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!Per wiki policy, Administrivia/SpoilersOff applies here and all spoilers are unmarked. Administrivia/YouHaveBeenWarned.
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UNMARKED SPOILERS AHEAD
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** The sorrow is reflected in his later matches. He even halfheartedly states "what's the point" before ending a fight in one move. Geoffrey confirms to James that his affable disposition is indeed an act in this moment.

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** The sorrow is reflected in his later matches. He even halfheartedly states "what's the point" before ending a fight in one move. Geoffrey confirms to James that his affable disposition is indeed an act in this moment.moment.
* Charlotte reflecting on how awful it is that there is all of this death and pain because of a tournament that seems to glorify it. None of it makes a lick of sense to someone as peaceful as her, and for a moment she feels just as helpless as the rest of the Youths to stop it.
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** The sorrow is reflected in his later matches. He even halfheartedly states "what's the point" before ending a fight in one move.

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** The sorrow is reflected in his later matches. He even halfheartedly states "what's the point" before ending a fight in one move. Geoffrey confirms to James that his affable disposition is indeed an act in this moment.
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-->'''Richard:''' Parents, who needs 'em, right? [[FreudianSlip I do.]]
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* Maxeral, the lead gargoyle of the AAAM's security, laments how because everything about his attributes and abilities are carved into his skull, he cannot act outside of their strict restrictions, and as a result he cannot uphold justice nearly as much as he'd like. It's part of the reason he puts so much trust in James.

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* Maxeral, the lead gargoyle of the AAAM's security, laments how because everything about his attributes and abilities are carved into his skull, he cannot act outside of their strict restrictions, and as a result he cannot uphold justice nearly as much as he'd like. It's part of the reason he puts so much trust in James.James.

* Even though he's later revealed to be the main saboteur, you can't help but feel bad for Richard Rainsford to an extent. His father, Avenant Rainsford, was a dragon slayer, and he viewed Richard's wizardly abilities as inferior to his own, claiming that wizards did everything the easy way instead of the "honorable way". [[WellDoneSonGuy Desperate to prove him wrong]], he won every single UWB tournament since its inception...but it never worked. And when he DID invite his dad to see, he just derided it as "a childish sport with fireworks". After ALL of this, it suddenly becomes apparent why the poor youth lost his mind and got it in his head that if he killed a lot of wizards before finding a WorthyOpponent, THEN he'd fit his old man's twisted views of honor.
** The sorrow is reflected in his later matches. He even halfheartedly states "what's the point" before ending a fight in one move.
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* Related to the above, when James and the youths visit Polybeus in the hospital, [[OOCIsSeriousBusiness he actually considers calling the case off.]] He then tearfully states that Polybeus' near death is all his fault, and that he should have never gotten anyone involved in the tournament to begin with. Serena and Margot thankfully snap him out of it, but he still spends the rest of the week in HeroicBSOD mode before Rodrigo decides to fix that matter.

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* Related to the above, when James and the youths visit Polybeus in the hospital, [[OOCIsSeriousBusiness he actually considers calling the case off.]] He then tearfully states that Polybeus' near death is all his fault, and that he should have never gotten anyone involved in the tournament to begin with. Serena and Margot thankfully snap him out of it, but he still spends the rest of the week in HeroicBSOD mode before Rodrigo decides to fix that matter.matter.

* Maxeral, the lead gargoyle of the AAAM's security, laments how because everything about his attributes and abilities are carved into his skull, he cannot act outside of their strict restrictions, and as a result he cannot uphold justice nearly as much as he'd like. It's part of the reason he puts so much trust in James.
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*** Even worse, Professor Bubos was unable to reach Gabriev in time because Dermberder was too busy getting toasted nuts to turn off the magical barrier. To think the boy could have lived if the dean actually took the situation seriously.
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*** On that note, just the fact that Gabriev, a kindly textbook KnightInShiningArmor, and the only person outside of the youths who was willing to help Polybeus see a better path to heroism, had to perish like that. Whomever the saboteur is, that solidified everyone's hatred of them.

