Interesting!
So you saved, did the Gamble option, didn't win, before the day passed you returned to the main menu, loaded your save pre gamble and tried gambling again and now the day won't progress?
What day are you on? Did you save during dialogue? Are you loading from one active game into another? (Returning to the main menu is how the game resets certain variables. If clicking +1 day buttons doesn't end with the day ending that means the underlying EndDay(); function got broken somewhere, which 90% of the time is tied in with a load issue.)
I can look into this issue this evening. I'm hoping it's just a loading from one active scene to another active scene issue bc that's an easy fix haha. If you don't want to wait for a new build, try exiting the game completely, reopening it and then loading into that file from the main menu.