heres what i did to get his route/good end:
- once you can skip class (by getting BAD STUDENT 4) go to the gardens or forest to meet bugbear and and choose accept to enter route
- meet bugbear at lunch/freetime for the 2nd meeting
- then approach him again during class (make sure you have 10 STR to be able to ask abt his smile for his success? end) ask his real name two times for crypto question
- during crypto choose the bugbear option, if you dont get the question you wont be able to continue his route (for me i kept retrying till i got crypto question)
- go to the library at 8pm after succesfully picking bugbear option
- 5th meeting is guaranteed at night after the library meeting
i did this like a year ago and i think it still works!! ^^