Why do we even celebrate Valentine's Day? Everything about it seems like it's tailor-made to make people miserable. The expectations are too high and the potential gifts too expensive. It's a recipe for disaster, but like well-intentioned lemmings, we rush to jump off that cliff every year in hopes of impressing the objects of our affection. Everyone's got their own story about a disastrous February 14, but these Redditors came together to share their experiences of V-Day woe. Some simply witnessed the catastrophe, while others were right at the center of it. Either way, one thing is for sure: each tale is more cringeworthy than the last.
1. Three’s A Crowd
I used to be a professional musician and the four-piece band I was in got booked for a Valentine’s Day event in a local bar. The guitarist invited his girlfriend down so they could be together on the night. Well, he was in for a surprise. What he hadn't counted on was his WIFE getting the night off work and coming to the show too, as a Valentine’s surprise.
Everything was fine for the first set of the night. Then the problems began when both the girlfriend and the wife met in the band room backstage. Most of the band escaped the obvious row that was coming and waited by the bar for the second set. What we saw next was the most outrageous show of a woman’s scorn anyone has ever seen!
The wife ran onstage and began trashing his guitars and all his pedals, leads, and amp. No one dared to stop her. She was rightly angry. Shortly after she left the stage, the girlfriend had her turn, destroying whatever was left of his gear. Between both cheated women, they caused around $2,000 worth of damage to his set up. Needless to say, we played the second set as a three-piece, but it was quite a show!
2. Swinging For The Fences
For Valentine’s Day this year, I made a big mistake. I made and gave a homemade card to someone who I’ve basically been very casually sleeping with for the last little while. I did it to show her that I’d be open to a little more of an emotional connection. Her response was devastating. She told me that she thought maybe we should be “just friends” from now on. So I ruined a pretty great casual gig trying to be a guy who has emotions…
3. Just Desserts
At the beginning of the evening, a man at our restaurant gave me a ring to bring out to his table with dessert. The couple began arguing before they even ordered and ended up screaming at each other in the restaurant. My manager made me ask the guy, as discreetly as I could, if he still wanted the ring with the dessert. It was that bad.
I didn't want to, but I asked. Big. Mistake. He then started to scream at me that of course he still wanted the ring. He was right, after all, it wasn't my business. So I brought out the ring. She said, "Are you serious?" and left. Then the man screamed at me again when I wouldn't let him chase after her and leave without paying.
In the end, the guy just threw the money on the table with a huge tip, but I think he just gave what he had and left. He had made such an insane scene that we had to give free desserts to the tables next to them to make up for ruining their evening. After the service, I told my manager I was never questioning a client's request again.
4. Let’s Get Down To Business
One year for Valentine’s Day, I was set up for a blind date by a friend. I arrived about 10 minutes early at the restaurant where we had planned to meet up. 40 minutes later, she strolls in, sits down, and says something so disturbing, it’s impossible to forget. Bluntly, she tells me: "I'll get straight to it. I don’t care who you are. I just need a father for my three kids." I immediately got up and walked out. Not exactly my idea of a romantic time!
5. 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.
6. Smoke Show
As a safety precaution, my girlfriend had her fire alarm linked up to the fire department’s system. On Valentine’s Day, I accidentally set the alarm off while searing scallops for our romantic dinner. In the middle of dinner, we got the surprise of a lifetime. Five firemen violently interrupted our dinner by breaking through her front door. One of the firemen was wielding an ax. Both embarrassment and laughter ensued.
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7. One Ring To Fail Them All
There was a couple seated a few places away from us. They sat far enough away so that we couldn't hear the conversation, but it was obvious that they were arguing. The waiter did his spiel on the set tasting menu and handed out a beverage list. The guy orders a bottle of vino for both of them and she interrupts with, "I'm good I'll just have water."
They continued over a very uncomfortable meal, during which he kept asking stuff. She'd respond with increasingly annoyed no's. The waiter returns and notices that appetizers hadn't even been touched yet. He tops off her water and his drink, then asks if everything was tasting alright. He finishes with an, "I'll give you guys some more time to enjoy."
She was now loudly enough that we could understand her now. "I can't keep doing this with you." She angrily forks into her appetizer and finishes just in time for the entree to arrive. The arguing continues, and the guy is looking increasingly nervous. Suddenly, he gets down on one knee. She said, "Oh God, no." He takes her hand to put the ring on it.
She snatches her hand away like he's lava. He still wasn’t reading the signals and said, "Will you do..." She bursts into tears. Everyone in the entire restaurant, who didn’t really understand the context of the situation, sighed an audible "Awww!" She said, "I can't believe you would even ask after what you did. I told you I needed space. I don't even know if I can trust you anymore."
After that, things were kind of a blur. I think she threw a couple of $20s on the table, then ran out. He stayed on the ground, still holding up the ring like he wasn't done proposing yet. The waiter returned with one of those sweet lava cakes topped with a little "She said yes!" thing. It was absolutely excruciating from beginning to end.
8. Sweet Ending
We had a classic of a couple coming in all dressed up and out for their romantic dinner, but as the meal went on they gradually got tenser and their muttered argument slowly became very loud. Walking back over to refill drinks or take plates seemed to make it even worse, but I couldn't just leave their (very small) table covered in the stuff.
By dessert, WWIII had broken out, and the evening ended with the guy getting a bowl of chocolate cake and ice cream emptied over his head. I still have no idea what they were arguing about, but the poor guy just sort of shoved a load of money on the table and ran out of there after his partner.
9. Oscar The Grouch
This Valentine’s Day, I made a point to be extra sweet to my husband all day long. I was constantly sending him lots of texts and snaps. We had decided to not buy gifts or anything for each other, which was totally fine. We went out for a quick dinner with the kids too, so that I wouldn't have to cook. Sadly, he was super grumpy the whole time, snapping at me repeatedly and generally being a jerk.
We get home, I do the dishes, get the littlest showered, and generally clean up. He is still being grumpy, and I am just ignoring it and pretending it's fine. I then looked in the fridge and saw that my dad had bought me flowers, as he does every year no matter what. My husband didn't tell me that I had received these flowers, though, so they were just sitting in the fridge all night without water.
