'I have about 100+ pictures of a wedding proposal gone wrong': 15+ dating disasters as told by the servers who witnessed the drama unfold

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Ben Weiss • Writer and Editor
Oct 29, 2023 2:00 PM EDT

Servers have to deal with a ton of unwanted nonsense on the job, but one perk of the job is that they get a front row seat to a wide variety of date nights gone wrong. From awkward first dates that turn out to be full of red flags to full-on marriage proposals that turn out to be complete failures, it seems like servers have seen the full range of possibilities that can occur on a date. Not to persuade people not to go out to dinner, but when someone says, "Just go out with them! What's the worst that could happen?" well, these stories are the worst that can happen.

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  • 01
    Table - "I once saw a lady throw red wine all over a guy's shirt and leave..."
    via Adrien Olichon

  • Various servers shared their sides of these dating debacles via this thread on r/AskReddit. My personal favorite has to be the guy who sat through the rest of his dinner with red wine all over him after his date threw her glass in his face. The food must have been really great for him to sit through a full entree in that state.

    Keep scrolling below for the rest of the stories. For more, check out this compilation of one-star reviews from various irate customers.

  • 02
    Font - r/AskReddit. Posted by u/Smash DudeBoi 4 Waiters, what dating disasters have you witnessed? 2.2k Comments
    via u/SmashDudeBoi
  • 03
    Font - RipGuts415 I was a waiter at a very famous, upscale restaurant and a gentleman approached the maitre'd requesting someone take pictures of him proposing to his girlfriend. Since I was the closest to the maitre'd I was tasked with performing this duty. After stalking the table for a solid hour the moment was inevitably approaching. I set up at an angle she couldn't see me and when he busted out the ring I started taking as many pictures as I could.
    via u/SmashDudeBoi
  • 04
    Font - Anyone who has tried to capture a once in a lifetime moment on camera knows that you're not really watching what's going on, you're just trying to frame the moment. After about 20-30 pictures I slowly realized that she was declining the proposal and the scene was quickly degenerating into a Five Alarm dumpster fire. However I was far enough away that I couldn't hear what was being said and couldn't be sure of what was transpiring so I continued taking pictures just in case. Finally I step
    via u/SmashDudeBoi
  • 05
    Font - He'd requested that I use my phone and send the best pictures to him. Needless to say he never approached us for the pictures and I have about 100+ pictures of a wedding proposal gone wrong somewhere deep in my iCloud photo bank... 9.2k Share
    via u/SmashDudeBoi
  • 06
    Font - lemongrassmacaroni. I worked at a bar in a hotel for 5 years. I had a table come down from their hotel room and sit at one of my pub tables for dinner. From the moment they sat down, you could tell the wife was furious about something. She was unbelievably pleasant toward me, but did not say a single word to the man at the table. I get their drinks and then their orders- he ordered steak and she ordered the sauciest pasta dish we had on the menu.
    via u/SmashDudeBoi
  • 07
    Font - About 20 minutes later (the wife still hadn't said a word to the man since they sat down) their food was done and my food runner set it on the table. Right as I was about to walk over to see if they needed anything else, I saw the woman stand up, say "Go yourself, John" as she picked up the plate of pasta and dumped it all over his head and down into his lap. Then she very calmly walked out of the bar and back up to her hotel room.
    via u/SmashDudeBoi
  • 08
    Font - I spent a few minutes helping the man clean up and got my manager to come handle the situation from there as it was way above my pay grade at that point. Later in the night, the woman came back to the bar without the man and we talked for a while. Turns out he admitted to cheating on her right before their dinner reservation. I never saw either of them again. 7.0k Share
    via u/SmashDudeBoi
  • 09
    Font - [deleted] I was bartender at a country club in college and I watched a woman curse her husband out at their table because the husband kept flirting with the waitress. She got REALLY loud and walked out. Keep in mind this was a nice restaurant at an upscale country club. The waitress felt it was all her fault but she told me the guy had been coming in there often and tipping her 100% of the bill everytime. 6.5k Share
    via u/SmashDudeBoi
  • 10
    Font - TheRelevantElephants I used to bartend at a yard house in the beforetimes Yard house is a corporate place that's basically a nicer sports bar with a ton of beer on tap with stupid, giant novelty glasses. I had a couple at the bar during happy hour drinking from one of the big glasses and they ordered some onion rings that were half price, he jokingly proposed with an onion ring and she started laughing and jokingly said yes Then he busted out an actual ring.....she wasn't laughing anymore
    via u/SmashDudeBoi
  • 11
    Font - frankylovee I used to work at a bar where 70% of the customers were on tinder dates. There was a line of two person booths along the wall when you first walk in. There were two dudes sitting by themselves in two different booths. Both of them were facing the door, one was in the first booth one was in the last booth. This girl comes in and walks up to the first booth, says hi to the guy, and sits down. They are chatting for about five minutes when the other guy who is sitting by himself c
