The times that stuck thing happened to me was related to talking to someone, for instance the director, or one of the teachers, maybe KAren even i can't remember. Maybe its not your case, but if it is, the solution for me was going to the main hall in school and clic skip classes and the person that you need to talk to will come to you.
I hope that helps.
Try going to the hall in the house and hit wait untill he shows. Its a similar trick to what I said above. If requirements are met, it will trigger. Read the desrciption, maybe there is a specific time. Try the trick mindlessly for week anyway