He remained super grumpy all day, and then just before he went to bed he texted me that he loves me and that I am the best wife ever. It was too little too late. I replied, "Who dis?"
10. What’s The Problem?
I had a brief stint as a waiter in high school. This one couple looks very sweet and loving, with no apparent problems. The girl got down on her knee and asked him to marry her. The man's response was chilling. He started laughing hysterically and explained to her that proposing is a man's job, not a woman's. She was furious.
She started screaming about how inappropriate that was, then got her stuff and stormed out. He looked completely bewildered.
11. Not Part Of The Plan
I took a bath and was all done up in some fancy new lingerie. My hair and makeup were completely pristine. I had been casually drinking for the better part of an hour and started getting dinner ready. The dinner preparations were taking longer than expected, so naturally, I drank to pass the time. Finally, when it was ready, I gave my boyfriend his plate, and we excitedly started eating and cuddling up to each other.
We were super excited because we were totally going to have some intimate fun together afterward. But my body had other plans. All of a sudden, while we were enjoying our meal, all of the drinks that I had consumed seemed to hit my system at once and I projectile vomited for a few hours straight before finally passing out.
12. Wing And A Prayer
A couple comes in and sits down in my section. I walk over just as the lady stands to go to the restroom and grab their drink orders. The lady goes to the bathroom and the gentleman says he knows what they want for appetizers. He orders boneless wings in two sauces. I run off to fetch their drinks and put their order in.
A couple of minutes later I'm returning with their appetizer. By this point, the lady had returned to the table. I set the basket down and she stares at it with surprise. "What's this?" I reply, "It's the appetizer that was ordered. Is it okay?" This woman turns to her partner and proceeds to loudly and thoroughly chew him out. How dare he order wings for an appetizer when he knew she wanted wings for dinner!
She runs on and on about how stupid he was for ordering wings first and I could just see the poor guy curl in on himself and slowly die inside. I stated I would give them a few more minutes and hurried away. The dinner was very tense and awkward after that. They barely spoke to me and I swear didn't utter another word to each other.
I felt so bad for the guy because he ordered wings since she obviously must have made it clear she wanted them and got torn a new one for it.
13. No Stalling
I went into the bathroom at a restaurant on Valentine’s Day and made a disturbing discovery. Not only was there a man in the woman's washroom, but he was also down on one knee, sobbing as he proposed to a woman in a bathroom stall. She said no.
14. Beating Around The Bush
My Valentine’s Day dinner was great, definitely one to remember. But it was all downhill from there. My girlfriend and I were in such a good mood from dinner that we decided to do something fun and exciting. We started getting romantic outdoors, just behind some bushes. That turned out to be a big mistake. My you know what is currently completely covered in poison ivy…
15. 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.
16. Eye Love You
I got ready to go out to dinner with my fiancé. I got all dressed up, did my hair and makeup, and looked great. I grabbed my perfume at the last second before we walked out the door and proceeded to squirt it in a full-on direct hit to my eyeball. It burned so horribly. Of course, my makeup was not waterproof and I completely ruined it by doing this.
It was half gone from that eye and it was noticeably red and irritated for the entire rest of the night. I had to keep wiping my face over and over again during dinner because it was watering. It was pretty distracting from the celebration of our love, but the ramen and sushi really made up for it and my eye smelled like the breath of angels all night.
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17. 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 absolutely deathly glare from the guy.
He hadn't proposed yet. She ruined it.
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18. When Everything Seems To Go Wrong
Oh boy, I think I've got a good one. I've begun to loathe Valentine's Day these last few years. My significant other, who usually expects me to do everything for Valentine's Day, surprised me this year with a pair of tickets to a sports game a few weeks before the big day. It was for an event that I had really wanted to see. But we had a huge fight in the days leading up to the holiday.
I got upset when she joked that my Valentine's Day plan would probably be some sort of boring dinner, a gift of chocolate and flowers, and planned last minute. I had already been planning to take her on a nighttime cruise and then brunch the weekend after. We ended up fighting and I told her I wanted to cancel those plans, since she never seems to give me credit for the time I put into doing stuff for her.
When Valentine's Day actually arrived, we were both so exhausted by the afternoon that we passed out and woke up a half-hour before boarding began for the cruise. We had to rush to get ready. It took a while and we barely made it in time—but then it got worse. We then realized we had shown up at the wrong location. Once we Ubered to the right location, the cruise had already left.
She was furious at me. She would barely talk to me for the rest of the night. Eventually, she brought up how stupid she would look to her friends who she had told about the cruise. I had gotten us a nice bottle of her favorite drink, so we had a glass of that and she fell asleep. Man, I freaking hate Valentine's Day!
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19. 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 jerk 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 jerk, 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.
20. Bet He Wasn’t Prepared For That Response
My now ex-boyfriend actually screwed up Valentine’s Day last year. I had planned a late dinner date about two weeks beforehand since we were only available in the late evening. I drove to his house and told him I was on my way. Yet, by the time I got there, he was still sitting in his bed in a t-shirt and shorts and said he was waiting for me.
I told him if he actually took the date and our relationship seriously then he would have already been ready. He then proceeded to argue about how it wasn’t his idea and that it shouldn’t be such a big deal that he wasn’t ready. At that moment, I decided that I’d had enough of him. So I got up, told him I was done, and left.
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21. Recipe For Disaster
One man, one very angry woman, one very full glass of merlot, and one impeccably white button-up shirt. You can guess what happened.
22. Phone Fail
A guy and girl come in. They order food and everything seems all good, then the girl leaves her phone and goes to the bathroom. The guy picks up her phone and starts snooping and the girl comes back and catches him red-handed. She is understandably angry and asks for their food to go. When she gets it she socks him in the chest and leaves. He paid for everything and quietly left immediately after.
23. Getting Down And Dirty
In high school, I went out for Valentine's Day one year with my then-boyfriend. We had been dating for almost a year at that point, but this was the first time that we ever really went anywhere. Typical high school relationship I guess. So we got dinner, and right before we left we exchanged presents. I was pretty excited about this.
