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* ''Fanfic/TheLastOfUsSeries'' (''Series/OnceUponATime'', ''VideoGame/TheLastOfUs''): Emma letting her pregnant girlfriend get killed is something that haunts her throughout the story.
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* ''[[https://archiveofourown.org/works/46883770/chapters/133792987#workskin You will always have a part of me nobody else is ever gonna see]]'': For Jotaro Kujo, his biggest regret was his decision in 1999 to distant himself from his wife and their daughter Jolyne in a misplaced effort to protect them from enemy Stand Users [[MagicIsAMonsterMagnet drawn to his Stand Star Platinum]]. Unlike in canon where it lasted to 2011 and left Jolyne with much resentment towards her father, [[PointOfDivergence the difference is that this distance ended 2 years when Jolyne came with her mother to the University her parents worked at, where she snuck to her office and let out a cry on how much he missed her]]. Jotaro [[MyGodWhatHaveIDone came to immediately regret his decision]] and worked with his ex-wife to spend more time with Jolyne as she grew up and get therapy for his [[ShellShockedVeteran PTSD from his time fightinf DIO and other Stand Users]], though by 2007 his past mistake still haunts him and Jolyne. [[spoiler:Even when the option of time travel comes [[SetRightWhatOnceWentWrong and the chance to prevent his decision to leave his family]], Jotaro declines believing he has no right to meddle with Jolyne's life]].
** One of the enemy Stand Users, Karina has a Stand that sends people back to the moments that they regret. Besides the major incident above, Jotaro also regrets going to Egypt to fight DIO and leaving his mother to face her illness alone (albeit because killing DIO was the surefire way to save her life), letting Avdol [[DefeatMeansFriendship fight and befriend Polnareff]] as he sees that [[spoiler:led Avdol to sacrifice himself to save Polnareff and Iggy from Vanilla Ice]], and keeping Polnareff LockedOutOfTheLoop about Avdol FakingTheDead and letting him believe [[ItsAllMyFault his impulsive attack at J. Geil led to the fortune seller's death]]
** Despite what BigBad Jeff thinks, the decision to fight DIO [[AvertedTrope isn't this]] for Jotaro, as Jeff hoped [[spoiler:to change the past so DIO can win the fight against Jotaro]]. While Jotaro does grieve that many of his friends died fighting DIO, he will not regret their decision to take down the great evil.
** One of the enemy Stand Users, Karina has a Stand that sends people back to the moments that they regret. Besides the major incident above, Jotaro also regrets going to Egypt to fight DIO and leaving his mother to face her illness alone (albeit because killing DIO was the surefire way to save her life), letting Avdol [[DefeatMeansFriendship fight and befriend Polnareff]] as he sees that [[spoiler:led Avdol to sacrifice himself to save Polnareff and Iggy from Vanilla Ice]], and keeping Polnareff LockedOutOfTheLoop about Avdol FakingTheDead and letting him believe [[ItsAllMyFault his impulsive attack at J. Geil led to the fortune seller's death]]
** Despite what BigBad Jeff thinks, the decision to fight DIO [[AvertedTrope isn't this]] for Jotaro, as Jeff hoped [[spoiler:to change the past so DIO can win the fight against Jotaro]]. While Jotaro does grieve that many of his friends died fighting DIO, he will not regret their decision to take down the great evil.
to:
* ''[[https://archiveofourown.org/works/46883770/chapters/133792987#workskin You will always have a part of me nobody else is ever gonna see]]'': For Jotaro Kujo, his biggest regret was his decision in 1999 to distant himself from his wife and their daughter Jolyne in a misplaced effort to protect them from enemy Stand Users [[MagicIsAMonsterMagnet drawn to his Stand Star Platinum]]. Unlike in canon where it lasted to 2011 and left Jolyne with much resentment towards her father, [[PointOfDivergence the difference is that this distance ended 2 years when Jolyne came with her mother to the University her parents worked at, where she snuck to her Jotaro's office and let out a cry on how much he she missed her]]. her father]]. Jotaro [[MyGodWhatHaveIDone came to immediately regret his decision]] and worked with his ex-wife to spend more time with Jolyne as she grew up and get therapy for his [[ShellShockedVeteran PTSD from his time fightinf fighting DIO and other Stand Users]], though by 2007 his past mistake still haunts him and Jolyne. [[spoiler:Even when the option of time travel comes [[SetRightWhatOnceWentWrong and the chance to prevent his decision to leave his family]], Jotaro declines believing he has no right to meddle with Jolyne's life]].
life anymore]].
