To lovers, what’s more important than spending a romantic day with the love of your life on valentine’s day? Everyone dreams of a perfect date full of romance on heart’s day. But not everything goes according to plan. While most couples spend memorable dates at romantic restaurants on valentine’s day, these lovers our 30 Reddit waiters served were unlucky instead.
#1 Nothing Beats a Valentine’s Break-up
I served at a Japanese hibachi restaurant and once had a couple come and the dude dumps her after the meal. She then gets up and throws up a trail probably a good 20 feet as she runs to the bathroom. The dude got up and left the girl and I was left to clean the mess. —moneybagmeisenheimer
#2 A Surprise Engagement Ruined
There was a note in our reservations that it was an engagement, they wanted champagne, a specific seat, a bunch of other stuff. The server comes up to the table with something like “so I read we’re celebrating an engagement, congratulations”. Confusion from the woman; glaring from the guy. He hadn’t proposed yet. She ruined it. —ChefHannibal
#3 Double the Rejection, Double the Pain
These two were on a date and the guy went to go use the bathroom, The girl just up and leaves after he went to the restroom. When the guy came back he sat around for a while until asking his waitress where she went. She replied by saying that she left. The guy then asked the waitress if she would go on a date with him. The waitress said no. —OffensiveGender
#4 A Marriage Rejection
He proposed, she said no. He cried and tried to change her mind for 20 minutes while she sat there stony-faced. She finally got up and walked out. He paid and left in tears. —SpinachandChickpeas
#5 Salty Dude Who Couldn’t Get a Seat Runs with the Reservation Book
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 P.M to 11:00 P.M. 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, 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 sh*t 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, 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” —danmatfatcat
#6 Busy Restaurant Having Three Major Events All at the Same Time
I had a section one V-day that had a marriage proposal, a 40th anniversary, and a breakup all at the same time. The break up was the worst. 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 hot turd. 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. I felt bad, he saw the celebrations going on at the other tables. —Odd-Examination
#7 A Valentine’s Gift from a Grandson
This was relayed to me by a close friend
Older Woman, probably in her upper 90’s with her teen-aged grandson at 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 woman.
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 and she did. They tipped my friend very well.
By happenstance, my friend ran into the young man some weeks later to find out the grandmother passed away a few days after that night, peacefully in her sleep holding a photo of her beloved husband. He was so happy he could make that night special to her. Said it was the only day he saw her smile since his grandfather passed away. He got the picture they took at the restaurant printed wallet-sized and carried it around with him in his wallet.
edit: Fixed some spelling and added more details after speaking with my friend again. I am not a great writer so this might diminish the story, I tried though. Thank you for the award! And I posted this to bring something a little different to the thread other than cheating spouses. It’s sad because the lady lost her soulmate of 70 something years, before Valentine’s day, which also would have been their wedding anniversary. —GodEaterSha
#8 Do Not Dine and Dash
It wasn’t disastrous for the couple as much as it was the restaurant. I used to work at a small southeastern 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 within 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. Stayed at the table for about two hours total and chatted.
They dined and dashed.
Edit: Had no idea there would be a ton of confusion over what a hush puppy was. In America (or at least the south) a hush puppy is a fried ball of cornmeal. I promise it tastes better than what it sounds like.
Also, for all those asking, it was a place called the Shrimp Basket. It’s a pretty small franchise. Sorry to break the hearts of all those that were guessing Waffle House or Captain D’s. —lacroixisbad
#9 His Valentine is a Ghost
I was eating in a fine dining establishment (Chili’s) several years ago. In the next booth was a really young guy who had a big bunch of roses on the seat next to him.
He kept looking at his watch, looking at the roses, and popping open a ring box for a peek at the ring.
He did this for a half-hour or so, then began calling and texting someone (presumably his girlfriend) over and over.
As we were waiting for our check, he hands my wife the roses, mumbled something, and walked out. Poor guy. —AZScienceTeacher
#10 A Friendly Date
I blew my car’s tire and my friend came in to bail me out. Were both straight dudes and forgot it was Valentine. Decided to have dinner and both were coming from important meetings so had suits on. We didn’t catch on until the end on how the entire wait staff thought we were just the cutest gay couple. —uReallyShouldTrustMe
#11 Public Embarrassment
Not my table, but back in my Olive Garden days, we had a man who looked to be in his mid-20s tap his empty wine glass with a fork to call for the attention of the surrounding strangers, then get down on one knee with a silver band in hand, and ask his girlfriend/date to “accept this promise ring.” She looked horrified start to finish. —LeapingMouse
#12 Valentine Medley
16 years in hospitality gives you some good stories.
