Bug: going on the fancy dinner date sets your money at zero regardless of how much money you have. It should just subtract the $100 for the food, not every dollar you have.
Does this game have a Discord?
Unfortunately, that is not the case. It's SUPPOSED to clean you out, regardless of how much money you have.
At the end of your dinner date, you're supposed to realize (I think it appears in yellow lettering), that if you keep dating her, she's going to clean you out or keep you broke, which then unlocks the getting smarter through online courses to get promoted within your job, so you can make MORE money... but not that much it seems...
So, it's doing what it's supposed to do... sucks, I know... after getting a lot of cash and all of a sudden, poof...