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In general there's no dead times, it's not a very grindy game.
99% of the time, when you don't advance it's because
- you're focusing on one girl (doesn't sound like that's your issue)
- you're not doing relaxation activities with them (sunbathing with maria, smoking with raven, etc).
- Failing that, do a quicksave (so I know we're getting the right save), and drop it either here or on discord (discord's easier for two way contact), and we'll have a look.