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1!!v4:
2* [[Franchise/LyricalNanoha Fate]] loses to [[VisualNovel/FateStayNight Archer]], despite her best efforts. She... [[https://tvtropes.org/pmwiki/posts.php?discussion=13792636210A84451500&page=783#19573 doesn't take it well]].
3* [[DarthWiki/UnchainedLightning Stormer's]] [[https://tvtropes.org/pmwiki/posts.php?discussion=13792636210A84451500&page=991#24765 reaction after]] a DoubleKnockout from [[DarthWiki/DiamondPhase Calia's]] impaling crystal finisher. [[spoiler: Thankfully, they get medical attention in time]].
4-->"[[spoiler:Looks like...we'll die together...my dear Chii...]]"
5* [[https://tvtropes.org/pmwiki/posts.php?discussion=13792636210A84451500&page=1216#30386 Yet another dramatic Puella Magi death.]] [[spoiler: Mami]] tries desperately to [[spoiler: save everyone around from her Witch Form, but is ultimately saved by Madoka anyway.]]
6* Pastry Person mercilessly keeps beating on Milo and Duckus (the duo of the VideoGame/DuckHunt dog and duck that appear in ''VideoGame/SuperSmashBros''), even though the two are exhausted, on the brink of death and pleading to be left alone, and had not done anything to him in the first place. Even merciless and sadistic [[WesternAnimation/MyLittlePonyFriendshipIsMagic Queen Chrysalis]] thought he was going overboard!
7* The tragic friendship between Mog from VideoGame/FinalFantasyVI and Walter from Anime/{{Hellsing}} that ends with Walter sacrificing himself to try and kill Porky.
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9!!V5 (Spinoff)
10* Starting [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=723#18062 here,]] [[{{VideoGame/Deemo}} the Girl]] is betrayed by [[{{VideoGame/Blazblue}} Hazama]] when the evil bastard {{Mind Rape}}s her, giving her a flashback of [[spoiler:her brother's untimely death.]] He then proceeds to kick her in the head... multiple times. It remains to be seen if there's any hope of recovery for the poor Girl. Also counts as NightmareFuel.
11* [[EldritchAbomination engie]] defiantly [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=1639#40974 self-destructs]] his drone to kill a vengeful [[KnightTemplar MIKI]], the dying shard contained within fleeing into the arms of [[ShipTease Daydre]].
12* The interactions between [[CatGirl Fem]][[CuteBruiser ji]] and The [[TheChessmaster Black]] [[DarkAndTroubledPast King]] can only end in tears. Start reading from [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=3176#79395 here]].
13** Speaking of the Black King... [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=3857#96418 Turns out his motive is also quite a sob story.]]
14* Sabitsuki has been KilledOffForReal, and it seems to have had an [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=5667#141653 unexpectedly profound effect on Engie,]] both in-game and in real life.
15* Starting [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=12812#comment-320295 here]], a mechanized [[Franchise/{{Godzilla}} Shin Godzilla]] is sent out by [[Franchise/SonicTheHedgehog Doctor Eggman]] to terrorize the Arena and finds opposition in the form of [[http://kaijucombat.com/wiki/doku.php?id=ckc_monster_list:scaos_the_sinkeeper Scaos the Sinkeeper]], a kaiju from the ill-fated ''VideoGame/ColossalKaijuCombat''. Scaos is an EmotionEater used as a dumping grounds for the negative emotions of an entire race, and understandably [[PoweredByAForsakenChild a pretty tragic figure]]. After a battle laden with enough character development to fill an arc, [[spoiler:Scaos finally [[HeroicSacrifice gets his]] "[[GoOutWithASmile good ending]]".]]
16* During a visit to the realm of dreams, Sarah is forced to [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=14405#comment-360103 fight her own sleep paralysis demon]] in order to open a path to the adjacent nightmare realm. During the battle, it knocks her unconscious ([[MST3KMantra don't ask how that works]]) and she ends up in a bar full of characters her player, [=Bolded1=], introduced whose story arcs were ultimately abandoned. It's a somber nod to his own inability to retain interest in given characters or series, with what feels like an in-universe half-hearted attempt to make light of the situation, like even the characters themselves have given up hope of returning to the spotlight.
17** It gets worse when "SAMAEL," a creature from a book Bolded intends to write, [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=14406#comment-360131 appears before Sarah while in the nightmare-queen's palace]] and tells her she will join the faces in the bar someday. It's immediately followed by [=KiriK=] playing out a ''very'' similar situation with a character from a novel-length story he nearly finished only to abandon, alongside the antagonist of a story that never got past the idea phase in 2016. The characters in the roleplay ultimately manage to shrug off these warnings and threats, but it should be clear the players weren't feeling so lighthearted and flippant when they wrote them.
18* Starting [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=14789#comment-369712 here]], Psyco's [[VideoGame/{{Undertale}} Chara]] comes under attack by Arachnos's [[VideoGame/{{Omori}} Omori]][[labelnote:note]]who, in this particular interpretation, is a barely sentient mass of grief and guilt that has been left behind after [[spoiler:Sunny committed suicide in one of the bad endings]], turning into a sort of [[AbstractApotheosis abstract]] emotional parasite that latches on to those who harbor deep-seated guilt and regrets, takes form in their mind, and [[EmotionControl amplifies their negative feelings]] until they [[DrivenToSuicide commit suicide]][[/labelnote]]. What follows is a BattleInTheCenterOfTheMind over the course of which Omori ruthlessly dredges up all of Chara's deep-seated regrets and sorrows and '''weaponizes''' them against the Fallen Child, all the while absolutely destroying them on an emotional level by [[BreakingSpeech giving a voice to all their insecurities and negative thoughts]]. It's not so much a battle as it is a long string of magic-assisted bullying, and Arachnos said that he felt disgusted while writing Omori's lines. [[https://tvtropes.org/pmwiki/posts.php?discussion=14315151240A21923900&page=14781 Just a few pages earlier]], Omori does the same to [[VideoGame/KirbyTripleDeluxe Taranza]] [[spoiler:'''[[TheBadGuyWins and succeeds]]'''.]]
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