possibly have restored D___t, but didn't because even He knows D___t wasn't a good draconequus...right in front of Havoc.
  • "Nightmare World: Broken Mirror" has one for an alternate Nightmare Mirror. After succeeding in destroying deceit in her world after a thousand years, she shuts down her defenses and allows the Princesses to come for her because she knows there's no place for the delusion she was a good pony in the world she's created. She can't hide from the monster she became to create her perfect world, so in the end she stops running from it and turns herself in.
  • Nightmare House. Totally optional canon. Totally sad how Nightmare Eclipse is holding down/back her "friends" with her shenanigans.
    • To wit, Nightmare Banneret wants a Nightmare Rarity but can never get one for some reason. Nightmare Manacle can't get away from the evil she's done and spends some times just staring out in guilt. Nightmare Whisper wants to end the punishment of discord. Worst of all is Nightmare Mirror, who absolutely KNOWS that they're killing ponies, that she's disgraced the Apple name, and that Eclipse is doing wrong, but can't see any other course of action to take.
  • Clover's Gaiden story has Clover's reaction to discovering Dandy and their son are fusing with her as a result of their wishes, leading to her feeling so scared lonely she wishes her Imaginary Friend to life so she won't be alone.
  • "Fluttercruel's Punishment" has several. Dark World!Fluttershy is forced to come to terms with the fact Fluttercruel was a psychopathic Serial Killer and needs punished for her crimes, despite the fact she sees Fluttercruel as her baby. Then we hear Stitch's life. Her father died by being put in a giant blender, Fluttercruel murdered her mother, then became obsessed with killing off her and her siblings one by one, ultimately capturing Stitch (after torturing and killing all but two of her siblings) and subjecting her to an And I Must Scream fate, extending her life just to prolong the torture. How could it get worse? She turns out to be Fluttercruel implanted in the timeline as punishment for her crimes. This results in her having an absolutely heartbreaking Heel Realization and My God, What Have I Done? reaction to it.
  • The Dark World heroes burying Wind Whistler after Paradox is expunged from her body. This is especially heartbreaking for Celestia, since she's still mentally a foal and thus had no idea what had happened to her friend or why she's dead.
  • Dark World's finale is bittersweet, because as happy as it is overall, it ultimately ends with a tearful goodbye between Twilight/Amicitia and her friends as she has to move on to do her duties elsewhere.
  • Amicitia being forced to nearly kill a younger Cadence (who's convinced magic is inherently evil) in self defense at the dawn of time.
  • A meta example: the owner of Neo Stream requesting that Alex delete his rebirth in chapter 36. Poor Neo Stream just can't catch a break...
  • Continuing the meta example in Chapter 36, LZ bringing up a number of painfully valid points on why the intervention with The Emperor of Man was a bad idea, leading to a heartwarming scene being tainted with Fridge Horror, and eventually deleted. It seems that contrary to the theme of the story, not everything can be redeemed or saved.
  • Another meta example is Alex and LZ's falling out. The two used to get along very well and be good friends, now it doesn't seem like they can talk at all without getting into fights over the fanfic. While it seems both sides have logical reasons, it's still sad to see two former friends at each other's throats.
    • Made even sadder with the revelation that LZ has spent a year or more suffering from clinical depression and anxiety disorder that likely contributed to the situation.
    • The fighting between the two got so bad that Kendell2 left the SA Arc due to not wanting to be forced to pick sides between his friends while they were fighting. Thankfully, it seems things between the two are at least trying to make up.
    • Really, the current state of the writing staff is really distressing. As mentioned above, the disagreements between main author Alex and LZ has turned into an outright feud. Fellow co-author Kendell2 has been forced to outright quit the project in order to avoid having to take a side in the feud between his two friends. Alexwalorn himself is at his wit's end, trying desperately to hold the staff together, blaming himself for everything that's happened. The only staff member who hasn't suffered a Creator Breakdown is Audio Adaptation author Louis Baldamont, and even that's iffy considering he hasn't been heard from in months.
