I was able to talk to the blonde haired girl about the teacher's stolen wallet and it gave me the indication that I needed to lower her health, but whenever I do that, the only dialogue option is to send her to the nurse.
At 60 health it says that I need to "hurt her and then ask." At 40 health it only gives me the option to send her to the infirmary. I have my power stat maxed out, so as far as I know, I always reduce her health by 20 per round of punishment. Is there a solution?
I got the black haired girl to say that her sister was falsely accused of stealing wallets, but before I did that I unlock the blonde haired girl's volunteer punishment and now I think that is keeping me from completing the black haired girl's quest to free her sister.