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* ''Franchise/AceAttorney'':
** In general, it's quite easy to accidentally put people down, especially when your assistant can [[InnerMonologueConversation read your mind]] or face, as shown in the fourth case of ''VisualNovel/PhoenixWrightAceAttorney'' if you answer "Yeah, you're useless".
--->'''Maya:''' I know... I'm no good for anything, am I, Nick? If I can't call my sister, I might as well not be here, right?\\
'''Phoenix:''' Um, well, actually... ''[thinking]'' (You don't know law, you don't have any trial experience or techniques... Yeah, you're pretty much useless... but I can't say that!) \\
'''Maya:''' It's okay Nick. You don't have to say anything. Your face said it for you. \\
'''Phoenix:''' ''[thinking]'' (Whoops!)
** In the third case of ''VisualNovel/PhoenixWrightAceAttorneyJusticeForAll'' [[spoiler:Acro turns out to have killed Russell Berry accidentally while trying to kill Russell's daughter Regina because she accidentally put Acro's brother Bat in a coma and is so naïve that she doesn't even understand what she's done. At the end of the case, Regina asks if Acro is going to come after her. The "correct" answer is to say "No," and to show her some evidence, but's there's no real reason you can't say "Of course he is!" and send her off in tears.]]
** Halfway through the case, you'll run into Franziska during the second investigation phase. For every irrelevant piece of evidence you present to her, she [[WhipOfDominance whips poor Maya as punishment]]. You can do this as many times as you like without any repercussions.
** In ''VisualNovel/AceAttorneyInvestigationsMilesEdgeworth'' Case 5, you run into the Steel Samurai, who reveals himself to be [[spoiler:[[TheDitz Larry Butz]].]] If you present the wrong evidence to him during the one investigation phase that lets you talk to him, [[spoiler:Larry refuses to look at your evidence because he's [[DistractedByTheSexy too busy staring ]] at [[MadScientistsBeautifulDaughter Franziska]]. Franziska promptly offers to "sear her image into his mind for eternity" by sending him on a "Whippity-Whip-Trip" into unconsciousness.]] This is probably the one time in which presenting wrong evidence in an investigation phase can be pretty satisfying... and [[SugarWiki/FunnyMoments hilarious]].
** [[VisualNovel/PhoenixWrightAceAttorney The first game's]] fourth case had two examples of this with the {{Butt Monkey}}s of choice being Lotta and/or Larry. At some point, Gumshoe will offer you either a dog (Missile), a fishing rod, or a metal detector to fish for Gourdy to find key evidence for your case. The ''correct'' choice would be [[spoiler:the metal detector]], but the two other options can lead to this. For Lotta, the player can take [[spoiler:the fishing pole, which Maya will use in the lake to fish for Gourdy, only to trip and fall, causing Lotta's cameras to react and waste ''more'' (very expensive) rolls of film than you already wasted earlier in the case]]. For Larry, the player can take [[spoiler:Missile, who will react automatically to the aroma of Larry's Samurai dogs the minute you get into the park, let alone the crime scene, causing the aptly-named poochy to run like a missile and chow down on all of Larry's hotdogs, making him lose his (at this point, already doomed) business. For added butthurt, you can also show Missile to Larry after the puppy ate his entire revenue]].
*** Lotta still gets misfortune even if you don't get the item. If you don't get it, Maya sneezes, setting off the camera anyways.
*** Another minor example from the same case: When you first start the case, Edgeworth refuses to let you defend him. After running around and gathering evidence for a while, Phoenix and Maya return to the Detention Center to speak with Edgeworth again. At this point, Edgeworth relents and asks Phoenix to defend him. The game continues regardless of your choice, but you can always choose to troll Edgeworth and tell him "Sorry, you missed your chance!", scaring him half to death and prompting both him and Maya to yell at you for your cruel sense of humour.
** In the third game's second case, examining the ceremonial sword will prompt Maya to strike Phoenix on the head with it. You can keep examining it, letting Maya repeatedly strike Phoenix on the head with it. One can only wonder how hard that head is...
** VisualNovel/AceAttorneyInvestigations 2 has the logic chess battles, which give you the opportunity to say needlessly cruel things to your adversaries. In particular, you can tell a broken down [[spoiler: Sebastian]] that he's a failure as a human being. [[spoiler: [[PressXToDie Take a wild guess as to what happens...]]]]