** One of the enemy Stand Users, Karina has a Stand that sends people back to the moments that they regret. Besides the major incident above, Jotaro also regrets going to Egypt to fight DIO and leaving his mother to face her illness alone (albeit because killing DIO was the surefire way to save her life),letting allowing Avdol to [[DefeatMeansFriendship fight and befriend Polnareff]] as he sees that [[spoiler:led decision is what led Avdol to [[spoiler:to sacrifice himself to save Polnareff and Iggy from Vanilla Ice]], and keeping Polnareff LockedOutOfTheLoop about Avdol FakingTheDead and letting which made him believe [[ItsAllMyFault his impulsive attack at J. Geil led to the fortune seller's death]]
teller's death]] for a period of time.
** Despite what BigBad Jeff thinks, the decision to fight DIO [[AvertedTrope isn't this]] for Jotaro, as Jeff hoped[[spoiler:to [[spoiler:so he can go to that moment and change the past so DIO can win wins the fight against Jotaro]]. While Jotaro does grieve that many of his friends died fighting DIO, he will not regret their decision to take down the great evil.
** One of the enemy Stand Users, Karina has a Stand that sends people back to the moments that they regret. Besides the major incident above, Jotaro also regrets going to Egypt to fight DIO and leaving his mother to face her illness alone (albeit because killing DIO was the surefire way to save her life),
** Despite what BigBad Jeff thinks, the decision to fight DIO [[AvertedTrope isn't this]] for Jotaro, as Jeff hoped
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[[AC:''Manga/JoJosBizarreAdventure'']]
* ''[[https://archiveofourown.org/works/46883770/chapters/133792987#workskin You will always have a part of me nobody else is ever gonna see]]'': For Jotaro Kujo, his biggest regret was his decision in 1999 to distant himself from his wife and their daughter Jolyne in a misplaced effort to protect them from enemy Stand Users [[MagicIsAMonsterMagnet drawn to his Stand Star Platinum]]. Unlike in canon where it lasted to 2011 and left Jolyne with much resentment towards her father, [[PointOfDivergence the difference is that this distance ended 2 years when Jolyne came with her mother to the University her parents worked at, where she snuck to her office and let out a cry on how much he missed her]]. Jotaro [[MyGodWhatHaveIDone came to immediately regret his decision]] and worked with his ex-wife to spend more time with Jolyne as she grew up and get therapy for his [[ShellShockedVeteran PTSD from his time fightinf DIO and other Stand Users]], though by 2007 his past mistake still haunts him and Jolyne. [[spoiler:Even when the option of time travel comes [[SetRightWhatOnceWentWrong and the chance to prevent his decision to leave his family]], Jotaro declines believing he has no right to meddle with Jolyne's life]].
** One of the enemy Stand Users, Karina has a Stand that sends people back to the moments that they regret. Besides the major incident above, Jotaro also regrets going to Egypt to fight DIO and leaving his mother to face her illness alone (albeit because killing DIO was the surefire way to save her life), letting Avdol [[DefeatMeansFriendship fight and befriend Polnareff]] as he sees that [[spoiler:led Avdol to sacrifice himself to save Polnareff and Iggy from Vanilla Ice]], and keeping Polnareff LockedOutOfTheLoop about Avdol FakingTheDead and letting him believe [[ItsAllMyFault his impulsive attack at J. Geil led to the fortune seller's death]]
** Despite what BigBad Jeff thinks, the decision to fight DIO [[AvertedTrope isn't this]] for Jotaro, as Jeff hoped [[spoiler:to change the past so DIO can win the fight against Jotaro]]. While Jotaro does grieve that many of his friends died fighting DIO, he will not regret their decision to take down the great evil.
* ''[[https://archiveofourown.org/works/46883770/chapters/133792987#workskin You will always have a part of me nobody else is ever gonna see]]'': For Jotaro Kujo, his biggest regret was his decision in 1999 to distant himself from his wife and their daughter Jolyne in a misplaced effort to protect them from enemy Stand Users [[MagicIsAMonsterMagnet drawn to his Stand Star Platinum]]. Unlike in canon where it lasted to 2011 and left Jolyne with much resentment towards her father, [[PointOfDivergence the difference is that this distance ended 2 years when Jolyne came with her mother to the University her parents worked at, where she snuck to her office and let out a cry on how much he missed her]]. Jotaro [[MyGodWhatHaveIDone came to immediately regret his decision]] and worked with his ex-wife to spend more time with Jolyne as she grew up and get therapy for his [[ShellShockedVeteran PTSD from his time fightinf DIO and other Stand Users]], though by 2007 his past mistake still haunts him and Jolyne. [[spoiler:Even when the option of time travel comes [[SetRightWhatOnceWentWrong and the chance to prevent his decision to leave his family]], Jotaro declines believing he has no right to meddle with Jolyne's life]].
