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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.
Sai is very observant, and is always focused on his missions.
Before dying, Shin told his brother that he had to suppress his feelings, and to live for the both of them.
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.
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.
Before that happened, however, Shin died of an unnamed illness and Sai's Root training suppressed most of the memories he had of him.
In the anime, Sai and Shin were forced to fight by Danzō but Shin, knowing that he was dying anyway, told Sai to report to Danzō that he had killed him in battle.
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.
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.
In doing so, Sai was able to start giving genuine smiles.