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1The actual episodes already had many sad moments, but the extended fic adds them a lot.
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3* Twilight reveals in the second chapter to Jewelius that she's planning to sing "Love is in Bloom" during the wedding reception, and she ends up singing it along with him. Then the entire wedding rehearsal incident occurs in the third chapter…
4* When Jewelius grills Shining Armor in the fifth chapter, the prince [[ArmorPiercingQuestion asks whether or not it was entirely Chrysalis's fault that the captain disowned his sister for trying to warn him]]. The ashamed Shining Armor ends up admitting that [[NotBrainwashed Chrysalis had no influence over that decision of his]]. Twilight makes a heartbroken expression as her brother hangs his head.
5* When Celestia is subdued by the Royal Guard, the wedding guests do nothing but glare resentfully at their once adored ruler. Crestfallen because of this, Celestia wonders if she's going through [[EtTuBrute the same feelings]] as Twilight (who's at the time lying unconscious on the floor) did at the rehearsal.
6** Suddenly losing her authority and prestige because of her nephew using her failures to denigrate her is implied to be such a shock to Celestia that she [[HeroicBSOD turns despondent]]. When she and the other disgraced heroes are sentenced in the next chapter, she remains silent for the entire scenario while her sister and the others try to speak for their defense.
7** In the 15th chapter, Celestia has become low-spirited due to everything that's happened so much that she's starting to be afraid Twilight is too much wrapped in Jewelius's influence. Cadance has to urge her not to give up on the hope of her faithful student coming around.
8* When the heroes' failed escape attempt [[NiceJobBreakingItHero succeeds in making them look as guilty as Jewelius says they are]], the wedding guests do nothing to help them and only look at them with disdain as the guards take them away.
9* When Jewelius sentences them to slavery, the Mane Five [[AintTooProudToBeg resort to tearfully begging for mercy]].
10* While he's being transported away from Canterlot, Shining Armor laments over being separated from Cadance, Twilight, and his parents. He also laments not being allowed to know if his sister (whom he last saw falling unconscious) is alright or tell her how sorry he is for renouncing her.
11-->'''Shining Armor''': [[IronicEcho I could've gained a wife. But instead… I just lost a sister.]]
12* Anytime Celestia, Spike, Shining Armor, or the Mane Five express remorse over shunning Twilight and inadvertently letting the invasion to happen. Celestia and Shining Armor also beat themselves over being unable to realize Cadance was imprisoned underground and impersonated by an imperfect impostor. [[GuiltComplex Shining doesn't even care to excuse any of his actions with Chrysalis' mind-control spell]].
13* Jewelius sends Spike the wedding cake toppers and Rarity her bridesmaid dress to rub salt in their wounds and remind them of the failures they were banished for.
14* Cadance telling everypony [[Recap/MyLittlePonyFriendshipIsMagicIDWIssue11To12 how Twilight secretly helped her and Shining Armor to become a couple years ago]] makes Shining Armor feel even more horrible about banning Twilight from the wedding. Cadance is understanding instead of angry with him, but when she asks him to reconcile with Twilight before they get married, it means in his mind that his relationship with the mare he loves depends on his reconciliation with his sister. The revelation of Twilight being a ShipperOnDeck toward her big brother and foalsitter since her fillyhood also makes the Mane Five better realize how utterly [[ItsAllAboutMe selfish]] their own behavior was during the wedding preparations.
15* The [[TheReasonYouSuckSpeech lashing out]] Twilight gives her brother, friends, and mentor in the 10th chapter. They came a long way to make amends with her by saving her from vengeful Changelings, and she bitterly renounces them as payback for how they treated her at the rehearsal. The point's driven home [[IronicEcho with their own parting words from the rehearsal thrown back at them]]. It is for Shining Armor a confirmation of what he has been fearing ever since his banishment; that his once-great relationship with his little sister has been ruined because of him.
16-->'''Applejack''': Twilight, please don't do this!\
17'''Fluttershy''': We're your friends!\
18'''Twilight''': No you're not! [[FalseFriend You only hang out with me because my connections could help you]]. You never cared about me or anypony else! I can't believe I fell for it for so long.\
19'''Shining Armor''': Twily-\
20'''Twilight''': And you can forget about me calling you my BBBFF anymore! In fact, [[IHaveNoSon I don't even have a brother]]. Now if you'll excuse me, I'm going to go check on the princess.\
21'''Celestia''': Twilight, I-\
22'''Twilight''': ''[[IronicEcho You]]'' [[IronicEcho have a lot to think about]].
23** What makes this worse is that Cadance just got injured and Twilight, mistakenly believing the others caused it by bringing her to Canterlot before Jewelius could reinstate her[[note]]as he had falsely promised Twilight[[/note]], is [[WhatTheHellHero calling them out for that]]. Though she was not happy about seeing them due to Jewelius corrupting her against them and responded with annoyance to the rumors they had heard about the Changelings chasing her, she didn't lose it before [[BerserkButton she found her beloved foalsitter lying injured on the floor]].
24* The revelation that [[spoiler: the large number of royal guards who were injured by the Changelings yet [[UndyingLoyalty remained loyal to the dismantled princesses]] were [[ThePurge murdered on Jewelius' orders]], with their relatives tricked into thinking they were casualties of the invasion that was their dismantled captain and Celestia's faults]]. Celestia and Shining Armor are utterly shocked by this as ([[spoiler: the latter had many friends in the Guard]]), feeling some responsibility over [[spoiler: the fate of their murdered loyalists]].
