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Servers Share The Most Awkward Dates They’ve Seen – Part 3

By Reuven Shechter
February 4, 2019

Shutterstock / Diego Cervo

Sometimes dates are just awkward. Whether they're first dates or a couple's 100th time going out together, something spoils the mood for them and everyone around them, including the restaurant staff. These cringy experiences are indelibly marked in the servers' heads, showing them how not to act in their own relationships. Explore these extremely awkward tales of dates gone wrong. Content has been edited for clarity.

A Surprising First Date

Shutterstock / Nejron Photo

Here comes the kicker: when I went to take some trash outside to the can, I caught them sucking each other’s faces like there was no tomorrow in the lot, propped up on one of their cars. I went inside to share the news with the staff that the date was a success; they were feeling the same way I was about the whole thing. We were all excited, too.

I figured they went home and shagged it out. Anyway, about thirty minutes went by and the waitstaff and I were leaving through the back door. WHAT DO WE SEE? The car they were kissing against was now fogged up and bouncing up and down in our parking lot. It was the funniest way this night could have ended. Moral of the story: don’t put judgments on people’s looks, and always try to shag on the first date.”

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The Bagged Salad Really Triggered Her

Unsplash / rawpixel

“I waited tables at the Olive Garden 10 years ago. A guy and his wife sat down at a table and immediately started arguing. Something about his affair and how a baby from it was costing them money. Finally, it culminated as I was bringing out their salad. As I walked away I heard the wife say:

‘Well, maybe if you hadn’t boned our son’s girlfriend and gotten her pregnant, we could afford to eat somewhere nicer than the goshdarn Olive Garden. Oh look, the highlight of my meals: Unlimited. Bagged. Salad. Maybe you could save up and we could go to Joe’s Crab Shack for our anniversary. Miserable man.'”

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Let’s Go Out…To Negotiate

Shutterstock / Rommel Canlas

“It wasn’t exactly a date, but I served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant where I worked at the time. They came before the dinner rush so they were pretty much my only table, and every time I’d check in on them, the wife was extremely angry and tearful and they were bickering about holiday schedules for their daughter, timeshares, or other issues.

It wasn’t the end of the world but it was extremely awkward to butt in to change our their forks or refill drinks while they were so emotionally charged.”

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His Nervous Tick Landed Him In The Hospital

Flickr / MPD01605

“The date initially seemed going well, but the guy was nervous and fidgety. He was rocking back on his chair a little as he would talk and eventually flew too close to the sun. He toppled his chair backward and knocked himself out cold. And peed his pants.

He had to be taken out of the dining room on a stretcher over the span of 20 minutes, while his Tinder date did the honorable thing and immediately went to the bar and ordered shots.

We gave them to her on the house.”

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Someone Loves Himself

Flickr / nan palmero

“I worked at an ice cream parlor, it’s kinda old-timey. There isn’t too much seating. Anyway, this guy comes in with a girl, they pay for their own cones and take a seat at two of the seven stools. The dude is talking and the girl is laughing and into it.

TWO HOURS LATER, THE DUDE IS STILL TALKING and the girl looks like she wants to cry or punch him in the face. 

Continue reading >>>

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