July 7, 2022 | Eul Basa

These Waiters Witnessed The Most Painful Valentine's Dates Imaginable

Folks in the restaurant industry deal with people from all walks of life in their jobs. They truly see it all, the best, the worst, the ups and the downs—it’s safe to say that there is little that will faze a seasoned waiter, though the stories that they take home with them often make us cry, or cringe. Among the most eventful days in the business is Valentine’s Day; a day of excitement, awkwardness, and emotions running rampant. Gathered below are tales from the tables of love, heartbreak, and everything in between.

1. Heartbroken at Hibachi

I served at a Japanese hibachi restaurant, and once had a couple come in. The dude breaks up with her after the meal. Oh, but it gets worse. She then gets up and vomits up a trail probably a good 20 feet as she runs to the bathroom. The dude got up and bailed, while the girl and I were left to clean the mess.


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2. A Friend Indeed

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


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3. No Chance

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 she went. She replied saying that she left. The guy then asked the waitress if she would go on a date with him.

The waitress said no. Yikes.


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4. Wrong Place, Right Time

They came in at lunch the day after, so it was pretty empty, but it was still for a Valentine’s Day date. They were both pretty nice at the beginning; the guy asked for a picture and whatnot. As the meal went on, the dude got more drunk progressively, and by the time I brought the check out, the woman was gone. I was pretty confused, but I quickly came to understand just what had happened.

When the dude gave me his card, he said, “I’ll give you a bit of advice. If you’re taking a girl out to break up with her, do it at a McDonald’s and not an expensive restaurant.”


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5. Cantankerous Camo

I was waiting on a couple in their early 40s on Valentine’s Day in an Irish Pub. The dude was dressed head to ankles in camouflage, and rude. She was decently dressed for a date at the pub and very pleasant. She thanked me for working on Valentine’s Day and said I probably have someone I’d rather be with, when he said, "Pfff! She's too skinny, who would want her?!"

I only spoke to her for the rest of the meal.


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6. Section Sorrows

The guy brought his high-class date a gift; a mini ceramic bear holding balloons. He presented it when I was at the table and she looked at it like it was a piece of stinky garbage. I just knew this was not going to end well. She left at the end of the meal and must have said something because he stayed at the table for another 40 minutes, head down, and crying. It was bad, but it was about to get worse.

While he was sitting there, there was a successful proposal one table over.


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7. Put Your Best Foot Forward

I work at a brewery/bar. One night a young woman comes in for a first meeting Tinder match. She orders her beer and chats with me a bit. Eventually, home slice strolls in; he strikes me as a bit of a meathead, but you see lots of people and I try not to judge. They say hello, officially “meet” each other and I ask if I can get him a brew. He orders one.

Somehow in the time it takes me to turn around, fill a pint, and set it in front of him, he’s already saying, “...So, don’t ever believe domestic abuse charges! My last three exes have all called the police on me.” Most people put their best foot forward on a first date. I can only imagine how charming this guy is once you get to know him.


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8. Unwanted Guests

Soho, NYC, Valentine’s Day 2009. Mid service, a guy in a cheesy jacket comes in with a full mariachi band, takes a knee in the middle of the restaurant, and proposes to one of the servers with a ring. The entire restaurant is watching, staff and guests alike. She instantly says no, mortified, and leaves the floor sobbing. The band continues to play while he half-hearted pursues her, but is stopped by the manager as he tries to enter the kitchen after her.

He exits shamefully while the band plays him off. The band sticks around for beers at the bar. Turns out he was her ex-boyfriend; they hadn't spoken in over a year and this was his attempt to win her back. We got drinks and laughed about it after service.

Valentine’s Day Disasters Facts Wikimedia Commons, Chidodj

9. Love & Chili’s

I was eating in a Chili's several years ago. In the next booth was a really young guy who had a big bunch of roses on the seat next to him. 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.


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10. Throw Your Hands Up

A guy proposed to his girlfriend and she said "no." But the story doesn’t end there. The guy threw his arms up and ran out of the building super dramatically. Later, while waiting for someone to pick her up, she told us it was completely out of the blue because they'd only been dating for a few months...


