How am I the stupid one? If you owe someone money as in the example Akio posted you don't physically have -5 dollars, you have 0.
You have no money and owe $5. The $5 is taken into account as an overall minus $5 from your balance, leaving you with -$5 dollars.
When you have a negative amount of money, that means that you owe more than you have. This is basic math.
You don't have physically negative five dollars, but you physically owe negative five dollars. I have no loving idea how you think somebody meant they could have physically negative five dollars and you're being a prick for insinuating they were