You know how we do the work study or get tutoring thing at 6 pm? Just click the first option (studying and chose whichever topic to study with, I chose the second option) , if you get another character that appears , don’t worry he will appear at 8 pm if you click to be in the library again, Bugbear will be there resting his head.
this can only be obtained if you done the Smile question since he asked you to meet you in the library
i might be wrong about some parts since I’m going off of memory and was the direction I chose !