Waiters are sharing the most awkward Valentine's Day dates they've witnessed on Reddit — and they will make you cringe

acollman@businessinsider.com (Ashley Collman)
A couple enjoys a Valentine's Day dinner at a Waffle House in Georgia in 2018.

David Goldman/AP

  • Waiters are sharing the most awkward Valentine's Day dates they've witnessed on Reddit. 
  • They include stories of failed proposals, cheaters being caught in the act, and couples getting into fights over ice cream. 
  • Visit Insider's homepage for more stories.

A Valentine's Day dinner has the potential to be very romantic, but also very awkward — especially for the wait staff.

In a thread on Reddit, a user asked waiters to tell stories of Valentine's Day disasters they've witnessed. Insider hasn't independently verified the stories, but they range from some truly cringe-inducing break-ups to surprisingly sweet botched proposals.

Here's a few of the best stories that were shared on the site. 

Obnoxious customers 

One waiter recalled a bizarre incident that happened during an especially busy Valentine's Day when he was working at a high-end Mediterranean restaurant. 

He said that the restaurant was completely booked and that walk-ins were only being seated if a reservation canceled. 

"Most of the customers were pretty understanding and either waited or simply left. One dude however kept pushing and pushing asking every 10 minutes how much longer until he is seated, constantly saying how he is a regular customer; and how his date is going to be there at 7 (he got there at 6)," the user said. 

At around 6:50 p.m., the user said that the guy lost it, walked up to the hostess stand, grabbed the reservation book, and walked out of the restaurant. Two of the owners ran outside to try and get the book back, but he was already gone.

The stories show how awkward Valentine's Day dinners are for both the couples and wait staff.

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"Even better is, two hours later, chaos is still running rampant and the dude shows back up saying he has a reservation for two. 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,'" the user recalled. 

Another Reddit user said one of the funniest Valentine's Days that they worked was during their time managing hotel room service at a hotel that offered a Valentine's Day multi-course room service package. 

"More than a few couples thought it was a good idea to call for the next course and then start having sex. 

"I had the 'privilege' of people answering the door naked, seeing sex toys strewn around and one where the other members of the threesome were carrying on in the background.

"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," the user wrote. 

Couples who weren't on the same page

Stories of rejection and couples fighting were a common theme among the waiters' stories. 

Perhaps the most bizarre incident involved a couple who playfully started dabbing some of their ice cream on each other during dessert. 

The waiter said the woman "flipped out" when her boyfriend switched the flavor he was using in the play fight, dipping into the chocolate ice cream. 

"You know I like chocolate the most, why would you waste it you idiot," the woman said. 

"In the end she stormed out 'cause the man couldn't comprehend how much she was blowing up the situation," the waiter said. 

Cheaters caught in the act

Valentine's Day can obviously be a tricky time for people cheating on their partners, and a few of the posts dealt with diners who were caught in the act. 

One bar back witnessed an awkward moment when a man got up to go to the bathroom while eating with his girlfriend on Valentine's Day. A "random woman" approached the girlfriend and informed her that she had recently matched with her boyfriend on Tinder and that they had "hooked up a week earlier." 

"The boyfriend returned to a drunk, sobbing and screaming girlfriend," the bar back wrote. 

Another Reddit user recalled a similar incident that happened while they were waiting tables in college. 

"I once saw a couple come in to eat, halfway through the dinner the man's wife shows up to surprise the couple. The wife took the wine bottle and poured the remnants on the husband's head, took off her ring and told the girlfriend she could have him," the waiter recalled.

A lot of the stories involved proposals that didn't go to plan.

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Proposals that didn't go as planned

Quite a few waiters witnessed men being turned down when they decided to propose to their significant other during Valentine's Day dinners. 

Reddit user SpinachandChickpeas recalled watched a woman turn down a proposal, and then sit there for 20 minutes while her boyfriend tried to change her mind. 

Another user worked as a pastry chef and prepared a dessert with the words "Will you marry me?" for a man who planned to propose to his girlfriend during dinner. It never saw the light of day because the girlfriend broke up with her boyfriend before they even got to the main course. 

Not all of the botched proposals ended in heartbreak though. One waiter told the story of a man who came into propose and threw up on his girlfriend when he got down on one knee.

"After the shock of what just happened, she still ended up saying yes," user KindSoul1 wrote. 

Awkward moments for the waitstaff 

Servers said they were sometimes the source of the awkwardness during Valentine's Day service. 

Reddit user Geckosandwine said that during one Valentine's Day shift, she set her hair on fire and spilled a full beer on a woman out to dinner with her husband. 

Luckily the husband knew how to lighten the situation. 

"Well now she has to take her pants off," he joked to the waiter. 

Another server said that a guy she was dating at the time made her Valentine's Day shift one of her worst. 

The Reddit user said that the guy she was seeing asked to take her out, but she declined because Valentine's Day is one of the busiest of the year and she needed to work.

So, out of spite, he took another girl out to dinner at the restaurant where she worked and sat in her section. 

"He then proceeded to spend the entire evening making a fool out of himself and making his date uncomfortable as he tried to make me jealous," she wrote. "Needless to say we didn't go out again. Ever."

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