Servers Share More Valentine’s Day Disaster Stories

Valentine’s Day is supposed to be the most romantic day of the year, right? Well, not always. As we know, where there’s build-up there’s disappointment. And VDay is definitely big on romantic build-up.
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From reading our previous article about Valentine’s Day disasters, you might remember a few cases when all that romantic expectation ended up with a colossal failure. Still, that doesn’t make those stories any less entertaining, so we figured bringing you some more of them couldn’t hurt.

Cruel Intentions

A waitress recalls when a teenage girl arrived at their restaurant dressed to the nines. Thinking it to be a first-love type date, the waitress offered to seat the young girl who excitedly produced a poorly printed invitation to the restaurant’s Valentine’s Day dance. Except that the restaurant had no dance…


The group of girls who set their unsuspecting classmate up giggled uproariously at a table nearby. With no way home, the waitress consoled the girl with a free dessert from the restaurant…

More Dessert for Me!

A waiter at a wine bar was wrapping up the tasting for a couple and ready to serve dessert when suddenly, the wife began screaming. Tossing the cheese board aside, she sprinted outside.

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The husband seemed nonplussed and asked for both of the desserts. He gleefully wolfed down both and then requested the final drinks, gulping them down in succession. Smacking his lips and wiping his mouth, he swiped his credit card and finally ran out after his wife!

Love Is Blind

We bet this couple wishes they could unsee this blind date. A pair of hopeless romantics tried their luck at a blind date on Valentine’s Day. Luck was the last thing that they were going to have.

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As they entered the restaurant, the waiter directed the guy to the table where his date was waiting. As he approached the table, both of their jaws dropped. They were each others’ exes!

The Diamond Duck

This restaurant on the Las Vegas strip was situated near a fountain that attracted a fair number of birds. A man thought it would be charming to propose to her by the fountain.


A duck that was in the fountain thought the ring to be irresistible and decided to help itself to it. After a wild “duck” chase, the ring was finally found in the fountain as the duck had dropped it before flying off!

Double Rejection!

This poor guy was seriously down on his luck. His date, obviously unimpressed with the evening, did the ultimate ghosting move and fled the restaurant when he went to use the restroom.


Very confused at the empty booth upon returning, he asked the waitress where his date was. She had to break the bad news that he had been abandoned. After a quick sigh, he asked the waitress if she’d like to go on a date, to which she, predictably, said no.

The Long Game

This Valentine’s Day disaster happened to the bartender. When he and his date sat down, a faulty bar stool left her slightly injured.


The bartender rushed his date to the hospital. Once there, the restaurant owner arrived with champagne and dinner to apologize. This led to a friendship between the three and the bartender and his date ended up being together for three years… until she decided she preferred their restaurant-owning friend!

The Saddest Glass of Water Ever

It took this guy a full five hours to accept that he had been stood up. He at first waited anxiously, scrutinizing the menu and distracting himself from his nerves. After a while, he eventually requested a drink and a glass of water for his expectant date.


Five hours later, after a meal and drinks all alone, the guy called for the check and for the waiter to remove the untouched glass of water from the table. Ouch.

King of Cringe

Did this guy think he was a Shakespeare character or something? Not content to ruin his date’s night, he decided to ruin every other customer’s night too. He stood up, tapped his empty glass with a fork, and made everyone observe the cringe-inducing tragedy.


Lowering to one knee, he held out a plain, silver band and asked his date to “accept this promise ring”. There were no claps, just stunned silence – including from his date!

Creepy Cupid

Wow. This slimy salesman took it to a whole new level of inappropriate. A guy arrived at this waitress’ restaurant on Valentine’s Day with a gigantic teddy bear and roses. Assuming it was her boyfriend, the other waiters called her over.


She quickly took cover after taking one look at him. She informed her colleagues that he was just the salesman that helped her choose her new car. No boundaries!

Presents Not Presence

Maybe this stud thought his presence alone would be enough of a gift. When this couple first arrived at the restaurant there was no sign of trouble. Both had expected glitz and glamour and certainly fit the part.