The most awkward:
My first job as a waitress, a guy wanted to propose to his girlfriend. He came in 2 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.
The most f**ked up:
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 at the table by the waiter’s station. It started out 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’ve fixed the till, but am unable to step away from this car crash.) 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 f**k this and noped out of there. I couldn’t even look her in the eye, just left her to leave in her own time.
Managing hotel room service where there was a valentines 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 having sex. Having to help with deliveries as reception f**k up the bookings; I had the ‘privilege’ of people answering the door naked, seeing sex toys strewn around and one where the other members of the threesome were carrying on in the background. After complaints of similar instances from my team I had to take action. I ended up having to call the offending guests and tell them if they could not respect my team by answering the door in at least a closed dressing gown they could come down and collect the rest of their meal from the restaurant. Bonus from the same night: had to call an ambulance for a woman with a dislocated shoulder. The guy admitted that they were trying to recreate a bukk*ke type scene in the shower using conditioner as the ‘cum.’ He slipped in the conditioner and fell on her. —_lilliput_
#13 Accidental Proposal
Old man proposed to an old woman. He tried to get off the chair to kneel, tripped, and fell and I assume broke something since he couldn’t get back up and we had to call an ambulance. My manager had to drive her 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.
Edited to add: I don’t know if she said yes, my manager didn’t get to see them at the hospital, only pass on her teeth to the nurse. Thank you kindly for the gold and silver though! —rancid_c*nt_bucket
#14 Do Not Assume Unless Otherwise Stated
A Girl that I worked with went to lunch on Valentine’s day at an expensive restaurant her boyfriend had gotten a reservation for, she got dressed up nice was going on about how sure she was that he was going to propose.
He broke up with her. —Makabajones
#15 How Not to Choose a Restaurant
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 one-year 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 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. —allthewrongwords
#16 Who Stole 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… It wasn’t there. I was freaking out big time. I asked everyone there if they knew what the f**k had happened to it. My assistant manager on-site had no idea, so I called my other assistant (who also had the safe code) and they didn’t know, either. Finally, my bar manager mentioned that one of the owners had been in earlier, and spent a little time in the office. So, at my wit’s end, I called the owner.
It turns out that he had seen the ring in the safe, and thought it was something a customer had left behind. Figuring that he had come into an extremely lucky situation, he decided (like the scumbag he was) that he’d take it for himself and save money on a gift for his wife on Valentine’s.
So, I asked the server and bar manager to help stall the couple. The server told them that we were going to do something special for their big date, and to hold tight.
I ran out, hopped in my car, and rushed to get the ring from the owner’s house (because he was – as I had mentioned – a scumbag, and didn’t want to be bothered with bringing the ring to the restaurant himself).
The bar manager went over to the table, and did some complicated, table-side cocktail mix that had a bunch of flair bartending tricks and ended with a flaming shot that, once dropped into the rest, made it smoke (I was really disappointed when I heard about all of this because I would have loved to see it instead of breaking a ton of traffic laws on my quest to get the ring).
Finally, I rushed back in after about 15 minutes of being on the brink of a heart attack, placed the ring on the dessert, and had their server take it out. At that point, just about the entire staff was watching the table, and when we saw the look on her face, my heart finally started beating again.
She said “Yes.” And, I started looking for someone else to work for the very next day. —Icmedia
#17 Ice Cream Fight
Had a man and woman sharing dessert and 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. —Yeetacus420
#18 The Legal Wife
In college, I waited tables and Valentine’s Day was always a good one in terms of tips.
I once saw a couple come in to eat, halfway through the dinner the man’s wife shows up to surprise the couple. The wife took the wine bottle and poured the remnants on the husband’s head, took off her ring, and told the girlfriend she could have him. —kobra_kyle
#19 Who’s Gonna Pay?
I was working for a higher-end chain steakhouse in the North West corner of greater Los Angeles (in the valley). Valentines is obviously one of the top 5 busiest days of the year for us, we did about 500 covers between 5 and 10 PM. It’s also a restaurant with a very open concept floor plan. Booths along the 4 walls of the restaurant and an array of tables in the middle with no partitions or anything between them. A younger couple (maybe mid 20’s) dressed to the nines came in shortly after we opened and were seated at 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 5 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 2 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 to 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. —tdkme
#20 Green With Envy
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 working in food service, you never get Valentine’s Day off and we’d just have to celebrate the day after or the weekend after.