    • And now it's spiked back up again. The saddest part is it seems like they just see one another as the bad guy and neither is willing to just let go of their grudge and move on. It's sad when the best it seems they could do is just pretend the other doesn't exist.
  • Mother Deer's entire situation. She's the Deer's Mother Goddess, like Tiamat is for the Dragons, and thus to her ALL deer are her fawns and she loves them. She's presently in a situation where she's has no choice but to lead a group of her children in a civil war against another group of them, and knows despite all the blood that's been shed, only MORE bloodshed is going to end it.
  • Pandora's Situation is hardly better, She effectively has to help Shining and Co. Euthanize her own child, and without even the comfort of it being merely dead, She had to help them erase it from existence, and is the only one who will mourn it. A brief flashback Shows that she feels she failed it.
  • In a dream, Shining is visited by his deceased uncle and a mare named Athena. Athena reveals that she was supposed to be his uncle's daughter, but because of his interactions with Shining, he never met her mother and she was never born. A heartbroken Shining is almost tempted to allow the Blank Wolf to erase him just so she can exist, but she tells him not to bother, because in the original timeline, she died young anyway.
  • The deaths of Sunset and Ranger, and the devastating effect it has on those left behind.
    • What makes it worse is they were engaged and Sunset was planning to introduce Ranger to her parents when they got to Equestria and how sudden it happens. One minute they're saving the life of a pilot...the next they're gone.
  • The Blank Wolf in the finale of the SA Arc. It's clear it doesn't want to delete Shining because it'd make a new Dark World, but it needs to do so to fulfill the purpose it was created for, and it seems disgusted with itself for developing desires of its own. And then, after being stripped of its immortality for hurting Cadence and fighting so hard to finish its dies, tears in its eyes as it looks towards one of the statues in the temple, implied to be its creator. Even Shining feels sorry for it and gives it a salute, knowing it was just like him: a soldier doing its duty.
  • In Reharmonized Pony POV Under The Stars part 2 the usually cheery Twilight Sparkle relates a nightmare she had where her friends and Ponyville asked Princess Celestia to put a seal on her horn so powerful that restraining that her magic and mana sense were effectively dead. The worst part? She found herself agreeing with their reasoning.
  • In "Reach For the Stars", Prince Blueblood talks about a time when he got lost in the caverns under Canterlot as a child. He managed to find his way back, earning his Cutie Mark in the process, only to discover that Celestia didn't even notice he was missing. As an adult, he has had many one night stands, but gets more and more disillusioned because they always leave before he wakes up.
  • In "Character Rerailment", Silver Spoon forced to act out the plot of "One Bad Apple", unable to control her body or even cry as her friends, the Cutie Mark Crusaders, get terrorized by Babs Seed.
    Silver Spoon's thoughts: Daddy! Something's wrong with me!...Listen to me daddy! Please! I'm not happy! I'm scared! Can't you see that?!
  • In Part 9 of the Wedding arc, the reformed Prince Blueblood mentions to the curious Interviewers that he doesn't see anything odd about not being invited to his cousin Cadence's wedding. Why? Because he knows he's a complete and utter embarrassment to his entire family and doesn't blame them for despising him.
    • Made even worse when in a previous chapter he meets Cadence (actually Chrysalis, of course) together with the Elements of Harmony. He tries for polite small talk, only for 'Cadence' to tear him a new one by telling everypony present — LOUDLY — just what sort of a selfish, petty, nasty little loser her cousin is. It's only made worse by the fact that the Elements cheer her every word. And then we learn that Chrysalis knows what she said was untrue; she just said it for some passing amusement.
  • Twilight being forced by Chrysalis to give Trixie a Breaking Lecture and not being able to do anything about it. What's worse, it's later shown Chrysalis intended to have Trixie murdered after this.
  • Moth's situation. She genuinely cares for her adoptive sister Bon Bon, Lyra, and the couple's adopted daughter Tootsie, and she's caught between her love for them and her crippling fear of Chrysalis and Celestia...
  • In Notes Get Scrambled chapter Scootaloo and Twilight go off together to find Twi's injured parents. Twilight tells Scootaloo she cast a 'find parents' spell right before she locks her into a chest to keep her safe. She then leaves to confront Chrysalis and rescue Shiny all by herself as a sobbing Scootaloo curses her for being a backstabber.