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11. The Good Grandson

My friend was working when an older woman, probably in her upper 90s came into his restaurant with her teen-aged grandson. It was a semi-classy restaurant. She was dressed to the nines and the grandson was in a nice button-up and dress slacks. As they got seated at their table the grandson placed a framed photo of what my friend assumed was the boy’s grandfather and husband of the older women.

Found out it would have been their 70th wedding anniversary but he had passed suddenly but peacefully a few months back. The grandfather had always wanted to take her to a nice restaurant but never had the time or money to do it. So, the grandson saved up his pay from the last couple of months and even got some donations from other relatives and took her to the restaurant. They ate dinner remembering all the good times with the man. They had my friend take a picture. They tipped my friend very well.

A few weeks later, he ran into the same young man by happenstance—and the man shared some news that made my friend burst into tears. He said that his grandmother passed away a few days after that night, peacefully in her sleep holding a photo of her beloved husband. He was so happy he could make that night special to her. He said it was the only day he saw her smile since his grandfather passed away. He got the picture they took at the restaurant printed and carried it around with him in his wallet.


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12. Over Prepared

During my first job as a waitress, a guy wanted to propose to his girlfriend. He came in two months before to book and had everything figured out. He planned to pop the question during dessert. We had champagne, balloons and sparklers prepped for the big moment. The time comes, he drops to one knee gives a speech about his love for her. He asks, she says no, puts the ring in her bag, finishes her dessert and leaves.

Quite possibly the most awkward thing I have had to witness—alongside around 200 other people. The manager gave him everything for free; he felt that bad for him. Cringed inside every time I saw him after that.


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13. Old Habits

An old man proposed to an old woman. He tried to get off the chair to kneel, tripped, fell and I assume broke something since he couldn’t get back up. We had to call an ambulance. My manager had to drive the woman’s teeth to the hospital separately because she had taken them out to eat her soup—lord knows why—and left them on the table in the confusion.


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14. Double Delivery

I was a delivery driver for a fruit bouquet company and I had two arrangements from the same guy. Routes were made for me and the truck was loaded so there was no way I could mess this up. I delivered both arrangements to each appropriate address. I headed back to the store to find the store owner and the guy who ordered them in an argument. This idiot put the wrong name on each bouquet. 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. Then the person who took the order. He ordered it ONLINE. All we did was import the order. I hate Valentine's Day because of that place, but man was that great.


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15. A Fishy Choice

Back when I served food at one of those super touristy seafood restaurants, I worked a Valentine’s Day double shift. For lunch, this younger couple came in celebrating their first anniversary. I offer my congratulations and proceed to do my usual spiel before taking orders. The girl is looking more and more dismayed the longer I talk.

Finally, I get to the end and ask if there are any allergies. She looks directly at her boyfriend and states, “Yes I’m allergic to fish and shellfish.” Then she looks over at me very sad. I made sure every aspect of her meal was fine for her. But It was that look of, “We’ve been dating a year and he still takes me to a restaurant that could kill me.” That really did it for me.


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16. Wine & Dine

In college, I waited tables and Valentine’s Day was always a good one in terms of tips. I once saw a couple come in to eat. Halfway through the dinner, the man’s wife shows up to surprise them. 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.

He tipped me a $100 bill.


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17. Favorite Flavor

I had a man and a woman in my section who were sharing dessert. The man playfully put a bit of the ice cream on her nose; she then did the same and he did it back once more, but with a different flavor of ice cream. She then flipped out at him because “You know I like chocolate the most, why would you waste it, you idiot!”

In the end, she stormed out cause the man couldn’t comprehend how much she was blowing up the situation.


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18. The Jealous Type

I was working as a waitress in a sushi restaurant and Valentine's Day was an all-hands-on-deck shift. This guy I had just started seeing wanted to go out, but I told him that while working in the food service, you never get Valentine's Day off and we'd just have to celebrate the day after or the weekend after.

I thought he’d take in in stride. Nope. I was dead wrong. 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 a fool out of himself and making his date uncomfortable as he tried to make me jealous.

Needless to say, we didn't go out again. Ever.