25* In the 12th chapter, as everypony waits for [[spoiler: Celestia's [[PublicExecution hanging]] to commence]], the chained and disgraced heroes are [[ShamedByAMob subjected to insults from Canterlot's citizens]] who blame them for what they suffered because of the Changelings' attack as well as everypony who lost their lives. [[CassandraTruth Nothing the desperate heroes say can convince anypony]] that [[spoiler: Celestia's hanging is wrong and that Jewelius is the true villain]]. Twilight herself doesn't really like to have [[spoiler: Celestia hanged]], but she claims that she has done all she can to help her former loved ones, and worse yet, her friends and brother's attempts to make her listen to reason only upset her to the point that she snaps, screams a BigShutUp, and bursts into tears. The citizens thus redouble their contempt for the captives, who sadly concede that Jewelius, manipulator though he is, has gotten everypony wrapped around his hoof - [[spoiler:until Celestia turns things around by apologizing to everypony and earning the crowd's forgiveness, which starts the ball rolling for Jewelius' eventual downfall]].
26** Lyra Heartstrings, Minuette, and Twinkleshine [[WhatTheHellHero call the heroes out]] for not caring about their disappearance and the Mane Five of shamelessly replacing them as bridesmaids. Shining Armor [[NotHelpingYourCase thoughtlessly tells them]] that Chrysalis claimed they were in the wedding only because they wanted to meet royalty. Offended that anypony believed such slander about her, Twinkleshine bursts into tears as the crowd's ire toward Shining Armor grows.
27--->'''Shining Armor''': I didn't mean to hurt her feelings!\
28'''Twilight''': But you did! Just like me.
29** Suddenly, an [[ProducePelting egg is thrown in the silent Celestia's face]]. The thrower turns out to be a filly who tearfully reveals that her parents were attacked by Changelings and are still in the hospital, blaming Celestia for it. A random mare then screams that her husband, a member of the Royal Guard, died. Celestia says nothing but feels pity and guilt.
30** When [[spoiler: Celestia is given a chance for final words, she sadly apologizes to Twilight and everypony else for failing them and everypony who lost their lives, accepting that perhaps she's not meant to be Equestria's princess anymore. She believes that she could have prevented all the suffering caused by Jewelius had she not placed her trust in the wrong ponies. [[FaceDeathWithDignity As a last token of love and caring]], she raises the sun and asks Twilight to take care of everypony for her. Twilight and the crowd are so moved by Celestia's remorse that they start demanding Jewelius to stop the execution. They're unable to change his mind and watch in horror as Celestia falls through the trapdoor. Fortunately, [[ShootTheRope Luna saves her sister]]]].
31* When the fugitives go seek shelter from Ponyville, it's revealed that Jewelius has been persecuting the entire town with raised taxes and trading prohibitions because it's the home town of the "traitorous" Mane Five. Nopony dares to walk in the streets anymore because Jewelius's soldiers might come to punish anypony who tries to go against the harsh laws or cause trouble just for laughs. Mayor Mare offers a hiding place in the town hall for ponies who resort to thievery in order to provide for the needy (one of the hiders is Scootaloo), the Cakes have barely enough food to feed themselves and their twins, and the Apples have been forced to harvest about all their apples without having the time to grow more for the starving ponies.
32* The moment Twilight finally realizes how [[spoiler:evil Jewelius -- her new friend, mentor and [[LoveInterestTraitor fiancé]] -- truly is]]. After [[spoiler: he has forced her into submission [[IHaveYourWife by threatening the lives of her imprisoned parents]]]], and she's left alone in the throne room, she breaks down, feeling the same sense of loneliness and betrayal like she did when she was abandoned at the rehearsal, with the [[MyGodWhatHaveIDone added guilt]] over treating her former loved ones the same way they treated her back then. Fortunately, [[spoiler: Raven Inkwell (who is actually a Changeling in disguise) arrives to get Twilight out of this predicament by freeing her parents and helping them escape]].
33* At the beginning of the 17th chapter, the Mane Five and Spike are on the verge of losing hope when they are unable to come up with a plan to stop [[spoiler: Jewelius]] without Twilight, admitting that the villain was right about them being nothing without her.
34* Crossed over with Heartwarming, the 17th chapter's reconciliation moment between Twilight and Shining Armor. She begins by [[ItsAllMyFault blaming herself alone]] over everything that's happened between them, tearfully saying that she'll do everything in her power to earn his forgiveness. Unable to just listen and let his sister take all the blame for herself, Shining Armor sheds more tears than her while speaking and tries to take all of the blame instead.
35-->'''Shining Armor''': How can you say all that?\
36'''Twilight''': BBBFF?\
37'''Shining Armor''': How can you put all this blame on yourself when most of it wasn't entirely your fault? How can you still call me that? How can you still love me after what I did?\
38'''Twilight''': You're my brother, I will always love you no matter what.\
39'''Shining Armor''': But you were right. You saw the signs, you tried to warn everypony, we didn't listen, but you were right. I made you look like such a horrible person in front of everypony. I kicked you out of the wedding that you set into motion a long time ago. I should've followed my instincts like you did. I should've known something was wrong with the bride. I should've listened to you and I'm sorry. I am so sorry.\
40'''Twilight''': Please, no more. ''[hugs her brother who reciprocates in kind, with Cadance also joining in]''
41* Though [[spoiler: Lieutenant Shackle]] undergoes a HeelFaceTurn and helps the heroes win the final battle, [[TheAtoner she is so wracked with guilt that she chooses to go to prison with the other conspirators and be a better pony after her sentence is served]].
42* Despite everything [[spoiler: Jewelius]] had done and his well-deserved end, the heroes — especially the three princesses — [[SympathyForTheDevil are saddened that he couldn't have been redeemed]]. He may have been evil, but [[spoiler: he was still the princesses' family]].

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