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*** On that note, just the fact that Gabriev, a kindly textbook KnightInShiningArmor, and the only person outside of the youths who was willing to help Polybeus see a better path to heroism, had to perish like that. Whomever the saboteur is, that solidified everyone's hatred of them.them.
** Afterwards, Polybeus' life goes down the tubes, with almost everyone in the school blaming him for Gabriev's death and his SurvivorsGuilt ripping at his soul. Sure, it brings him closer to his friends, but even they can't do much to salvage his reputation.
** And just when things can't get any worse, his fight with Miguel, just when he's about to score a decisive victory against the jerkish wizard, ends with HIM getting blasted by the saboteur's scheme, nearly killing him and putting him in the hospital.
** After he recovers, he's found by Charlotte talking with Gabriev's mom, still reeling from the guilt of surviving when someone much more deserving of the hero's title didn't. The grieving mother comforts him regardless, and gives him her son's helmet as a TragicKeepsake.

* Related to the above, when James and the youths visit Polybeus in the hospital, [[OOCIsSeriousBusiness he actually considers calling the case off.]] He then tearfully states that Polybeus' near death is all his fault, and that he should have never gotten anyone involved in the tournament to begin with. Serena and Margot thankfully snap him out of it, but he still spends the rest of the week in HeroicBSOD mode before Rodrigo decides to fix that matter.
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* The brutal CurbstompBattle Miguel inflicts on Ivan not only establishes the older wizard as a scumbag, [[HeroicBSOD but it leaves the poor conjuror's self-esteem in tatters]], not helped by Polybeus' constant passive-aggressive jabs from earlier.

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* The brutal CurbstompBattle Miguel inflicts on Ivan not only establishes the older wizard as a scumbag, [[HeroicBSOD but it leaves the poor conjuror's self-esteem in tatters]], not helped by Polybeus' constant passive-aggressive jabs from earlier.earlier.

* Polybeus just can't catch a break in this story. [[TraumaCongaLine Everything seems to go absolutely wrong for him at every turn.]]
** First, he's dressed down harshly by James for always talking down to Ivan. Not too bad, as he learns quickly from it. But then the pressure of the tournament starts getting to him, his self-esteem issues bubbling up to the surface (not helping that his first victory was an undignified GroinAttack). Then, during his fight with Gabriev, he falls face-first into the mud, humiliating him like never before. It actually causes him to cry in shame before [[HopeSpot Gabriev gives him the encouragement he needs]]...minutes before the brave knight is killed horribly by the saboteur's cursed glyph. Polybeus can only hold the dying Gabriev as he dies.
*** On that note, just the fact that Gabriev, a kindly textbook KnightInShiningArmor, and the only person outside of the youths who was willing to help Polybeus see a better path to heroism, had to perish like that. Whomever the saboteur is, that solidified everyone's hatred of them.
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* It's minor, but when James tells Helseng that having twenty friends is quite a lot, there's a slight twitch in her shoulders and fingers, as if she's shocked and saddened at such a statement. Why this is so is not explained, but it's implied that there's more to Helseng's story than we know, and it isn't pretty.

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* It's minor, but when James tells Helseng that having twenty friends is quite a lot, there's a slight twitch in her shoulders and fingers, as if she's shocked and saddened at such a statement. Why this is so is not explained, but it's implied that there's more to Helseng's story than we know, and it isn't pretty.pretty.

* The brutal CurbstompBattle Miguel inflicts on Ivan not only establishes the older wizard as a scumbag, [[HeroicBSOD but it leaves the poor conjuror's self-esteem in tatters]], not helped by Polybeus' constant passive-aggressive jabs from earlier.
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** Later, [[WelcomeBackTraitor most of the students make him feel very unwelcome]], no doubt because of what he helped do.

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** Later, [[WelcomeBackTraitor most of the students make him feel very unwelcome]], no doubt because of what he helped do.do.

!!Tournament of Death

* It's minor, but when James tells Helseng that having twenty friends is quite a lot, there's a slight twitch in her shoulders and fingers, as if she's shocked and saddened at such a statement. Why this is so is not explained, but it's implied that there's more to Helseng's story than we know, and it isn't pretty.
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* Polybeus seems like a comedic blowhard who obsesses way too much over his one-sided rivalry with James...but then he talks to Ivan about it, and it's obvious that [[IJustWantToBeSpecial he's just really desperate to owe up to his culture's idea of legendary heroes.]] He ends up ranting about how great heroes [[VirtueIsWeakness don't need friends]], and how they are the only people who matter. Judging by the tone of his voice and a previous statement about [[FreudianSlip how not everyone can be born lucky or gifted]], he has little faith in his own ability. He even lashes out and insults Ivan's lack of ambition compared to him, [[KickTheDog wondering how James could befriend someone who he sees as a drab coward.]] The Ruslovakian is justifiably upset by this, but seeing Polybeus tearfully beat himself up over not being able to solve the SnipeHunt James gave him produces no shortage of pity on his part.

