* Pinkie's HeroicBSOD.
* Chapter 9. Specifically, when [[spoiler: Rainbow Dash has her wings broken by a thug and passes out, only to later wake up and find [[OutOfCharacterMoment Mare-Do-Well crying over her]] while she attempts to patch them up.]] [[ItsAllMyFault "I'm sorry. I'm sorry. I'm sorry. I'm so sorry."]]
* When [[spoiler: Rainbow Dash rejected Pinkie Pie]], this troper died a little inside.
* [[spoiler:Pinkie Pie after TheReveal. Not only is she mentally fragile, but ''she knows exactly how bad it is.'' She's completely unable to help herself and is convinced that she's damaged beyond repair.]]
* Chapter 21. [[spoiler: It's painful seeing Rainbow Dash and Pinkie Pie (to a lesser extent) exchanging verbal barbs with each other, calling each other out on what they did during the story. You wonder for most of the chapter if their formerly strong friendship will survive at all. Turns into a CrowningMomentOfHeartwarming when Rainbow Dash refuses to give up on Pinkie as a friend.]]