** One of the enemy Stand Users, Karina has a Stand that sends people back to the moments that they regret. Besides the major incident above, Jotaro also regrets going to Egypt to fight DIO and leaving his mother to face her illness alone (albeit because killing DIO was the surefire way to save her life), letting Avdol [[DefeatMeansFriendship fight and befriend Polnareff]] as he sees that [[spoiler:led Avdol to sacrifice himself to save Polnareff and Iggy from Vanilla Ice]], and keeping Polnareff LockedOutOfTheLoop about Avdol FakingTheDead and letting him believe [[ItsAllMyFault his impulsive attack at J. Geil led to the fortune seller's death]]
** Despite what BigBad Jeff thinks, the decision to fight DIO [[AvertedTrope isn't this]] for Jotaro, as Jeff hoped [[spoiler:to change the past so DIO can win the fight against Jotaro]]. While Jotaro does grieve that many of his friends died fighting DIO, he will not regret their decision to take down the great evil.
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* ''Fanfic/PapaBear'': Tom seems remorseful that he didn't do enough to try and stop Marinette's bullies at school (trusting that the teachers and faculty would put a stop to it), which is why he's so determined to help Adrien escape Gabriel's custody.
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* ''Fanfic/SleeperHitAU'': Aizawa [[ForWantOfANail expelled Midoriya under false pretenses]] in order to ensure there was room in Class 1-A for his protégé Shinsou once he proved himself in Gen Ed. Then the League of Villains attacked his class at the USJ, resulting in [[spoiler:Asui and Mineta dying at Shigaraki's hands]]. Suffice to say, Aizawa deeply regrets his decision, wondering how different things might have been if he hadn't kicked Midoriya out.
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* ''Fanfic/SleeperHitAU'': Aizawa [[ForWantOfANail expelled Midoriya under false pretenses]] pretense] in order to ensure there was room in Class 1-A for his protégé Shinsou once he proved himself in Gen Ed. Then the League of Villains attacked his class at the USJ, resulting in [[spoiler:Asui and Mineta dying at Shigaraki's hands]]. Suffice to say, Aizawa deeply regrets his decision, wondering how different things might have been if he hadn't kicked Midoriya out.
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* ''[[https://www.fanfiction.net/s/13376549/ Echoes of the Dark]]'' gives Neptune an AdaptationalAngstUpgrade that causes her to view the events of ''[[VideoGame/HyperdimensionNeptuniaVictory Victory]]'' and ''[[VideoGame/MegadimensionNeptuniaVII VII]]'' as her ''two'' Greatest Failures - the former because Neptune's selfishness and stubbornness during an argument with her adoptive daughter Peashy [[ForWantOfANail inadvertently caused a chain of events]] that led to Peashy being brainwashed into working for the villain for ''ten years'', and the latter because Neptune herself was brainwashed into working for the villain and almost ''killing her own sister'', with Neptune especially giving herself a hard time regarding the fact that [[BreakingSpeech the things she said]] to her sister while brainwashed are what Neptune actually ''does'' feel, [[BeneathTheMask but is ashamed of]].
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* ''[[https://www.fanfiction.net/s/13376549/ Echoes of the Dark]]'' gives Neptune an AdaptationalAngstUpgrade that causes her to view the events of ''[[VideoGame/HyperdimensionNeptuniaVictory Victory]]'' and ''[[VideoGame/MegadimensionNeptuniaVII VII]]'' as her ''two'' Greatest Failures - the former because Neptune's selfishness and stubbornness during an argument with her adoptive daughter Peashy [[ForWantOfANail inadvertently caused a chain of events]] events that led to Peashy being brainwashed into working for the villain for ''ten years'', and the latter because Neptune herself was brainwashed into working for the villain and almost ''killing her own sister'', with Neptune especially giving herself a hard time regarding the fact that [[BreakingSpeech the things she said]] to her sister while brainwashed are what Neptune actually ''does'' feel, [[BeneathTheMask but is ashamed of]].
