Three things are guaranteed in life for hospitality workers: death, taxes, and stress around the holidays. Perhaps none more so than Valentine’s Day, when the perfect storm of filled reservation books and customers with high expectations leaves many a server white knuckling throughout the night.

For your morbid curiosity, we’ve rounded up the most painful and gruesome Valentine’s stories from hospitality workers around the web.

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1. Finders Keepers

As a restaurant worker, being asked to participate in somebody’s engagement can be both a fun and nerve-wracking experience. When Reddit user Icmedia was asked to hide a ring in the dessert one Valentine’s Day, they were surprised. The wings-and-pizza place they managed was not the kind of place you’d expect somebody to pop the big question. But, ever the good sport, our hero agrees. The bachelor dropped the ring off a day early, and it was safely tucked away in the restaurant’s safe.

Fast forward to Valentine’s day evening, and the two lovebirds arrive. “They're so obviously in love that she didn't seem to notice or care about the fact that he had brought her to a middle-of-the-road place with a sports-bar atmosphere.” The couple orders entrees and champagne, while our hero uses their chef skills to whip up a special chocolate strawberry tart.

“I went to the safe to get the ring, and... It wasn't there. I was freaking out big time. I asked everyone there if they knew what the f*** had happened to it… Finally, my bar manager mentioned that one of the owners had been in earlier, and spent a little time in the office… It turns out that he had seen the ring in the safe, and thought it was something a customer had left behind. Figuring that he had come into an extremely lucky situation, he decided (like the scumbag he was) that he'd take it for himself and save money on a gift for his wife on Valentine's.”

While our hero rushed across town to retrieve it, the restaurant staff went into DEFCON 1. The bar manager filibustered with a complex tableside cocktail that ended with a flaming shot. Against all odds, our hero arrives back in time to plant the ring like nothing happened.

“At that point, just about the entire staff was watching the table, and when we saw the look on her face, my heart finally started beating again. She said ‘Yes.’ And, I started looking for someone else to work for the very next day.”

2. Spoiling the Big Moment

Of course, losing a ring is not the only way a proposal can go wrong. When a customer tells you they’re celebrating an engagement in their reservation notes, most restaurants will oblige them with a “congratulations” and a glass of champagne on the house.

However, as told by reddit user ChefHannibal, this is a dangerous assumption to make.

“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.”

3. Caught in a Love Triangle

As hospitality workers, we try not to judge those whose choices in life are different from our own. Reddit user misfits90 was working as a delivery driver for a fruit bouquet company, when, one Valentine’s Day, a customer ordered two arrangements for two different recipients.

“Routes were made for me and the truck was loaded so there was no way I could mess this up.” Both arrangements were delivered to their appropriate address.

However, when our hero arrives back at the store, they find the owner and customer in a heated argument. It turns out the customer had mixed up the two recipients' names when submitting the order online. While this may not seem like too big of a deal, our hero gathers that the two women who received bouquets probably weren’t supposed to know about each other.

To make matters worse, the bouquets had a phone number listed below each name. So after a revealing phone call was made between the two women, the customer found himself in hot water. While we don’t know what happened after this exchange, we can assume this man did not have the Valentine’s Day evening he was expecting.

4. “IF I Can’t Eat Here, No One Can!”

There are things they don’t teach you in school but are only learned through life experience. Always having a reservation on Valentine’s Day is one of them. Though sadly, many people still seem to forget.

As Reddit user danmatfatcat recounted, the high-end Mediterranean Bistro they worked at was completely booked up. Those who showed up without a reservation were told they could only be seated if a reservation was canceled. Most people were understanding, however, there was one gentleman who “kept pushing and pushing asking every 10 minutes how much longer until he is seated, constantly saying how he is a regular customer.”

“We insisted that once a table was available, and all the customers before him were seated, he would get a table, but because of the amount of reservations, we couldn't guarantee he would even get a table at all. At about 6:50 the guy loses it, fast-walks up to the hostess stand where the reservation book is, grabs the reservation book, and practically runs out the front door… Two of the owners ran outside to follow the guy and try and get the book back, but by the time they got out he had already left the parking lot.”

With the only copy of the reservations now gone, and 4 more hours of Valentine’s Day dinner still remaining, the staff is in utter disarray. (Sidenote, this is why we always recommend our customers use a cloud-based reservation system.)

Fortunately, the staff got some closure later in the evening when the angry customer showed back up, still trying to get a table.

“Three of the five of the owners (all brothers) escorted the dude and his date out to the parking lot and banned him from the restaurant permanently. They even took a picture of him and posted it in the window saying ‘Do Not Serve This Man’”

5. X-Rated Room SeRVICE

Of course, restaurants and delivery services aren’t the only hospitality businesses that are prone to chaos on Valentine’s Day. Hotels too can see a whole lot of unpredictable activity. Especially when they’re offering a special Valentine’s package, as one redditor’s hotel did.

The package included a multi-course meal that would be delivered to each couple’s room one course at a time. However, mid-way through the meal, our hero found that more than a few couples had gotten bored with the dinner and started shifting towards activities that were more… adult. “I had the 'privilege' of people answering the door naked…” (The rest of this sentence is NSFW, but you can read the original post here.)

“After complaints of similar instances from my team I had to take action. I ended up having to call the offending guests and tell them if they could not respect my team by answering the door in at least a closed dressing gown they could come down and collect the rest of their meal from the restaurant.”

I guess the party was over.

A Less Eventful Valentine’s Day

That concludes our round-up of Valentine’s Day horror stories. If you’ve been unfortunate enough to experience your own story, let us know in the comment section below (that is, if you aren’t too traumatized to speak of it).

Also, for restaurant and hospitality operators who want to take the stress out of future holidays we recommend using Science On Call, the tech support platform for restaurants. We take care of all the technology needs of restaurants, including POS, online ordering, phones, internet, printers and more. You focus on your food and your guests, and we’ll do the rest.

Hospitality Horror Stories: Valentine’s Day