Akaashi seems to be the closest person to Bokuto, often getting dragged into his antics whether he likes it or not. The setter is often tasked with dealing with Bokuto's mood swings, and Akaashi can predict which of Bokuto's moods will surface with each move. Akaashi can tell when Bokuto's playing is off, even if it's something small. They also hang out together outside of practice in school, despite Akaashi being a second year. Although Bokuto can get immensely annoying, Akaashi continues to hang out with him nonetheless. They also seem to be closely involved with each other, as shown when Akaashi reminds Bokuto that he failed his math exam and Bokuto exclaims that Akaashi promised not to tell or when Bokuto suddenly threw off his jacket and Akaashi immediately caught it, suggesting he's used to it.
He also seems to have a list of Bokuto's weaknesses and ways to help him memorized.