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1'''As a Moments subpage, all spoilers are unmarked [[Administrivia/SpoilersOff as per policy.]] Administrivia/YouHaveBeenWarned.'''
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3* Before Catarina's change and her timely intervention, all of the main characters lead unhappy lives:
4** Keith is a bastard child, and his mother abandoned him to the custody of his nobleman father, where he suffered even more. It got worse when his earth magic emerged, which he injured his half-siblings and thus spent his formative years being a recluse. In the game, it would get worse as Catarina and her mother would treat him like crap enough that he grew up as a playboy. Fortunately in this series, [[SugarWiki/HeartwarmingMoments this lead to another type of moment...]]
5*** In the ''Verge of Destruction'', this will get worse for Catarina who regained her memories of her former life ''too late''. Since everything in this timeline followed the game up to the first bullying event, the Claes family is still incredibly strained, she still bullied Keith for years, and he ends up becoming a playboy. So when Catarina tries to apologize and calls him "little brother", Keith lashes out and rejects her, since she did nothing but mistreat him most of their lives, and thus he wants nothing to do with her. Unlike Maria or Geordo, who both have good cause to believe Catarina's change-of-heart is sincere, Keith is too broken to notice or care. The very ''idea'' that Catarina would try to be nice to him after making his life hell for years makes him vehemently angry.
6** Alan grew up being constantly overshadowed by his older twin brother Geordo that results in having self-esteem issues, which lead him seeing the latter's genuine compassion and praise to him as insulting.
7** Geordo might have fared better than Alan, but [[IntelligenceEqualsIsolation his extremely high intelligence]] and ability to see right through most facades still makes him unable to enjoy life, and he can't relate to other people's struggles. He also suffers from MiddleChildSyndrome because his two elder brothers (Geoffrey and Ian) are the focus of everyone's attention, while his younger twin brother Alan was [[SoapOperaDisease bedridden]] back when he was a kid and thus had to be tended to. To make it even worse for Geordo, Alan is pushing him away because his insecurities prevent him to see his older twin brother's attempts to connect with him as nothing but his desperate need for family and company. It's even worse in the game world, where he is forced into an engagement with [[RichBitch Catarina]] that will make his life more empty than ever.
8*** [=S2E05=] puts Geordo's problems in an even harsher light. He wasn't "just" [[LonelyAtTheTop bored]] and [[MiddleChildSyndrome ignored]], he also felt ''betrayed''. By ''his own mother'', no less. It is a sobering reminder that despite being WiseBeyondTheirYears, Geordo is still a child who needs his parents' attention.
9** Mary and Sophia are being bullied for being the daughter of a marquis' commoner second wife and being albino, respectively. The badmouthing is too much for them to bear enough that they retreat alone and find solace in gardening (Mary) and in books (Sophia).
10** Nicol endures hearing forced sympathies to other people by claiming that Sophia is nothing but a burden to him, which is clearly untrue. He gives up on convincing others otherwise since he believes that no one will understand him anyway. And although his issues are already ironed out thanks to Catarina, the first person who shares his sentiment, his unrequited love for her causes him heartache more than he is willing to admit.
11* Maria being born with a rare and powerful magic should be a blessing. Instead, it tears her family apart and isolates her from her peers. Then to make things worse, when she gets to magic school, she's bullied for being a commoner.
12** A flashback shows that she once tried to make friends with her classmates by making them sweets, but when she presents her sweets to them, they all just leave the room without saying a word to her.
13* Atsuko. Welp, her case is a triple whammy.
14** The anime only briefly shows how she was in a FriendlessBackground before she met the "Monkey Girl". The light novels reveal ''why'': she was [[StockShoujoBullyingTactics bullied]] a lot throughout grade school as she had [[LonersAreFreaks never been able to befriend anyone]] due to being {{socially inept}}, and the bullying eventually [[BulliedIntoDepression caused her to become]] [[ShrinkingViolet social phobic]]. The way she described her social difficulties implies it's an issue she's always had, which indicates it's probably not something she has conscious control over. The worst thing is [[IJustWantToHaveFriends she still yearns for friendship]], which means she was forced to [[{{escapism}} seek solace]] from books while tuning out everyone she actually sees because they're too uncomfortable for her. Made even worse when she reincarnated as Sophia, she ends up having the same problems as her: being ostracized because of something that they didn't even ask for, which in Sophia's case, it is her albinism.
