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• Erstin's death in the anime. There's a reason episode 17 is the Wham Episode.
• Watching Aoi get attacked by a mob and walk to her death to protect Mashiro. Even if She Got Better, it still hurts to watch.
• The end of episode 25, when Arika is reunited with her mother at last...and has to destroy her corpse and the system using it.
• Erstin's death in Mai-Otome. You know the writers are serious when they play a montage for you, replete with equally sad music.
  • And then, over the next few episodes, It Got Worse as all the cheerfully irresponsible behavior that used to be played for laughs stopped being funny. This troper was depressed for hours.
  • Also when Arika meets her mother for the first and last time in her life: (Arika twirling around girlishly) "Hey, mom! I'm a real Otome! It suits me, doesn't it?" And then the vision where Arika runs into her mother's loving embrace for just a fleeting instant. Both Mashiro and the viewer has a hard time keeping the promise not to cry.

• A private moment between Alyssa and Miyu, in which Miyu tries to reasssure Alyssa that Natsuki cares for her, but Alyssa remains unconvinced, and tearfully tells Miyu that she's all she has. Arika witnesses this scene, and is so disturbed by the possibility of crushing that hope that she's initially reluctant to fight against Miyu in the combat exhibition. Similarly, the part when it seems as though Miyu is about to die protecting Alyssa.
• The real Mashiro's death scene.