Nope. 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. —venustas
#21 Three Years Wasted
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 3 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. —t97brandt
#22 My Sister’s Lover
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, got pissed and started to rant about how she should have gotten over him sleeping with her sister already. . . . we had to ask him to leave.
Edit: Oh I have a good story if you don’t mind me sharing. Not on V-day though. We had a guy come in and asked us to write “will you go to the prom with me.” She said yes so happily! I think they ended up engaged 2 years later since we started to see rings on their fingers. They were lovely regulars and I wish them the best. —TheThrowawayFox
#23 Leave if You Must
Saw a couple have a full-on argument at a restaurant. I wasn’t their server but the table was directly in the center of the restaurant and they were certainly loud enough for everyone to hear. My manager kindly asked them to leave and the guy’s response was to yell “I’ve been wanting to do that sh*t for 2 years now” and stormed out —PackersFan8712
#24 Ooops, Wrong Girl
A few years ago, I had finished my shift at a pub I was working at, and sat at the bar with a drink. There were still a few couples sitting 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.
Guy: “Hannah, will you marry me?” He kneeled in front of his girlfriend, she was sitting down. Girl: “Hannah? Who the f*** is Hannah?” She yelled, threw her drink at him, and walked out. Guy paid and walked out, looking very red. —Skyre_Rose
#25 Is it Sweet or Creepy?
I was hosting at a really busy brunch place and Valentine’s Day was one of our busiest days. We had a full waitlist with tons of people in the lobby when this dude walks on with this huge teddy bear and a bouquet of roses. He said he wanted to drop them off for my coworker so I let her know he was there but understandably she was running around so it took a bit. While waiting, a bunch of folks waiting for tables complimented him on how sweet he was to do that for his girlfriend and how jealous they were. It was kind of cute.
When my coworker finally was able to come up front there was a lot of “awww” and such. Again, we were slammed so she ran back after taking the items and it was back to work for all of us. When it died down, I asked her how long she was dating her boyfriend for and she 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 f**king disturbing. —sadolan
#26 A Different Girl on a Different Date
Happened to my poor co-worker;
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.
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 didn’t think anything of it. We never saw the guy again. —Vesploogie
#27 Free Drinks for Heartbreak
It was like a movie. I was bartending at an Italian restaurant (not a fancy one, but still) and it’s pretty much full of valentines dates. A guy walks in and sits at the bar by himself, looking pretty down. He asked for a whiskey, so I poured it, 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 hr bus trip between cities) and he sure surprised her. She was in her dorm room f**king 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 the raptors with him. Never saw him again. —rjwyonch
#28 My Date Walks on All Fours
Serving at a touristy restaurant about 5 years back. Had a call for a reservation including “myself and my service dog”. Okay. No problem. I actually like “one tops”, even on Valentine’s, they’re usually quite nice and just want to be treated well despite taking up a table meant for 4+ people. I agree to take it while all the other servers are complaining about the reservation only being for one. Anyway. Hours later, in walks this drop dead gorgeous woman, with a full-grown man in a dog mask and full leather suit (complete with leather tail) being LED on ALL FOURS behind her. She nonchalantly gives her name, it’s on the reservation list, and so the hostess just…leads her to her table…
I walked up to them, being super professional (I was so stoned it wasn’t really phasing me) and this woman just orders like 200$ worth of random apps, entrees, and a bottle of higher-end merlot. Of course, there were stares, of course, other tables inquired and/or complained, but he was such a well behaved “service dog” and i never mentioned it or asked questions or stared, and I sh*t you not, that lady tipped me 100% in cash with a twinkle in her eye as she left. 10/10 would wait on them again. Not really a “disaster” in the traditional sense, but…disaster nonetheless. —CamoCricket
#29 Free Shower, I Guess
Was the Chef at a pretty fancy place. We did 4-course tasting prix fixe and were always booked to the brim for Valentine’s. The owner was out of town and the place was packed during our first seating when the pipes to the apartment above the restaurant burst. Nasty, cold water rained on everyone and everything. The fire department came. The owner said to give everyone champagne, clean the place up and keep going. As if anyone wanted to continue their meal soaked through on a cold ass night in ceiling water. —AntiqueAccountant3
#30 One Word, Run
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, 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, and somehow in the time it takes me to turn around, fill a pint, and set it in front of him, he’s already saying,
“…So don’t ever believe domestic abuse charges! My last. Three. Exes. Have all called the police on me.”
Most people put their best foot forward on a first date. I can only imagine how charming this guy is once you get to know him. —Laser_Dogg