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

via twenty20/hannahmcswain
via twenty20/hannahmcswain

1. Death By Hot Sauce

I worked in a restaurant that had a huge selection (150+)of hot sauces. We sold them by the bottle but customers could sample any of them and use them on their food. A couple came in, the guy started bragging about how much he loved hot sauce and how he never found one that was too hot. He asked for the hottest one we have. I brought the bottle to his table, he filled a spoon with the sauce and made a big production of how he was going to eat it. I told him not to, the hostess told him not to, the waitress serving the next table told him not to… he put it in his mouth, started choking and gagging, puked on the table then passed out and did a faceplant right into the puke!! We called 911. He woke up right away and kept gagging for a while. He refused treatment when the paramedics showed up. They left without even ordering a meal! The girl told one of the restaurant staff that it was their first date.

2. Unwelcome News

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

3. Calling Mommy

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.”

4. The Dine And Dasher

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

5. A Failed Proposal

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.


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