I was going to a fine arts school at this point, so I had made him something in class that I was really proud of and hid a gift card to a store he loved inside. Meanwhile, he gave me one of those $5 stuffed animals from Walgreens and just kind of threw it at me, with no card or anything. After that, we were walking to the car and he was practically taking up the entire sidewalk.
So I'm trying to walk through the mushy grass in heels. It had been raining and I was trying to steer clear of the muddy parts as much as I could. But then, disaster struck. I fell in the mud, practically ruined my dress, and he laughed at me. The worst part was that he didn't even take the present I worked so hard to make for him. He "accidentally" left it at my house when he dropped me off.
I still have it to this day.
24. 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 9-1-1 which we do immediately. Turns out, this girl’s boyfriend just did this to her, and from what I could tell this probably wasn’t the first time.
So, after law enforcement shows 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 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 taken his card as he was out of town on a business trip. Never one to defend a guy like that, I told her where she could find her husband. Fun times.
25. Silent Night
I witnessed one of the most awkward dates on Valentine's Day from a table that sat across from us. Both the guy and girl were on their phones the entire night, when the waitress came to get their food order neither even looked up at her to order. I was close enough to them where I would be able to hear their conversation.
Not a word was ever said. The girl at one point abruptly stood up and left (me thinking she was going to ditch the guy) but she came back and sat down. Again no exchange of words, not even a " where did you go?" That couple finished before us, and when the bill came they both awkwardly stared at it and didn't touch it.
The waitress came back 10 minutes later to check on them and said something like " I'll come back when you are ready" with the most uncomfortable smile on her face. Finally, the guy just takes the book bill thing and puts his card in. They leave.
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26. Love Hits The Brakes
I've worked in restaurants for 14 years, so you know my worst Valentine's Day story is going to be a doozy. One time, I had a guy ask me to help him bring the ring and champagne after dinner so he could propose to his girlfriend. Being a woman and wanting to witness the romance, I hid around the corner so I could kind of peek at them.
They were lovey-dovey all through dinner and everything seemed good and I fully expected her to say yes when he asked. She didn’t. In fact, the woman did not react well at all. She told him no and that she was planning on breaking up with him. She added the only reason she was on this date with him is that he said he bought her something special for Valentine's Day.
She thought he was going to buy her the car she asked him for, and she was going to dump him next week. Then she said since you didn't get the car, she's dumping him now and she left! The guy was devastated! I felt so bad for him. I will remember her for the rest of my life because how could I not? What a greedy woman.
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27. A Good Run Of Bad Luck
When I was 17, my boyfriend of a year broke up with me over the phone while I was visiting my dad in another city. An hour later, my mother called me sobbing because she'd had a knock-down-drag-out fight with her boyfriend. Meanwhile, my stepmom had been yelling at me, and then called into work by her heinous boss even though it was a Saturday.
My poor shell-shocked father, dealing with three crying women, tried to make it better by taking my stepmom and me to a movie at the end of the day. But my stepmom was really late getting out of work, so we missed the movie we had wanted to see. Instead, we had to settle for something none of us really cared about seeing, just so we'd have something to do.
I thought it couldn’t get worse, but I was so, so wrong. After the movie ended, we went to dinner. My dad dropped my stepmom and me off in front of the restaurant and then pulled around the corner to park. In the process, he was hit by an oncoming car. He was fine, but the car was totaled. That was just the cherry on top of what was already an unforgettably awful day. It was by far the worst Valentine's Day ever.
28. 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."
29. A Slight Change Of Plans
I would have to say that the worst Valentine’s Day that I’ve ever experienced was probably the one where my girlfriend stopped by a “friend's” house after dinner for “15 minutes” just to “say hi” and ended up completely ditching me and spending the night there. But don’t worry, she said. They were just friends. Yeah right…
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30. Do Or Dine
I was a waiter at The Pasta House. At this time, another server was pregnant and trying to cover as many shifts as possible before she had the baby. In February, she asked if she could work Valentine's Day for me and I said sure. Dinner reservations fell through for my date and me so we decided to see if I could get a table at the restaurant where I worked.
I walked in the door only to see that they were absolutely slammed. The place was FULL of customers. As I came in, my manager said, "Thank God you got my message. She we went into labor and we need you to take tables." I told them I wasn't there to work, but to go on a date. My boss was so mad that I didn't get to work that he fired me. On Valentine's Day!
31. Dress For Unsuccess
My wife and I were out for Valentine's day and the couple next to us were having a breakup dinner. Oh, and it got worse. They were breaking up right before their impending wedding. She was in an early 90s prom dress. He was in a suit jacket and tie. She was loaded and getting loud about losing the deposit for the reception hall. She finally took a swing at him and the host escorted them both out.
Her poofy dress knocked over a couple of drinks on the way out. What an emotional rollercoaster.
32. 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.
33. 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 hurt 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.
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34. 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.
35. A Case Of Mistaken Identity
In sixth grade, I had a crush on a girl and I wanted to send her a rose. Rose deliveries were something that my school always had available as a tradition. However, I didn't want her to know that it was from me. My handwriting is incredibly distinguishable and I was really shy back then, so I paid one of my friends a dollar to write her name and "Happy Valentine’s Day, From Your Secret Admirer" on the card.
He went to the desk set up at lunch and turned in the card. Everyone at my lunch table watched as one of the teachers delivered the card to Lauren. We continued to watch as she received the card, then she smiled and giggled with her friends. She then jumped up and ran to the desk where they were selling the card and roses.
She wrote some stuff down and then ran back to her table. A few moments later, the teacher got up and walked over to my table. To my surprise, she gave a card to my friend, the one that I paid to write the note. It was from Lauren. She had recognized his handwriting and wanted to go on a date with him. He got up and went to her table to accept the offer.
Jerk. They went on a date, and were "dating" as much as sixth-graders can be for the rest of the year. She then moved to El Paso, Texas with her family at the end of the school year, never to be seen or heard from again by any of us. Unrequited love is a painful thing. And I haven't had a good Valentine’s Day ever since.
36. 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.
