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I have played all but one ending and loved it (The nurse's ending broke my heart) but I can't figure out what the edgy thing Demayo wants. No one else seemed to have this problem and there was nothing in the read me guide, so it seems i'm just the idiot, though i would really like to be able to finish their route

Ohh I'm so sorry. I should have included that in the read me! You have to show them your diary. Because you're super emo haha