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unfortunately you can’t meet him at the library after the midterm announcement if you haven’t triggered the bugbear question in crypto (since the question itself becomes the topic of conversation when you do meet him), so you need that to continue his route :) 

according to the guide, asking him about his real name during the midterm announcement should ensure the bugbear question later on, though if you’re lucky, you can get the question before meeting him in class (like i did), hope this helps!

god i had the same problem with barnaby's fail end CG...i failed more than 5 times to get it before giving up lmao, but i found a comment below me with the steps that helped me get it if you haven't seen it yet. hope this helps :)
(credit to @/Nokayo)

1st meeting (class):

"hi" & "comment on how interesting the play is"

2nd meeting (class):

"compliment barnaby's notes"

3rd meeting (6:00 PM library, work on class project with barnaby)

"disagree"

4th meeting: (6:00 PM library, work on class project with barnaby)

"go to the door"

he still avoids you if you try to approach him in class after this, but it should give you the CG you're looking for

if you can’t find him during lunch, then try looking for him during free time or when you skip class in the locations specified. there’s a very good chance you’ll find him eventually while skipping class as you only have 1 class with him, so i recommend building up on BAD and skipping frequently. that’s how i initiated most of his events after my second interaction with him.

as for how i got the second interaction, it might’ve been luck, but i literally just chose his icon when it was time for lunch and it initiated it for me. when i did, it took me to the garden, so maybe try going there more often? 

if you’re still having a hard time finding him after doing his first interaction in s.o.m then it might just be the rng messing with you atp :’) or your game is bugged, this has been happening to a lot of people tho so if in doubt, just reinstall 

i believe you have to trigger his route first by approaching him in study of malediction (which is the only class you'll ever have with him) so afterwards you'll have to initiate events with him either by having lunch with him, skipping class, or during free time.  some places he frequents are: library, garden, forest, and kitchen. hope this helps :)

just a small little note for bugbear's route: the smile question is NOT required! if you're unsure if you have enough points for his success ending then by all means stack up on STR for it, but don't worry if you don't have enough for it, i got his success ending without it :)