37. The Big Sick
I had been dating this guy for almost a year and this was the first Valentine's Day where I wasn't single. He went to a different college than I did, and he lived about two hours away from me. I was planning on driving out there on Valentine's Day so that we could spend the day together. He came out to visit me the weekend before, but then I got violently ill.
I spent the whole weekend throwing up bile and, when I finally went to the hospital Saturday night, doctors made a disturbing discovery. I had diabetic ketoacidosis. I spent the rest of the weekend plus some of the week in the hospital. This delightful now-ex boyfriend grudgingly came out and visited me in the hospital after I whined at him for a while over the phone.
He didn't want to drive to Seattle to see me, because he was afraid of driving in the city and it was a pain in the butt for him. I was released the day before Valentine's Day, and he still expected me to drive out to him. Did I mention that I’d been missing both school and work, because I could barely walk without passing out? I needed time to recover.
We ended up getting into this huge fight because he was being such a selfish jerk. I'm still bitter about it three years later.
38. 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.
39. Will The Real Secret Admirer Please Stand Up?
My worst Valentine’s Day of all time was the one where I discovered that the Valentine’s cards that I had been receiving for years from “my secret admirer” came from a truly disturbing source. They were, in fact, from my parents. As much as I love my parents and appreciate this gesture from them, it was also crushing to realize that I didn’t actually have the secret admirer out there that I always thought I did.
40. 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.
41. Food For Thought
This is not a joke, it’s a real story I heard from a friend in real life. Somebody’s boss gave his wife a cabbage as a Valentine's Day gift. He then showed it off to everyone in the office, and bragged that he had come up with an inexpensive gift that could be used practically for the sake of cooking. Meanwhile, his wife secretly complained to an employee over the phone about how much she hated it.
I’m gonna go out on a limb and guess that this was not a good Valentine’s Day for that couple…
42. 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 law enforcement 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.
43. The Fruits Of Your Labor
For Valentine’s Day, I bought her this fancy edible fruit arrangement last week because she said she’s always wanted an edible arrangement. I was in for the surprise of my life. She dumped me just a few hours later. I still don’t know why. I had spent the entire Valentine’s Day up to that point wondering what she was doing and fantasizing about her sending me a text saying that she was thinking about me.
I also contemplated leaving her flowers and a card at her door, just to show her how much I cared. But screw that, she didn’t even thank me for that edible arrangement. The whole experience was absolutely devastating, and it took me a very long time to recover. On the bright side, I've lost ten pounds since the breakup, so I guess I can choose to look at the glass half full instead of half empty!
44. 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. That's when we learn the disturbing truth. It 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.
45. A Rose By Any Other Number
On my way to see my girlfriend for Valentine’s Days, I stopped off to get a rose, as per tradition. When I was paying, I found out that I could buy two for the price of one, so I thought hey why not! That turned out to be a bad move. Turns out in the country she is from, presenting someone with double roses is apparently something that is only done at funerals. Yikes.
46. 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 on 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 on. He got the picture they took at the restaurant printed and carried it around with him in his wallet.
47. 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.
48. Code Red
During the afternoon on Valentine’s Day, while I was still at work, I deployed some new computer code to a production program without doing as many preliminary preparations as I probably should have beforehand. It worked fine for about five hours, so I went home thinking that everything was running smoothly. Then, five minutes after my wife and I sit down for our romantic dinner, my phone blows up with complaints from work and I have to go into the office for a few hours.
Lesson learned.
49. Head-Banger
One of our favorite regular customers brought in her boyfriend for the first time and in her excitement, she bumped into a table and knocked someone’s cup off, which isn’t bad but in her haste to pick up the cup she hit her head on the corner of the metal table and cut her forehead open. It looked like a horror movie scene.
We cleaned her up and gave them a stack of free food cards because she’s awesome and we love her.
50. Checking Out
Yesterday in the grocery store I worked at, an angry couple came in right at 11:59 p.m., and tried to buy some booze after midnight. Our machines won’t let us do that after midnight. The couple got angry at each other and kept calling each other names in front of me. Finally, she says: “I’ve had it! I hate you anyway! I’m dumping you!” Guy: “You aren’t hot anyway!” Neither bought anything and scurried off.
Happy Valentine’s Day.
51. Not Using His Noodle
So, I had some guy who couldn't understand the concept of ravioli. He kept asking if we served "hollowed out spaghetti" (his words) and stuffed it with lobster. I said no, but we did use pasta. He kept reiterating that he wanted pasta. It finally dawned on me, "Sir, do you think that spaghetti is the Italian word for pasta?"
His date was unimpressed, but I finally get him down for an order of lobster ravioli, even though he still seemed unaware of what he was ordering. After he got his food, ate one of the ravioli, he said to me, like I was the dumbest guy on the planet, "Bro, all you had to do was tell me that they were Boyardee’s. I know what those are."
52. Material Girl
I was just getting off of work around 3 p.m. so I headed to do some grocery shopping and I saw a guy looking frantically through his shopping bags so I asked if he needed help with something. He confessed that he had bought a Wal-Mart necklace for his girlfriend because she told him if she didn't get something expensive she would leave him.
He had purchased it, but he had taken his eyes his bags for a moment and when he checked his bags again, the necklace was gone. He told me he had just been laid off and didn't have the heart to tell her no. I felt about an inch tall, helping him try to find a cheap necklace, knowing that no matter how good a guy or how bad a circumstance, some people are so materialistic that someone giving their all is still not enough.
I hate Valentine's day, I wasn't single last night, but boy I feel heartbroken for that guy.
53. Ring Of Fire
I worked at a fine dining restaurant years ago. A middle-aged guy came up to me, handed me a gorgeous sapphire and diamond ring and asked me to have the pastry chef include it with his companion's dessert. The chef found beautiful blooms to decorate her dessert plate and placed the ring in the middle of one. Her reaction, however, wasn’t what anyone expected.
She saw the ring, took it out of the flower, and placed it on the table. Then, she picked up her fork and started to eat her dessert without saying anything at all. The ring must have been an extravagant apology on his part and she was having none of it. I was tempted to say that if she didn't want the ring, I'd take it off her hands!