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19. The Match

A couple sitting at the bar were enjoying their night out. The man got up from his barstool and left for the bathroom. As his girlfriend was alone—and absolutely wasted—at the bar, a random woman approached and revealed that she recently matched with the woman’s boyfriend on Tinder and had hooked up a week earlier. The drunk girlfriend refused to believe this story, so the woman showed her his Tinder profile and their conversation. The boyfriend returned to a drunk, sobbing and screaming girlfriend.

I felt like I was watching a reality TV show, it was incredible. The poor girl was basically carried out of the bar by her boyfriend of three years whom she just discovered has been cheating on her for who knows how long. It was the most dramatic moment I have ever experienced and it was absolutely none of my business.


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20. A Painful Response

I once saw two failed marriage proposals on the same Valentine's Day. The first one simply said, "No I can't do this." and walked out. But the second one was worse. She stared like a deer frozen in the headlights for an excruciating 30 seconds before muttering, "Let's talk about this later." They stayed for the rest of their 6-course V-day special dinner, eating and making painful small talk.


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21. The Critic

As the evening winds down, someone calls in saying they're a professional food critic and demanded to speak to the manager. After a 15-minute call, the manager tells us the "critic" rated us a B- and said the food was good, but the service sucked. He said he would leave that last part out of his review if we comped his meal and gave him vouchers for free meals in the future... but he refused over and over to say where he worked.

Confused, the manager talked to the server... who confirmed that the guy ate alone, ran her around ragged while shamelessly hitting on her, and left zero tip—he wrote his phone number on the tip line. The real reason behind his antics? He wanted free food because the server didn't call him immediately for a date...


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22. Too Soon

Ex-barista here, hope that is close enough. Some guy on Valentine’s Day came in and asked us to write on the cup, "Will you marry me?" It did not go well. 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, was furious and started to rant and rave. When I heard what he said, my jaw dropped.

He kept going on and on about how she should have gotten over him sleeping with her sister already. We had to ask him to leave.


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23. What’s My Name?

A few years ago, I had finished my shift at a pub I was working at, and I sat down at the bar with a drink. There were still a few couples sat in the restaurant, but the boss let me clock off early. I had a pint before leaving, and at a table nearby, it sounded like a proposal was about to happen. A few people went quiet listening in...then it happened.

The guy says, "Hannah, will you marry me?" He kneeled in front of his girlfriend; she was sitting down. That’s when the girl yells, "Hannah? Who the heck is Hannah?" She threw her drink at him and walked out. The guy paid and walked out, looking very red.


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24. A Nice Night Out

I had a table of two people, probably in their mid-40s last year. It took 45 minutes for this couple to get their entrees due to our kitchen being way too slammed. When they were dropped at the table, they immediately asked for to-go boxes because they told their babysitter they’d be home by a certain time. I overheard the wife say, “Well I guess this is why we don’t celebrate Valentine’s Day.” The worst part was that they weren’t angry, just... very sad.

My personal feelings about dining out on Valentine’s Day aside, I felt so horrible that this couple clearly had put in an effort to have a nice night with each other only to have it go that way. To make up for it, we comped their meals.


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25. The Escape

I work in a small, fine dining restaurant. A man from my table goes to the restroom and is gone for a while—probably 10 minutes? Which for a restaurant is a while. As I’m passing by the restroom he whispers, “PSSSS!” Ushering me to the side and hurriedly telling me that he needs to leave through the kitchen because his wife’s best friend was sitting near him and his date, who of course as I learn then and there, is not his wife.

We box the remaining courses up and do a walk of shame through the kitchen. He’s furious, she’s crying, all while the rest of us are stifling our laughter. He ended up tipping well on the prix-fixe, which was nice.


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26. Throwing A Fit

Me and my wife both waited tables in college and she happened to work for a very nice, romantic Asian/Southern fusion place in town. Valentine's Day was overbooked, of course, and one table, a guy and his date had to wait about 20 minutes to be seated. He's complaining already as they are seated, so she knows this will be extra fun on one of the busiest evenings of the year.

They order and he insists he wants his filet mignon WELL DONE. Person of good taste, right? Anyway, she places the order as asked and continues on her way. Food comes out. The guy is very upset that the filet is still slightly pink in the middle. My wife pulls the plate and assures him the kitchen will correct the error. She takes it back and Chef says, ok, we can handle that. He hands it off to grill cook who re-fires it.