    via u/SmashDudeBoi
  • 12
    Font - thisnameisfineiguess. I was bartending at a restaurant in San Francisco. This guy came in and ordered a vodka martini. He downed it and ordered another. Halfway through his third he called his wife and asked for a divorce. After he hung up we talked about the Red Sox (I'm from Boston). 3.7k Share
    via u/SmashDudeBoi
  • 13
    Font - [deleted] Not a waiter but I saw a first date next to me. In short, girl states she has an allergy to pineapple, guy says OK in a "I don't believe you" kinda way. At some point he scraped some pineapple glaze off his dessert and onto her spoon when she popped outside to make a call. She comes back and eats without noticing too much, has a severe reaction. Guy freaks out and tries to run but gets stopped by my girlfriend who is suspicious of him. Manager administers the girls epipen and am
    via u/SmashDudeBoi
  • 14
    Rectangle - Ive_got_spirit. I worked fine dining in Vail Colorado. I once saw a lady throw red wine all over a guys shirt and leave. He sat and continued eating his spaghetti plate. No 3.2k Share
    via u/SmashDudeBoi
  • 15
    Font - thinkdeep. Bartender for a couple on a Tinder date. They talk for about an hour, he goes to the bathroom but left his jacket on the back of his chair with his wallet and keys in. She stole them, stole his car, and went shopping. That poor refused to call the cops for an hour because "it was going so well." I felt bad for him. 1.6k Share
    via u/SmashDudeBoi
  • 16
    Font - imk . Couples fight in restaurants a lot. That or maybe they argue everywhere. I couldn't say. I worked as a waiter for years and I could not begin to count the number of arguments I saw. But one guy comes to mind above all of them. This guy must have been 50-60 years old and got angry with his lady. He actually threw a and stomped off and was wandering around the restaurant and looking back at her and scowling. It was like a child throwing a temper tantrum, but most children aren't even
    via u/SmashDudeBoi
  • 17
    Font - o jeezy_peezy. Bartender here. A couple on a blind date took their seats directly across from the dishwasher so I had to pretend I couldn't hear him (40+, balding, overweight, and drunk) asking her (30+, pretty, friendly, and level-headed): "Listen. I see you over there, just amazing and gorgeous, and I'm wondering what you're seeing in me. What do you think?" She smile/cringed and made an effort to sidestep his questions and change the subject at least 3 times, while he ordered shots of
    via u/SmashDudeBoi
  • 18
    Font - BunnyKerfluffle I watched a proposal in the dining room of the hotel I worked at. Everyone was eagerly awaiting the dessert and ring box to be brought out. She saw the box and just started saying nononononono, and told the crushed groom, we need to talk. People who initially were clappi just slowed to a dead silence. She ended up going back to the room, collecting her things and leaving, while he cried at the table for a few minutes. It was super depressing for all the staff, guests and t
    via u/SmashDudeBoi
  • 19
    Font - Tyaltir I was a bartender at a restaurant that specializes in seafood. This couple came in and it was obviously a first date, they were both very awkward. They ordered a few dishes, one of them was a dish with Crystal Shrimps (peeled, without the actual hard shell, but still with head and whisker things and stuff). The guy proceeded to eat the entire shrimp. Like, head and tail and everything. It was as crunchy and horrible as you can imagine. 733 Share
    via u/SmashDudeBoi
  • 20
    Font - sadekuu Saw a proposal take a turn when the guy put the ring in her champagne, she drank the champagne quickly unknowingly and started to choke. Guy performs a heimlich maneuver and the ring pops out only to fly into someone else's food. Guy had what appeared to be two heart attacks but in the end the lady did say yes Side note because of the almost death they got free dessert and they laughed about the whole evening saying "till death do us part for real" and they wanted no beverages at
    via u/SmashDudeBoi
  • 21
    Font - Wowza7125. Not my story, but my partner just told about this happening at his work. We live in a pretty large university college and one time a guy came in with a plant for a date. He sat with it at the table, ordered it food, drinks, and dessert. He was a total gentleman to the plant. Turns out he lost a bet with his frat brothers. 607 ↓ Share
    via u/SmashDudeBoi
  • 22
    Font - InkMage94 I worked briefly as a waiter at a semi-nice place near me. I had a couple come in for a date who we've seen there a few times before (I think it was their regular dating place). She was very clearly sad, and was talking about how her uncle was really sick and was probably going to pass away soon. He decided to pull out the ring and pop the question anyway. Seriously, dude? Read the room. 567 Share
    via u/SmashDudeBoi
  • 23
    Font - yooyootrain. Not a waiter, but once witnessed a woman ghost her date at the end of the night. It was a fancy jazz club, and the couple racked up what I assume was at least a $500 bill (there was a TON of wine and they went through a few expensive entrees). When it came time to pay, the woman snuck out while the man was in the bathroom, and just disappeared. The dude was distraught :( 400 Share
    via u/SmashDudeBoi

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FAILS first date dating fails server askreddit relationships couples breakup reddit thread online dating Reddit tales from your server ghosting toxic relationship dating
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