Naruto
With all of the nostalgia associated with this anime, I think that it hurts my heart more than any other. It's not just that, but all of the "what could have been" scenarios, you know? Thinking about how things might have been if Naruto had been raised by his parents, if Sasuke had grown up with Itachi, if Gaara had grown up knowing the truth about his mother... the Naruto feels are simply never-ending!
Honorable Mentions
Those sad moments in anime are what makes those high points all the more meaningful and capture our hearts! Here are some of my other favorite heartbreakers because I'm an emotional masochist! I don't wanna spoil anything, so I tried to be vague...
Akame Ga Kill! *spoilers*
That's a nice character. It'd be a shame if someone... killed them... I remember Lubbock was when I lost it; I'm not sure if it was losing him, or if it was the fact that that was when I lost hope, but I needed a break after that... Tatsumi, though, was probably the worst because, even after I accepted that there would be no survivors, I still had a sliver of hope for him... So much for main character status </3 ;;
Assassination Classroom
Who else is still trying to heal from this one? From the beginning, there was always an uneasiness for me, that they couldn't carry on forever, with this deadline looming overhead. Then the truth about Korosensei was revealed, and they tried so hard to save him, all for nothing! You almost forget that these are mere middle schoolers, with all that they go through, and then, seeing them all break down like that, I felt tears roll down my own cheeks as my heart broke for them, especially my poor Nagisa </3... okay, I'm gonna stop now ;;;
Orange
So I'm actually only about halfway through this one, but I think it definitely makes this list! I can't imagine how Kakeru must feel, or Naho or Suwa, or any of the characters, really, but especially Kakeru! I hope Naho and Suwa are able to save him, heal him...
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