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Waiters Expose the Most Awkward Dates They Unfortunately Witnessed

As a waiter, you get an intimate view of a lot of different relationships. You might witness a proposal, a birthday, a big new job announcement, the options are limitless. It's a beautiful thing, to be able to partake in so many joyful occasions. However, waiters don't get to pick and choose, they're there for the good stuff as well as everything else. At least they get paid.

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  • Rectangle - Posted by u/Flavor_Town_ 11 days ago 19 @16 E 18 S 15 29.4k Waiters/waitresses of Reddit, what's the most awkward first date you had to witness first hand? 6.5k Comments Give Award Share 94% Upvoted ...
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    The waiters and waitresses of Reddit were asked to share the most awkward first date they had the luxury of witnessing. As a customer at a restaurant, you hope that your waiter doesn't pay much attention to your relationship...but unfortunately, we are all humans, and awkwardness can be very clear sometimes.


  • Font - sophiegitt 11 days ago S Not a first date but we did have a guy come into our steakhouse on a Saturday night at 7 pm with NO RESERVATION. He then told us on the spot he was going to propose to his girlfriend. We had to seat them somewhere awful, it was right next to the bathroom and when he got down on one knee, looking around nervously, absolutely no one noticed. Him and his gf kept waiting for the rest of the restaurant to see them and go quiet or even clap for them but not a single per
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    Ah, it's the rudeness for me. How do people not realize that we girls notice how the guy treats the waiter. It's a major red flag when he is disrespectful, entitled, or a flat-out D-bag. Honestly, what's the point of not being nice? You have to pay either way, and they're giving you a service. Tsk tsk. 


  • Font - stopbeingatotalbitch 11 days ago I had a guy ask me to take a video of him proposing to his girl. Everything went fine until it was time to review the video. Turns out, I never actually recorded. Lmfao I died a little on the inside but asked if he wanted me to record the entire thing again, since it was definitely staged (real proposal but staged). He politely said no, I apologize once more and left awkwardly. 315 Reply Give Award Share Report Save

  • Font - WhatOnceWas396 11 days ago Just saw one on Valentine's Day. The date seemed to be going very well, actually, not awkward at all. They talked non-stop, no lulls in conversation, they were laughing, carrying on, and just generally having a good time. In fact another server and I were laughing about how obnoxiously loud they were. Then I heard the gentleman say “...and obviously you're not still married... right? Please tell me you're not still married," she said "well, actually..." and then
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  • Rectangle - Ashley_42 11 days ago 2 4 e 8 S A teenage couple sharing an ice cream and holding hands very awkwardly. After they finished the ice cream they kept talking about their - very adventurous - sexual fantasies. They were around 14 years old. Super awkward to have to interrupt them to ask if they want anything else. 1 14.5k Reply Give Award Share Report Save
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  • Rectangle - BigFuturology 11 days ago Didn't happen to me but I was working while the bartender got to experience it. Guy and girl came in, super weird chemistry all night. The guy is obviously trying to impress her by being a huge douche and she looks like she's just pretending to not hate it so the date will end faster. At the end of the night, she says she'll take an Uber home and he awkwardly leaves without her. She then waits for the bartender to come back over, orders another cocktail, and
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  • Font - RAM_592 11 days ago · edited 11 days ago I had these two people that were there on a first date. After the appetizers this poor man got the shits and was going back and forth to the bathroom all night. There was only a few other people in the restaurant at the time so it was noticable and they were chuckling everytime he got up. I honestly felt so bad for the guy. 8.8k + Reply Give Award Share Report Save
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    Via u/RAM_592

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  • Rectangle - tottaly_not_masters 11 days ago · edited 11 days ago 26 I legit saw the guy try to roofie the girl. Like not even trying to be hidden about it. He 13 O & 10 More did it right in front of me. The girl went to the bathroom and I was cleaning the table next to them. I saw him take the powder out and slip it inside the drink. Another thing too, it was a pizza place. Who tries to roofie someone in a pizza place! Edit: yes I called the cops. Jesus I like chaos but I'm not an animal 16.1k R

  • Font - Bluegunder 11 days ago · edited 11 days ago At a restaurant i worked at, there was a white guy and a black guy on a first date. They were sitting in a booth and having a good time. White guy gets up to go to the bathroom. When he came back he sat in the wrong booth with a different black guy. Took him a minute to realize it was a different person. The person he was on a date with was not happy at all. They tried to salvage the date, but it didn't work. 2.2k + Reply Give Award Share Report
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  • Font - stocky_stegasaurus 11 days ago · edited 11 days ago Worked at a pub connected to a brewery in college. Dude comes in with a stunning woman, I mean she's absolutely gorgeous. Whole time they're sitting at the end of the bar, and you can hear the guy talking about how he has a room for them next door at the hotel in downtown. So they decide to go to the brewery next door, gonna pull a little dine and dash. They got over there and didn't realize we are on the same system, so he orders a coup

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  • Rectangle - joellyy 11 days ago At the end of the dinner, 2 couples on a double date dine and dash. I chased them down, and the girls had no clue, their dates had told them they already paid. The girls ended paying, the guys had no cash. 9.6k Reply Give Award Share Report Save
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    Via u/joellyy

  • Font - themerrypaek 11 days ago · edited 11 days ago I used to work at a sushi restaurant in Anchorage, and there was a girl who would come about once every few weeks with a different guy. Every single time, she ordered a heodubbap, which is like a rice-salad-sashimi bowl, and it was GIANT. I've only ever seen a handful of people ever finish the entire thing in one sitting. She would finish the whole thing (with CHOPSTICKS) and always ask for a spoon towards the end. It was always fun watching t
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  • Rectangle - fraxiiinus 11 days ago · edited 11 days ago O 2 14 23 2 & 39 More Not a first date, but when I first started bartending I had a woman who was very obviously stood up. She got there, ordered a drink, and would look around every once and a while. I saw her use her phone a couple times and her mood just got sadder until she finally put her phone upside-down on the bar and ordered food an hour later. I wiped what I could off her bill then paid the rest myself, told her it was on the hous
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  • Font - newguy1787 11 days ago O 2 2 A couple was shown to their table, and the guy was on the phone the entire time. I normally wait until guests are off their phones to give my spiel, the specials and such and take a drink order, but he didn't show any sign of getting off the phone. I take the order, which the guy just holds his hand over the phone, talks over his date. When I come back, she attempts to order an app, our house specialty, and he tries to say the portions are large enough without
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  • Font - justacomment12 11 days ago The guys card declines. I didn't want to embarrass him so I waved him over near the credit card machine so it would look like he needed to go to the bathroom. He told me to try it again and I assumed he was going to move money over on his app. He went back to his date. Card declines again. The machine prints a receipt that states the reason for decline... "insufficient funds". I keep trying 4 more times. I go over to the table and say "I'm having an issue with t
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  • Font - frankylovee 11 days ago : 4 I worked at a bar where like 50% of our business was from Tinder dates. This one time, two guys came in separately and sat at different tables by themselves, along the same wall. They were both facing the door and clearly waiting for dates. Eventually a woman comes in, walks up to the closest guy, sits down and they start chatting. They start ordering drinks. After -5 minutes, the other guy, who is still waiting by himself, gets up and walks over to the couple.
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