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 shikamaru and naruto
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I think Naruto's past is más tragic because he didn't get too see his parents and knowing that the Kyuubi inside him killing his parents and the whole village makes it even worse.

-anyway it took me a lot of decision to choose between naruto and sasuke, honestly sasuke is really sad too because sasuke's family got murdered por his OWN brother and also he was betrayed por his own brother and his way of losing his family members was very tragic. Sasuke was also tortured por Itachi's mangekyou sharingan and he got to see how Itachi killed his own parents and im not saying that...
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