The plate comes back out five minutes later. The guy is even more irate. HE CAN STILL SEE PINK!!! Sends it back once more. The chef is done with this guy at this point and has the grill cook turn the thing into a charcoal briquette. The runner takes the plate out to the table ASAP. As it's being dropped off, my wife is talking to another table on the other side of the room, reviewing the wine list.

The guy takes the burnt steak in his hand, stands up, and THROWS IT ACROSS THE ROOM at my wife while yelling about how terrible the service and the chefs are. Dead silence in the room. All eyes are on the guy. Guy's date is starting to tear up. He yells again about not paying, grabs his date's arm and leads her out of the building.

I hope the date made it home safely. That guy had serious issues.


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27. The Surprise

I was working as a duty manager and one of the tills kept dropping off the network. As I was trying to fix it, I could clearly hear the conversation of the table by the waiter’s station. It started sweet enough with her excitedly telling 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. By this point, I'd fixed the till but was unable to step away from this car crash. It turns out she stopped taking the pill without telling him, thinking she could turn him around. He said he knew she could be a little nuts sometimes but this was next level.

He told her it was over and she could send someone to collect her things as he wanted nothing more to do with her. He called me over to pay the bill and just left. The guy never even shouted, he just calmly went screw this and got out of there. I couldn't even look her in the eye, just left her to leave in her own time.


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28. The Request

A guy and his date came in for Valentine’s Day. They had a great time, ate a lot of food, drank a lot of wine, and got along really well with my co-worker, who was their server. About two months later they come back in and request my co-worker again, who happily says yes to serving them. He goes up and greets them, the guy introduces his wife to him, and my co-worker mentions something about how much he enjoyed serving them on Valentine’s Day.

They go quiet. The wife gets up and leaves, the guy just lowers his head. It turns out he had brought his mistress in on Valentine’s Day, but my co-worker didn’t realize he was with a different woman this time around so he didn’t think anything of it. We never saw the guy again.


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29. The Pale Blue Dress

A couple came into my hibachi restaurant since it was the "fanciest" place in town. The young woman was all decked out in a spangly, light blue satin cocktail gown and he was in a suit and tie. They wanted to sit at the grill for the show but still ordered a ton of sushi and drinks, so their section of the table was extremely full of dishes. I'm talking multiple mixed drinks and waters for both of them, soup and salad bowls for both of them, appetizer plates, sushi plates, soy sauce trays, and their entree plates.

The hibachi seats 12 and its basically a bar ledge around the grill for a table, and we were slammed so there was no extra room. I barely managed to talk them into letting me take the empty dishes as they finished with them, but it hardly helped. The chef starts his show and dude is super into it, demanding to be included.

So, the chef flicks a shrimp at him. In his effort to show off and catch it in his mouth, he manages to miss it completely and crashes into the table sending food, drinks, and a full bottle of soy sauce on a plate right into his date's pale blue satin covered lap and everywhere else. It was a complete mess. She was screaming and crying, the other couples that had their meals ruined were all upset.

He's blaming me, and the busboys and I were just trying to clean up and salvage what we could of the service. It was truly awful.


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30. The First Valentine’s Day

I waited on one of the owners of the restaurant I was working at with his girlfriend and her tween kids—kind of weird, but they probably couldn't get a babysitter. He had been dating this woman for several months, but it was his first Valentine's Day on a date that wasn't his wife, who had passed away, in decades. I don't think he was ready yet, but he was there to support the business.

He broke down crying during dinner and it was heartbreaking. They left early.


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31. Check the Paperwork

I was hosting at a really busy brunch place and Valentine's Day was one of our busiest days. We had a full waitlist with tons of people in the lobby when this dude walks on with this huge teddy bear and a bouquet of roses. He said he wanted to drop them off for my coworker so I let her know he was there, but understandably she was running around so it took a bit.

While waiting, a bunch of folks waiting for tables complimented him on how sweet he was to do that for his girlfriend and how jealous they were. It was kind of cute. When my coworker finally was able to come up front there was a lot of "awww" and such. Again, we were slammed so she ran back after taking the items and it was back to work for all of us.

