Restaurant Servers Share The Worst Valentine’s Day Disasters They’ve Ever Witnessed

Valentine’s Day is supposed to be filled with love, joy, and all those other good gooey emotions. While many couples get to enjoy a nice, romantic night out together, things don’t quite always end up going as well as planned.

These servers went on Reddit to share the most disastrous Valentine’s dates they’ve ever seen.

Lots Of L’s Taken In A Row

photo of empty restaurant
Photo Credit: Unsplash / Nick Karvounis // Text Credit: Reddit / OffensiveGender
Photo Credit: Unsplash / Nick Karvounis // Text Credit: Reddit / OffensiveGender

“These two were on a date and the guy went to go use the bathroom. The girl just up and leaves after he went to the restroom. When the guy came back, he sat around for a while until asking his waitress where his date went. She replied by saying that she left. The guy then asked the waitress if she would go on a date with him. The waitress said no.”

A Whole Year And He Didn’t Know That?

lobster on a plate
Photo Credit: Unsplash / Toa Heftiba // Text Credit: Reddit / allthewrongwords
Photo Credit: Unsplash / Toa Heftiba // Text Credit: Reddit / allthewrongwords

“I served food at one of those super touristy seafood restaurants. For Valentine’s Day lunch, this younger couple came to celebrate their one year anniversary. I offer my congratulations and proceed to do my usual spiel before taking orders. The girl looks increasingly dismayed the longer I talk. Finally, I ask if there are any allergies.

“She looks directly at her boyfriend and states, ‘Yes, I’m allergic to fish and shellfish,’ and then looks over at me very sadly.”

Really Jumped The Gun On That One

bartender pouring a glass of champagne
Photo Credit: Unsplash / Steve Daniel // Text Credit: Reddit / ChefHannibal
Photo Credit: Unsplash / Steve Daniel // Text Credit: Reddit / ChefHannibal

“There was a note in our reservations that it was an engagement, they wanted champagne, a specific seat, and a bunch of other stuff. The server comes up to the table with something like, ‘So I read we’re celebrating an engagement. Congratulations!’

“Confusion from the woman; glaring from the guy. He hadn’t proposed yet. She ruined it.”

Okay, But Why Was He Trying To Propose At A Chili’s?

exterior of a chili's restaurant
Photo Credit: Callaghan O’Hare / Bloomberg via Getty Images // Text Credit: Reddit / AZScienceTeacher
Photo Credit: Callaghan O’Hare / Bloomberg via Getty Images // Text Credit: Reddit / AZScienceTeacher

“I was eating at a Chili’s on Valentine’s Day. A young guy next booth had a big bunch of roses. He kept looking at his watch, looking at the roses, and popping open a ring box for a peek at the ring. He did this for a half-hour or so, then began calling and texting someone (presumably his girlfriend) over and over.

“As we were waiting for our check, he hands my wife the roses, mumbled something, and walked out. Poor guy.”

That’s An Intense Reaction To Have

drawing of candy heart with
Photo Credit: Unsplash / Patrick Perkins // Text Credit: Reddit / moneybagsmeisenheimer
Photo Credit: Unsplash / Patrick Perkins // Text Credit: Reddit / moneybagsmeisenheimer

“I served at a Japanese hibachi restaurant and once had a couple come and the dude dumps her after the meal. She then gets up and throws up a trail probably a good 20 feet as she runs to the bathroom. The dude got up and left the girl and I was left to clean the mess.”

He’s Definitely Fallen For Her

ambulance driving on street
Photo Credit: Unsplash / Jonnica Hill // Text Credit: Reddit
Photo Credit: Unsplash / Jonnica Hill // Text Credit: Reddit

“An elderly man proposed to an elderly woman. He tried to get off the chair to kneel, tripped, fell, and I assume broke something. Since he couldn’t get back up and we had to call an ambulance.”

Well, That’s Uncomfortable

man holding open ring box
Photo Credit: Unsplash / Nick Karvounis // Text Credit: Reddit / Jukka_Sarasti
Photo Credit: Unsplash / Nick Karvounis // Text Credit: Reddit / Jukka_Sarasti

“A guy proposed to his girlfriend and she said no. The guy threw his arms up and ran out of the building. Later, while waiting for someone to pick her up, she told us it was completely out of the blue—they’d only been dating for a few months.”

He Got What He Deserved

bouquet of flowers
Photo Credit: Unsplash / Lorena Schmidt // Text Credit: Reddit / misfits90
Photo Credit: Unsplash / Lorena Schmidt // Text Credit: Reddit / misfits90

“I was a delivery driver for a floral company and I had two arrangements from the same guy. The routes were made for me and the truck was loaded so there was no way I could mess this up. Delivered both arrangements to the appropriate address.

“I headed back to the store to find the store owner and the guy who sent these in an argument. This idiot put the wrong names with each address and it was on the card with the arrangement. Along with the phone numbers. So both women called each other and then called the guy. He tried to say it was my fault.”

This Is A Whole Mess

woman holding her pregnancy belly
Photo Credit: Unsplash / Freestocks // Text Credit: Reddit / _liliput_
Photo Credit: Unsplash / Freestocks // Text Credit: Reddit / _liliput_

“She told him she was pregnant. He went quiet and didn’t say anything for a bit and then asked her what the plan was. She said she was keeping the baby. He said he didn’t want kids and had told her this. She got upset and said she thought he’d be happy and change his mind when he found out.

“Turns out she stopped taking the pill. He told her it was over and she could send someone to collect her things because he wanted nothing more to do with her.”