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* ''[[Fanfic/TheSpectacularSpiderManLostInGotham The Spectacular Spider-Man: Lost In Gotham]]'': Peter considers his failing to save Ben as this, internally regarding it as "his greatest shame". Bruce later tells Peter that he considers [[WeUsedToBeFriends Harvey Dent]] becoming Two-Face as this.
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* ''Fanfic/TheBridge'':
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* ''Fanfic/TheBridge'':''Fanfic/TheBridgeMLP'':
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[[AC:''Film/OmenIVTheAwakening'']]
* ''Fanfic/AlwaysVisible'': Galbraith blames himself for Delia's death because he could not disobey mister chief inspector Schaeymoure's orders to leave her family's home, which results in the poor baby falling into the hands of an incompetent F.B.I. agent.
* ''Fanfic/AlwaysVisible'': Galbraith blames himself for Delia's death because he could not disobey mister chief inspector Schaeymoure's orders to leave her family's home, which results in the poor baby falling into the hands of an incompetent F.B.I. agent.
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[[AC:Franchise/MarvelUniverse]]
* Invoked in ''Fanfic/TheAmazingSpiderManTruePurpose''; while not his greatest failure, Spider-Man talks with Hope Summers about the death of Sally Avril, the short-lived ‘Bluebird’, as an example of why he feels responsible when people he cares about join him in the field.
* Invoked in ''Fanfic/TheAmazingSpiderManTruePurpose''; while not his greatest failure, Spider-Man talks with Hope Summers about the death of Sally Avril, the short-lived ‘Bluebird’, as an example of why he feels responsible when people he cares about join him in the field.
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* ''[[Fanfic/StarWarsVsWarhammer40K Star Wars vs. Warhammer 40K]]'': Davik Thune was present at the Fall of Cadia prior to his elevation to Chapter Master of the Crimson Razors and clearly regrets being unable to prevent Abbadon from destroying the planet, leading him to embrace the zealotry and bloodthirst of his predecessors when before he was a severe detractor of them.
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* ''[[Fanfic/StarWarsVsWarhammer40K Star Wars vs. vs Warhammer 40K]]'': Davik Thune was present at the Fall of Cadia prior to his elevation to Chapter Master of the Crimson Razors and clearly regrets being unable to prevent Abbadon from destroying the planet, leading him to embrace the zealotry and bloodthirst of his predecessors when before he was a severe detractor of them.
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** Sora believes that not noticing Riku's self doubt prior to ''VideoGame/KingdomHearts'' is his, since it led to Riku's FaceHeelTurn during that game.
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** Sora believes that not noticing Riku's self doubt prior to ''VideoGame/KingdomHearts'' ''VideoGame/KingdomHeartsI'' is his, since it led to Riku's FaceHeelTurn during that game.
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* ''Fanfic/AbraxasHrodvitnon'': [[Characters/AbraxasHrodvitnonMonsterX San]] isn't proud of the many, many horrors he committed on many alien planets and on Earth when he was part of Ghidorah, but his greatest shame is the psychological agony that he unwittingly inflicted on [[MoralityPet Vivienne]] whilst turning her into his [[TwoBeingsOneBody new sister]].
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* ''Fanfic/AbraxasHrodvitnon'': [[Characters/AbraxasHrodvitnonMonsterX San]] isn't proud of the many, many ''many'' horrors that he committed on many alien planets and on Earth when he was part of Ghidorah, Ghidorah before his HeelRealization, but his greatest San's ''greatest'' shame is the psychological agony that he unwittingly inflicted on [[MoralityPet Vivienne]] whilst turning her into his [[TwoBeingsOneBody new sister]].
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* ''[[Fanfic/OneDayAtATimeFanfic One Day at a Time]]'':
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* ''[[Fanfic/OneDayAtATimeFanfic ''[[Fanfic/OneDayAtATimeNyame One Day at a Time]]'':
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* ''Fanfic/AClashOfNEETs'': For [[LightNovel/{{Konosuba}} Aqua]], it was [[spoiler:reincarnating [[VideoGame/WorldOfWarcraft Arthas Menethil]] to give him a second chance at being a hero]]. ''Everything'' that has gone wrong for [[Literature/ASongOfIceAndFire Westeros]] since then has been a direct result of that well-intentioned but poorly thought out choice, and the Septa Cecily's Guide on it makes it clear that she ''knows'' it too; the main reason all of the Children Of Destiny are chosen from her Champions, rather than the other goddesses', is because she sees this as her mess to clean up.
to:
* ''Fanfic/AClashOfNEETs'': For [[LightNovel/{{Konosuba}} [[Literature/{{Konosuba}} Aqua]], it was [[spoiler:reincarnating [[VideoGame/WorldOfWarcraft Arthas Menethil]] to give him a second chance at being a hero]]. ''Everything'' that has gone wrong for [[Literature/ASongOfIceAndFire Westeros]] since then has been a direct result of that well-intentioned but poorly thought out choice, and the Septa Cecily's Guide on it makes it clear that she ''knows'' it too; the main reason all of the Children Of Destiny are chosen from her Champions, rather than the other goddesses', is because she sees this as her mess to clean up.
