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Waiters Are Sharing The Most Awkward Dates They've Witnessed And What The Actual Heck

"Once appetizers came out the man thought it would be a good idea to serve his wife divorce papers."

Look, most of us will experience a really awkward date night out at some point in our lives. However, you never really think about how your bad date might become a full-on story to the waiters serving you.

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So this week when Reddit user StittDownAndListen asked, "Waiters and Waitresses of Reddit, what is the most awkward date you have ever witnessed at work?", it really put in perspective that a bad, weird, or just plain AWKWARD date night out affects more than just the couple.


Anyway, here are just a few of the absolute WILDEST stories:

1. This surprise serving:

"I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. Once appetizers came out the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar, but I did bring out tissues for the wife, who was breaking down. I ended up boxing up their dinner. The guy paid, but I do not envy that ride home."


2. This O.G. proposal:

"A guy proposed to his girlfriend at Olive Garden. When he got down on one knee and opened the box, she was shaking her head and then just stared silently. It must've been a whole 30 seconds of pure silence, but it felt like an eternity. Then, the guy proceeded to describe the ring, how much it cost, the different aspects of it, etc. Finally, the girl just said, 'No.' The guy sat back down and they tried to finish their dinner."


3. This other O.G. affair:

"I waited tables at Olive Garden 10 years ago. A guy and his wife sat down at a table and immediately started arguing. Something about his affair and how a baby from it was costing them money. Finally it culminated as I was bringing out their salad. As I walked away I heard the wife say,

'Well, maybe if you hadn't boned our son's girlfriend and gotten her pregnant, we could afford to eat somewhere nicer than Olive Garden. Oh look, the highlight of my meals, UNLIMITED. BAGGED. SALAD. Maybe you could save up and we can go to Joe's Crab Shack for our anniversary, asshole.'"


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4. This first date duck out:

"There was a couple sitting at the bar together, it seemed like it was a first date. I was in the back rolling silverware and, after about 30 minutes of them sitting together, the dude came running into the back and asked, 'There’s an exit back here, right?' He then proceeded to bolt out of the back door. We were all flummoxed. The girl sat at the bar alone for AT LEAST another 45 minutes before she left."


5. This glass attack:

"There was a couple at my work having drinks. The girl went to the bathroom, came back, and admitted that she’d been sleeping with the guy's brother. Glasses were thrown across the room and they both got kicked out."


6. This talker:

"A couple sat down and, from the girl's body language, you could tell she was into him. However, as the date progressed, she closed off, sat pretty much sideways, and was playing on her phone. Her body language shift occurred over an hour and a half because he didn't stop talking the entire time. She gave some nods in response and even perked up a few times to try and contribute to the conversation, but his monologue never stopped."



7. This familiar face:

"I was bartending a day shift at an upscale Italian place. This couple came in, started drinking, and were VERY flirty with each other. I wasn’t quite sure why, but the man seemed familiar. Midway through their lunch the woman used his name and it dawned on me that the man was the husband of my previous boss. I asked if he was “Mark” from “that restaurant on the way to the beach?”

He said that he was NOT, but the woman he was with insisted on making it awkward and peppered me with questions like, 'I’ve heard the owner of that place is crazy, did you know her?' Turns out, she was purposely trash-talking 'not-Mark's' wife."


8. This proposal gone wrong:

"I waited tables in this fine dining restaurant. It was pretty common for people to propose there, so much so that we had a system for the whole thing. One guy came in and wanted to do the ring in the champagne, but I talked him into doing a dessert alternative that doesn't result in a sticky ring and champagne on the floor.

Anyway, I brought out the ring and the woman said, 'Dammit, I've told you before I'm not marrying you.' He flipped, but she stayed super calm about it. He left, she ate the dessert, and he eventually came back, paid, and they left together."


9. This unnecessary orderer:

"Some older couples have a habit where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn't work with younger couples. Basically, I was serving a younger couple (early 20s) who seemed pretty early in their relationship. They were ordering drinks and the guy ordered the girl's drink for her. Far from being dazzled by him knowing what she wanted, she said 'Well, I'd actually like a latte, not a coke... But fine, whatever, if I don't get a say.' He responded angrily with, 'Oh sorry, have what you want then!" She got her latte and he glared at me.'


