'We know you're single. Can you come in [for] an extra shift tonight?': 15+ Valentine's Day dinner disasters, as told by servers

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Ben Weiss • Writer and Editor
Feb 11, 2024 8:00 AM EST

Everyone knows that there are just as many disastrous Valentine's Day dinners as great ones. Something about the commercialism of the fake holiday creates a bizarre mix of emotions, unrealistic expectations, and a weird amount of stakes despite, you know, the meaning of the holiday to be virtually empty. 

However, instead of hearing about all the Valentine's Day fails from the perspective of the couples themselves, let's looks at these dinners gone wrong from a more objective viewpoint. These servers and bartenders shared what they believe to have been the most memorable Valentine's Day fails they have witnessed via the following r/AskReddit thread. Some of these stories involve failed proposals, the accidental unveiling of secrets, and even a few all-out screaming outbursts. 

Keep scrolling below for the full stories. When you're done, feel free to take a look at this collection of memorable if not bizarre high school reunion encounters.

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  • 01
    SpinachandChickpeas. 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. 21.7k Share
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  • 02
    r/AskReddit Posted by u/Hamsternoir Waiters what Valentine day disasters have you witnessed?
    via u/Hamsternoir
  • 03
    Theholynun I saw a couple have a full blown argument in the middle of the restaurant. The woman stood up, took her ring off, threw it at him and walked out. The man continued his meal, had dessert and then paid the bill, left a pretty big tip for the inconvenience and left! 50.4k Share
    via u/Hamsternoir
  • 04
    jimmyjohnjohnjohn. 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. 43.9k Share
    via u/Hamsternoir
  • 05
    lacroixisbad 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 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. Stayed at the table for about
    via u/Hamsternoir
  • 06
    ryanzbt not really a disaster but this guy came in and said he was waiting for his date, he stayed for 5 hours waiting and she never showed, he eventually ordered for for himself and asked that I remove the other glass of water from the table, he said it was their first date 34.6k Share
    via u/Hamsternoir
  • 07
    banville 750. Not a TOTAL disaster, but still not good. Had a table of two people, probably in their mid 40s last year. Took 45 minutes for this couple to get their entrees due to our kitchen being way too slammed. When they were dropped at the table, they immediately asked for to-go boxes because they told their babysitter they'd be home by a certain time. I overheard the wife say "well I guess this is why we don't celebrate Valentine's Day". The worst part was that they weren't angry, just...
    via u/Hamsternoir
  • 08
    My personal feelings about dining out on Valentine's Day aside, I felt so horrible that this couple clearly had put in an effort to have a nice night with each other only to have it go that way. (We comp'd their meals, btw). EDIT to clear up some timing issues. I should've added more context to this the first time but wanted to keep it simple. They made a reservation but unfortunately got seated about 10 minutes late, they ordered a round of drinks while looking over the menu, then a salad cours
    via u/Hamsternoir
  • 09
    DirtyDratini. 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. 31.6k Share
    via u/Hamsternoir
  • 10
    venustas 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
    via u/Hamsternoir
  • 11
    PackersFan8712. 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 guys response was to yell "I've been wanting to do that for 2 years now" and stormed out 28.5k Share
    via u/Hamsternoir
  • 12
    verry rjwyonch. 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:
    via u/Hamsternoir
  • 13
    he had come to the city to surprise his girlfriend for Valentines (about a 5 hr bus trip between cities) and he sure surprised her. She was in her dorm room fone of his friends from high school. He didn't know what to do, so he just walked into the first place that sold . I spilled as much whiskey as he wanted and watched the raptors with him. Never saw him again. It's cliche, but it happened. Edit: "watch the raptors" isn't a euphemism... We watched the basketball game. 28.1k Share
    via u/Hamsternoir
  • 14
    epiultra Someone showing up for a date and you both realize about 30 minutes in she ain't coming. "Drinks on me buddy". 27.5k ↓ Share
    via u/Hamsternoir
  • 15
    allthewrongwords. 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 she
    via u/Hamsternoir
  • 16
    Vesploogie Happened to my poor co- worker; A guy and his date came in for Valentines 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 Val ntines Day. They go qui
    via u/Hamsternoir
  • 17
    Turns out he had brought his mistress in on Valentines 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. 24.4k Share
    via u/Hamsternoir
  • 18
    Background_Extra52. Not really much of a disaster, but last year my work called me up, "hey buddy, we know you're single, can you come in as an extra shift tonight?" 23.2k Share
    via u/Hamsternoir
  • 19
    SpinachandChickpeas. 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. 21.7k Share
    via u/Hamsternoir
  • 20
    5+1) grub_en Bus boy on Las Vegas Strip, An attempted proposal. Dude tries to set up sign with gf's friends for her to show up and see the ring near a fountain. Duck stole the ring, they found it 2 hours later as he dropped in the fountain. She still said yes. Free drinks where given. ↑ 19.4k ↓ Share
    via u/Hamsternoir
  • 21
    Makabajones 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. 17.8k Share
    via u/Hamsternoir

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FAILS dating fails single askreddit relationships valentine divorce breakup reddit thread Reddit toxic relationship dating Valentines day
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