30 Valentine’s Day Disasters As Seen By Waiters

Not a waiter, but in my strip club bouncer days we had one of our regulars get suited up and bring flowers in one V-day to try and woo one of the dancers. It did not work.

Pro-tip: If every time y'all hang out it involves you giving her money, she is not in to you.

Ex Barista here, hope that is close enough. Some guy on Valentine 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.

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 sat in the restaurant, but the boss let me clock off early. I had a pint before leaving, and at a table near by, 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 was kneeled in front of his girlfriend, her sat down. Girl: "Hannah? Who the **** is Hannah?" She yelled, threw her drink at him and walked out.

Guy paid and walked out, looking very red.

A guy did a backflip and asked a girl to be his valentine... she declined. I walked up to him and asked if he was fine, he said it took him a week to perfect.

Two failed marriage proposals on the same Valentine's Day.

The first one simply said "no I can't do this," and walked out.

The second one 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.

While working at a sushi bar in college I witnessed a blind Valentine's day date where the guy who showed up was already the girls ex-boyfriend.

I set my hair on fire and spilled a full Stella on a lady. I work in a causal fine dinning steak house. Luckily for me, the lady I spilled the Stella on was super understanding and her husband said from across the table “well now she has to take her pants off”. Sooo that could have gone worse for me.

Old man proposed to old woman. He tried to get off the chair to kneel, tripped and fell and I assume broke something since he couldnt 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.

A 16 year old boy proposed to a 15 year old girl with a cheap ring in the whipped cream of her dessert. She said yes.

Not my story, but a co-worker (which happens to be my cousin) told me this story.

One day a guy enters the taco restaurant were we worked at, he was a waiter so he goes on to bring the menu to the table. The guy (20 ish) says he's waiting for someone, so he's gonna wait to order a full meal, but as waiters we are taught to insist a little more and sell something. So the guy finally orders the cheapest item on the menu (a small carne asada taco, just one). A few hours went by, the dude's date still hadn't arrived, and every 20 or so minutes he would order another one of those small tacos. Eventually the owner of the place, who is a really cool dude and has been a friend of my family for years, tells the waiters "look at this poor sucker, if the girl never arrives, I'll pay for everything he has ordered myself"

So another hour and a half goes by and this dude finally gives up and asks for the check. He looked pretty sad so as a waiter of his age, my cousin told him everything he consumed was on the house. He smiled and left good tips anyway.

Stay strong guys (or gals) if she/he has you waiting that long, she/he's probably not worth it anyways.

Small, fine dining restaurant: Man from my table goes to the restroom and is gone for a while (probably 10 minutes? Which for a restaurant is a while). As I’m passing by the restroom he’s all “PSSSS!” Ushering me to the side and hurriedly whispering that he needs to leave through the kitchen because his wife’s best friend was sat near he and his date, who of course as I learn then and there is not his wife. We box the remaining courses up and do a walk of shame through the kitchen. He’s pissed, she’s crying, all while the rest of us are stifling our laughter. He ended up tipping well on the prix-fixe, which was nice.

A Girl that I worked with went to lunch on Valentines day at an expensive restaurant her boyfriend had gotten a reservation for, she got dressed up nice was was going on about how sure she was that he was going to propose.

He broke up with her.

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 awhile until asking his waitress where she went. She replied with saying that she left. The guy then asked the waitress if she would go on a date with him. The waitress said no.

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 flavour of ice cream. She the 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.

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.

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 blanket 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 says:

Waitress +Member(dad) present

Baby first name and member’s last name

And the date.

Soho, NYC, V Day 2009. Mid service, 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. Band sticks around for beers at the bar.

Turns out he was her ex, 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, and she banged the bartender later.

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 attention of the surrounding strangers, then get down on one knee with silver band in hand , and ask his girlfriend/date to “accept this promise ring.”

She looked horrified start to finish.

Worked at a chain bbq restaurant, was a line cook but could see in the dinning room. Had a lady and her kids(early teens) come in turn to be seated. She started to freak out, crying, yelling and left. Turns out the table in the corner was her husband and another lady in a date.

Younger couple came in for what I can only assume was a first date. Ordered a pizza but never ate, caught up in conversation I guess? Guy must’ve been feeling confident bc about 2 hours in he gets up, goes to the bathroom, and then decides to sit next to her in the booth rather than across from her where he was before.

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

Please refrain from doing this.

I was a 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***ing disturbing.