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
“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?
“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
“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?
“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
“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
“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
“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
“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
“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
“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
“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 🙁
“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”
“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
“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
“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
“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
“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
“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
“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!
“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?'”