Sanguine likes Boss! He's a genuinely cool guy and he's super easy to get along with, and he can easily see why so many people are swooning over him— he's cute and charming, and while Sanguine doesn't have a crush himself, he respects the hell out of everyone else's. That being said, he gets the impression that Boss is the kind of guy to take too much on his own shoulders, to the point of his own detriment. He knows for a fact that Boss doesn't get enough sleep, and it worries him.

He doesn't blame Boss at all for bluescreening after that last game— while he doesn't know the extent of Boss's affections for Maki and A, he knew that he was fond of people on both teams. He regrets that wasn't more he could have done to help Boss, and wants to try and be there for him in the future.

And he would totally be willing to give guitar lessons.

How would Boss feel if people actually did start drugging him with sleeping potions?