I don't remember that particular part of the story very well, but I'll do my best to give some advice and hope it works. If you want to progress a specific girl, check every area at every opportunity. Some events trigger only on certain days of the week, at a specific time of day, while doing a specific activity. If you aren't sure about a specific event, try saving before each action for an entire week, and reloading the save if you do not get the event you are hunting for. I know it's a lot of trial and error, but for some events it's the easiest way to do it.
If you are talking about increasing a girl's level after a punishment event, save before the punishment and try various things in order to reach max on each punishment stat, reloading (or hitting the restart from beginning button) if you don't reach the stats required by the end of the punishment. Some punishment's require various things to be purchased online before you can succeed in maxing out the stats as well, so check the online shop.