  • Octavia's reaction to the destroyed concert hall.
    • From the same chapter, Chrysalis forcing Shining to attack Twilight, and nearly forcing Sweetie to kill herself.
  • Scootaloo gets her Big Damn Heroes moment and manages to save Sweetie Belle, only for Chrysalis's control over the filly to be too strong for her love to break. You can practically feel the pegasus filly's heart break...
  • Rarity trying to break Sweetie Belle free from Chryalis's influence. As she goes on, she realizes that Sweetie's Stockholm Syndrome is partially derived from a grudge towards their parents for being gone so much and for Rarity throwing the tiara at her earlier. Luckily she manages to break Sweetie free.
    • In an odd way, Chrysalis gets a moment of this when Sweetie finally shakes off her control: she screams in agony and pain, and collapses with tears rolling down her face, unable to understand what happened and why she feels that way.
  • Garnet wondering if she and Gag will be able to get a happy ending.
    • Why does she wonder that? Because so far she's seen two friends die before their wedding day, another two get brainwashed by an evil Queen and replaced by said queen respectively before theirs, and a third couple who she doesn't even know where they are or if they're safe. She's come to wonder if Misfit Platoon is simply cursed to have tragedy strike them before their wedding day. Poor girl.
  • Weaver exposing herself and her siblings as Changelings by taking Kabut's One-Winged Angel serum and injecting it into herself in order to expose him to the counter-agent Garnet developed. Though Garnet managed to save her, she fully expected it to be a Heroic Sacrifice. What makes it worse is that her siblings offered up some of their love to try and save her, she refused because she didn't want them to die.
  • The backstory of the changeling trio. They left the Hive after realizing that the changeling way of life was wrong, and have tried to live as best they could without hurting anypony.
  • The group voting on whether or not to send Chrysalis an option to surrender. They do, but Chrysalis rejects it, leaving Sweetie heartbroken.
  • Chrysalis talking with Maua.
  • Chrysalis's Villainous Breakdown continues, and reveals her deep-seated self-loathing.
  • The good kind when Shining is freed.
  • One of the captured changelings breaking down in tears when she is denied Revenge on the Brought Down to Normal Kabuto for killing her brother.
  • The fact that Hercules is a noble being, yet chooses to follow his oath to Chrysalis despite his own self-admitted desire for a peaceful end to all this. Word of God even describes him as someone who could have been a hero if things were different.
  • Chrysalis's sadness at no longer being able to hear Maua's voice.
  • Cadence's flashback to her crystal pony incarnation.
  • The CMC have to watch Chrysalis die as she refused any offers for them to save her. It's particularly heartbreaking for Sweetie Belle, who truly wanted to be Chrysalis's friend, and Silver Spoon, who kept imagining Diamond Tiara in place of Chrysalis. At least Chrysalis's good side was reincarnated as a Blank Slate alicorn filly zebra...
  • General Lone Ranger. Seeing just HOW he completely lost his mind is heartbreaking, especially when you learn that the death of his son, Private Ranger, was what completely pushed him over the edge. Alex Warlorn is quite good at making the readers feel empathy for even the most monstrous of villains in the series.
    • Then you realize that he was the one who had left the flowers at Private Ranger's grave, which was made clearer by a small edit the author did later. Even in the depths of his madness, he still genuinely cared about his son and grieved for him.
  • The Reveal that Scootaloo's parents have been looking for her, but haven't been able to find her.
  • In the latest chapter, poor Scootaloo vanishes, not just from Ponyville, from reality itself. And no one can even remember her name. Not even her hero, Rainbow Dash. On the other hand, Dash remembers that she doesn't remember, and it inspires her to find out just what the hay is going on.
  • Flutternice's treatment of Discord, who by then is just happy she's still alive and long since made a Heel–Face Turn can be hard to watch. As is her gradual breakdown when they discuss it with her.
