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Yes, throw out the whole concept that Naruto called Sakura his girlfriend in front of his father, also throw out the smile he gave her at the end of the chapter and toss away one of the most important themes in Naruto which is to never give up and persevere even though everything in to world seems to be against you and you would get that scenario. You are thinking WAYYY too much into it, that scene has about a 0% chance of happening in my eyes.
Naruto would say something more like: I don't know the feelings of losing someone so special and I don't know what I would do if it ever happened. I also have a girl I love named Sakura, she is one of the many shinobi standing out there on the battlefield and I don't know what I would do without her... but, at the end of the day, I made myself a promise, and that was to bring a smile on her face no matter what the situation.. and no matter how tough it is for me personally. Do you think Rin would be happy with what you have become? Do you think Rin would like this Obito? I think no matter what Rin would want what's only best for you and that is to live your life to the fullest even though she isn't here to celebrate it with you.
Dear Lord, that was brilliant! That should be part of Naruto's talk-no-jutsu.
Naruto is challenging Obito's "I am no one. I don't want to be anyone!" statement. When Rin died, Obito rejected his entire self, like his dreams and his ambitions. Naruto doesn't like that because exactly because dreams and ambitions are so important to him. When he was all alone, his dreams and ambitions were all he had. Without those, he would have simply withered away and become the dead end kid that many people saw him as.
