Valentine’s Day is a day of love and romance, but not for everyone. For some, Valentine’s Day is a day for broken hearts, breakups and blowups. Workers and patrons at restaurants and bars have a front-row seat to some of the most awkward, abysmal and just plain awful Valentine’s Day moments, where attempts at love don’t always have a fairy tale ending.
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. 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. 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.
3. 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.
4. 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.
5. No Stalling
I went into the bathroom at a restaurant on Valentine’s Day and made an…interesting discovery. Not only was there a man in the woman’s washroom, he was down on one knee, sobbing as he proposed to a woman in a bathroom stall. She said no.
6. 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.
7. 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.
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. 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.
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. Living Large
I used to work the drive-through at Burger King and I overheard this conversation on Valentine’s Day while taking a car’s order. Girl: “Get me a #3.” Guy: “It’s Valentine’s Day baby, you can supersize it!”
12. 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!
13. 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 90’s 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.
14. Wasted Space
I worked as a hostess at a busy higher-end restaurant. I was working at the front door with my friend. The place was packed and the waitlist was extremely long. A woman came in by herself and was a little upset to have to wait for a table. Since she was only a party of one, we found a space for her at the bar while she waited. It was about an hour wait for a table. While sitting tight for a table, this woman proceeded to get completely wasted.
She kept coming up to us and asking about her table and we kept updating her about the time. While she was standing there, a group of people came in and we sat them right away because they had reservations. She then started yelling at us and dumped her drink on my friend’s head. The manager did not kick her out. We still had to accommodate her.
15. Ex’s and Oh’s
I’ve seen a doozy or two in my time as wait staff at El Nonno’s. The worst one is when my girlfriend came in with my best friend. I thought they were there to surprise me. Nope, this was their way of telling me that they’re dating each other now. And I was stuck as their server. But this pales in comparison to when they visited the restaurant the next time.
So my now ex-girlfriend and ex-best friend came in again and had their wires completely crossed. My ex-girlfriend thought she was going to get a marriage proposal, but my ex-friend came to the restaurant to come out of the closet and confess his love for me. Then three was the time my boyfriend and my former boss came in together, and I naively thought this was a surprise.
It turns out they both forgot I worked there and came in to have an affair. My ex-boss was cheating on his wife, and my boyfriend was cheating on me. That restaurant was insane.
16. 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.
17. A Bad Reaction
As a bartender, I saw a guest in the restaurant throw up on his steak not even a minute after it was placed in front of him. His date kept surprisingly calm for that scenario.
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.
19. 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.
20. 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.”
21. 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.
22. 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!
23. 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.
24. Raw Responses
So the pizza place I work for cuts all the pepperoni pizzas into hearts and we had to make about 450 of those, plus 250 more pizzas, in four hours. Our slogan is “Take and Bake”, so we make the pizzas and you take them and bake them at home. Several times, we had people get their pizzas at the end of the line and go “It’s not cooked.” Deadpan, my coworker looked at them and said “Yes.” to every single one of them.
Also, I took a phone call, and I said “When will you be coming to get your pizza?” and she goes, “Actually I’d like it delivered.” Needless to say, we didn’t deliver it, and she hung up.
25. Sweet Nothings
Last year I worked at a high-end sweets shop. Everything is top-notch as advertised, it was what people were willing to do for it that scared me. Chocolate covered strawberries? $50 per box of four. We couldn’t keep them in stock, and more than a few sweaty husbands begged us to make more and throw them in any container we had.
One guy walking in on Valentine’s morning offered to pay us double, even without the fancy romantic packaging (we didn’t take it). We had also sold a big embroidered heart-shaped box for nearly $100. One guy asked us how much it cost, left, and came back later with his friend. He’d asked him for a loan. To buy V-Day chocolates. Relationships are wild.
26. Abrupt Ending
One of my friends is a server at a fancy restaurant in my city. He said that on one Valentine’s Day, he walked by a table and heard the boyfriend say, “Well, once again, I’m sorry to disappoint” in a really nasty tone. Things got real awkward and quiet for another 20 minutes, then the couple got their check and quickly walked out.