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* Polybeus seems like a comedic blowhard who obsesses way too much over his one-sided rivalry with James...but then he talks to Ivan about it, and it's obvious that [[IJustWantToBeSpecial he's just really desperate to owe up to his culture's idea of legendary heroes.]] He ends up ranting about how great heroes [[VirtueIsWeakness don't need friends]], and how they are the only people who matter. Judging by the tone of his voice and a previous statement about [[FreudianSlip how not everyone can be born lucky or gifted]], he has little faith in his own ability. He even lashes out and insults Ivan's lack of ambition compared to him, [[KickTheDog wondering how James could befriend someone who he sees as a drab coward.]] The Ruslovakian is justifiably upset by this, but seeing Polybeus tearfully beat himself up over not being able to solve the SnipeHunt James gave him produces no shortage of pity on his part.part.

* Zebul Blaa, a dark elf and RecurringExtra, breaking down in tears in front of Charlotte when he confesses to being TheMole for the Summer Prince. All he wanted was to be free from having to choose allegiance with either the Seelie or Unseelie court, and he ended up aiding in a horrible racket. It's obvious that Charlotte recognizes his reasoning as being very similar to her own problems.
** Later, [[WelcomeBackTraitor most of the students make him feel very unwelcome]], no doubt because of what he helped do.

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** Later during the Samhain ball, she tells James how she and her kind can never truly be too far from Fairyland. They either live as humans, Ettercaps, or they die. All she wants is to experience the human world, and she just...can't.
-->'''Charlotte:''' You know what I feel like? I feel like a [[TarotMotifs star]]. An observer, stuck high above the world in an empty void. If I try to reach out to the world below, I'll fall in flames and diminish to nothing.
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* Polybeus seems like a comedic blowhard who obsesses way too much over his one-sided rivalry with James...but then he talks to Ivan about it, and it's obvious that [[IJustWantToBeSpecial he's just really desperate to owe up to his culture's idea of great heroes.]] He ends up ranting about how those who don't perform heroic deeds are forgotten and thrown to the wayside, and even [[KickTheDog insults Ivan's lack of ambition compared to him.]] The Ruslovakian is justifiably upset by this, but seeing Polybeus tearfully beat himself up over not being able to solve the SnipeHunt James gave him produces no shortage of pity on his part.

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* Polybeus seems like a comedic blowhard who obsesses way too much over his one-sided rivalry with James...but then he talks to Ivan about it, and it's obvious that [[IJustWantToBeSpecial he's just really desperate to owe up to his culture's idea of great legendary heroes.]] He ends up ranting about how those who great heroes [[VirtueIsWeakness don't perform heroic deeds need friends]], and how they are forgotten the only people who matter. Judging by the tone of his voice and thrown to the wayside, and a previous statement about [[FreudianSlip how not everyone can be born lucky or gifted]], he has little faith in his own ability. He even [[KickTheDog lashes out and insults Ivan's lack of ambition compared to him.him, [[KickTheDog wondering how James could befriend someone who he sees as a drab coward.]] The Ruslovakian is justifiably upset by this, but seeing Polybeus tearfully beat himself up over not being able to solve the SnipeHunt James gave him produces no shortage of pity on his part.
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** Later, when Oomlowt is taking Evelina up to task with Dermberder, Margot tearfully tells her that she's supposed to be a teacher instead of the cruel monster she's been to her specifically. Anyone who's felt abused and put under unrealistic expectations by their own teachers can relate.

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** Later, when Oomlowt is taking Evelina up to task with Dermberder, Margot tearfully tells her that she's supposed to be a teacher instead of the cruel monster she's been to her specifically. She's quick to note how for all of her scolding, she's never offered any advice on how to be better. Anyone who's felt abused and put under unrealistic expectations by their own teachers can relate.

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** Even after putting on a fantastic display in defiance of Evelina, Margot still ends up running away and finding a place to sob from the sheer hatred she's developed for the local SadistTeacher. Thankfully, James is there to pick her up.

