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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.
In the anime, it was shown from his Infinite Tsukuyomi dream that his greatest desire is to fully rediscover his emotions and connect with as many people as possible through it.
He later appeared to show genuine anger while explaining to Sakura about Naruto's feelings for her and later when she lied to Naruto about the predicament with Sasuke and trying to use a fake confession to get him to give up on Sasuke.
Before Shin's death, Sai created a picture book that would depict all the opponents they faced and illustrate the feelings that they shared for each other.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.Due to this training and his lack of social experience and personal initiative, Sai has great trouble in understanding how bonds between people can motivate others.He often showcases this confusion after thinking about why Naruto would go so far to save Sasuke, a traitor, even though Naruto had not been ordered to do so.