This post from 2011-2013 is my favorite all time chowthread.
There may be no more stories 800+ posts later, but if there are, bring them on!
I have a cringeworthy story that is funny in retrospect, from back when Juniors in Westwood (LA) was still open. My husband and I had a casual dinner only to be presented with an extraordinarily large tab. When we asked the waiter, he took back our bill to investigate and it turned out that he had charged to our card another table's dinner, and our dinner to their card. They were a party of six. He talked to them about the mixup first, and then came over to explain it to us. After the explanation, he asked whether we minded if he just left things as they were, and didn't re-run the cards. He said he proposed this to the other table as well, and they were ok with it!