Servers Share The Most Cringeworthy Dates They’ve Ever Witnessed

Bad dates just aren’t awkward for would-be lovers. They’re also horribly awkward for the poor souls with the misfortune to serve drinks, take orders, and generally keep their “happy face” on even as things fall to pieces. We’re speaking, of course, about loyal restaurant servers. Reddit asked food service workers of the Internet to share the most awkward dates they’ve ever had the misfortune (or pleasure) of seeing on the job. The main takeaway? The human race should stop proposing at restaurants unless we’re 100% sure the significant other will say yes.

Split the bill for these 42 delicious stories about the most awkward dates ever seen by servers.


42. That’s Not What We Mean by Get a Room

I work at a Japanese restaurant, and one couple comes to mind. It was the "worst" for everyone else involved. We offered "private" rooms that have sliding doors, and this couple clearly was hitting it off very well...

to the point that after a few drinks, she had moved to his side of the table and they just went at each other's faces & bodies for about two hours.

They could have done all that with the doors closed and it would have been less cringey—still cringey nonetheless—but no, the sliding doors were wide open for all the patrons to see. Kids, big groups of people, waitstaff, runners, etc...

If I remember correctly, they tipped pretty bad too, so it was not a fun time.

alwaysfrozen

Cringeworthy Dates facts

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41. No Points for Trying Too Hard

This is actually a story where the (somewhat awkward) guy was doing pretty good until my boss screwed it up for him.

So there was this couple on a first date, seated at a table in the back. At first, I didn't think much of it, wasn't even aware that it was a first date until the restaurant's phone rang.

A man called to let me know his son was there on his very first date ever (the son was in his late 20s). Obviously, this was a big deal to him and he called the restaurant to make sure we would do our best to make sure they have a pleasant evening.

My boss heard and instantly went to the kitchen in order to make sure they would get a "special treatment." What followed was plates with rose petals, red hearts etc. etc. Way over the top.

When serving the plates, my boss even mentioned the phone call. To finish it off, the desert came complete with fireworks and all that.

The idea was sweet, but obviously this was way too much for a first date of two people who were basically just getting to know each other. As the evening progressed, the girl was visually put off by my boss trying too hard. Poor guy.

Up until then he had been doing quite well, the pair seemed to have a lovely evening. Until my try-hard boss entered the scene that is.

The girl was polite toward the end of their date, but it was obvious there was not going to be a second date. And it wasn't even the guy's fault, other people ruined it for him. I felt so sorry for that dude...

Zafuso

Cringeworthy Dates facts

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40. Let’s Split the Check and Literally Everything Else

I guess you could call this a couple date. I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered.

Once appetizers came out, the man thought it would be a good idea to serve his wife divorce papers.

I did my best to avoid that side of the bar. I did bring out tissues for the wife, who was breaking down. I ended up boxing up the dinner. The guy paid, but I do not envy that ride home.

ThereandBack22

Cringeworthy Dates

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39. Heartbreak in Any Language

Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears.

She whips out a pen and starts writing paragraph after paragraph angrily. It was awkward because I kept having to come back to the table since they ordered multiple courses.

He was just eating and signing while she was hunched over the table writing away while crying. When they finally left, they tipped me pretty well, so I guess it wasn’t too bad?

midgetT-rex

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