10 servers reveal the wildest things they’ve seen on Valentine’s Day

  • Valentine’s Day can be a bummer for servers.
  • They have seen fights, breakups, and dates being stood up.
  • Here are some of the saddest and wildest stories.

Although a lot of Valentine’s Day dates include two people, it often involves a third party – your server. And for many servers, Valentine’s Day can be one of the most overwhelming, yet interesting, nights to work in the service industry.

From breakups and demanding proposals to fights and insult slinging, these Reddit threads show just how eventful a V-Day shift can be. Here are stories from servers that prove working on Valentine’s Day is as unpredictable as love itself. Just a reminder, these are just for fun, as INSIDER can independently authenticate these stories.

One server witnessed a fight

“We were super busy that night, but everything was going well until the fight. We had two large parties in a certain section that was [separated] from our more intimate tables. It was a party section.

“Halfway into the meal one girl wraps a chain around her fist and goes after a girl in the other party. Everyone ran out and the manager still [had] their bill with him when I quit.” – Redditor kykyjelly

Another saw someone stood up and felt his pain

“I once waited on a guy on Valentine’s Day who was obviously waiting for his date to show-up. He had to be middle aged, 40s perhaps, and this was in the days before mobile phones (1997 maybe?).

“Anyway, it was a busy night, and he kept checking his watch and he had a rose sitting on the opposite plate – and he kept waiting, and waiting, and waiting. He got more and more sad as the night went on.

“He eventually ordered a meal, by himself, and it looked like he may cry by the end of the night … I paid for his meal out of my own tips that night. It was one of the saddest meals I ever waited on.” – Redditor gopher33j

The ‘karate kids’ left this server’s restaurant in disarray

” … Last year we had a group we call the ‘karate kids’ come in half an hour before closing time. These are kids that run all over the restaurant, are given enough money to empty the toy machines (once when they showed up – again, completely unannounced – we had bouncy balls flying all over the restaurant in the middle of dinner rush: bouncing off walls, flying between the liquor shelves behind the bar, hitting other customers. You’ve never seen anything like it, I promise).

“[They] left candy wrappers all over the tables and spilled milkshakes splattered on booths and walls. Of course, the parents have money and never tip. Anyways, 100 of them showed up right before close.

“We close at 11 p.m. and I was there until 1 a.m. I crushed an enormous piece of ice cream cake at the end of the night by myself as I did my check out that shift. Never forget V-Day 2014.” – Redditor kogx3

This server got tricked with fake money

‘I was so busy I didn’t even think of checking.’ Trong Nguyen/Shutterstock

“Super busy at one point and a table came to pay a $US140 bill with two $US100 bills. Stood there for change and seemed super nice. When I go to cash out later I realise both were fake. I was so busy I didn’t even think of checking.

“I had three different $US100 bills and that’s the only table who paid with two of them and they were faked in the same way. Happy Valentine’s Day to me. My boss is making me pay the $US200 out of my own pocket.” – Redditor dahnjenika

A guy asked this server for a booster seat to give to his date

“I was serving a couple probably in their mid-20s. It was Valentine’s Day and they were arguing a lot. The guy ended up calling me over to the table to calmly ask me, in front of his date, ‘Do you have a high chair or a booster seat since someone wants to act like a child.’ I was speechless, she wasn’t. They left soon after that.” – Redditor Puddin__pop

One server witnessed things get awkward after the appetizers were served

“I was working cocktail and had a couple sat at a small high top. The girl’s having a great time and the guy is being quietly polite, they get cocktails and appetizers, I’m having a good time with them.

“And then suddenly the girl is very much not having a great time and holding back tears while the guy politely and apologetically asked to pay out. I guess they [drove there] together because they just say there waiting for me to get back. It was so awkward.”- Redditor Ambitus

Drinking champagne
Not every dinner ends with champagne. Getty/Pascal Rondeau

This server helped with a proposal involving an ‘enormous diamond’ speared between the olives of a martini

“Most anxiety-inducing 10 minutes of my serving career – waiting for the bar to make a martini while I had somebody’s engagement ring in my pocket. The hubby-to-be wanted it speared between the olives, and it had to have been at least a carat.

“I was terrified to let it out of my sight. Naturally, the bar was backed way the hell up so I have to go by the table and say ‘Sir, ma’am, that martini is coming right up. RIGHT UP,’ the subtext being ‘Sir, don’t worry, your enormous diamond is safe.’ Drink delivered, ring in place, and she said ‘yes.'” – Redditor matchy_blacks

This server watched a date end in tears

“On my first V-Day I had a couple disappear from their table. I found them arguing by the bathroom doors. They end up breaking up and then I had a puffy-faced guy crying at my table. This all happened before the entrees arrived. We ended up comping his meal and boxing it up for him.” – Redditor krrusty

One server witnessed a girl immediately shut down a proposal

“A couple came in on Valentines Day with no reservation. They got seated at the bar, ordered some drinks and appetizers, and they were sitting there chatting and laughing. It seemed pretty normal.

“After finishing their appetizers, the guy dropped to one knee and pulled out a ring. The girl immediately shut him down. He didn’t so much as get a word out before she was saying, ‘nope. nope. nope.’ She grabbed her coat off of the back of her chair and was putting it on, still saying ‘nope’ over and over. She practically RUNS out of the place and does not look back.

“He looked gutted. Paid the bill and walked out, staring at the floor the whole time” – Redditor macklackey

Engagement ring
Proposing in public can be risky. Shutterstock

Another heard an awkward date.

“We saw a horrible date happen between a woman and a man, where he simply would not stop talking about air-conditioning repair. Anytime there was a pause in their conversation, he started right up with the AC repair and installation facts. The woman would try to steer the conversation into movies, books, Mexican food, friends, and he would say nothing. It was soooo awkward to watch, it hurt.” – Anonymous Redditor