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[[AC:''WesternAnimation/RickAndMorty'']]
* ''Fanfic/RestInPiss'': Piss Master's Daughter feels she should have done more to help her father and be a part of his life, which could have prevented his suicide. It is revealed that Piss Master always welcomes his daughter to visit him, but she never takes him up on that offer which she now regrets because she misses him. Before the incident that humiliated him on the internet, Piss Master told his daughter he was going after a 'notorious villain' with a long list of defeated heroes. She realized now that it was a suicide mission, and looking back now, she should've known he was on the edge. Piss Master's Daughter regrets not stopping her father before he ever went, asking him how he was doing and taking a bigger interest in his life. Finally, after Piss Master was embarrassed on the internet, his daughter regretted not contacting him to comfort her father. Piss Master's Daughter revealed that her father attempted to contact her after he was humiliated by the human on the internet, she made fun of her father on her podcast and ignored his texts and calls up until they stopped coming, and then the guilt hit her. Piss Master's Daughter visited her father only to find a man impersonation her father, realizing that her father killed herself and the man was trying to spear her feeling by assuring her that her father was ok and if anything happened to him it was not her fault she was heartbroken.
* ''Fanfic/RestInPiss'': Piss Master's Daughter feels she should have done more to help her father and be a part of his life, which could have prevented his suicide. It is revealed that Piss Master always welcomes his daughter to visit him, but she never takes him up on that offer which she now regrets because she misses him. Before the incident that humiliated him on the internet, Piss Master told his daughter he was going after a 'notorious villain' with a long list of defeated heroes. She realized now that it was a suicide mission, and looking back now, she should've known he was on the edge. Piss Master's Daughter regrets not stopping her father before he ever went, asking him how he was doing and taking a bigger interest in his life. Finally, after Piss Master was embarrassed on the internet, his daughter regretted not contacting him to comfort her father. Piss Master's Daughter revealed that her father attempted to contact her after he was humiliated by the human on the internet, she made fun of her father on her podcast and ignored his texts and calls up until they stopped coming, and then the guilt hit her. Piss Master's Daughter visited her father only to find a man impersonation her father, realizing that her father killed herself and the man was trying to spear her feeling by assuring her that her father was ok and if anything happened to him it was not her fault she was heartbroken.
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* ''Fanfic/CorAutemAurora'':
** [[VideoGame/FinalFantasyXV Gladio]] only arrives to Lestallum only after [[spoiler:Ulldor has killed Jared and raped his sister Iris]]. The realisation that he was not there to pretect his only remaining family completely destroys his self-confidence.
** Sora believes that not noticing Riku's self doubt prior to ''VideoGame/KingdomHearts'' is his, since it led to Riku's FaceHeelTurn during that game.
** [[VideoGame/FinalFantasyXV Gladio]] only arrives to Lestallum only after [[spoiler:Ulldor has killed Jared and raped his sister Iris]]. The realisation that he was not there to pretect his only remaining family completely destroys his self-confidence.
** Sora believes that not noticing Riku's self doubt prior to ''VideoGame/KingdomHearts'' is his, since it led to Riku's FaceHeelTurn during that game.
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[[AC: ''Literature/GrandmasterOfDemonicCultivationMoDaoZuShi'' / ''Series/TheUntamed'']]
* Lan Xichen is at the center of two of these in ''Fanfic/ForgetMeNotDontLeaveMeBehind''. Yue Liu's greatest failure was leaving him behind when she fled her captivity. Lan Qiren's greatest failure was letting him down as a child and not giving him the care he deserved.
* Lan Xichen is at the center of two of these in ''Fanfic/ForgetMeNotDontLeaveMeBehind''. Yue Liu's greatest failure was leaving him behind when she fled her captivity. Lan Qiren's greatest failure was letting him down as a child and not giving him the care he deserved.