Better Valentine’s Day Than Most People Get

car with flat tire
Photo Credit: Unsplash / Denny Muller // Text Credit: Reddit / uReallyShouldTrustMe
Photo Credit: Unsplash / Denny Muller // Text Credit: Reddit / uReallyShouldTrustMe

“I blew a car tire and my friend came to bail me out. We’re both straight dudes and forgot it was Valentine’s Day. We decided to have dinner and both were coming from business meetings so had suits on. We didn’t catch on until the end on how the entire wait staff thought we were just the cutest gay couple.”

I Can Feel Secondhand Embarrassment

Olive Garden restaurant exterior
Photo Credit: John Greim / LightRocket via Getty Images // Text Credit: Reddit / LeapingMouse
Photo Credit: John Greim / LightRocket via Getty Images // Text Credit: Reddit / LeapingMouse

“Back in my Olive Garden days, we had a man who looked to be in his mid-20s tap his empty wine glass with a fork to call for the attention of the surrounding strangers. He proceeded to get down on one knee with a silver band in hand, and ask his girlfriend/date to ‘accept this promise ring.’

“She looked horrified start to finish.”

His Poor Wife 🙁

bottle of wine
Photo Credit: Unsplash / J McKinney // Text Credit: Reddit / kobra_kyle
Photo Credit: Unsplash / J McKinney // Text Credit: Reddit / kobra_kyle

“I once saw a couple come in to eat and, halfway through the dinner, the man’s wife showed up to surprise the couple. The wife took the wine bottle and poured the remnants on her husband’s head, took off her ring, and told the girlfriend she could have him. He tipped me $100.”

You Can’t Exactly Change That “No” Into A “Yes”

woman holding up diamond ring
Photo Credit: Unsplash / Jeremy Bishop // Text Credit: Reddit / SpinachandChickpeas
Photo Credit: Unsplash / Jeremy Bishop // Text Credit: Reddit / SpinachandChickpeas

“He proposed, she said no. He cried and tried to change her mind for 20 minutes while she sat there stony-faced. She finally got up and walked out. He paid and left in tears.”

Good On Her For Dropping Him

plate of sushi
Photo Credit: Unsplash / Andraz Lazic // Text Credit: Reddit / venustas
Photo Credit: Unsplash / Andraz Lazic // Text Credit: Reddit / venustas

“I was working as a waitress in a sushi restaurant on Valentine’s Day. This guy I had just started seeing wanted to go out, but I told him we’d just have to celebrate the day after or the weekend after.

“He got so upset that he went and asked a different girl out, came to the restaurant I worked at on V-Day, and sat in MY SECTION. He then proceeded to spend the entire evening making his date uncomfortable as he tried to make me jealous.”

That’s Such A Lazy Proposal

photo of coffee shop from above
Photo Credit: Unsplash / The Creative Exchange // Text Credit: Reddit / TheThrowawayFox
Photo Credit: Unsplash / The Creative Exchange // Text Credit: Reddit / TheThrowawayFox

“Ex-barista here—some guy on Valentine’s Day came in and asked us to write ‘will you marry me?’ on the cup. She looked at the cup while he went down on one knee. She said nothing, put the cup back down, and just walked away shaking her head.

“He, on the other hand, got pissed and started to rant about how she should have gotten over him sleeping with her sister already…we had to ask him to leave.”

All That Practicing For Nothing

man doing a backflip
Photo Credit: Unsplash / Douglas Bagg // Text Credit: Reddit / beejeko
Photo Credit: Unsplash / Douglas Bagg // Text Credit: Reddit / beejeko

“I was working at the mall where a guy did a backflip and asked a girl to be his valentine. She declined. I walked up to him and asked if he was fine; he said it took him a week to perfect the move.”

She Really Misjudged That One

paper heart ripped in the middle
Photo Credit: Unsplash / Kelly Sikkema // Text Credit: Reddit / Makabajones
Photo Credit: Unsplash / Kelly Sikkema // Text Credit: Reddit / Makabajones

“A girl that I worked with went to lunch on Valentine’s day at an expensive restaurant her boyfriend had gotten a reservation for, she got dressed up nice and said she was sure that he was going to propose. He broke up with her.”

Alexa, Play “I’m In Love With A Stripper” By T-Pain

man holding a bouquet of flowers
Photo Credit: Unsplash / Angelo Pantazis // Text Credit: Reddit / BigBodyBuzz07
Photo Credit: Unsplash / Angelo Pantazis // Text Credit: Reddit / BigBodyBuzz07

“Not a waiter, but in my strip club bouncer days we had one of our regulars get suited up and bring flowers in one V-day to try and woo one of the dancers. It did not work.”

It’s A Disaster In The Making

girl's hand with engagement ring on
Photo Credit: Unsplash / Simon John-McHaffie // Text Credit: Reddit / DirtyDratini
Photo Credit: Unsplash / Simon John-McHaffie // Text Credit: Reddit / DirtyDratini

“A 16-year-old boy proposed to a 15-year-old girl by having us put a cheap ring in the whipped cream of her dessert. She actually said yes.”

I would like to know if they’re still together. If anyone has any idea, my DMs are open.

Nothing Like Being Reminded How Alone You Are!

man talking on cellphone
Photo Credit: Unsplash / Антон Шариков // Text Credit: Reddit / Background_Extra52
Photo Credit: Unsplash / Антон Шариков // Text Credit: Reddit / Background_Extra52

“Not really much of a disaster, but last year my work called me up and said, ‘Hey buddy, we know that you’re single: can you come in as an extra shift tonight?'”