I have a crazy one (seemed crazy to me).
Today I called to pay a medical bill from wife's pregnancy. The bill was ~$4k. We had $2500 in an HRA, and were going to pay the remainder out of pocket. So, I call the billing department, start giving account numbers and amounts, etc. The woman asks me "have you asked for a discount on this bill?" I'm like, "uh, no?" So she gives me a number to call, tells me to request a discount because I am paying in full. I call this number, ask politely for a discount, hold for 20 seconds, they come back with a THIRTY FIVE PERCENT DISCOUNT, eliminating all but $70 of the ~$1400 we were going to pay out of pocket.
HOLY SHIT. This is a thing???