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As the evening wore on, the woman grew more agitated. The reason for the argument became evident: she began yelling at her partner for not buying her a Valentine’s Day gift. She poured the last of her wine over him before storming out!

Holding a Grudge

Fragile egos were on full display at this Valentine’s Day dinner. What was a run-of-the-mill dinner between two lovers boiled over into a self-entitled meltdown from one-half of the couple.


When the bill came, the waiter asked the couple if he should split the bill. This question enraged the female companion, who began scolding him and writing out a scornful letter supposedly for the manager. After being forced to leave, the resentful customer phoned the restaurant repeatedly to object!

Unfortunate Cookie

A boyfriend thought the most romantic way to propose to his girlfriend would be to conceal the engagement ring in a fortune cookie. He enlisted the help of the waiters to do this.

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The waiter sat the cookies in front of them, and the boyfriend assumed the one closest to him was the engagement ring. He took it, got down on one knee, and cracked open the wrong cookie! Thinking it was a cruel joke, his girlfriend had to be consoled.

Acts of Kindness

Here’s something heartwarming to balance out the disasters! This waiter overheard a very young boyfriend phone his friend to see if he could bring him cash as he realized he could not afford the restaurant bill for him and his girlfriend.


The waiter mentioned this to the manager, who said he would take care of it. The young man settled the bill and left smiling with his date. The manager revealed to the waiter that he allowed the kid to pay whatever he could and paid the rest himself. Mensch!

Dad’s Favorite Restaurant

How good must the food be if you’re willing to risk your entire family finding out about your affair? An elderly gentleman brought his far younger companion to have Valentine’s Day lunch at this particular restaurant. Seems innocent enough, right?

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That evening, a family came for dinner and the waitress could not help but recognize the father’s face…it being the same man from earlier! A mortified expression washed over the man’s face once realizing he had the same waitress.

The Mariachi Misery

A mystery man made a grand entrance into this New York restaurant with a Mariachi band following him. They strolled through the restaurant towards one particular waitress who was trying to hide. The mystery man cornered her, kneeled, and presented her with a ring.

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Turns out to be her ex-boyfriend, thinking that the gesture would win her back. It did not. The man left, the mariachi band sat at the bar and drank and his ex-girlfriend went home with the bartender!

The Escape Artists

These two deserve each other. A customer requested the waiter to hide the engagement ring in what is known as a “hush puppy” – a ball of fried cornmeal. That should have been the warning sign right there.


The couple arrived with family in tow, and the woman luckily found the ring before biting into the hush puppy. The wait staff congratulated them and served them for a full two hours before the whole family dined and dashed.

They Don’t Need It

This hopeful fiancé arranged for the restaurant to use pricey chocolate and gold leaf to spell out the words “Will You Marry Me?” on the dessert tray to pop the question right at the end of the couple’s magical night.


Just when the cooks are putting the finishing touches on the dessert, the table’s waiter comes into the kitchen and informs them that she dumped the poor guy before the main course!

The Hijacker

One selfish woman tried hijacking an elderly couple’s table reservation. The woman ignored the reserved sign, sat herself down, and even tried to get rid of the “Reserved” sign. When the waiter demanded she leaves, she tearfully pleaded with him to give her the table as her boyfriend was going to propose, but they never booked.


Realizing she couldn’t stay, the woman began swearing at the waiter. She did get a standing ovation from the other customers as she stormed out.

Don’t Forget Your Dentures

An elderly gentleman planned to propose to his equally elderly beloved over dinner. His knee joints were not up for the challenge of kneeling, and he took a tumble. The ill-fated future fiancé could not rise, and the restaurant staff had to have the ambulance called.


When the ambulance had left, with the man’s female companion in tow, the staff noticed that she had left her dentures behind on the table. The restaurant manager drove the poor woman’s teeth to the hospital to return them to her!

Wedding Day Blues

Getting married on Valentine’s Day, now that’s a bold move. A newlywed couple arrived at the restaurant fresh from their wedding. So fresh, in fact, that the wife still had on her wedding dress.

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The couple hauled their luggage into the restaurant and collapsed exhausted into their seats. The waiter warmly congratulated the couple, who didn’t even acknowledge her. Onion rings were the only item they ordered, and they sat in silence for an entire hour before leaving.

