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

6. Random Violence

One Summer I worked at Cheddar’s. A couple in probably their late 40s walked in and sat at one of the high top tables in the bar area. The man ordered a shot of whiskey and a beer, the woman a diet coke. When the drinks come he takes the shot, takes a pull on his beer, and backhands his SO so hard she fell out of her chair. He just sat there calmly drinking his beer until his arresting officer arrived.

7. He Ordered For Her

Couple sits down at my table. Do the usual greeting. Ask them if they would like to start out with a beverage. The female replies, “coke, please”. The male stops her, interrupting “uh, make that a diet coke. I’ll take a jack and coke”. The date didn’t get any better.

8. The One Night Stand

The worst I’ve served by far. I worked at a breakfast place so we got a lot of one night stands awkwardly making small talk, but that was mostly just funny. I became really good at figuring out how far into a relationship a couple was. Anyway, this pair. They came in and sat themselves (we had a host) and then the dude asked to switch tables. You chose that one, though! Anyway, he orders the drinks. One water with extra lemon for the gentleman, two small orange juices for the lady, even though I explained it would be cheaper to get a large, but he declined. When I went back, he asked for more sugar and lemons. He had used all twelve-fifteen packets of sugar (and sweet n low, and cane sugar, and equal) in his water with extra lemon. Their food order was insane. Every ticket I took at that place usually cost about $5-10 per person, and this guy’s ticket was at around $30. His girlfriend’s was $8, including the OJs. Time comes to pay and he stares at the girlfriend. She pulls out a card, which comes back declined. She starts crying when he says he doesn’t have money. She goes outside, calls her mom, calls her bank, whoever. She’s screaming on the phone for about twenty minutes. While she’s melting down outside, dude comes up to the register and throws down a wad of ones. “Here.” And leaves.

9. The Nervous And Sweaty Guy

First date for a couple in their late 20’s. Started smoothly, the obvious first date jitters and awkwardness but nothing odd.

Ten minutes later they order and the guy is sweating bullets, really nervous. I checked on them about 5 minutes later and he’s looking distinctly off.

He didn’t make it to 20 minutes. He shat himself and ran out leaving the girl sitting there in shock and pretty upset.

The story was she had been set up on the date by a friend, who’d told her that he was nice, but extremely shy and nervous. Apparently it was all good until he needed to talk about himself, then shit city occurred. That chair went straight to the dumpster.

10. No Way To Ignore This

A couple in their late 20s was having a quiet discussion in their booth and were going from their table over to the bar to use the phone and back to their table. Then suddenly the woman yells “YOU BROUGHT A HOOKER INTO MY MOTHER’s HOUSE YOU COCKSUCKER” and storms out.

Restaurant is dead silent, and me and the bar tender just look at each other and burst out laughing and the guy shuffles back to his table.


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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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