When it died down, I asked her how long she was dating her boyfriend. Her response sent chills down my spine. She casually replied, "He's not my boyfriend. He was the salesman where I just bought my car and I think he got my workplace from the paperwork." That was pretty freaking disturbing.


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32. The Cliché

I was bartending at an Italian restaurant and it's pretty much full of Valentine’s dates. A guy walks in and sits at the bar by himself, looking pretty down. He asked for a whiskey, so I poured it and told him it was on the house because he looked like he needed it. He proceeds to tell me his story. He had come to the city to surprise his girlfriend for Valentine’s, about a 5-hour bus trip between cities, and he sure surprised her.

She was in her dorm room sleeping with one of his friends from high school. He didn't know what to do, so he just walked into the first place that sold alcohol. I spilled as much whiskey as he wanted and watched basketball with him. I never saw him again.


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33. Taco Time

One day a guy enters the taco restaurant me and my cousin worked at. My cousin was a waiter so he goes on to bring the menu to the table. The guy, around 20 years old, says he's waiting for someone, so he's going to wait to order a full meal, but as waiters, we are taught to insist a little more and sell something. So, the guy finally orders the cheapest item on the menu—a small carne asada taco, just one.

A few hours went by, the dude's date still hadn't arrived, and every 20 or so minutes he would order another one of those small tacos. Eventually, the owner of the place, who is a really cool dude and has been a friend of my family for years, tells the waiters, "Look at this poor sucker, if the girl never arrives, I'll pay for everything he has ordered myself." So, another hour and a half goes by and this dude finally gives up and asks for the check.

He looked pretty sad so as a waiter of his age, my cousin told him everything he consumed was on the house. He smiled and left good tips anyway.


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34. Odd Family

My first day of work on the floor at a country club was the weekend after Valentine’s Day. There was a lot of buzz in the back about this adorable family, where every year the mom brought the son out to a nice dinner at the club and the father brought the daughter to the men’s section for a dinner—which shows how much pull the guy had since women weren’t allowed in that part of the club. It was their Valentine’s Day tradition. The kids are both 14 or 15 years old.

I’d also been filled in on the gossip that the waitress I replaced had left to have a baby. She was really young and there was a blanket of disapproval from the staff and a lot of the members. I’m serving the mom and son in the more upscale dining room, but getting drinks from the bar where the dad and daughter are, so I’m around both groups.

I’m bringing a bottle of wine to the mom when a woman walks in with a baby in a carrier and starts handing personalized golf balls out to people as a birth announcement sort of thing. She hands one to the mom at the table and one to the son and walks off when the mom knocked her wine glass to the floor and starts whisper-shouting at the son.

People are congratulating the new mom, and pretending to be friendly, and then each table seems to go perfectly quiet one after another. I go to the bar to get a new wine glass and see a man duck over to the dad’s table and say something to him. The man gets up without saying a word, even to his daughter, and dashes into the men’s locker room, leaving her sitting at the table.

The whole room goes quiet, but nobody intervenes as the old waitress goes over to the table, hands the girl a golf ball, says a few words I can’t hear then walks out of the club. The girl starts sobbing. Eventually, the mom seems to have remembered the daughter, because the brother comes and leads her out, and they all leave together.

When I was clearing the table, I read the golf ball, which was a birth announcement—outing the dad from the family as the father of the waitress’s baby. Yikes.


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35. A Mean Date

There was a couple that was meant to be having a proposal dinner. The guy had rung to book a table and had let us know he was going to propose during dessert. He’d given the ring to the kitchen staff so we could bring it out with a cake, and he’d got some balloons and streamers too. Anyway, he walks in a couple of steps behind his partner—everyone has big grins for them both, but he grits his teeth and shakes his head, surreptitiously dragging his finger across his throat pantomime style. Great.

Oh, and lucky me, they’re seated in my section. It’s obvious she was bloody furious with him about something; she spends the first half of the meal seething quietly, and the second having a constant pop at him. While she was in the bathroom, the manager made me double check he didn’t want us to bring the ring out or anything. “Heck, no!” was his response. I felt really bad for him, she really was mean!


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36. Mad Management

I was managing a hotel room service where there was a Valentine's package that included getting each course of the special menu delivered to your room. More than a few couples thought it was a good idea to call for the next course and then start getting freaky. Having to help with deliveries as reception messed up the bookings; I had the “privilege” of people answering the door naked, seeing adult toys strewn around and one where the other members of the “fun” 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.


