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General
- Any time Pikachu feels like he's failed Ash. From fighting Ash after being captured by the Iron-Masked Marauder's Dark Ball and Shadow-fied, to watching Ash die during the Scuffle of Legends, to losing to Wallace's Greninja.
Kanto
- Ash finds out the fate of his father from Ho-Oh.
- Delia gets Reminded, and has to come to terms with Ash constantly getting into life-threatening trouble even though he is just a child.
Johto
- Molly pleads for her imaginary Eevee to not make a Heroic Sacrifice, as she has grown attached to her.
- Cubone being tormented over being the Sole Survivor of her family is worthy of a few tears, especially when Ash enters her inner world and sees how dreary it is.
- Pikachu gets captured in a Dark Ball by Vicious, tortured into a Shadow Pokémon, and forced to fight Ash.
- May distresses over the possibility of another trainer selecting Blaziken (who is still a Torchic at the time) as their starter before she does, which would cause her to lose him.
- Ash's guilt over Latios dying in the original timeline. It was so bad for him that he did not celebrate any of his birthdays after that because Latios' death occurred on his birthday.
Hoenn
- May misses Manaphy, who was like a son to her, when reminded of him by a seawater-scented incense.
- Oak's Charizard and Dragonite sharing a moment thinking about their deceased comrade Arcanine, and the reality that both of them will probably outlive Oak as well.
- Ash finding the last location his father was seen, marked by a memorial stone, and then him inviting his mother, Latios, Latias and Keldeo over to pay their respects.
- There's a lot of panic going around during the Delta Episode, with people around the world potentially seeing their doom coming right for them. Special mention goes to Marill, who had just recently laid her egg.
Sinnoh
- In the Jewel of Life special, we get to see multiple timelines where the heroes failed somehow due to the changes in the past, like one where the Meteor from the Delta episode wasn't fully deflected.
- During the Battle Finale, every time a member on Ash and Co.'s side is badly injured enough to be withdrawn is this, especially considering the stakes thus far.
- In the Battle Finale, the reaction shots of Ash's friends to his death.
- Especially Mawile, and her anguished cry of "DAD!".
- Sceptile insisting to Meganium that he has to get back out there, and Meganium refusing since he's too badly injured and she doesn't want to lose him too.
- Lucario enters Tranquil Fury as he wields Kari against the second, still controlled Creation Trio. None of his usual quips, no sarcasm, no observations, just silent efficiency.
- Absol goes ballistic with grief, and fury, and guilt because every moment where she couldn't perceive Team Galactic crashes into her at once. She throws herself into the fight and is only guided still by her disaster sense because she refuses that the same thing that killed her trainer will befall any of her other friends.
