The weather has been determined BEFORE you sleep at 10 PM.Hey man I kept trying and loading the save (10pm on a Tuesday) then try to sleep and nothing triggers. Affection with Anna is 203 and Progress Points: 12.
Any ideas?
As I've written before, it's determined when you start a new day. So, you can save and reload a billion times in your case: if the corresponding day is in fact a sunny day, you'll never trigger the rainy day event for the current day at this point of the day (i.e. 10 PM).