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37. Full of Complaints

It was my first week serving and I was trying to do everything by the books. This normal-seeming couple is satisfied throughout the meal and I ask if the check would be together or separate, big mistake. I figured it would be together and go to the gentleman but not wanting to assume I asked. They say together; no big deal, I go get the check and drop it off.

I come back and she's writing a paragraph about how I shouldn't have asked. I grab my manager. She stops by the table and the crazy lady complains. They leave, the gentleman tips me well and seems embarrassed at the situation. The crazy lady fills out our survey complaining and calls the store three times after to complain.


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38. Seat Swappers

A younger couple came in for what I can only assume was a first date. They ordered a pizza but never ate; just caught up with a conversation, I guess. The guy must’ve been feeling confident because about two hours in he gets up, goes to the bathroom, and then decides to sit next to her in the booth rather than across from her where he was before.

I swear to you, she then got up and used the restroom about 10 minutes later, and when she came back, she decided it would best if they didn’t sit next to each other and sat in his original place. Please refrain from doing this...


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39. Don’t Forget the Pizza

I worked at Pizza Hut and the guy asked if I could bake a ring into the pizza. I politely declined. Their waitress did, however, put their ring on the pizza before bringing it to the table. The girl saw the ring, got mad, yelled at him for proposing at a Pizza Hut and walked out. He asked for a box, took the pizza and went after her.


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40. A Matter of Perspective

The place I worked at in college was a pretty nice establishment and a romantic destination because our view overlooked the entire city. It was also located at the top of a five-star hotel that had several projectors cycling through what was going on around the hotel in the lobby. There was no footage from the gym or pool so it was relatively tame and we never had a privacy issue. The best you’d ever get were people eating, walking around the lobby or drinking at the bar.

Anyway, a guy walks in with his wife and asked to be seated in a secluded area. Well, you can imagine since it’s busy and it was Valentine’s Day, we didn’t have those, so he basically waited an extra hour to make sure he was seated in the back corner. It’s my section, I take their drink order and take care of them, though the husband was gone when I returned and I didn’t see him go to the bathroom. Thinking nothing of it, I go to the bar to get the drink and see ALL of my coworkers huddled around the monitor above the bar along with everyone else in there.

Sure enough, I found the husband as he was underneath the table, going to town. The only problem was the camera above their table had a clear view because it was situated in the corner. So now the entire hotel lobby can see, as it cycles between us in the bar laughing, people checking in and our romantic couple dining on each other.

More and more people start to notice and the bar fills up. This includes back of the house staff like dishwashers and the line cooks. Eventually, it also brings out my manager who runs over to their table, tells them what happened and they both run out mortified. But before they do, the husband tries to stand up too quickly and flips the table, ruining all the plates while also exposing that his fly was down and his you-know-what is out.

He’s yelling at my manager, the hotel manager, who came up when he saw it in the lobby, and security unzipped as he’s escorted out. So yes, a disaster for them but man they made a lot of people laugh that night.


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41. The Sky is Falling

I was the chef at a pretty fancy place. We did a four-course tasting prix fixe, and were always booked to the brim for Valentine’s. The owner was out of town and the place was packed during our first seating when the pipes to the apartment above the restaurant burst. Nasty, cold water rained on everyone and everything.

The fire department came. The owner said to give everyone champagne, clean the place up and keep going. As if anyone wanted to continue their meal soaked through on a cold night covered in ceiling water.


Valentine’s Day Disasters Facts Flickr

42. The Hush Puppy Heist

It wasn’t disastrous for the couple as much as it was the restaurant. I used to work at a small Southern franchise restaurant, it wasn’t anything you could mistake for upscale. We had someone call in and ask if we could fry the ring he was planning to propose with in a hush puppy. Extremely weird request, but we said sure. They come in to eat with their families, she gets her order of hush puppies, doesn’t choke on the ring and seems excited enough. They stayed at the table for about two hours total and chatted.

Well, after all that trouble—they dined and dashed. Ugh.