54. Clean Humor
For Valentine’s Day, I bought and gave my girlfriend a promise ring. In return, she got me some cookies, which doesn’t sound like much but it was more than fine in my book. I came over to the apartment that she shares with her sister to spend three hours with her. Thanks to her sister threatening to throw a fit, I was forced to spend two of those hours cleaning the kitchen.
55. Insult To Injury
I was eating in a restaurant on Valentine’s Day and saw this guy kneel to propose. We were all happy for them until the girl said no. She used some lame excuse, something along the lines of, “Mike, I just don’t think that you’re the one, you know? Poor Mike is all sad and gets up to leave. He comes back two minutes later to get his wallet and sees her doing something shocking.
Literally minutes after turning down a proposal, this girl is talking to the waiter at the restaurant and, get this, swapping numbers with him. Mikey grabs some random couples’ drink and throws it on the floor yelling about their year-long relationship ending. He then stormed off and she just grabs the nearest guy and jams her tongue down his throat.
56. 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.
57. 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.
58. 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...
59. This One Is Sad...
My friends and I met up at this big food court to hang out. One of my pals got there an hour early and saw this one dude with a bouquet and a giant teddy bear. Almost five hours later we came back to the food court for lunch and the guy was still there with no date. He left shortly after and we watched him make a call, throw the flowers at the ground, pick them back up, and leave.
60. This One Takes The (Cheese)Cake
My wife and I went to Cheesecake Factory for lunch, in a bid to avoid the crowds. Next to us, a dude got down on one knee and proposed (yes, in a Cheesecake Factory). The waitress was filming it, people were watching, she saw the ring and started crying, he smiled, and all looked good. Oh, how wrong we were. When my wife and I left 20 minutes later, she was still crying, covering her face, and he wasn’t smiling anymore.
I couldn’t hear well enough to know what they were talking about, but they kept speaking in low voices. Didn’t look good.
Shutterstock
61. 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.
62. Forget Me Not
I walked into a grocery store which was pretty packed with frantic-looking Valentine’s Day shoppers. I walked in at the same time as another man with a confused look on his face and I heard him say out loud to himself, “Man, the store is pretty packed for a Friday evening.” Then, we both turn the corner and are met with all of the last minute flower arrangements and Valentine’s cards layout.
I see the man completely freeze and again out loud, he says “Oh.. no... no no no! Today is Valentine’s Day? Oh no!” As he quickly runs to the chocolate section, joining the rest of the panic-stricken dudes with the same looks on their faces. Hope those dudes are all still alive this morning.
63. 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.
64. Location Revealed
I worked a 14-hour shift then wanted to meet up with my boyfriend afterwards to give him his Valentine’s Day gift. He gave me an address and when I showed up, my jaw dropped. I realized it’s a sleazy strip club (he did not tell me what it was and only gave me an address that I used to call an Uber). So I went inside, balloons and gift in-hand, I found him, dropped off his gift and Uber’d back home alone.
65. 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 it's 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.
66. Nothing Special
Had a woman come into a fine dining restaurant and tell me she was allergic to allium (garlic, shallots, etc), processed sugar, gluten, and salt. It's a four-course prix fixe menu for $150/person. Her partner had an excellent meal and such a wonderful experience. She essentially had crispy rice, steamed broccoli and cauliflower, pepper rubbed Arctic char, and skipped dessert. She did not have a wonderful experience.
I would have felt bad for her, but we go out of our way to give them the menu ahead of time, call to confirm that you're okay with the reservation and menu, and approve that the $150 price was legit. But that wasn't good enough for her. She just kept throwing a stink because she must have expected us to create an entirely new menu just for her and it should have been just as amazing as the other food our 250 guests were eating. In the end, I charged her full price and got that 20% tip.
A note for those who don't restaurant often: Don't assume you're special on a holiday where everyone thinks they're special. You're not that special.
67. Sparks Fly
A few days before Valentine’s Day, I turned around in class and semi-creepily asked the girl behind me if she wanted me to plug her laptop in for her. The previous Tuesday, she had asked me to do that since I sit next to the only working outlet in that classroom. When I asked her out of the blue, she just looked at me like I was a freak or something and said "...sure."
My intention had been for this move to lead us into a riveting conversation on the subject of grounded electrical sockets, because I had previously noted her that laptop charger had a ground pin despite the fact that this building was constructed before those were the norm—so they may have retrofitted the sockets without actually adding proper support for this.
Riveting, I know. I can’t believe this didn’t work out. I even had a few amusing anecdotes about the International Space Station’s electrical power system. Obviously, that was going to make her fall in love with me and be my Valentine because that’s totally how normal human conversations work. Yet, despite this elaborate plan of mine, somewhere in the gap between me finishing my question and her saying "...sure," I realized that this was a terrible idea…
68. 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 quieted 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.
69. This Hits In The Feels
I was with a girl who was absolutely in love with me. She was already talking about marriage, pets, kids, etc. On our third Valentine’s Day together, during dinner, I looked at her and it hit me. I realized that I had lost any feelings I had for her. Nice girl, cute, treated me great, would've made a fantastic wife. I just lost those feelings.
It sucks to know it's not your fault the way you feel, but to also realize that this poor soul is going to be crushed. It's been five years and I still feel like garbage for that.
70. 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.
71. She Didn’t See The Light
I once asked a girl out on Valentine's Day with a gift that I had hand made. I built it with LED lights and a microcontroller. I then soldered it. The whole nine yards. Yet, despite all this effort that I had put in, I did not get to go out to dinner with her on Valentine’s Day in the end. I got rejected by her. And it still hurts to this day.
72. Faking It
I was at a fast-food place alone on Valentine's Day because I'm a lonely guy. The dude in front of me straight up asked the cashier if the cook could make the best looking burger possible because he forgot he was cooking for his wife and wanted to pass it off at home as though he made it for a romantic dinner. Oh, buddy.
73. Bad News And Good News
I had a man who was verbally inappropriate at his wife at my table, and I don’t mean talking over her and being rude. I mean saying things like, “What do you think you’re doing you stupid bimbo?” and, “I’ll give you $36,000 to get out of here right now you piece of slime.” I had four different tables complain about them and we eventually asked them to leave.