Spicy Wings

A customer brought his date to a grilled chicken restaurant and was hostile from the moment he entered. We assume he was thirsty as he demanded three bottles of wine!


When his chicken turned out to be too spicy, he accused the waiter of insulting him, prompting the “meathead” to hurl the wine bottles at him! Other men in the restaurant stopped him after a lengthy fracas. His date luckily made her escape in the middle of it!

Waiter’s Revenge

A regular at this restaurant, who was well-known for never leaving a tip, had an infamous reputation for bringing multiple women to the establishment.

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Tired of no tip, one waitress took it upon herself to tell the truth about the regular’s many, many dates and flings. His date caught the drift and left when he was in the restroom. He returned to an empty table and begrudgingly paid the bill (sans tip, of course), and never returned.

Annie, Are You OK?

This one is a lesson to those who may need to slow down on dating for a while. A customer reserved an exclusive Valentine’s Day dinner in the wine cellar of a fancy establishment. The chef was specially requested to write “Congratulations, John & Annie” on their dessert tray.

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Valentine’s Day rolls around, and sure enough, the couple arrives for their – or rather John’s – long-awaited date. But that date was not with Annie, and we will never know what compelled the guy to take a different girl.

The Mood Dampener

Two different couples sat in booths adjacent to each other at this restaurant. Both booths had taken advantage of Valentine’s Day, and the respective boyfriends had it in mind to propose.


After an excited “yes” from the first girlfriend, the boyfriend from the other booth thought he might have a chance. But, alas, he received an emphatic “no” from his girlfriend. The celebrations from the first booth added to the awkwardness and no one left the restaurant very happy.

She’s Seen Way Too Many Movies

When this delivery driver arrived at the designated address, he learned that this wasn’t your typical Valentine’s Day meal.


It turns out this was an attempt to make the husband jealous as his very brassy wife pushed past him and said the delivery driver was the only man to have got her something for Valentine’s Day. After the wife offered a tip, the driver quickly made his getaway. We wonder if this at least pushed the husband to be more romantic in the future, otherwise, he might lose his wife to any delivery boy.

Mashed Potato Hair

This waiter found himself a casualty of a jealous boyfriend. A valentine’s day breakup is something we will never personally understand, but it happens. After the breakup, the girlfriend and one of the waiters were hitting it off.


The ex-boyfriend did not appreciate his girlfriend moving on so fast, and so… in front of him. A poor waiter who wasn’t even involved retold the story, found himself covered in mashed potatoes.

What a Gentleman

We’re starting to think some of these aren’t disasters but blessings in disguise! A woman, seemingly treating her date to Valentine’s Dinner, was left red-faced when her card got declined during payment. You’d expect her loving date to be understanding, right?

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After half an hour of trying anything she could think of, the now exasperated boyfriend threw his hands in the air and yelled, “Fine! I’ll pay!” He paid in cash and made sure to leave barely any tip. Classy.

The Tire-Slashing Sleuth

This guy was as bad at adultery as his wife was at sleuthing. Valentine’s Day saw some high drama for this waiter as he reminisced when a guy and his date had their dinner destroyed when his wife came marching in with their three children in tow!


After verbally and physically attacking the pair, the woman made her way outside and proceeded to slash the tires of what she assumed was her husband’s lover’s car. You guessed it – it wasn’t the right car.

Valentine’s Parole

A waiter picked up odd vibes from this couple on Valentine’s Day. The woman was upbeat and friendly, while the boyfriend was aggressive. 

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All it took for the guy to explode finally was the waiter bringing the woman the wrong drink. The boyfriend threw the drink across the room and upturned the table. The woman begged and pleaded with them not to call the authorities as her boyfriend had just been released! Maybe he wasn’t quite ready to be released?

Nice Ring, I Think I’ll Keep It but Not on My Finger

Eight weeks before Valentine’s Day, a customer arranged to make his proposal memorable with this restaurant. The eager boyfriend pulled out the ring when the day arrived and asked for her eternal commitment. The woman did not stop chewing her dessert while saying “no.”