Valentine’s Day Disasters Facts Flickr

43. The First Cut is the Deepest

So, as anyone in the service industry knows, you generally just do not make plans on certain holidays because you will have to work, no matter what. I had not had a date on Valentine's in probably 7 years, so when my boss gave me the day off, I was surprised and posted something dumb on Instagram about it. I got a DM from a girl I knew but not very well, asking me out for Valentine’s, and she was really cute so I figured why the heck not.

Things went so wrong, so quickly. We get to the restaurant, grab a drink in the bar while we wait on our table, and took a shot to get the social lubricant flowing since we don’t really know each other very well. I pay our bar tab, and we move to the table. To set the scene a bit, this place is a really nice steakhouse and they have these dark red, diamond pattern booths that are fluffy, with buttons at each point of the pattern.

The moment we sit down, my date lets out a blood-curdling scream like she had just been stabbed. She grabs her arm and her hand comes away covered in blood, and she looks so confused and I have no idea what the heck just happened. I look around thinking someone just stabbed her but everyone around us is seated just staring over at us. I move over to her side of the booth and grab the napkins off the table to find where she is cut.

The entire back of her upper arm is sliced from elbow to shoulder. One of the buttons had broken off of the wall and the snapped metal fastener was exposed so when she sat down her arm ran all the way down along it. She is panicking, I am trying to stop the bleeding, while the people around us figure out what is going on and call 9-1-1 for us. The manager comes over and is immediately a defensive jerk until he sees that it was his booth that did the damage.

The paramedics show up, I get the owner's info from the manager, and we spend the night in the ER where she needed something like 80 stitches. We both are exhausted at this point when a guy walks in with flowers, champagne and a bag of takeout food from the restaurant we had left. It was the owner of the restaurant coming to make sure we could have the Valentine’s meal we had missed out on.

Sure, it was probably because he was afraid to get sued but it was still really welcomed after how bad the night had become, so quickly. She and I ended up dating for almost three years and became good friends with the owner. The cherry on top? They became such good friends, that she ended up hooking up with him. That was the last I heard from either of them.

Woo, Valentine’s. I have stuck to working those nights ever since.


Valentine’s Day Disasters Facts Shutterstock

44. In the Bad Books

I worked at a pretty high-end Mediterranean bistro. My second Valentine's there, it was probably the busiest night I've ever worked as a server. We had reservations that booked basically the entire restaurant including the bar and patio from 4 PM to 11:00 PM. No walk-ins were to be seated unless a reservation was canceled, or someone with a reservation didn't show up.

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). 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 number of reservations, we couldn't guarantee he would even get a table at all.

At about 6:50 the guy loses it. I couldn’t believe what happened next. He fast-walks up to the hostess stand where the reservation book is, grabs the reservation book and practically runs out the front door. Now everything is going to complete mayhem because the only copy of the reservations for the night that is barely half over is gone. 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.

Even better is the fact that 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."


Valentine’s Day Disasters Facts Wallpaper Flare

45. Rotten to the Core

One Valentine’s Day, I was working the night shift at a hotel and this woman comes down with a cut above her eye looking like she just went a few rounds in the ring with a boxer. The woman starts sobbing and asks us to call the cops which we do immediately. Turns out, this girl’s boyfriend just assaulted her, and from what I could tell this probably wasn’t the first time.

So, after the cops show up and haul the dude off, my manager offers her a different room on comp as we need to leave the guy’s stuff where it is for him to pick up the next day. She accepts, and I go up with the woman to help her collect her stuff and move to the new room. There were a bunch of bottles of alcohol in the room, and she donated them to the front desk staff. I got a bottle of Hypnotiq and some vodka. My manager got a bottle of Patron.

The cherry on top of everything? The dude’s wife called later that night saying someone had stolen his card as he was out of town on a business trip. Never one to defend an abuser, I told her where she could find her husband. Fun times.


Espionage FactsShutterstock

46. The Ring

I was the manager of a wings-and-pizza place with a full bar—definitely not the kind of place you'd take someone for a "romantic" Valentine's Day dinner, but it was still busy because some people aren't very tactful. We had a guy who had called ahead and asked if we could put a ring in a dessert for him and of course, we obliged. He dropped the ring off the day ahead and I put it in the safe in our office to keep it secure.