I’ve never seen anything like it before, at one point the guy went to the restroom and I went up to the wife and asked if I could help in any way and if she was alright. I’ve never wanted to assault someone in my life more than that piece of garbage. We also had something really good happen when our chef and her girlfriend got engaged at the end of the night! It kind of balanced it out.
74. 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 vibrators 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.
75. 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.”
76. Dog Days
One year on Valentine’s Day, I thought it would be cute to take my dog along with me to a dinner date. We were on our way to the local Sonic, which was the only restaurant we had in our area. Sadly, while walking toward the restaurant, my dog got hit by a car. He was a really cool dog too, he just got a little excited. It was really sad.
77. 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.
78. A Messy Breakup
I bartend. I'm assuming this couple was on a date. They just ordered their food. In less than 10 minutes of their date, I saw the girl take a drink and throw it on the guy. It hit the people behind him, the walls, and it soaked the floor too. She immediately walked out in tears. The guy's face as he just sat there soaked was indescribable. It was the most movie-like break up I've ever seen happen in real life.
79. Sounds Like A Case Of Mixed Massages
A few years back, my girlfriend spent the two weeks leading up to Valentine’s Day talking about how she doesn't like Valentine's Day and gifts. She went on and on about how it made her upset because it brought back memories for her of a previous relationship that she didn’t care to remember. Because of this, I got her no present and just gave her a massage when the big day came.
Starting the very next morning, I was getting tons and tons of messages from her friends talking about how sad and angry she was that I didn't even get her a single flower…
80. 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.
81. A Not So Beautiful Day In The Neighborhood
The dude who lives in the apartment above me must have really screwed up Valentine’s Day this year. I can hear him and his girlfriend arguing up there at least once a week, and they can get pretty darn loud at times. Ironically enough, my own boyfriend had just called me for some over-the-phone intimate time, since we're long distance.
Just as our conversation is starting to get steamy, we suddenly hear someone upstairs yelling: "IT'S VALENTINE'S DAY! AND YOU DIDN'T GET ME ANYTHING! THIS IS THE SECOND YEAR IN A ROW. I WANTED TO WAKE UP TO FLOWERS OR CHOCOLATE OR A CUTE TEXT OR ANYTHING BUT I GOT NOTHING! IF YOU CAN'T GO TO WALGREENS AND JUST GET ME A $3 CARD, SOMETHING IS WRONG WITH YOU!"
Usually, when I hear this couple arguing, the guy always has some rebuttal to scream back at her after she attacks him. But this time, I hardly heard a peep out of him.
82. 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.
83. Just Desserts
I brought a girl back to my house for dinner and a movie on Valentine’s Day. I had previously made a "bet" with her wherein if she won, I'd make her dinner and bake pie, but if I won, she had to make out with me. Either way, win-win, right? So we finished dinner and went back into my bedroom to watch the movie we had planned to watch.
Midway through the flick, she said, "I'm still a bit hungry—I think I'll go grab a quick bite of the leftovers." She got up and went into the kitchen. I decided about 45 seconds later, as my stomach rumbled, that that sounded like a great idea. When I arrived in the kitchen, my jaw dropped. There she was, standing over my silverware drawer, emptying everything into her purse.
I was shocked. I asked her, "What the heck are you DOING?" She giggled and replied, "Oopsie!" I'd have been angry already, but the girly giggling just put me over the edge. I walked up, looked in her bag, and saw that she'd only managed to grab some of the inexpensive silverware so far. At that point, I reached over to the counter and grabbed a slice of the pie.
I looked her in the eyes and said, "Don't forget your dessert." While holding her gaze, I dropped the pie into her purse and smashed it up as best I could with the sides of the purse to make sure it got in there nice and good. I kicked her out and never saw her again.
84. 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.
85. Mixed Messages
I went out on a date with this girl in her first year of college on Valentine’s Day. For some reason I'll never fully understand (maybe she was trying to sabotage the date), she chose for us to see the movie Borat. For those of you who just don't know any better, there are certain people you go to see Borat with, and there are people you don’t.
I will never get over the awkwardness of trying to be romantic while Borat gets tea-bagged by a ginormous foreign man. Yet, it still got worse than that. Just beforehand, we were sitting at cafe next door, chatting. It was going pretty well regardless of her movie choice, which had the potential to ruin the night. Suddenly, I saw this guy I knew from high school.
He walked up to say hello and ask what movie we were seeing. I told him "Borat" with a straight face, and he said, "Ohhhhhhhh, no! That's a terrible first date movie." God, I still think about how this girl replied to him. Before he could say anything else, this girl said, "Oh we aren't on a date." No, I just picked you up, bought your food, and bought you a movie ticket.
86. 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.
87. A Cutting Remark
I had a date on Valentine's Day when I was 16. Being young and poor, we went to an Applebee's My date ordered off the kid's menu and got herself some chicken fingers. Embarrassed by this, I did what I could to steer the conversation away and try to have a pleasant evening. When the meal finally came, I noticed she couldn't cut her own food.
Noticing the look on my face, my date got upset. In an annoyed tone, she said, "I just learned how to do this last week, okay?!" After further conversation during which she claimed I couldn't have been in pre-calc in my public school because she was only in Algebra II in her private school, I decided to pay the bill and leave.
88. Love Hurts
Worst Valentine's Day I ever saw? Easy. I once witnessed a full-blown divorce discussion, in which the woman left and the man finished the last three courses of their tasting menu when she waited for a taxi in our lounge.
89. Something’s Fishy
My date and I were having a nice dinner of salmon and roast potatoes at a dining hall on Valentine’s Day. As he started talking about his day, I took a bite of salmon and felt a horrible pain slide down my throat. Not knowing what the heck that was, I tried drinking some water. Deep in my throat, I felt like I was being attacked, and every gulp only made it worse.
Then, I made a chilling realization. This must be that stupid thing my mother had always warned me about when eating fish—that you have to be careful of fish bones or they will get stuck in your throat. Well, darn. I spotted some potatoes on my plate and started shoveling them in my mouth; you know, to try and knock the bone out or push it down. Then the guy started telling a joke.
