- Derpy's backstory. Born to loving parents, who disappeared during a storm, she was then forced to stay with Countess Glass, who emotionally and physically abused her for years due to her 'deformity' until she ran away. Hoping she'd be left in peace, after one night where she becomes very drunk and has a one-night-stand, she becomes pregnant and has no idea who the father is.
- Fancy Pants' parents died begging Cascadius to spare their son, but he could make no promises.
- Similarly, Blue Murder is desperate for this to be One Last Job, but Cascadius can't promise that.
- The murder of the old Bearers in Lost Reflections is all heartbreaking, but Addie's death, desperately apologising to the already-dead Zipadee for panicking and triggering the trap that killed them both is particularly gut-wrenching.
- The fate of Trilby. Handed over to insane cultists because her father got arrogant, we don't see much of what is done to her, but Royal Flush keeps asking Cascadius about her, and even that little information is enough. By chapter 9, she barely remembers her name, and wishes for death.
Tear Jerker / The Rejuvenation Play