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This woman’s hunger must have matched her callousness. She actually took the ring from him, threw it in her bag, and finished her meal! She could have at least let him keep the ring he bought…

Money Talks

A waitress found herself in an awkward situation when the man at the table she was serving kept displaying highly inappropriate pictures to her on his phone. Each time the waitress returned, he would show an even racier image. 

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The waitress eventually called her manager. Upon seeing the man, the manager quickly informed the waitress that the inappropriate guy was actually a politician’s son and any confrontation would end up in a lawsuit.

Tinder Proof

Modern technology outed one boyfriend’s mischievous ways. The boyfriend and his girlfriend spent  Valentine’s Day sipping on cocktails at a local bar. When the intoxicated boyfriend went to the restroom, a woman approached his girlfriend and claimed to have recently dated her boyfriend.

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After opening her Tinder app to prove their conversations, the mystery woman removed the girlfriend’s doubts. The boyfriend returned to his now hysterical girlfriend, whom he had to throw over his shoulder and carry out the bar.

Love Comes in All Sizes

We thought we’d throw in a cute story to let you catch your breath from all the calamities. A curious couple would frequent this particular restaurant every Valentine’s Day. What made them unique was that the wife stood over six feet tall while her husband touched on five feet tall.

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The couple was incredibly amorous, and as the waiter recounts, the husband would nestle into his wife’s bosom after dinner and usually drift off. Ok, somewhat weird but endearing at the same time.

That’s a No, Then?

This public proposal did not go as planned, as this girlfriend responded to the romantic proposal by – wait for it – laughing.

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The affronted boyfriend demanded an explanation as to why his girlfriend was rejecting him. She was growing increasingly embarrassed by his spectacle as he spiraled into a blubbering wreck, growing louder and louder demanding an answer. We think his reaction was very indicative of why she said no.

Can’t Buy Me Love

May we have a moment’s silence for this trainwreck? Perhaps this man thought that a five hundred dollar meal and a three hundred dollars worth of wine would make his girlfriend see the light?

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After splurging on the finest food and wine for his partner, he dropped to one knee and, grinning like a Cheshire cat, popped the question. His girlfriend remained unmoved, but why?  Apparently, she had better options. The boyfriend leaped to his feet and screamed the awful truth.

White as a Sheet

A woman was left dejected as it appeared her date had ghosted her mid-date after going to the bathroom and not returning for a full twenty minutes. Taking pity on her, the manager offered to make her meal complimentary.

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That is until somebody notified the waiter that the guy was still in the bathroom…and in need of a roll of toilet paper! This guy was no ghost, but he did need a white sheet!

Heart-Shaped Steak

In the tackiest marketing ploy ever, a steakhouse cut a section out of their sirloin steaks to resemble a heart. It worked – they were back to back with guests and soon ran out.

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One customer who was deadset on having his heart-shaped steak had a hissy fit when the waiter informed him that they’d sold out and he’d have to order something else. The man folded his arms, glowering, while his wife ordered and ate in silence.

A Hairy Situation

What is it with cheaters bringing their paramours to the same restaurant they bring their partners to? This two-timing halfwit brought his mistress and his wife to the same restaurant within twenty-four hours of each other.

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The wait staff recognized him from the day before and noticed that his partner’s hair was now brown rather than blonde as previously. Paying her a compliment, the waiters commented how good it looks, to which the wife immediately realized her husband’s philandering ways.

Saying the Wrong Name

Having finished his shift early, a bartender decided to hang back and have a beer before heading home. A tipsy customer first staggered to his feet and then wobbled down to one knee. His gleeful partner sat dreamy-eyed.

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Disbelief washed over his girlfriend’s face as he said the words, “Hannah, will you marry me?” but not the good sort of disbelief. Screaming, the girlfriend demanded to know who Hannah was! The guy was left soaked in booze as she poured her drink over him.

Parting Shot

A couple held no punches as they erupted into an argument in the middle of the restaurant. Both sides did not hold back and were screaming wildly over each other. As the fighting was so loud, the manager requested that the couple leave.

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Without missing a beat, the husband retorted that leaving is what he has been aiming to do for two years! We don’t think he was referring to the restaurant. At least the manager helped this guy finally get what he really wanted.