  • Lord Tirek making his father be Forced to Watch the rest of the surviving Centaurs, including his own wives be butchered, tortured, and killed. Doubly so since his father did love him genuinely, only to see him become a complete and utter monster that annihilated their people.
  • Seeing that that Adagio and Melody used to be genuinely Friendly Rivals makes what ultimately happened to both parties. In the end, the two both had their lives ruined and neither ever saw one another again.
  • Wishful's Heroic Sacrifice to stop the Green Smooze.
  • Phobia briefly expressing grief while he explains to the CMC that Void was taken by the fog. He's really Havoc and Void is really Entropy. He's lost his wife and he doesn't know where she is. The CMC think he's just an ordinary colt, but during this moment, he sounds old.
  • Button Mash doesn't realize that his memories of hanging out with the CMC and dating Sweetie Belle are fake and the result of the rumors spreading. He thinks that the fog caused Sweetie Belle to gain amnesia about him. Sweetie Belle doesn't have the heart to tell him the truth and tells him that he's correct. It's going to be even more heartbreaking once he DOES realize the truth.
  • When Featherweight reveals that Diamond Tiara has become a Nightmare and is one of the ones responsible for what's happened, Button Mash tells the others that they shouldn't tell Silver Spoon about it because it would be too painful for her.
  • Despite the fact that Umbra's wolf was trying to erase them, the CMC are horrified when they have to let Blanky destroy it. Even though it was a monster and not a corrupted being, Apple Bloom wonders if this action makes them monsters.
  • Pipsqueak's ship, the MoonPearl, is destroyed, and Sweetie Belle reluctantly orders Blanky to leave them and look after his group.
    • It can be upsetting to see just how weary and worn Razzaroo is when she saves the CMC progress after the above event. Even her ship's damaged, showing just how much the chaotic world has taken their toll on her body and psyche.
  • Bon Bon's reaction to Tootsie being badly wounded by Venus. Yes, Tootsie has helped bring about an apocalyptic event and tried to kill the CMC multiple times, but she's still Bon Bon's child and no parent should have to see that. On top of it is Tootsie starting to have a Heel Realization.
  • Everything about Applebloom seeing her family's condition due to the Rumors. It's so bad it gets to the point the filly nearly goes Nightmare as a result.
  • Princess Celestia, turned evil by the rumors, cruelly makes Sunny Day realize that she's not a real pony by pointing out the holes in her memories. The poor girl has a breakdown until Luna mercifully makes her fall asleep.
  • Tootsie and Alula finally realizing that they were the bad guys all along, and how much it impacted them.
  • Applebloom choosing to separate herself from the rest of her group except Button to make sure they don't get hurt in the upcoming final battle.
  • In chapter 54, it turns out Button Mash knew along that his memories of his past friendships with the CMC and others were not real. What's worse is that he has no delusions like the Fake Princesses did. Not helped that in his sorrow and desperation, he tried goading Apple Bloom into fighting. He argues that if they break the curse and change the world back to normal, he'll essentially be erased and a new Button Mash who doesn't love nor remember Sweetie Belle will be left in his place. "I don't wanna die!"
    • Even though they finally dealt with that problem, now Apple Bloom is the only one to face Nightmare Diamond and Discord, with the "despair" that many have said that lies at the top of the World Tower.
    • Apple Bloom's brief Heroic BSoD when it's revealed Diamond broke the press before she ever even got there. Thankfully she fixes it, but still...
  • When the Rumors curse is broken, King Sombra and the Umbrum are trapped again, but Radiant Hope vanishes into thin air. The only thing Sombra is concerned about is whether or not his wife was real. Some positive beings created by the rumors like Harry the Bear vanish as well. Several duplicates of the Doctor and his friends would have vanished if Apple Bloom hadn't sent them to a new universe, but they Never Got to Say Goodbye.
  • Even armed with the ability to change reality, Apple Bloom still couldn't get Queen Chrysalis to repent.
  • Starlight Glimmer realizing she doesn't know her own daughter at all.
  • Havoc's avatar pleading with Discord, practically begging him to redeem himself, even asking him to lie and just SAY he'll change. And Discord's refusal because he says he doesn't want or deserve to be redeemed. And Havoc's last line, "I lost my oldest son, I won't lose my youngest."
