Sometimes progress needs a couple days to pass before the event unlocks. Usually 3 or less, but occasionally up to 7 days. If you've let 7 days pass and it isn't triggering, go hour by hour from after school to dinner (wait, check her room, wait...)
Also, make sure to check YOUR room. I've misread the progress hint more than once.
Also, make sure to check YOUR room. I've misread the progress hint more than once.