Well, my plan backfired, and once again, the pain became much, much worse. By now, it felt like someone had driven a screwdriver into my throat and was occasionally shoving it in deeper. When the guy finished his joke, he paused as he looked at me, awaiting laughter. I burst into tears. He said, "That bad, huh? I'm sorry... I-I've got other jokes..."
I managed to whisper that I had a fish bone stuck in my throat. He blinked. "But it's boneless salmon." I didn't really know how to respond to that, so I just stared at him with tears running down my face. He then said, "So uh...do you want to leave? What do you want to do?" and I whispered that maybe if we just got more potatoes, it would go away.
Three plates of potatoes later, I still had a fishbone in my throat, plus I was overly bloated. I never want to see a potato again in my life. This guy just watched in confusion while I ate potatoes and cried. When I looked up, he asked if it was still there. I nodded. At some point, we decided to go back to my room. Then, as we passed by the salmon station in the dining hall, he made it so much worse.
He pointed at the sign: "See? It's boneless." I didn't respond. When we got to my room, I called my mom and she said I needed to go to the hospital to have it removed. Freaking out, I turned to go and he insisted on coming with me to make sure I'd be okay. Sweet, right? Well, once we got there, he wouldn't leave. We waited six hours before any doctor or nurse would even see me in the ER.
When a doctor came, it was some practicing med student who, without looking, said that most people think the bone is still there when it's not. Apparently, salmon bones don't show up on X-rays, so he told me to go home. I refused, having just had the bone partially dislodge then re-lodge, punching a second hole in my throat. He said too bad, then went to get me check-out forms.
Then, the resident doc came and reamed the student out. I was thinking, "Oh thank god, they're actually going to fix me now." He told the student, "No, we won't release her until we're sure it's really gone; she could choke or it could puncture her lungs." Okay, really scary, but okay, they were going to fix it. So the doctor took me into a room and the student came trooping in after him.
He brought in this weird box thing with a long cord and a slightly larger thing on one end. He told me that, luckily for me, there was this new technology that can pick up salmon bones, and all they have to do is stick the cord through my nose and down my throat. I was not a fan of this idea. Even worse, he said he didn't have time to do that, and that it would be "good practice" for the med student to try it for his first time.
All the med students and all the nurses in the freaking ward came in to see this new technology, which made the med kid nervous. His hands were shaking. They sprayed some numbing stuff into my nose (most of it missed) and then the kid with shaking hands tried to stick an electrical cord down my nose while 15 people watched.
That's when the pain came. The med student said, "There's resistance," but the nurse urged him to just keep pushing. At this point, I had two holes in my throat and an electrical cord up my nose that was too big to fit, but the guy was still jamming it in. I started crying again. Not sobbing or anything, just tears rolling down my cheeks out of sheer pain. This apparently freaked the kid out more, and my shaking got worse. I didn't need to see it; I could feel it in my nose. Once the camera finally went in, the kid looked through and said he could see the bone. "Uh-oh—it's right there, in her vocal cords. That could mean serious damage," he noted.
So he took it out and the docs arranged for an ear, nose, and throat doctor to come in the next morning and remove it. They said they couldn’t do it themselves because they could permanently damage my vocal cords. Awesome. Here's the kicker. The 15 folks watching the cord procedure all wanted a turn. The resident doc came in and told me how important it was that people got the experience.
So I felt bad and gave all of them permission—all 15 of them—to practice with the cord thing on me. This was an hour and a half ordeal of them sticking the cord in my nose and pulling it out again while lecturing each other on technique and such. The entire time, the poor guy I was on a date with was sitting in the waiting room.
He must have been there for about eight hours, and on a school night no less. A nurse came in, gave me a pill, and said it would "relax" me before the operation. This was about the time when the nurses realized I had someone waiting for me in the waiting room. Finally, they told him he could come back to the room where I was and visit me.
The next morning, they put me under, got the bone out, and sent me on my way. During my classes in the afternoon, I had a spontaneous nose bleed that was pretty bad. I tried to cover it up with tissues until the person next to me turned, saw a ton of bloody tissues, and freaked out. I left. The guy texted me several days later and kindly asked if I wanted to try re-doing our first date. I told him I'd be happy to.
90. 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.
91. A Wild Ride
This was several years ago before everyone had cell phones. A cell phone would've made things tremendously easier, now that I think about it. So this girl saw me on a personal ad and. hit me up. We seemed to hit it off. She was a little older than I was and her picture made her look a little bigger than I'd normally go for, but whatever.
It was kind of weird that she wanted to pick me up—on Valentine’s Day no less—rather than meeting somewhere, but I was still game. I should've stopped everything when I saw that dingy old Honda Civic roll up. The girl ended up being a LOT older and a LOT heavier than I expected. I didn't say anything though because I didn't want to offend her.
So I got into her car, which was full of trash, and we set out. She told me she needed to swing by her place and I said sure, whatever. Her place was in the rough part of town, which creeped me out. She invited me inside and I figured it was better than sitting in the car waiting. So I joined her inside, which is when things really took a turn for the worse. It turned out, her boyfriend and kid were living in her apartment, neither of whom she mentioned to me before. Her boyfriend was remarkably laid back about me wandering in; meanwhile, her kid was toddling around, oblivious.
Sometime later, we headed to the car. She started driving and we began discussing where to go for dinner. I recommended a really nice restaurant, but she said it was too fancy. I also suggested a quirky hole-in-the-wall that's kind of gross but has fantastic food, but she didn't want to go that way. She suggested Taco Bell. I make a noise that was somewhere between "uhh, okay" and "really," which she took as me agreeing, and so we went to Taco Bell.
At this point, I was just happy to not be in her neighborhood. I ordered a couple of tacos, and, being the gentleman, I paid when she ordered what seemed to be half the menu. Then, she said she needed to use the bathroom. That was my chance. Without even thinking about it, I was out the door and halfway down the block before I even realized what I was doing.
