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The greatest change in his personality, however, came after he encounters his reincarnated brother.When Shin is used as a living bomb by Deidara, Sai became truly enraged for the first time and attacked Sasori and Deidara mercilessly, showing genuine rage on his face.Sai had read somewhere in a book that giving somebody a nickname would bring you closer to that person and develop your friendship, this resulted in Sai hurting Sakura Haruno's feelings, because he called her "ugly", stating the first true character trait that came to his mind.This also nearly led to enraging Chōji, while eating barbecue with Team Asuma and Team Kakashi he nearly called him "fatso" before Naruto covered his mouth before he could finish.When first introduced, Sai was distinguished by his total lack of emotion which he often masks with a false, cheerful, yet transparent façade.After much mental conditioning and training while in Root, Sai had suppressed almost all of his emotions, laying all of his loyalty to whoever commands him, and thus making it easier for him to accomplish dangerous, unpleasant, or unethical missions.Realising he was offending people by saying characteristics that came to his head, Sai decided to take a different approach by saying the opposite of what came into his head.In this way, at the same event Sai called Ino "gorgeous" (although he truly meant to call her "ugly"), much to Ino's surprise, Naruto's relief, and Sakura's outrage.
This was due to his inability to realise the difference between a rude statement and a true statement.
In doing so, Sai was able to start giving genuine smiles.
Wanting to experience personal bonds for himself, Sai sets out to make as many friends as he can.
Sai organised the book so that his and Shin's portraits would be located at opposite ends of the book, and in the centre pages would be a picture of them holding hands.
Some time after the loss of Shin, Sai forgot that this was his intention, and the picture book was left unfinished, though he could never bring it upon himself to discard the book.