Keeping It in the Family

A customer asked his barista to write “Will you marry me?” on his girlfriend’s takeaway cup. The barista did so obligingly, handing the girlfriend her coffee while the guy got down on one knee. The girlfriend simply placed the cup back on the counter and turned to walk out.

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The guy, having become enraged, began shouting that his girlfriend should forgive him for having had an affair with her sister! We’re shocked that a cup of coffee didn’t solve that.

The Creepy Critic

A restaurant manager received a call from someone claiming to be a food critic. Seemingly displeased with what he claimed was “poor service”, the supposed critic threatened to leave a scathing review.

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The critic refused to divulge the publication he worked for. After investigating, the manager found that the “critic” had been a lone Valentine’s diner who tried to hit on the waitress. As if that’s not worse enough, the guy left his phone number instead of a tip!

All Dining and No Dashing

Forgetfulness put a damper on this poor couple’s Valentine’s after a husband discovered that his wallet was not on him after he and his wife finished an extravagant meal worth three hundred dollars.

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It was an hour’s drive back home in rush hour traffic for the poor husband while his wife embarrassingly sat in the middle of the restaurant. The staff took pity on her situation and snuck her drinks and snacks to bide the time.

Revenge Is a Dish Best Served…Warm?

Valentine’s Day is no ordinary workday for restaurant staff. As it is one of the biggest drawcards of the year, staff usually find it impossible to take time off. A waitress’ boyfriend found this out the hard way when she had to cancel their plans.

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Seeking petty revenge, he arranged a date with another woman at his girlfriend’s restaurant. His attempts at making her jealous backfired spectacularly as he found himself the one left in the lurch from both women.

The Great Valentine’s Day Famine

Marketing is a fine art…and so is budgeting. A newly acquired restaurant tried to rake in a crowd as it advertised the Valentine’s Day special of a three-course meal for almost twenty dollars.

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The waiter recalls having to refuse entry to a couple after couple due to the crowd and having to rebuff any requests for food from the customers – as they had run out within the first two hours!

The Sad Shrimp Saga

We’re wondering why all-you-can-eat seafood seems to be a Valentine’s Day thing. This time, it wasn’t all-you-can-eat crab but rather shrimp. Just over half an hour after the couple began eating, an argument ensued and the woman was wailing.

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The guy, seemingly untroubled by her sorrow, continued to order bowl after bowl of shrimp all the while his gloomy partner sobbed. Sensing defeat, the woman made her exit while her knight not in shining armor continued ordering his shrimp.

That’s No Pearl

Oh boy, this request was seriously lost in translation. Cooks at a seafood restaurant didn’t understand that they were to place the engagement ring on a lobster claw and not inside the lobster itself.

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The boyfriend, who was to propose, was sweating bullets when he realized the ring was not on the claw and called the waiter to ask where it was. At that moment, his girlfriend shrieked as she chomped down on all eighteen karats of the diamond ring.

He Wishes It Was a Racehorse

This V-Day disaster happened not to a waiter but to a carriage driver. A man paid for an hour’s carriage ride to propose to his partner. Half an hour into the ride, the man reveals the ring and asks her the sacred question… to which she replied, “Absolutely not”! 

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The next half an hour back to the barn, the driver discreetly tried messaging his coworkers to remove all of the celebratory decorations that were waiting for the couple!

The Vegan

A bachelor booked a table at a high-end steak restaurant for Valentine’s Day even though he was single, confident by Valentine’s Day he could take someone out.

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It turns out that he found a girl last minute and it was their first date. He requested his date to keep her eyes closed until being seated so he could surprise her with the upmarket restaurant. Upon opening her eyes and realizing she was in a steakhouse, she yelled that she was a vegan and made a very sudden departure!

No Tip, No Memories

An enthusiastic customer set up a restaurant booth to propose to his girlfriend. The accommodating waiter went out of his way to make it memorable. The hopeful fiance handed the waiter his phone and asked him to film the proposal. However, the screen locked as he was about to pop the question.

