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Waiters And Waitresses Reveal The Most Awkward Dates They’ve Ever Witnessed

Paddy Clarke 6 Apr 2020

Going on a date, whether it be you and your partner's first or fiftieth, can be a wonderful experience where you can relax and spend time with the person you love. However, they can also go agonizingly poorly!

One strangely curious person took to Reddit to ask serving staff what the most uncomfortable date they had ever seen was, by asking, "Waiters and Waitresses of Reddit, what is the most awkward couple date you have ever witnessed at work?"

And the internet responded... and it responded with some truly toe-curling responses! Please find below a series of stories that will make you want to either hold your partner closer or just curl up into a ball and die!

1. Running Out The Backdoor

Unsplash | Kenny Luo

"There was a couple sitting at the bar together - seemed like it was the first date. Maybe after 30min of them being together, I'm in the back rolling silverware and the dude comes running into the back and goes, 'There's an exit back here, right?' and proceeds 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." ⏤ HappyLittleTrees17

A surprising amount of people were sharing stories about how they had seen people sneaking out of the backdoor of places to get out of dates. I simply couldn't do that, I always thought it was something that happened on TV shows, not in reality! Has this ever happened to you, or have you done it? Let me know if you're brave enough to admit it!

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2. One Man Getting Drunk, Singing A Song, And Proposing In The Worst Way Possible!

Unsplash | Bogomil Mihaylov

"I work at a dinner theatre, and we usually do proposals where we set up a 'random draw' where the 'winner' comes up on the stage to win their prize, and are then surprised by their partner who proposes. It's usually sweet. This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We agreed to let him do it.

"We do the fake draw, the woman comes up on stage in front of 400 people, and the music starts. This guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes. Usually, this gets a round of applause, but not after that trainwreck of a performance.

"The poor woman was just holding her face the entire time and starts shaking her head and says "No, what's wrong with you?" She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on the mic is 'Well, that's that'." ⏤ AgainstBelief

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3. Serving "Energy Vampires" On A Date

Unsplash | Marek Studzinski

"Couple came into the restaurant dressed very goth. I was running the cash register just a few feet away. They proclaimed to everyone that they were energy vampires, but not to fear them because they won't hurt us. They said they didn't need our food for sustenance, but enjoyed the tasted.

"After ordering the meal they politely asked the waitress if she would stick around for a second so they could feed off of her aura. The waitress said ok and gave me a side glance over her shoulder that I knew meant 'I better get a good tip for this'... The couple clasped each other's hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in the seats and sighing as if they had just had a turkey dinner. The waitress was indeed tipped well for her delicious energy." ⏤ hexiron

I cannot even watch documentaries about those people who pretend to be vampires, it always just makes my whole body tense up from the cringeyness.

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4. "I'm Having A Really Nice Time But..."

Unsplash | Paul Hanaoka

"First date, I would estimate college age. They’re eating and the girl says 'I'm having a really nice time, but my friend just texted me and asked me if I wanted to hang out, and I said yes, so I actually have to go'." ⏤ youngandstarving

Now, I'm famously bad at picking up romantic hints; however, something tells me that this person might not have actually been having a "really nice time". Well, either that or she is a complete sociopath.

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5. Seeing Their Boyfriend On A Date

Unsplash | Davids Kokainis

"Late to the party but I will share my story. Had a couple come in one night and everything seemed to be going fine. We just hired a new server who was training and I asked her if she had any questions. She was still nervous about greeting tables so I told her she could shadow me and watch what I do. We go over to the couple's table and all I hear from the new server is “YOU F*CKING BITCH I KNEW YOU WERE CHEATING ON ME'.

"Turns out the guy was her bf on a date with his side chick and he didn’t know she just got a job there. She didn’t get fired for what she said." ⏤ CigarJpug

I think it is astounding that the new server in this story didn't get fired for this. It is very good of their manger to have understood the situation!

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6. The Guy Never Stopped taking

Unsplash | Kristina Flour

"They sat down and, from the girl's body language, you could tell she was into him. As the date progressed she closed off, then sat pretty much sideways, then was playing on her phone. The body language shift occurred over maybe 1.5 hours. He didn't stop talking the entire time.

"She did give some nods and 'uh huh's' in response; even perked up a few times to contribute. But his monologue never stopped." ⏤ TheStankTank

The point of a date is to get to know the other person, not to wax lyrical about yourself for hours on end. And, I know that some people panic and keep talking out of nervousness, but you really need to remember to listen to the other person and not completely dominate the conversation.