15** [=S1E07=] shows some of the aftermaths of Monkey Girl's death. Atsuko looks vacant and despondent at Monkey Girl's funeral. Later, while walking home, Atsuko reads the last text she ever received from her friend and breaks down crying, saying she doesn't know how she'll be able to go on without her friend. Considering Atsuko's status as a pariah (something she also suffered in her next life as Sophia) due to her [[NoSocialSkills crippled social skills]], the fact that Monkey Girl is the first friend that she made really hammers her heartbreak over losing her. This is also an InUniverse example; Sophia [[ImCryingButIDontKnowWhy cried subconsciously when she dreamed about it]], and even though she forgets most of it upon waking, she feels what little she remembers of it "a profound sense of sorrow and pain gnawing away at my heart."
16*** Acchan's wish for ReincarnationFriendship in the novel is heartbreaking on its own.
17--->''So... if life is like... the stories I read... If one day, my life were to end, and if I were to be reincarnated...\
18Then... please. I’d like to be with that girl... to be her friend. Just one more time.\
19And live those [[ArcWords peaceful days]], together with her... Just one more time.''
20* [=S1E09=] has Anne's past. Her mother (who by the way conditioned her into becoming a YesMan as a survival mechanism) died in a house fire and she got burnt as a result. What did her father say to his bastard daughter after that? He told her that ''she was of no use to him'' in a political marriage and told her to leave. Shortly after she was abandoned to the House Claes. It was so bad that she started referring to herself as a ''tool''.
21* After being told about Dark Magic, Catarina has a nightmare where she comes across the dead bodies of her friends. She begins breaking down, wishing she'd just accepted her destruction end if it meant they'd live, before she wakes up.
22* When Catarina is put into a magical coma, all of her friends are gathered by her bedside. They begin thinking of how much she means to them, and then begin feeling helpless and useless, blaming themselves for not being able to protect her.
23* Atsuko and the Monkey Girl's farewell [[DreamApocalypse when the latter is waking up from her coma]] is particularly bittersweet. While they are still technically together as Catarina and Sophia, neither of them are aware of that and their original relationship is effectively gone, at least for the time being.
24-->'''Atsuko:''' Goodbye, and thank you, my precious best friend.
25* The instigator of the magic coma above is the StudentCouncilPresident Sirius Dieke, or rather Raphael Walt. His DarkAndTroubledPast is this and NightmareFuel.
26** He was a bastard son of Marquis Dieke, but he led a happy life with his mother. That happiness was cruelly destroyed by the Marchioness Dieke, the wife of the marquis, who kidnapped both mother and son in order to save her sickly son Sirius (who looked like Raphael). The plan to save her sick son required dark magic to transfer Sirius's soul to Raphael's healthier body. In order to give a mage dark magic, a ritual was done where Raphael's mother was sacrificed in front of Raphael's eyes.
27** Sirius's soul was transferred to Raphael's body, but all it did was give Sirius's memories to Raphael because Sirius had already died before the soul transfer was completed. Raphael was forced to impersonate Sirius in order to keep himself from being killed by the Marchioness. His dark magic emerged after some time.
28** He initially wanted revenge, but was about to let go of his anger and move on when the dark mage responsible for the ritual (who the Marchioness had killed in order to cover up her crimes) manipulated Raphael's anger and grief and made him continue his revenge against their shared enemy. The dark mage's thirst for revenge is so great that he forces Raphael into acting against Maria and Catarina, even though they did nothing to wrong either of them, solely because their influence is making Raphael have second thoughts.
29** And if the BadEnding of his secret route is achieved, he will end up losing himself and killing ''everyone'' (the main cast). He will be held responsible (and in his bad route, have blood on his hands) for the questionable things that he had done throughout the series that he had little to no control over. Small wonder he left the academy under the guise of receiving medical treatment. Even after the truth comes out, he still blames himself for what happened despite being as much of a victim as Maria and Catarina.
30* In ''Verge of Destruction'', hearing Catarina's thoughts and genuine anguish about the person she used to be is truly heart-wrenching. In the main series, Catarina can refer to herself and the game character as essentially different people, since Catarina didn't really have a long history of wickedness before she turned eight. ''[=VoD=]'' Catarina ''can NOT'' say the same. She is well aware that it was ''her'' who did all of those horrible things, even though she can't remember why or what she hoped to gain from it. Seeing her genuine sorrow when the people she's wronged [[ReformedButRejected don't give a damn about her apologies]], along with her declaration that she ''must'' try to apologize and make amends (doom flags or not) because she could never live with herself otherwise is extremely sad and compelling.

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