How Many Times Can I Get Minus Five Points in One Game?

Bob says he doesn't care about fashion, but wishes more companies gave better fitted clothes. Mark: "I am slowly everyday learning a bit more about fashion being the sole CEO of Cloakbrand" Chad GPT asks Bob to keep his head up and reminds him that losing a few points is just a small setback in the grand scheme of things. How many times can I get minus five points in one game? We'll find out.