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7. Turning Up Late And The Leaving Immediately

Unsplash | Yogas Design

"When I was bartending this guy came into the bar on a weeknight, average looking guy, late twenties. He sat down and asked for a drink and told me he was nervous because it was his first date in 3 years and they had met on tinder. He arrived 20 minutes before her expected arrival to get rid of some of his nerves...two hours passed and he waited for her with no text or call explaining she would be late.

"This woman walks in, walks up to the guy and I'm thinking 'wow! She really came!'. She looks at him and says 'Are you Joe?', the guy replies yes and gets up to properly greet her looking incredibly excited...she says 'no thanks...' and just leaves.

"What a foul creature. Joe(not his real name) and I proceeded to get way too drunk for a Tuesday. Poor average Joe." ⏤ Corticulture

If there is ever an understandable reason to get drunk as hell on a Tuesday, this is it. How could anyone be so barefacedly rude and horrible to someone like this?

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8. Another Incredibly Failed Proposal

Unsplash | Austin Pacheco

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

"Anyway, long story short. I bring the ring, she says 'Dammit, I've told you before I'm not marrying you.' He flips, she's super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the f**king dessert; eventually, he came back and paid and they left together. Super awkward." ⏤ Lampmonster1

Someone in the comments wrote, "In college, my friends would do this, stage a small argument, and have the guy rush out and the girl just sit there looking depressed as a way to get food comped." However, the server in the story explained that they were guests of the hotel so everything just went on the bill anyway.

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9. Knocking Themself Out Cold And... Worse!

Unsplash | Francisco Galarza

"Date seemed going well, but the guy was nervous and fidgety. He was rocking back on his chair a little as he would talk and eventually flew too close to the sun. Toppled his chair backwards and knocked himself out cold. And peed his pants.

"He had to be taken out of the dining room on a stretcher over the span of 20 minutes, while his Tinder date did the honorable thing and immediately went to the bar and ordered shots. We gave them to her on the house." ⏤ ANPhiK

This is one of those comedies of error situations where everything keeps getting inexplicably worse. I imagine that while they were carrying him out, the paramedics dropped him and knocked a plate of spaghetti all over his face.

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10. Nothing Special!

Unsplash | Penny Michalski

"I was eating at a restaurant and heard the hostess ask a couple she was seating if they were out for anything special. The husband replied, 'No, it's just our anniversary.' It has inspired my father in law to drop that line almost anytime he goes out to eat now." ⏤ geewhizz90

I hope more than anything that the guy in the story meant it as a joke also, otherwise he was in for one hell of a frosty evening.

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11. Ordering Food And Drinks For Their Date

Unsplash | Jeanie de Klerk

"There's a habit of some older couples 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 some younger couples. I was serving a younger couple (early 20s), who seemed pretty early into the relationship. They were ordering drinks and he orders her drink for her. Far from being dazzled by him knowing what she wanted, she didn't want any of it

"'Well I'd actually like a latte, not a coke. But fine whatever, if I don't get a say...'

"He responded quite angrily with 'oh sorry, have what you want then!

"She got her latte and he glared at me. They ate and left. Not been in since, I'm sure they're doing well." ⏤ Durnovarian

Guys, please don't do this. No one wants to have their food ordered for them, and you're not living in the 1950s. Good God this one made my toes curl!

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12. A Very Strange Dynamic

Unsplash | Jonathan J. Castellon

"Chiming in late, but one comes to mind. I had a mid 40's man with a young and attractive mid 20's woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary. After possibly 45 mins a lady storms into the bar, and immediately goes up to them. She grabs the man by the shoulder and says 'you... You're a c**t' and walks out. The man turned to his perceived date and says 'yeah, she does that' and then left the room, leaving his date to sit there, staring blankly into oblivion until she left. Odd." ⏤ LSDnoiseparty

There was a lot of debate in the comments of this one as to whether this was genuinely a man cheating on his wife, or whether it was all part of a fetish prank/game that the couple were playing.

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13. The Hour-Long Fondue Breakup

Unsplash | Nerfee Mirandilla

"I worked at a fondue place. 1.5-2 hour meal for two people. Four courses, the works. Couple came in and he had pre-arranged with us to present an engagement ring with the chocolate course with melted chocolate on the plate spelling 'Will you marry me?' Also roses and other embellishments on the plate.

"Apparently the entire meal she was explaining to him how bad he was at being in a relationship. Too needy, too emotional, somehow also didn’t spend enough time with her and wasn’t connecting with her? It was an hour-long breakup speech.