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The quick-thinking waiter used his own phone and promised to send the video. After they left, the waiter realized no tip was left. Needless to say, the fiance didn’t get his video!

Burger Ring

Is that Burger King or Burger…Ring? A burger joint might not be the most romantic place to propose, but each to their own. A highly insistent customer demanded that staff place the engagement ring he bought for his girlfriend inside the burger itself.

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The staff advised against it, but he insisted, and they complied. As expected, things went very wrong. The ill-fated girlfriend swallowed the ring, and paramedics were called. The foolish boyfriend then threatened to sue the restaurant for negligence!

Husband’s Stakes Were Too Low

A waitress at a waffle house recalled when a cute, elderly couple walked in the door. It soon became evident though that the wife was seething with resentment.

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Immediately upon being seated, the wife loudly exclaimed (with some very colorful language) for all to hear that she was in disbelief that her husband would bring her to eat steak at a waffle restaurant to celebrate Valentine’s Day. We side with her on this one. Raise your stakes, buddy!

The Jig Is Up

Scamming a restaurant should follow the same principle as “lightning never strikes twice”. A pair was caught red-handed trying to swindle a restaurant out of a free meal.

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The con involved the couple selecting a restaurant on Valentine’s Day and faking a proposal in order to score a free meal. Mindlessly, the couple tried it at the restaurant they scammed the year before! This time around, keen-eyed staff recognized them and told them to get the hell out!

The Heedless Husband

This anecdote might be our favorite yet. A customer called this restaurant to make a Valentine’s Day reservation. The waiter, somewhat confused, informed the man that the date was the fifteenth of February and that he had already missed Valentine’s Day.

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Without missing a beat, the man sheepishly responded with, “Yes, I know that, but my wife has made it clear that I better not forget next year’s!” Let’s hope his long-term memory is better than his short-term!

Not the Backseat They Were Expecting

A police car’s backseat is undoubtedly not the kind of backseat most Valentine’s Days dates end up on! A couple spiraled into an argument so heated that the staff asked them to tone down or leave during dinner.

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The resentful man simply walked out of the restaurant, leaving his penniless partner to pay. She begged the manager to wait for her partner to return. Which… he never did. The manager called for the police, who walked the jilted lover out.

Special Delivery

A waiter overheard a female diner enthusiastically announce her pregnancy to her boyfriend who sadly did not share her delight. After getting over the shock, he reminded his girlfriend that he was explicit about not wanting children.

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She was under the illusion that upon finding out she was pregnant, her boyfriend would be overwhelmed with paternal feelings and abandon all his child-free ambitions. Boy was she wrong. Guess it wasn’t a good idea after all.

Sound Advice

Who is so oblivious to breaking up with someone on Valentine’s Day of all days? This hapless boyfriend decided Valentine’s Day would be the most suitable day, and an upscale restaurant would be a reasonable breakup venue.

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The couple seemed radiant, snapping selfies and sharing their food until the boyfriend, now tipsy, began getting a bit loud. Eventually, the woman left in a fit. When the waiter went over to deliver the check, the boyfriend handed him a business card and advised him not to waste money at an expensive restaurant when dumping a girlfriend.

What Did He Say?

This particular restaurant only permitted (costly) three-course meals to be ordered on Valentine’s Day. A couple sat in stony silence with their food untouched and their plates pushed to the edge of the table.

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What DID her boyfriend say to her? No one should ever comment on other people’s weight or eating habits. Especially not boyfriends. And on Valentine’s day of all days? What has this girl done to deserve this?

Whisk(ey) the Blues Away

A bartender took pity on a very dejected-looking patron sitting at the bar and offered him a whiskey on the house. The kind gesture got the patron to spill his guts and said he was in town to surprise his girlfriend for Valentine’s.

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It was indeed a surprise for both of them as he walked in on his girlfriend in a very compromising position with another guy. At least he got free whiskey out of this!

Not So Sweet

An innocent-enough-looking couple shared a very normal Valentine’s Day Dinner, packed with smiles and giggles and sweet nothings. Things took an odd turn when the waitress began to notice the guy’s voice rising.

