No
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He doesn't have a girlfriend in Naruto. He just has pairings that people support. I don't think he'll ever have a girlfriend.
Naruto Shippuuden does not have "Seasons". It has Sagas (like all Anime series') The Saga in which Naruto defeats Pain is called the "Pain Invasion Arc".
Chapters 430 to like 444. The way the chapters are im guessing that it how much is about Naruto vs. Pain.
obviously yes, because Naruto was only able defeat pain because of the nine tailed fox. Pain defeated Naruto, but Hinata came , got herself killed and Naruto became enraged. Then the fox cam out and gave pain a hard time. pain still beat him in while naruto was in 6 tails mode. Then Naruto's 8 tails came and pain probably would not have been able to handle him. When Naruto was transformed back to himself he was healed by his father!!!! So pain was then wounded, weak and couldn't control any other paths but the deva path. Naruto then defeated him because he had all his strength left while pain was not strong. Naruto's Nine tailed fox cant be counted because naruto does not control it and it runs wild.
No, they are not even girlfriend and boyfriend. So they can dump.