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** Even after putting on a fantastic an amazing display in defiance of Evelina, Margot still ends up running walking away and finding a place to sob from the sheer hatred she's developed for the local SadistTeacher. Thankfully, James is there to pick her up.up.
---> '''Margot (face buried in her hands):''' I hate her, I've tried my whole life not to hate anyone or anything, but I hate her. I hate her more than anything in the world, James. I hate her, I hate her, I hate her!
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* Charlotte admitting to James that she envies humanity because they are not bound to the incredibly strict rules of Fairyland. It doesn't help that she cannot decide which of the fairy courts to pledge loyalty to.
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* She's rather blase about it, but Gretchen's backstory isn't very nice. She was approached by her fellow villagers for miracles, and she gave them the means to do so. But they didn't listen to her rules, and [[NeverMyFault proceeded to blame her for their mistakes.]] [[ThenLetMeBeEvil She turned them into toads to give them a real witch if they wanted one so badly.]] Sure, the spell didn't last long and she went for the AAAM afterwards, but still.
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* It's mostly sweet when Ivan declares on the Treadscar Path that James and Gretchen are his best friends after having just met them, but the two know [[FriendlessBackground what this implies.]] And really, it applies to them too.
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** During the rest at the Treadscar Path, James explains it to Ivan and Gretchen by using an old folk myth about a queen having two daughters, one of which is a dragon due to a witch's curse. He all but states that he feels like the dragon, being born one way but feeling like another, and altogether feeling like the body is a prison. Oh say, can you say TransTribulations?
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** Later, when Oomlowt is taking Evelina up to task with Dermberder, Margot tearfully tells her that she's supposed to be a teacher instead of the cruel monster she's been to her specifically. Anyone who's felt abused and put under unrealistic expectations by their own teachers can relate.

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** Later, when Oomlowt is taking Evelina up to task with Dermberder, Margot tearfully tells her that she's supposed to be a teacher instead of the cruel monster she's been to her specifically. Anyone who's felt abused and put under unrealistic expectations by their own teachers can relate.relate.

* Polybeus seems like a comedic blowhard who obsesses way too much over his one-sided rivalry with James...but then he talks to Ivan about it, and it's obvious that [[IJustWantToBeSpecial he's just really desperate to owe up to his culture's idea of great heroes.]] He ends up ranting about how those who don't perform heroic deeds are forgotten and thrown to the wayside, and even [[KickTheDog insults Ivan's lack of ambition compared to him.]] The Ruslovakian is justifiably upset by this, but seeing Polybeus tearfully beat himself up over not being able to solve the SnipeHunt James gave him produces no shortage of pity on his part.

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** At one point, when his friends bring up the ChangelingFantasy in relation to the kidnapped students, he states that there were times when his parents must have believed he himself was an imposter of their kid. Maybe they even WANTED to believe it.

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\n** At one point, when his friends bring up the ChangelingFantasy in relation to the kidnapped students, he states that there were times when his parents must have believed he himself was an imposter of their kid. Maybe they even WANTED to believe it.it.

* The HORRIBLE treatment Margot gets from Professor Evelina. All because she needs a gauntlet to control her unstable fire magic. The teacher spends every opportunity she has criticizing and belittling her like she were an unwanted pest. James has every reason to feel infuriated.
** Even after putting on a fantastic display in defiance of Evelina, Margot still ends up running away and finding a place to sob from the sheer hatred she's developed for the local SadistTeacher. Thankfully, James is there to pick her up.
** Later, when Oomlowt is taking Evelina up to task with Dermberder, Margot tearfully tells her that she's supposed to be a teacher instead of the cruel monster she's been to her specifically. Anyone who's felt abused and put under unrealistic expectations by their own teachers can relate.
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* UNMARKED SPOILERS AHEAD*

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* UNMARKED SPOILERS AHEAD*
AHEAD
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Just because it's an AffectionateParody of the WizardingSchool genre doesn't mean there aren't moments that make you go "oof".

*UNMARKED SPOILERS AHEAD*

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!!The Meddlesome Youths

* The implications throughout that James has AbusiveParents. No, scratch that, abusive transphobic parents. Time and time again, it's clear that they only saw him as Elizabeth. While he's glad to leave it all behind, he can't help but feel more than a little bad about it.

** At one point, when his friends bring up the ChangelingFantasy in relation to the kidnapped students, he states that there were times when his parents must have believed he himself was an imposter of their kid. Maybe they even WANTED to believe it.

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