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His very shocked date sat stunned as he scolded her for not caring about the harmful effects of sugar and that her apathy was dooming mankind. Embarrassed, his female companion fled, and he actually chased her! He returned the next day to pay. Guess he’s a gentleman?

Freudian Slip

This waiter did this all to himself! The only customers he was serving that evening that weren’t a couple were what the waiter assumed to be, mother and son. The evening went uneventful until it came time to pay.

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Handing the check to the young gentleman, the waiter said, “It’s so sweet of you to take your mom out for Valentine’s!” If looks could kill. It did indeed turn out that they were a couple just with an…age difference.

What a Washout

A relatively upscale restaurant hosted an exclusive Valentine’s Day event complete with set meals. Water pipes in the top levels of the building burst, and the restaurant, being on the ground floor, was utterly washed out.

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The owner said to supply as much champagne as anyone wanted and keep acting normal. What can we say? Hypothermia sure is romantic, especially if you have to hug each other to keep warm.

Take Off Your Birthday Suits, Please

A room service waiter saw it all when a couple decided to seriously make the most of their Valentine’s Day hotel package. The couple did not care that the wait staff witnessed some of their very unorthodox displays of passion.

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After the wait staff had been exposed to guests in various states of undress, the manager lay down the law and insisted that if the guests did not cover up for staff, they would have to retrieve their own food and drinks.

Golf Ball Revenge

A couple would bring their two teenage children every Valentine’s Day and sit at different tables – the mother with the son and the father with the daughter.

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A waitress, who had been on maternity leave, arrived unexpectedly and began handing out golf balls to all the customers announcing her child and partner’s name. The father quickly disappeared. On the golf balls were her name and his name as the child’s father!

Worst Ringbearer

Hiding the ring under the table seems like an odd choice, but we guess the guy was trying to shake things up? This man’s plans were foiled by good intentions. Another customer walked past the table and spotted something on the floor.

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In an act of kindness, the customer reached down, picked up the engagement ring box, and smilingly said to the couple, “I think you guys dropped something!” Proposal ruined!

Anyone Seen Mr. Krabs?

Waiters had a somewhat tragically comedic Valentine’s Day when a woman brought her young son instead of her husband to their all-you-can-eat crab leg Valentine’s Dinner. The child’s parents had a war of words before the dinner, and she opted to take her son as company instead of her husband.

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Eating her feelings, the mother devoured the all-you-can-eat crabs’ legs until the manager had to bar her from eating anymore as they were running out of supply for customers!

Triggered by Chocolate

A waiter was watching what seemed to be a cute exchange between a couple whereby the husband dabbed a spot of ice cream on the tip of his partner’s nose. She, giggling, returned the favor and plopped some on his.

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He did it once more, but this time with the chocolate ice cream. His partner lit up like a volcano, screaming, “You know I like chocolate! Why would you waste the chocolate, you idiot!”

Homewrecker Gets Wrecked

Valentine’s Day is usually a gold mine for waiters to receive tips. This particular waiter did not expect the payday he was about to receive when a seemingly innocent dinner turned into a divorce.


The couple he was serving was chewing blissfully away when the man’s wife showed up the next minute. After pouring a bottle of wine over her husband’s head, she yanked off her wedding ring, gave it to the mistress, and said she could have him.

A Terrible Surprise

A devoted boyfriend went the extra mile to propose. He convinced his girlfriend he would be out of town on Valentine’s Day but had arranged a surprise engagement with her friends and family.

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Along with several family members and friends, the boyfriend hid in the apartment, waiting for his girlfriend to arrive home. She eventually did – in the arms of another man! Wow, this is so awkward and cringy we’re surprised it wasn’t already written into a Nextflix show.

The Ring-Off

A local dive bar did not expect to be entertaining a Valentine’s Day wedding proposal. Nonetheless, a hopeful fiancé asked the staff to help arrange a surprise proposal for his girlfriend.

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The manager stored the ring in the safe. However, the bar owner came across it and, thinking that it was a lost and found item, decided that it would be great for his girlfriend! After hunting it down, the manager retrieved the ring, and the proposal was a success.

