48 Waiters Share The Most Cringeworthy Dates They’ve Ever Witnessed

16. “Call Me Daddy”

Working at a big chain restaurant I’ve encountered several of these but the one that sticks out the most is one where there was this old overweight man and a younger woman probably half the mans age. Right from the get go the woman orders a Long Island and I could tell something was up with these two but didn’t really think much of it at the time. It was when she proceeded to order not one but two more long islands (at this point I was regretting getting her that last one). They finished their meals, she was pretty intoxicated but not belligerent. I bring menus for dessert and as I’m presenting them the woman asks if they can order dessert to which the old man replies, “only if you call me daddy,” as I’m standing there. He then gives her the I’m gonna fuck you eyes she starts this half hearted giggle and I decided that I stayed at the table probably 2 minutes too long and told them I’d be back. They ordered dessert so I’m assuming she called him daddy.

Fast forward about two weeks later the old man shows up with some other girl half his age so I’m assuming he has a lot of daughters he likes to take out to eat, or you know, hookers.

17. Paid For Her Silence

We have a guy that comes in with a hooker (always a very young looking Asian girl) every other Wednesday for lunch and then his wife and him come in Friday night. He is always in my section and tips me very well for my silence.

18. The “Fucking Disgrace”

Used to wait/tend bar at a chain restaurant where after a few weeks you would get to know the regulars. This is in the UK so tipping wasn’t terribly high but there was an elderly couple that would come in every Tuesday and Friday for fish and chips with a few pints and a gin and tonic. After they arrive and order their usual, a couple seat themselves at the table next to theirs and begin their small talk. They were both twenty somethings and from their mannerisms it was clear that it was still early days for them. The guy is talking just a little too loudly and the conversation was all about him. “Oh yeah I used to make loads of money playing poker at casinos, I made so much that I’m now barred from all the ones in town. “I can totally bench press like 300lbs.” Basically the guy kept bragging about about shit the entire time and wouldn’t shut up.

The main thing he kept talking about was how much he could drink, since the girl ordered a beer as well and he latched onto it talking about how he could outdrink all his mates and he fucking LOVED beer. The elderly guy at the table next to his kept rolling his eyes at me every time I passed by, when I took their plates away his wife whispered “This is torture!” Eventually the guy has started to get quite drunk from trying to drink pint after pint in the space of an hour or so. When I come over to clear their plates and ask if they want anything else the girl begins to ask for the bill before he cuts her of asking for another pint. She quietly reminds him that he’s had five or so already and he tries to jokingly reply with “Bitch I can drink as much as I want.” Without a word the girl immediately storms off leaving the guy looking shocked as hell. The elderly couple leave their money on the table but before they leave the man turns to the dumbfounded braggart and just says “Son, you’re a fucking disgrace.”

19. The Honeymooners

I used to wait at a country house hotel. It was pretty fancy, silver service, all of us in dickie bows and waistcoats so we tended to get the “upper crust” of society. This really friendly couple came in, very much in love and my boss whispers to me to be extra nice as they had just gotten married that day.

It was just themselves, no wedding party, bit strange, but they seemed very happy so whatever. I served their 4 courses and left them to it.

As I was collecting their deserts however I noticed a, chillness in the air. The next time I walked through the area, the woman was gone, the man just sitting there downing the wine.

The next morning, the man came downstairs, alone, and ate his meal, staring out the window. What was meant to be a week stay (their honeymoon) turned into me bringing their bags down to the car that day. They both sat in and drove off. I’ll never forget the….quietness. They both tipped and thanked me though, which was nice

Bit more information, they were both in their late 30’s early 40’s. And the night porter heard them arguing…loudly.


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  • http://radiatepositivelife.wordpress.com Natali

    This was probably the most entertaining thing I will read all week!!!

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