Waiters/Waitresses of Reddit, what's the worst date you've ever waited on?

I work at a 5 star (on a good year) restaurant that serves mostly the upper middle class. This night is one I will never forget.

This couple walks in one day. Automatically I noticed something weird. They were in torn up rags and looked as if they hadn't showered in 2 weeks. I am not one to judge so I went and asked them what they wanted to drink. The man ordered the most expensive glass of wine we had at the restaurant! I did not want the man to get in trouble for not having enough money to pay, so I repeated the price to him but he was firm with his request. His date ordered a coca cola. I bring the drinks and go on waiting my other tables while keeping an eye on them to see what kind of people they were because I was truly intrigued. The date automatically took off her shoes and was barefoot, even walking to the bathroom at a single point. The man was sipping his wine while picking his ear wax and brushing down his scruffy hair. I took their order for the appetizers, and observed their behavior more (they ordered the two most expensive appetizers). I came with their appetizers and put it on their plates. Their eyes lit up and as soon as I walked away, they dug in. I could tell that both of them lacked a little not of etiquette, but they seemed to know how to eat without making a mess. While eating, the woman was playing with her toes, and the man was on his phone, occasionally letting out a fart. The night went on in this fashion until it was 11pm and they finished. Their bill consisted of a very expensive wine, coca cola, semi expensive appetizers, fillet mignon, lobster with a side of black caviar, and a sea food scampy. When I handed it to them, I was very curious as to what their reactions would be. The bill was around 800$-850$. I saw the woman to her pants and pull out a ragged thrift shop looking wallet, but the man urged her to put it away. He pulled out money clip and gave 1000$ in cash and told us to keep the change. Then they walked out of the restaurant, with their stomachs filled. The other waiters had noticed this odd couple as well and were in awe that a pair in such ragged clothing could afford such a meal like that. The restaurant has a clear view of the valet and 20 seconds after the man gave his ticket to the valet driver, a brand new white porshe pulled up and the man and his date for in. Everyone was shocked. That was the weirdest couple I have ever served, and it has taught me not to judge people purely on physical attributes and traits.

Hope you enjoy this!

/r/AskReddit Thread