The Book Thief

Note: being a customer doesn’t give you the right to exceptional, extraordinary treatment. This was not obvious to one diner at this particular restaurant who arrived on Valentine’s Day without a reservation.

Getty Images Photo by mark peterson/Corbis via Getty Images

After being very persistent for almost an hour, he thought the best way to get a spot would be to sabotage the reservations by stealing the reservation book. Staff gave chase, but the nimble suitor outran them only to return later, insisting he’d booked a table!

For Heaven’s Hake!

In celebration of their year together, a couple went to a particularly high-end seafood restaurant. The waiter, joining what is to be a joyous moment, offered his congratulations and well wishes. But then…

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After delivering his sentiments and speaking at length about the specials, recommendations, and suggestions, he proceeded to ask if either of the pair had allergies. Turning her head slowly towards her boyfriend, the woman stated, “Yes. I’m allergic to fish and shellfish.”

Indecent Proposal

A young waiter found himself in a real-life instance of an indecent proposal on Valentine’s Day. But it wasn’t a marriage proposal. When the check arrived for the couple, the husband asked the young waiter if he would be interested in engaging in their… bedroom activities!

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The waiter, who added that he was raised very conservative and very Christian, quickly declined without giving it a second thought! Here’s hoping the tip made up for the insult!

Fruit Infidelity

Nothing is sacred to a cheater; not even Valentine’s Day. A driver, who had to deliver fruit bouquets ordered from the same man to two different women, dutifully did so.

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The half-time husband, half-time paramour, and full-time fool mixed up his home address with his mistresses’ address. The two women called the number on the bouquet card and unraveled the man’s philandering.

Jerry, Jerry, Jerry!

We’re sure the waiters thought they might be on the set of Jerry Springer when they witnessed this catastrophe. Beaming with hopeful expectation, a man put his cutlery down, reached into his pocket, and displayed the diamond ring to his girlfriend.

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She began sobbing. Rest assured, these were not tears of joy. As he uttered the words, “Will you marry me?” his partner said in a wail, “I’m pregnant.” The man’s shock was only beginning as her second sentence followed, “And you’re not the father.” Ouch.

Premature Proposal

Champagne? Check. Specially reserved spot? Check. Throw in the candles, the petals, the ambient lighting, and all the right elements were in place for the perfect Valentine’s Day proposal.

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Having read the restaurant memo that it was a proposal, the waitress approached the beaming couple and congratulated them on their engagement. Instead of a warm thanks, the waitress got a bewildered look from the girlfriend and incensed scowl from the boyfriend – he had not yet proposed!

My Wife’s Friend Is Out There!

This Valentine’s Day dinner went very wrong for a two-timing husband. The waitress, who was working this particular couple’s table, noticed the man leave to the restroom and not emerge for almost fifteen minutes.

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At one point, she heard a “psst!” and the man motioned her over to the restroom door. Pleadingly, he asked her to help him escape as his wife’s friend had arrived and would see him with his date – who was the wife’s best friend.

Sad Violin

An overeager boyfriend tried to persuade a restaurant to orchestrate the cliché of all cliché proposals, complete with an engagement ring in the glass of bubbly champagne. The restaurant, worried about liabilities, politely refused.

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Determined to make the evening special, the guy had a violinist enter the restaurant and play while he proceeded to get down on one knee. Shocked, his female companion screamed,” This is our third date!” and stormed out of the restaurant.

Partner Starter

One amorous couple could not wait for the main course and decided to, shall we say, “tuck in” before the food arrived. The cameras that broadcast a general live feed of the dining area caught the couple in their risqué act!

Getty Images photo by Henrik Sorensen

Staff ran to alert them, and the husband sprung up and knocked the table on its side – destroying all the plates and starters on the table! The pair, who was furious rather than embarrassed, had to be escorted out by security.

It’s Platonic!

On his way home from work, a (very straight) man had the misfortune of his tires blowing out. Stranded, he called his (equally straight) friend to assist him.

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As a gesture of thanks, he offered to buy his friend dinner. Both still in their suits from work and unawares of it being Valentine’s Day, the two made their way to the nearest restaurant. It only dawned on them that the entire wait staff thought they were on a Valentine’s Day date!

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