Yeah thats what I do every night but let me show you what I do to advance and it seems to like... not pop up at all.You need to sleep on your bed every nights to advance the day.
I wake up. > Go to School > Go to class > Recess > Talk to teacher to get out of recess > class continues > afternoon > I go to Racheal's house to boost her love meter > Go back home > Go to my room > sleep > Next day will prompt the Hero to say "I got to go to school" line. I did this a lot of times and it still seems to never be weekends...