* ''VisualNovel/BoyfriendToDeath'': You can attack [[NiceGuy Ren]] in the basement if you have a knife during Strade's route; [[VideoGameCrueltyPunishment Strade will be]] ''[[SarcasmMode very]]'' [[SarcasmMode pleased with you]].
* In ''VideoGame/CoffeeTalk'', you can deliberately serve the wrong drinks to your customers, and in Episode 2, there's an achievement for making Riona walk out on you for not getting her orders right too many times.
* In ''VisualNovel/DanganronpaTriggerHappyHavoc'' and ''VisualNovel/Danganronpa2GoodbyeDespair'', there is an additional mode that works like a dating sim. At certain points during those modes, the students will end up talking to the main character about their pain, fears, frustrations, vulnerabilities, and insecurities all on display, while the only available command involves agreeing or disagreeing with these internal reflections. Depending on the context, it's possible to make the main character of both of those games say some incredibly mean things to the other students.
** In the following game, ''VisualNovel/DanganronpaV3KillingHarmony'' Shuichi's Free Time Event with Tenko Chabashira will either end with Tenko knocking Shuichi out cold, or if you're feeling extra sadistic, tell her to shut up.
* Darkly {{parodied}} and sort of deconstructed in ''VisualNovel/DokiDokiLiteratureClub'' when [[spoiler: Monika makes fun of the horrible things that happen to other characters because she thinks [[MediumAwareness they're just game characters anyway]] so it doesn't matter. The creator has [[https://www.youtube.com/watch?v=bPw9cMWkAMs pointed out]] she's missing the point that this is the kind of game where the player [[VideoGameCaringPotential gets attached to the characters]], so she expects you to laugh along with her. Also {{inverted}} because now it's a character doing it and the player meant to feel uncomfortable.]]
* In ''VisualNovel/KatawaShoujo'', most dialogue choices aren't unsubtle enough for you to really do anything awful on purpose, but [[spoiler:the single choice in Shizune's route, explicitly giving you the opportunity to cheat on her with Misha, her best friend who is also in love with her]], certainly takes the cake.
* Just ''playing'' ''VisualNovel/LongLiveTheQueen'' is cruel, because your cute little magical girl princess is [[NintendoHard going to die an awful lot of horrible deaths]]. However, you can also use her to commit acts of gleeful wickedness against other characters. Among other things, you can force a woman into marriage, abuse the servants, ramp up punishments in hopes of discouraging assassination attempts, execute people at random, and reduce a woman to tears by blaming her for her daughter's death. The game actually has, alongside the various in-game stat meters shown to you, a hidden Cruelty stat which, if sufficiently increased, allows you to do ''even more'' awful acts, up to and including sacrificing your thirteen-year-old cousin to a kraken[[note]]this can alternatively be done ''without'' already being a vicious bitch if you learned certain information during that playthrough, but if you don't have that information and you haven't made the protagonist sufficiently callous, ''she will refuse to do it''[[/note]] or [[spoiler:murdering your own father]].
* ''VisualNovel/MinotaurHotel'': The whole point of the Ruthless route. You can be an absolute dick and perform several KickTheDog moments towards Asterion, which will cause him to eventually realize how doomed his situation is.
* In the third ''VisualNovel/PurrfectApawcalypse'' game, you play as a VillainProtagonist who's sadistically murdered others in previous games so you naturally get a lot of options to be cruel, including but not limited to: making a dog girl violently sick by putting chocolate in her cake, severely injuring another dog by putting nails in the baseball you throw to him, stalking the cat boy who rejected you and killing him so that you can get your body back from him (long story there), and even summoning a GodOfEvil to [[TheEndOfTheWorldAsWeKnowIt start the apocalypse]].
* The game ''VisualNovel/{{Sprung}}'' gives the player character mace which has absolutely no purpose within the game except for the player to spray it in people's eyes and see them cry. Becky also gets the equipment necessary to set somebody on fire (this does result in a game over).
* ''VisualNovel/SyrupAndTheUltimateSweet'': Between eating the candy girl in your basement, handing that candy girl off to your rival who's slowly eating her into nothing and refusing to help, and telling your rival that you hate her, there's a lot of it. Although it all leads to various [[DownerEnding downer endings]].
* Half of the fun of playing ''VisualNovel/WinterShard'' is the freedom it gives the player to be the evilest, sickest bastard imaginable if they want to play Frederone like that. [[NoCanonForTheWicked It won't get you anywhere near the True ending, though.]]

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