27. Trying To Impress
We had a reservation for a kid’s birthday party on the bus (our restaurant has an old-school bus fitted with retro tables). A preteen couple comes in and the guy gets mad because we told him we couldn’t seat them on the bus due to the reservation. He tried to force his way up after being told repeatedly no. Pretty sure he was trying to impress his date, who watched this all unfold and looked completely mortified.
28. 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.
29. One Man’s Trash…
A few years ago my family and I bought some ice cream and when we went to throw the wrappers in a garbage can on the street, we found a perfectly intact and nice bouquet inside. We got the bouquet out, and we could tell it had been thrown out recently. There was a card but it only had the name of the florist on it. So we took it with us.
We had to meet with my grandma and her boyfriend right after, and they were like ”Why are you bringing us such a nice bouquet out of the blue like that?” and we were just laughing as we just picked it up from a garbage can. We told them the story and they kept the bouquet for a week.
30. 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.
31. 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.
32. 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.
33. 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.
34. “Utter Madness”
I ran the front desk to a hotel solo one Valentine’s Day. It was utter madness. We sold out with reservations, and there was a solid stream of locals coming in expecting to get rooms and then arguments with their disappointed dates when they were informed that we were booked solid. There were complaints from travellers just passing through and an older couple staying for a sports event about “loud amorous noises” emanating from rooms near theirs.
The phones were ringing off the hook from people looking to book Jacuzzi rooms when everyone in the city had been reserved in advance. There was a ridiculously inebriated guy getting dropped off in a taxi expecting to get a room after we’d sold out. He was irate and yelling, “What am I supposed to do now? Go sleep in the streets?”
Someone thought it would be a great idea to dump a trail of glitter and rose petals down an entire hallway leading to their room. And this was just the 3-11 p.m. shift. R.I.P. third shift and the morning housekeepers.
35. Table Service
When I was a server/bartender we had a frequent escort come to our restaurant. It was pretty obvious she was an escort as this restaurant was in a wealthy neighborhood and she would be with a different man every time. Once when I served her she said to me I’d make good money if I joined her company. So on Valentine’s Day, she came in…
She was wearing big, gold hoop earrings, breasts hanging out of a floral dress and fake designer bag. She sat down with an elderly man who I figured was married because he was wearing a wedding band. Anyway, long story short she was doing something inappropriate to the man under the table. The manager kicked her out and she never came back
I was in McDonald’s and I see two people at a table having a Valentine’s Day date with a red tablecloth and candles with fancy napkins and their order number card on the table. Honestly, props to them. Looked fun.
37. 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.
38. 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 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.
39. 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.
40. Skin Deep
We’re in the last hour of service, but we’ve about emptied out. A couple sat at the bar for about 30 minutes before ordering potato skins two minutes before closing and then asked me to remake them twice. They gave me some dirty looks when I put all my ‘go home’ stuff near them, so I said, “I’m not sure if anyone told you, but it’s my Valentine’s day too”.
41. 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.
42. Love Requires Patience
I work at a pizza place, where we served heart-shaped pizzas for Valentine’s Day. They took twice as long to put in a pan, and nobody was allowed to order ahead of time. Online orders weren’t going through properly so we had some customers waiting for their pizza for a solid 40-50 minutes. Short-staffed on delivery drivers as well. Overall pretty stressful.
43. A Waiting Game
A group sitting at a table next to mine had an absolute meltdown because their food took too long to arrive. Most of them just left and the last few asked if they could just box it up and leave when the food arrived. They got it all on the house.
44. Breaking The Silence
I was working in an extremely quiet, high end bar a couple of years ago, one couple was sitting in a corner booth having a screaming argument. Very, very awkward.
45. Don’t Make Eye Contact
I’ve seen too many Valentine’s Day couples who spend 99% of the time looking at their phones. So sad. So lonely.
46. Take The Good With Bad
I work at a small local Mexican restaurant. I can’t think of any disaster that happened at work for Valentine’s Day, but my girlfriend did dump me before I left for work. Then a girl from one of my tables left her number so the universe is looking out for me.
47. 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.
48. 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.
49. 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.
Her: Man, this is a great steak!
Him: Did you say this is a great date?