History TearJerker / Dimension20

'''Tula:''' [[TheReasonYouSuckSpeech "You are so obsessed with power, obsessed with control, that you have taken this whole family and demanded that every bad thing that has ever happened to us was]] ''[[TheReasonYouSuckSpeech our]]'' [[ItsOkayToCry fault. If you were]] ''[[ItsOkayToCry really]]'' [[ItsOkayToCry strong, you would be able to be sad when bad things happen!]] [[TheReasonYouSuckSpeech Instead of demanding that there was something we could have done!]] It is a big, big forest, and we are just stoats."\\

'''Tula:''' [[TheReasonYouSuckSpeech "You are so obsessed with power, obsessed with control, that you have taken this whole family and demanded that every bad thing that has ever happened to us was ''our'' fault. If you were ''really'' strong, you would be able to be sad when bad things happen! Instead of demanding that there was something we could have done!]] It is a big, big forest, and we are just stoats."\\

*** Pasha N., despite being trained as a forensic scientist, is stuck filing stimuli for the evidence room and had never moved past the tragedy that claimed her brother.

* The deaths of the Rocks Sisters, even though they happened years before the beginning of the series. By all accounts, they were all {{The Ace}}s in their respective field, and as the flashbacks show, they were among the most heroic characters in the world, making them TooGoodForThisSinfulWorld.

** The reveal of the assassination target as [[TooGoodForThisSinfulWorld Queen Pamela Rocks of Candia]]. Her terror and confusion when she recognizes her attacker makes it worse.

