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Over time, Sai came to think of Shin as an older brother and looked up to him.
Unfortunately, the final step in Root training called for the two to fight to the death to eradicate all remaining emotions.
In the anime, an attempt to gain a powerful fūinjutsu after seeing the Third Hokage sacrifice his life in an attempt to defeat Orochimaru, led Danzō to supervise Sai while he learned how to use the Sealing Technique: Tiger Vision Staring Bullet, noting that it would be dangerous as he would have to use "emotional energy" in order to make the technique stronger.
Sai struggled greatly with this endeavour as it conflicted with his training and, consumed by negative emotions, his training was seemingly left incomplete.
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.
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.
This was due to his inability to realise the difference between a rude statement and a true statement.
During his time in Root, Sai was ordered to eliminate a large number of individuals that posed a threat against Konoha.
At the time he was assigned to Team Kakashi, the last assassination he performed was of Unmo Samidare.
After spending more time with Team Kakashi, Sai comes to appreciate bonds, particularly the bond that exists between Naruto Uzumaki and Sasuke Uchiha, though Sai would come to have his doubts about Sasuke when he began to commit crimes on an international scale, which Naruto would suffer for.
This causes him to break out of his emotionless shell and start to remember the times he had with his own "brother", Shin.As per standard Root training, Sai was conditioned to remove all emotions and as such, has difficulty connecting with others.