  • Apple Bloom was able to make it so Starlight was able to save more lives when the Disaster hit, by making sure everypony evacuates. As she tries to delay the inevitable at the cost of her own life, Starlight says goodbye to her friends and family, with some parting words for her best friends...
    Mom, Mrs. Hackney, Logan, Slipknot, I love you.' She continued to work like mad at the controls. Even just a few seconds more was something. 'Patch, Clover, Melody, Sweetheart, Bon Bon, Bright Eyes, let's have some cookies at the clubhouse later. We can invite Lance, Teddy, Ace, oh and Dandy, Cookie, and Buddy too I guess.' Not much time left. 'Everypony... I... I'm sorry... please live. Bright Eyes for goodness sake, don't blame yourself.' Going critical. 'Bon Bonyou'rebeautiful! Melodyyourock. Cloveryou'renotMeadowlarklite! Sweetheartyouwerethebestofus. Patch,goodluckgirl.
  • Flash Sentry's recent solo chapter implies that he came from the human world sometime not long after Legend of Everfree to tell Princess Twilight that he was moving on from her. Whatever method he used to travel between worlds not only sent him back in time to before the point where Twilight became a princess, traveled to his world, and met him in the first place (which means he can't tell her any of this until at least after she comes back from there or else he'll cause a Temporal Paradox), but it screwed up his memories so bad he only now remembers why he left, and he didn't take it all that well. He also comments on how the human Filthy Rich from Legend of Everfree wasn't wearing a wedding ring, and expresses sorrow at the thought that the human Diamond Tiara's parents are having marital troubles.
  • "Mistakes of the Goddess of Music" has Cadence's heartbreak over Morning Star's fall to evil, since she and him were extremely close to each other before and she loved him as her little brother.
  • Discord admitting that on some level he genuinely did feel empathy for his brother Destruction, even if he refuses to accept his role in the events that lead to Destruction's death.
  • Diamond Tiara, a little girl, being rather obviously suicidal during the Final Battle and wanting to die.
  • Wallflower's backstory is absolutely tragic. Her 'not noticed by anyone' issue includes her parents. Trixie forgot she existed after they had a genuine moment. Wallflower is messed up, but there's a very good reason for it.
  • Sunset's reaction to her friends' memories getting wiped. Especially when it happens to Princess Twilight too.
  • Wallflower's Heel Realization is this for multiple reasons. As is her being so frightened of it being a Hope Spot she is genuinely afraid Sunset has forgotten her again next time they meet.
  • Sunset losing her memories of the human world as in canon, but especially because Wallflower begins to see how horrible what she's doing actually is, adding to the heartbreak of the moment.
  • Golden Tiara's reaction to seeing Nightmare Nhilus.
  • Sweetie Belle's reaction to Rarity's Heroic Sacrifice. And just the fact Rarity did it to begin with, given how she's forced into it and that she's clearly scared by the fact she's going to.
  • The original Rarity is gone, merging herself with the Spirits of Dark Magic to end their threat forever and save Diamond. While she gets a reincarnation, it's acknowledged they're not her even if they have her memories.
  • Discord's death manages to be this, as he willingly allows himself to be erased and Dissy to be the sole remaining personality to be Reincarnated through Pinkie Pie. Especially since Shady sees him off silently.
  • We find out that the gods have been desperately trying to help Tempest Shadow all this time but she subconsciously refuses any and all help.
  • We find out Applejack the First crossed the Despair Event Horizon after Discord killed Galaxia and Mimic, possessed Wind Whistler, and broke a piece of the Rainbow of Light permanently. She was so lost in her despair she genuinely overlooked what good she did at Surprise's farm and thought she'd be going to Hell when she died. Thankfully, Majesty changes that when she arrives in Heaven.
  • Meta: The author Alex Warlorn is retiring from writing fanfics after the Finale Arc is finished.
  • Meta: Alex Warlorn has become disillusioned with the original show, and is only finishing the fic out of a sense of duty.

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