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10. This ice cream disaster:

"I worked at an ice cream parlor — kinda old time-y, not much seating. Anyway, a guy came in with a girl, they paid for their own cones, and took up two of the seven stools. The guy was talking and, at first, the girl was laughing and into it.

CUT TO TWO HOURS LATER, DUDE IS STILL TALKING. The girl looked like she wanted to cry or punch him in the face. The guy never asked her a question. Never let her say more than a few words before he'd stomp out her 'rude interruptions.' Finally I said, 'Hey guys, we close soon. I hope you have a nice day, but we need to mop.' I watched them walk down the street and he was STILL TALKING. Like, get a room with yourself, guy. You're obviously the man of your dreams."


11. This divorce settlement:

"I served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant I worked at at the time. They came before the dinner rush, so they were pretty much my only table, and every time I’d check in on them the wife was extremely angry/tearful and they were bickering about holiday schedules for their daughter/timeshares, etc. It wasn’t the end of the world, but it was extremely awkward to butt-in to change out their forks or refill drinks while they were so emotionally-charged."


12. This emergency exit:

"A gorgeous blonde woman in her late 20s was sitting with a very well-manicured looking man in his mid-40s. He was polite, talkative, and super into her, but you could tell that she wasn't reciprocating the feelings. The guy went to the bathroom and she quickly picked up her phone, frantically called someone, and begged for a pickup ASAP. The gist of the call was that the guy was her mother's coworker and her mother had set the date up. About 15 minutes later, a guy her age came in, threw some cash on the table and excused them. She cited some vague emergency and was escorted out."


Comedy Central

13. This I'm NOT lovin' it moment:

"I worked at McDonald's and a couple came in. The woman sat down and the man tried to order. There was lots of 'umm'-ing and 'ahhh'-ing over what he wanted to buy, then he ordered two meals, we gave them to him, and he went to sit down. What followed was a 10-minute shouting match about how he wouldn’t take the woman on a ‘proper date’ and how messed up a McDonald’s date was. Guess he ordered the wrong thing?"


14. This flirty facade:

"I worked at a Chili’s and, one Valentine’s Day, a girl gave me her number while her boyfriend was in the bathroom. I came back and had to deal with her being sweet to him the rest of the dinner. I did not call or text her, but it was weird every time she’d flirtatiously look me."


15. This absolute mess:

"When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person.

Right in the middle of their dinner (and in the middle of our Friday night dinner rush) this poor guy stood up, tapped his wine glass to get EVERYONE'S attention, and then proceeded to tell EVERYONE what a fantastic person his girlfriend was. The whole time this is happening, she was just sitting there with the most bored look on her face. Then the poor guy pulled out a ring, got on one knee and asked her to marry him. She gave him the most disgusted look imaginable and said, 'THIS is the ring you expect me to say yes to? Could you be any cheaper?'

She got up and walked out, leaving the poor guy just kneeling there. I didn't charge him for the meal."



16. This affair to remember:

"Not a waiter, but I was working as a supervisor in a restaurant. There was a couple that came to lunch everyday and, everyday, they went to the bathroom together for like 20-30 minutes, so we all assumed they were having sex. It was inappropriate, but there was nothing we could do. Then, one day the woman came to the restaurant with another man. That man was her husband, which made for a pretty awkward moment."


17. And finally, this horrible request:

"A couple was at a table with two crying children. I went up and started with, 'How are you doing tonight? What can I get you started with to drink?' The father then said, 'Do you have a shotgun back there so I can blow my head off?'

The wife’s glare at him was the scariest thing I’ve ever seen, I honestly hope that man is still living."


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There ya have it! Have you ever witnessed a horrible date while working in a restaurant? Heck, even just a restaurant patron??? Share your stories in the comments below!

Some thread entries have been edited for length or clarity. H/T Reddit.

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