A little later on, from a distance, I saw her burst out of the Taco Bell, look around, then start shouting for me to come back. Then I saw her get in her car. I thought she was just going to go home, but no... she started looking for me. This particular Taco Bell was on a main drag that backed up to kind of a residential neighborhood, so I wound up hiding behind some hedges and shrubs as she patrolled the streets.
This went on for two or three hours, with me skulking in the bushes as she circled the block. I've dodged officers that were less determined. I managed to work my way back to my building, only to find her waiting in her car out front. Luckily, she didn't know about the back entrance, so I snuck in that way and left all my lights off.
I locked and barricaded the door because she refused to leave. The sight of her lurking in the parking lot at that late hour prompted one of the neighbors to call the authorities. She still refused to leave. She called the officers a number of interesting profanities and, judging by the screaming I heard from the parking lot, they decided to take her in for disturbing the peace.
92. 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.
93. Oceans Away
I convinced a girl who I was crazy about to go out on a date with me on Valentine’s Day. I knew I had to make it count. We lived by the ocean and she had dropped the hint that she had never been out on the pier at our local beach. Challenge accepted. I nervously drove her down to the beach and we proceeded to slowly walk out on the pier together. I should have known it would all go wrong.
She seemed hesitant from the beginning. We stopped near the end of the pier and I leaned against the railing over the water while she stood back a bit from the edge. She didn’t really seem into it at all. Awkwardly, I said, “This is a great view, huh?” just as two pigeons flew up and landed at our feet. “Sweet, chicks dig birds,” I thought to myself.
To my horror, the birds began to make passionate pigeon love in front of us while neither of us spoke. I had never witnessed such violent passion. I quickly scanned around and saw a couple holding roses on the other side of the pier. “Awesome, they look romantic; chicks dig romance,” I thought to myself. We quickly walked away from the surprisingly forceful pigeon action and stood next to the happy couple.
The man and woman were holding each other, but something seemed off. I glanced up and noticed that they were sobbing. The girl I was with noticed too. As we were both looking, the couple took their roses and cast them into the sea. I had posted us up next to a darn funeral; some kind of sea burial. Between animal lovemaking and this, I had executed one of the worst V-Day dates of all time.
Just as I had accepted my failure, my date started getting fidgety. Based on her body language and her expression, it dawned on me that she hadn't told me about the pier as a “hint,” but because she was terrified of it. Turns out, she had a fear of heights and the ocean. That pier will forever be a monument to my most unsuccessful date.
94. Pizza Prognosticator
I used to work at a very local, family-owned, pizza place. It was packed and we only had two counter girls (myself and my girlfriend, whose dad owned the restaurant). We had a special on these really cute heart-shaped pizzas. One couple ordered one of them and my girlfriend brought it out, but got bumped because it was so crowded.
When she dropped the pizza it broke clean in half which I have to admit was super weird because it was sliced into eighths. The girl who ordered the pizza had a zodiac tattoo and was wearing a bunch of crystals. She got up immediately, pointed at the pizza and started yelling about how it was a sign and stormed out of the store after breaking up with him. We think he dodged a bullet.
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95. It’s Not A Competition
This is something that happened to me directly. I thought my boyfriend and I had agreed to get each other small gifts; like chocolate and flowers, you know? I came home from work to a bunch of red ribbon-covered boxes with over $7,000 worth of gorgeous jewelry inside them. Do you know what I got him? A $25 gift card to Applebee’s. I really thought I was being clever.
96. 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.
97. You Think You've Had a Long Flight?
Just got on a flight in London headed to Vegas. Sitting next to my GF and she wants to show me something she has planned for the trip so gets out her phone. It opens to the Messages and shows a chat with a guy (I know him) saying how much she is gonna miss him and how she doesn't wanna go away with me anyway. The doors close on the plane and that was a really fun 10-11hrs...
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98. Plan B
My worst Valentine’s Day ever was back in high school with my first boyfriend. We had been dating for eight months or so, and I told him a week before about how excited I was since this would be the first Valentine's day I'd had a boyfriend for. We also made plans to hang out at his place after school when the big day came.
So I got the recipe for his favorite cookies from his mom and made them. I also baked him brownies, got his favorite candy bars, and put them in a big heart-shaped box. On the outside of the box, I wrote a bunch of reasons as to why I liked him. On Valentine's Day, I gave him his present and he told me that he didn't get me anything. That’s when I learned the harsh truth.
Apparently, he had thought that I was joking about being excited for Valentine's Day. I thought that this was a pretty lame excuse, since I had clearly put a lot of effort in and I'm also known for being crazy excited over holidays. But whatever. He liked his present and I'd get to spend time with him that day, so I acted pretty chill about it.
After school, he wound up ditching class early to go play video games with his friends; and he completely forgot that I was supposed to hang out with him. I stood outside his last class like a fool waiting for him to come out, and he never did. His teacher let me come inside and use his phone to call my boyfriend's parents and ask if he was there.
He was, and they came and picked me up. But instead of taking me to their house, they took me home because my boyfriend wound up leaving right after I called to go to his friend’s house. I don't know why I didn't break up with him right then and there. If I could go back in time, I would definitely let my former self know that I could do better than that guy.
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99. Valentine’s Lost
My mom has been a waitress for more than 25 years and has worked her fair share of Valentine's Days. She says she's sen a lot of sad stuff, but it's the worst when little old men or women come in and eat alone because their husband or wife had passed recently and they just sit there and cry. My mom will sit down with them and give them hugs.
100. Flowing With Emotion
A woman was eight months pregnant. A guy brings her in for Valentine's Day and has the mariachi band sing their love song. He pulls out the expected ring and she says yes. Things looked perfect! Only spicy Mexican food is perhaps not the best choice when your eight months pregnant. She hurriedly shuffled to the restroom five times. The fifth, she...didn't quite make it.
It's a tiny community, so I met them years later at a wedding party. I walked up and introduced myself. I mentioned I had met them years ago. "I was there years ago when y'all got engaged. The emotions were just... flowing that night?" The husband laughed until he cried, the poor wife just covered her face in shame.
101. Misunderstandings
Her: Man, this is a great steak!
Him: Did you say this is a great date?
Her: ....no
Sources: Reddit, , , , , , , , , , ,