* In "Heartache on the Celestine Sea", Gorgug and Zelda have a surprisingly realistic argument over the phone that ends with Zelda apparently dumping Gorgug. It's not a shouting match but Brennan plays Zelda and her hurt feelings extremely well. Particularly wrenching is how Zelda calls Gorgug out on seeing himself as a loser despite literally being a rock star who saved the world. It's a weirdly real moment after a relatively whimsical episode.
* Fabian, after a particularly awful fight with his father's nemesis, gets all but 3 of his father's followers killed, barely escapes with his life, and has his pride obliterated, stuck in an HeroicBSoD. After realising his rash actions have endangered his friends and caused him to nearly die twice, he rips up his Owlbear jersey, a symbol of the things that he deserved through his amazing abilities, and takes off his father's eyepatch, feeling like he doesn't deserve them.
* "Pirate Brawl" is one of the darkest episodes of the entire run, featuring the Bad Kids taking loss after loss to enemies far stronger than them, ending on Ragh's disabled mother possibly about to be murdered by the Shadow Cat. It ends on an extremely depressing note, as the Bad Kids are left to pick up the pieces after learning just how bad things can get.
* Aelwyn Abernant's condition when Adaine finds her is truly disheartening: she's one level of exhaustion away from dying, she's lost the ability to form long-term memories, and is completely powerless. Worst of all, her father, who'd up until this point played ParentalFavoritism in her favour, is completely fine with the fact that she's been tortured for months, even denying that this is torture because they haven't directly caused physical harm on her.
** The relationship between Adaine and Aelwyn moves from simply antagonistic to tragic in this season. After seeing the cruelty that their parents usually reserved for her enacted on Aelwyn too, and that in her broken state, her sister wanted to help her escape, Adaine tries to rebuild their sisterhood. When she cares for her in the hot springs of Kei Lumennura, she uses Detect Thoughts on her, and sees that for all her life, she bore an overwhelming self-hatred for her inaction against their parents' mistreatment of her younger sister, but that the only feeling that was stronger was her fear that they would also direct the abuse towards her if she spoke up, creating a constant feed loop of self-loathing and fear. Her state of mind is, aptly, a bombed out city in ruins.
* Riz's time in Hell outside of the humour of the courtroom shenanigans boils down to a brutal manipulation by first Kalina, and then, unintentionally by his dead father, to destroy the image of his father he never really knew, as he was killed when Riz was very young. Riz crying as he says 'solving clues helps' is, whilst mostly played for laughs, is pretty heartbreaking
** That said, it makes the reveal about Riz's dad all the sweeter, and their interactions in 'My Green Heaven' all the more heartwarming
* Every living main character's deepest fears are exposed in the Nightmare Forest:
** Fabian has always expressed the desire to put his name on the face of the world. However, we learn in the Nightmare Forest that he fears more than anything to be helpless, and his friends not even remembering him, leaving the proud half-elf screaming Gorgug's name in fear. Tying into his greatest fear, he then has to confront Chungledown Bim, a living reminder of his weakness. It marked him so much that [[OOCIsSeriousBusiness he hugs Gorgug harder than he's ever hugged anyone before]].
** Riz, just having witnessed Kristen's death, runs out in the forest all alone to chase her killer. The chase cuts short when he meets Baron again, who lays him a [[BreakThemByTalking verbal beatdown]], arguing that they were made up as a lie to hide the fact that he was being left out by his friends, and says that they'll always leave him for somebody more important, as he was nothing more than a ball.
** Fig has to watch as the AnthropomorphicPersonification of her carefree rocker girl facade binds her and abandons her friends to the forest. While walking, it belittles her all the way, and even taunts her with the idea that Ayda will leave her as soon as she finds out "the real you".
** It's revealed to the audience that Gorgug struggles with the idea that he's still alive, and this isn't some DyingDream where he gets all these wonderful friends and gets to be awesome and popular. It then goes right into the general impostor syndrome that he's feeling regarding his ability to do Artificer work correctly and his general intelligence. When he's faced by a puzzle in order to advance further into the forest, he struggles to get it right, and for getting help from the sphinx that gave him the puzzle, the latter shows him a vision of his parents casting out their whole family after they express concern over them adopting this child.
---> '''Digby and Whilma's extended family:''' Will it not break your hearts when inevitably, the child grows to know only rage?
** Adaine, suffering from an anxiety attack, is too scared of something that haunted her entire life to come back, and represses it. The result is the forest making her believe that she's failed in getting to the heart of the forest due to not accepting to face her biggest fear, and make it seem like she's outside the briar wall, bringing back her insecurity about her worth. Her future self's representation, a lonely elf in widower's garb who has watched everyone she grew close to die of old age at least, shows us that she dreads more than anything else to be alone, incapable of growing new bonds. Future Adaine's trembling voice when she talks about her parents adds even more tragedy to the encounte, like she's just a broken teenager who could never grow up.
---> '''Future Adaine:''' I don't know why I was so easy to discard ...
* Siobhan, similar to the Jawbone moment from Season One, starts crying when confronted with the fact that Adaine's family abandoned her and possibly didn't love her.
* Ayda's dream. She felt, due to her UsefulNotes/{{autism}}, completely alone, isolated, weird and different to everyone else, and felt a great amount of pressure from her past selves to be like them, having been forced to raise herself. When she met and fell in love with Fig, all that changed. The dream counteracts Fig's anxiety about the front she puts up, by means of the fact that Ayda, isolated from the culture of Spyre, saw Fig for who she was and immediately fell in love with her.
* The above moment, similar to the Sandralynn moment from Season One, makes Emily Axford start genuinely crying, and it's just as heartbreaking.
* After trying and failing to persuade their father into simply leaving Adaine behind, rather than doling out the "punishment" he has planned for her, Aelwyn audibly becomes increasingly torn. Backed into a corner by their father's demands to "scour" Adaine's mind for info, eventually all Aelwyn can blurt out is "[Adaine] is just... she's a baby" to Angwyn's confusion. Apart from the sheer, desperate pleading in this moment, it implies that situations like this have been playing out in the Abernant family since Adaine was very young. And those same moments still weigh heavily in Aelwyn's mind.
* This line, when Aelwyn casts Detect Thoughts on Adaine and sees what the wreckage of her mind looked like before Adaine restored it:
--> '''Adaine:''' [[ArmorPiercingQuestion Would you be my big sister?]] I would really like for you to be my big sister.
* In the epilogue, Jawbone offers Adaine adoption papers so he can become her legal guardian. The moment is so emotional that Siobhan bursts into tears instantly.