Tear Jerker / Romance and the Fate of Equestria

• The death of Granny Smith. It's particularly hard due the fact she didn't die of sickness or old age, but while saving Applebloom from Crazyface.
  • Now considered Harsher in Hindsight due to the author's own death of his grandmother.
• Rainbow Dash's reason for sleeping around is mostly due to her own insecurities.
• Annihilara's entire backstory is just full of it seeing as how she's the Princess of Suicide.
• Oddly enough, despite Discord being mostly an Anti-Villain and even betraying the Mane Six, it's hard not to feel bad for the guy once we see how Queen Chrysalis treats him.
• Rainbow Dash confessing her relationship between her and Derpy to her father who doesn't believe that relationships can last. Even worse once he reveals that has no idea who her mother is and thinks that he was doing her a favor by keeping that information. In the end, she pretty much disowns him as her father and gives his cloak that she kept with her to Derpy as one of her first belongings.
• Rarity’s death. Having been around for 195 chapters and was in depression for all of it to the point she had admitted she wanted to commit suicide. In the end she died not with a finished arc, but in a Heroic Sacrifice by saving Pinkie Pie. It’s sadly realistic in how death can just happen and you can just figure it out due to story.