Well this is the problem here, I have already finished this quest once. However, due to my clumsiness, I overwritten that save. Now I wish to replay the game but I could not get the staff mission about Ruth to update. Since this is happening, I could not vote to change the rules in the Friday meeting session.
It did not reset everything tho. First, The new save doesn't have the old headmaster quest, but I didn't care that much about it. Then there is my main problem, in order for me to progress further I would need to finish two staff quests. I have finished Sally's quest and now I am left with Ruth's. However, I have talk to Ruth and I am already left with no conversation option, yet the quest didn't update. Because of this, I cannot gather information to blackmail her.