"We come around the corner with candles lit and the chocolate fondu and the engagement ring on the plate, the table next to them did everything they could to wave us off, I was holding a camera to capture the magical moment...which never came. He tried to get his prepared remarks out, but it was so bad we eventually left the dessert at the table and tried to act like nothing had happened. She left before the check came." ⏤ Jps1023

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14. Surprise Divorce Papers

Unsplash | Kelly Sikkema

"I guess you could call this a couple date. 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. I did bring out tissues for the wife who was breaking down. I ended up boxing up dinner. The guy paid but I do not envy that ride home." ⏤ ThereandBack22

One other service employee replied to this comment by explaining how shocked they were at how often breakups happen in restaurants, writing:

"Breakups happen a TON more often than I would assume as a server. I've had a couple of memorable ones One lady (a bit on the thick side) was waiting at a table. She said it was a blind date. He came in...she waved...he turned and left. I bought her a shot of tequila that night. Another one was a man and woman having a seemingly normal meal and wine. Out of nowhere, I hear her stand up super fast and her chair fell...she tossed her wine directly in his face like in the movies. She left."

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15. Figuring Out Someone Has Been Having An Affair

Unsplash | Denny Müller

"In law school I always worked the Sunday morning shift at the restaurant in town and it was always so dead but I’d bring homework so it was mostly ok. Every other week, this couple would come in and order G&Ts and nachos and sit for hours talking about how attracted they were to each other, their sex life, and would joke about sneaking around and what not. I never thought much of it.

"Until one day, I walked into the dining room from the kitchen and saw the lady had already been seated in a booth facing me. Her dude’s bald head was across from her, facing away from me.

"I approached the table, about to ask the love birds if they wanted their usual, when the dude turned around and IT WAS A DIFFERENT DUDE. The lady looked at me sheepishly as he mentioned to me it was his WIFE'S birthday and they had never been at my restaurant before lmao." ⏤ [Deleted]

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16. Making An Uncomfortable Toast To The Entire Restaurant

Unsplash | Scott Warman

"When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date. Right in the middle of their dinner, this poor guy stands up, taps his wine glass to get everyone's attention, and then proceeds to tell EVERYONE what a fantastic person his gf is, how much he loves her, and how lucky he is to have her in his life.

"The whole time this is happening, she is just sitting there watching him with the most boring look on her face. It was so weird. Kind of like, 'Yeah, tell me something I don't know'. Then the poor guy pulls out a ring, gets on one knee and asks her to marry him. She gives him the most disgusted look imaginable and says 'THIS is the ring you expect me to say yes to? Are you retarded? Could you be any cheaper?' Then she gets up and walks out, leaving the poor guy just kneeling there." ⏤ Penya23

This person went on to say that they didn't charge them for the meal. Also, they went to explain, "a hostess at the restaurant knew the guy personally. Apparently it took him a really long time to get over it."

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17. Game-Show-Style Tinder Dates

Unsplash | Kon Karampelas

"A girl brought two tinder dates and played them off each other game show style. They seemed to be unaware this was what would happen. Splitting the bill was hilarious." ⏤ [Deleted]

I cannot believe that both of the guys stayed for the whole meal! I'd have had to nope the hell out of there upon realizing what was going on.

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18. Flirting With Waiter

Relevante design | Unsplash

"A girl hit on me in front of her bf when I was serving. The bf walked off after staring her off and the girl awkwardly sat there alone for a while. I asked a 'girl' friend to take over her table, coz it was too awkward." ⏤ [Deleted]

I mean, I don't think that I would be able to sit there politely if the person I was on a date with started flirting with the waiter, would you?

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19. Flirting With The Waiter 2: Electric Boogaloo

Unsplash | Kate Townsend

"I had a middle-aged couple who seemed perfectly nice. The man asked me where he could go to smoke. I pointed him in the right direction and then started heading back to the kitchen which was in the same direction. He followed me and told me that the woman with him was his ex-wife. Not knowing how to respond, I said it was nice that they got along so well. He told me she just pretended to seem nice and was actually a terrible person.

"I was feeling uncomfortable enough, but then he started to ask my age, if I had a boyfriend, what I was doing later. Thankfully, I could excuse myself to the kitchen. However, serving that table was awkward after that especially since she kept touching and complimenting him." ⏤ Rosepetals7

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20. Asking For A Shotgun

Taylor | Unsplash

"I don’t really know if this counts because I think they were married. At a table with two crying children, 'how are you doing tonight, what can I get you started with to drink?'

"Father: '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." ⏤ RhodeIslandisFake

Which one of the stories on this list made you want to reach for this gentleman's hypothetical shotgun? Be sure to let me know in the comments below, and even share some of your own awkward date stories if you feel brave enough!

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