Fast forward to Valentine's Day. The couple shows up, and 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 on the most romantic day of the year. They ordered champagne—well, the local winery's best sparkling white—entrees, and it was almost time for dessert.

I had used my chef skills to whip up a special chocolate strawberry tart that wasn't on the menu, just for this occasion (because why not try to make their night at least a little fancy?) I went to the safe to get the ring and my blood ran cold. It wasn’t there. I was freaking out big time. I asked everyone there if they knew what the heck had happened to it. My assistant manager on-site had no idea, so I called my other assistant—who also had the safe code—and they didn't know, either.

Finally, my bar manager mentioned that one of the owners had been in earlier, and spent a little time in the office. So, at my wit's end, I called the owner. 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.

So, I asked the server and bar manager to help stall the couple. The server told them that we were going to do something special for their big date, and to hold tight. I ran out, hopped in my car, and rushed to get the ring from the owner's house, because he was, as I had mentioned, a scumbag, and didn't want to be bothered with bringing the ring to the restaurant himself.

The bar manager went over to the table, and did some complicated, table-side cocktail mix that had a bunch of flair bartending tricks and ended with a flaming shot that, once dropped into the rest, made it smoke. I was really disappointed when I heard about all of this because I would have loved to see it instead of breaking a ton of traffic laws on my quest to get the ring.

Finally, I rushed back in after about 15 minutes of being on the brink of a heart attack, placed the ring on the dessert, and had their server take it out. 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."

I started looking for someone else to work for the very next day.


Valentine’s Day Disasters Facts Shutterstock

47. Missing in Action

A younger couple (maybe mid 20’s) dressed to the nines came in shortly after we opened and were seated in a table basically in the dead center of the dining room. They were very friendly and pleasant and I could tell that for them, dining at our restaurant was a really special treat, so I did everything in my power to make it special for them.

When they’re done, probably around 7, I brought their check which was around $300. When I came back to pick it up the guy had a super embarrassed look on his face and he said he thinks he left his wallet in the car and the woman, who is embarrassed for him, doesn’t have anything with her because her dress had no pockets and she didn’t bring a purse.

So, he goes out and five minutes later comes back in looking pale as a ghost. He has left his wallet at home and asks if he can call back later with payment info. My GM won’t let this fly because there’s no collateral of any sort he can leave, so the guy has to drive home TO BURBANK to get his wallet while the woman waits, with her hair done and her red lipstick and her pretty dress, In the middle of the dining room on Valentine’s Day.

Now, on the best day with no traffic (never happens) it’s at least 40 minutes each way from our restaurant to Burbank. She was there for almost two hours waiting for this guy. We were all so embarrassed for her that the staff kept discreetly slipping her drinks and little amuse-bouche bites from the kitchen. It was one of the most awkward things I’ve ever seen in a restaurant.

When he finally got back, he was super apologetic to us and her, he paid the check and tipped like 30% and they left. It was pretty obvious it was an honest mistake but I still think about that couple from time to time and wonder how things worked out for them.


Awful First Dates FactsShutterstock

48. No Reservations

There was a note in our reservations that there was an engagement; they wanted champagne, a specific seat, and a bunch of other stuff. The server comes up to the table saying something like, "So I read we're celebrating an engagement, congratulations!" She gets a confused look from the woman; an absolute death glare from the guy.

He hadn't proposed yet. She ruined it.


Valentine’s Day Disasters Facts PxHere

49. Pastry Proposition

Not a waiter, but I was a pastry chef at this big resort in Cape Cod. We got a special order from this guy who was coming in for his anniversary, which happened to be Valentine's day. He wanted his dessert to have, "Will you marry me?" written on it so he could pop the question when it came out. He called ahead to the front and back kitchen and even came in himself that morning to make sure it was good to go. The whole crew was behind him.

We had cooks coming in all night to ask if it had happened yet. I wrote the inscription on the plate and dressed it to the nines with gold leaf and expensive chocolate. I'm taking a picture of the plate just before it's set to go out and notice our head waiter come in with a weird look on his face. My blood ran cold when he opened his mouth. He said plainly, "They don't need it."

She broke up with him before the entrees even hit the table.


Valentine’s Day Disasters Facts Shutterstock

Sources: 1, 2

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