Tear Jerker / A Growing Affection

Get the Kleenex...
  • The deaths of Karin and Yori.
  • Sakura's rant to Rock Lee about how "she does NOT love Naruto" at first starts off as just Laser-Guided Karma catching up to her until it becomes clear how much she regrets the missed opportunity.
  • Kankuro's death is extremely painful. Of note is Naruto admitting that he and Kankuro had a running joke based on Naruto's dislike for Kankuro at the Chunin Exams, prompted by the latter's "I like you, kid", and while he knew they both knew it was a joke but that Naruto wishes he had taken it back before Kankuro died.
  • Gamabunta's death.
  • Jiraiya calls Tsunade up to tell her that he's found Orochimaru's body and to say goodbye, since killing Orochimaru's body will set off all the traps he's set up around it or Jiraiya will simply bleed out afterwards.
  • Sasuke regains control of his body long enough to say his goodbyes and to hold it still for Naruto to kill. There's also the fact that no matter what else happened by that point, Sasuke was going to die no matter what ANYBODY else did.
    • When Naruto learns that Jiraya is dead and watches as he accompanies an at-peace Itachi, Sasuke, and the other four Hokages to death with the Shinigami, Naruto BSODs so hard he briefly becomes an Empty Shell.
  • When Sakura gets her arm ripped off when Pein storms the Leaf village. Not only does Naruto lose his shit when he watches it happen, but the Pein path doing it to her was aiming for her stomach first...but rethought it because he had a mission to fulfill.
  • We get to see all of what Gai could have been... and it hurts. Gai wins all of his little bets with Kakashi, who accepts his penalties without issue; Gai killing Kisame the first time they met so Itachi could have brought destroyed Akatsuki before it became truly dangerous; Gai becoming the fifth Hokage ushering an era of peace and vitality; Gai watching Naruto become Hokage and him issuing Neji, Tenten and Lee their Genin squads; a pair of children who look suspiciously like Hana and Shizune with his eyebrows. Thankfully, he's allowed to take this last image with him to the next life.
  • Gouki, heavily injured but still in one piece, chooses to end his life by forcing Sakura and Hinata to seriously incapacitate him and have his last of kin, Naruto finish off. He wishes them well and his last words are to his wife, Kohaku.