There seems to be a bug when you're going to school through the park in the morning and the two bad girls ask you to buy them booze. If you click on them more than once, they seem to give you the booze money each time. Then you go and get the booze, give it to them, and they leave. You still seem to have the rest of the booze money, which means you can't go to school or end the day, so that save is f'ed. Happened to me on a playthrough as Poppy's slave.