* In Chapter VII, [[color:green:Lyra]] is forced to watch the ugly breakdown of the relationship between her two best friends, as Twilight and Moondancer are too different to get along without [[color:green:Lyra]] mediating between them.
* In Chapter VIII, [[color:green:Lyra's]] infatuation towards Morning Dew and its ForegoneConclusion.
* In Chapter IX, Twilight completely breaks down upon realising that [[color:green:Lyra]]'s curse is what destroyed her friendship with Moondancer. “First Moondancer, and now you? I d-don't know what's worse: losing friends or losing the memory of why they'll never return...” The fact that her memory is wiped of their conversation moments later does not make this any better.
** The same chapter has [[color:green:Lyra]]'s own breakdown in [[spoiler:Bon Bon]]'s arms after her brief visit to the realm of the Unsung, though this one's at least half tears of happiness, since it's triggered by an [[CrowningMomentOfHeartwarming extremely moving act of kindness]].
* Any time we have to recap what happened to [[color:green:Lyra]] during the first few weeks of the curse. Whether it was her running around in a blind panic trying to get ''anypony to notice her'', setting buildings on fire as a desperate plea for attention, falling into a state of near starvation and madness or how she once got desperate enough to contemplate suicide....well, its pretty hard to read.
* When you're reading through [[color:dodgerblue:Comethoof]]'s [[ApocalypticLog diary]], you just know it can't end well. That said, when you get to the point where [[spoiler: he becomes forgotten too, even to his love of his life]], its heartbreaking. Even though Penny is continually sure [[color:dodgerblue:Comethoof]] is an evil rebel who's come to eat her, the Sarosian watches over her for weeks, trying to get her to recover, until [[spoiler: she eventually dies since she was pregnant with his now half-existent foal]]. He falls into pure madness shortly after.
** The story is sad enough to make [[color:green:Lyra]] glad she wasn't in a relationship before coming to Ponyville.
* In Chapter XII, the death of Granite Shuffle and [[color:green:Lyra]]'s attempted eulogy for him.
* Towards the end of Chapter XV, [[color:green:Lyra]]'s breakdown over her seeming inability to [[spoiler: help Snips and his family get away from his abusive father]].
* In Chapter XVII, [[color:green:Lyra]] [[spoiler: saying goodbye to Nebulous, her father. The fact that he's forgotten her ''and'' divorced from his wife since the curse began makes it even worse.]]
* The ending, just that ending.[[spoiler: Lyra chooses to sacrifice herself to ensure that everything she did remains. DownerEnding indeed, though the alternative options would have been worse.]]
** Made worse when you realize there was the fourth option for Happy Ending. [[spoiler: Dawn's Advent, the last song, brings the Unsung pony back to normal by making it like they were never Unsung. However, it was part of Firmaments which imprisoned and kept Aria Unsung. This could mean that Cosmic Matriarch left a failsafe, in case Aria was not dead. All Lyra had to do was to make Aria play Dawn's Advent and it would be as if Aria was never Unsung, never creating Unsung realm and never Unsinging any ponies, like Comet Hoof or Lyra. This may also make Discord never appear in changed universe and Nightmare Moon to never happen. Neither Lyra nor Aria have even thought of this solution]] Now, you are allowes to cry, realizing that this makes the story truly a tragedy.