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Sai was orphaned as a child and recruited into Root, a secret branch of the Anbu under the leadership of Danzō Shimura.
There, he was raised and conditioned to have no personality, personal connections, or a name; "Sai" being given to him for the purposes of joining Team Kakashi.
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 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.
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's social awkwardness tends to get people angry, because he often speaks without considering his words and their effects on people.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.