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17 Servers Share The Most Awkward First Dates They've Seen

The world has no shortage of bad first dates. Sure, a bad date is disappointing. But on the plus side, finding out someone sucks from the moment you meet them is a real time saver. And when you get knocked down, you can always get back to swiping on tinder.

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  • 1
    Text - 3 days ago edited 2 days ago CaptainWisconsin 13.4k points Couple years ago, I was tending bar at a high-end steak joint. A pretty brunette walked in and sat down at the bar. After fixing her a cocktail, I asked if she'd like to see a dinner menu. She explained that she was waiting for a date. A few moments later, the guy arrived carrying a large bag. It was immediately obvious this date was their first Their conversation was lurching from forced to downright painful when he reached into
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  • 2
    Text - daveyhh 5.4k points 2 days ago I was hanging out at Starbucks and witnessed a horrible date. She was Japanese and he started off by showing her his shirt with sumo wrestlers on it, then would ask questions like... what's your favorite sushi? Do you only speak Japanese? How do you say toilet in Japanese? They have sumo in Japan right? Did you see my shirt? It was so amazingly awkward I bought another cup of coffee to listen to the entire thing.
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    Text - lachrym0se 12.0k points 2 days ago This isn't as bad as some of the others but the guy and girl arrived separately and it seemed like they were meeting for the first time at the restaurant. They sat down then the girl excused herself and went to the bathroom. The guy ordered drinks for them both while she was gone then, after like 30 mins, ordered two meals. It was so obvious she wasn't coming back but he kept calling her and eventually just left all the food and drink untouched and paid
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  • 4
    Text - ugh_you_bastard 4.2k points 3 days ago I once saw a guy try and impress his date by pretending to know about wine. He then proceeded to pronounce every single wrong one. I don't even know how I would phonetically write out his butchering of Chablis and Sauvignon Blanc. Date looked at him like he'd just taken a shit on the table
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  • 5
    Text - horton_hears_a_homie 1.9k points 3 days ago Girl was obviously super into guy, and he seemed like he was at least somewhat interested. They both talked and joked with me, overall great table. Cut to the check, I ask if it will be together, and the girl smiles at the guy. He promptly says, "No, separate please." Her face dropped, and he blatantly wrote his number on the check with a little note for me. That poor girl almost cried as she quietly shuffled out the door. What an ass he was.
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  • 6
    Text - 2 days ago voice_of_craisin 11.2k points Bartended for a decade. For a while I was at a medium range Italian restaurant. More than once I saw a first date go awry because one of the two drank too much Most memorable was a woman who started downing rum punches. They were at a table so I couldn't see them and I guess the waiter had forgotten his "red light, yellow light" training (I don't know if they still do that) After the sixth one I asked if these were all going to the same person and
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  • 7
    Text - Muffinbeans 4.1k points 2 days ago I'm a bartender at popular burger and wine bar. I had an older gentlemen (about 60 years old) come in on a Wednesday evening and order a bottle of wine and two glasses as he's waiting for someone to show. This other older woman shows up a short while later and both of them hit it off. They sat themselves right behind my POS so basically anytime I had to ring something in I had a front row seat to their date. Both of them crush 3 bottles of wine and sit t
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  • 8
    Text - el_pobbster 10.6k points 3 days ago Oh man, thanks for asking this one, I've got a great one Happened at my former restaurant. Reservation for 6:00, young guy comes in a few minutes early, tells me he's kind of nervous because it's a first date and he hasn't had many before, bla bla bla, kind of sweet really. Anyways, girl arrives about half-an-hour late, and proceeds to get very, very drunk. About mid-way through the meal, she answers her phone, takes the call, and starts talking about h
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  • 9
    Text - foppishyyy 4.1k points 2 days ago Couple in their mid-twenties comes in, it's obviously a first date but they seem to really like each other and are getting along well. I wasn't serving them however, I was serving the table next to them. About halfway through their meal I notice them holding hands over the table. Cute. Then, the guy lifts her hand to his lips and kisses the back of it. A bit of an outdated gesture, but still cute I guess. The woman seems slightly confused but goes along w
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  • 10
    Text - notasugarbabybutok 3.4k points 3 days ago I've shared this story before, but I once had two very young (like 15 at most) teenage boys come into my place for what was clearly their first date together, if not their first date ever. maybe 20 minutes into their date one of their mothers showed up, realized it was a boy her son was on a date with, and started screaming and crying about she didn't understand how he could do this to her and didn't he know she wanted grandchildren, etc, etc. jus
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  • 11
    Text - onionslut 7.5k points 2 days ago He reached for his water and punched it directly into her lap
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  • 12
    Text - noodles_the_food 7.2k points 2 days ago There was this young guy eating dinner with his mom. I noticed they seemed weirdly uncomfortable and distant but didn't think much of it. Turns out the lady was not his mom. He had met her on a dating site and had been VERY clearly catfished. The lady was at least a good 20 years older than him When she left the restaurant he stayed behind and told me about what happened then asked me out. I politely declined but agreed with him that that was a real
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  • 13
    Text - bucket_of_frogs 3.2k points 2 days ago Not a waiter bu... Me and my GF sat next to an obvious first date at a Pan-Asian fusion restaurant (Zen in Durham, UK). She comments that her main course wasn't quite what she expected and thought it'd be spicier. He then snaps his fingers above his head VERY loudly so half the restaurant turns round to look and a waitress rolls her eyes and goes over. He demands that they COOK IT AGAIN AND MAKE IT HOTTER. Next thing, there's half a dozen Thai waitre
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  • 14
    Text - 2 days ago alixphoenix 3.1k points Girl and guy came into the barbecue restaurant I worked at. They met at the door exchanging the usual "Hi, nice to meet you!", etc. The guy was a complete dick. She ordered ribs and he said "do you want to keep that hot figure of yours or look like that chick over there?*points to slightly overweight woman* then, when they were waiting to pay he starts flirting with the chick behind them. She deadass waited until he paid then left without waiting for the
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  • 15
    Text - theiafall 6.5k points 2 days ago witnessed a cpl on their first date having a few drinks. started making out by the 3rd. dude cried by the 4th started sucking on her finger. cried again. abruptly ran out of the bar and down the street. she paid CAME BACK 2 WEEKS LATER i pretended not to recognize him to be nice, and he brought it up! 'i think you served me on a date 2 weeks. ago' 'uhh i dunno man i serve alot of people' 'yea it was you, remember? i cried and ran away?' bruh
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  • 16
    Text - Yeebees 2.6k points 2 days ago I'm a host at a restaurant but my first week working a gay couple got in a fight in the middle of their meal, drawing attention from everyone in the restaurant. Before my manager could step in and stop it one stood up and shouted "YOU'RE THE REASON MOST PEOPLE ARE STRAIGHT" and left. Ive always thought about how it is both a roast or compliment depending on sexuality
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  • 17
    Text - Zeruvi 5.5k points 2 days ago I'm not service staff but I often eat/drink alone and people watch, and first dates are almost always painfully obvious Worst one I ever saw, two people who were probably perfect for each other; they were both completely self absorbed. How completely? They both started stories and kept telling them at the same time. They weren't even listening, just talking at each other. I was enraptured by the sheer insanity of it, I didn't eat for like 45 minutes as they b
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