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Restaurant Servers Describe The Worst Dates They've Ever Witnessed

Black and white photo of a server dressed in all black peering through a window.
Photo by Ian Taylor on Unsplash

I have been a waiter on and off for many years.

The things I've seen!


I've witnessed both the best and the worst of humanity.

But nothing compares to watching awkward or bad dates in real time.

I could tell if the chemistry was going to be on or off in mere seconds.

Break-ups, make-ups, marriage proposals, and even a death or two.

Love ain't easy at "The Olive Garden."

Redditor Common-Sprinkles9328 wanted to hear from all of the restaurant servers out there, spill some tea, they were asked;

"Waiters of Reddit, what 'well this is going horribly' dates have you witnessed?"

No Coke?

"I've seen a bunch but the best was when a guy brought in a canned Pepsi and just asked for a glass with ice. He then offered one to his date.

"It did not go well."

- ElHamburglare

Excuse Me Lol GIF Giphy

She Left

"The man tried to order for his date, she didn’t like that, but it was early in the date so she said nothing, he ordered an expensive appetizer that she didn’t want, only he ate it. She looked not impressed but still seemed to be trying to feign interest. It came time to order dinner, and he tried to order something expensive for her: surf and turf."

"She said no thank you; she was a vegetarian (something established before the date) and wanted the vegetarian dish. He didn’t back down and insisted she have the surf and turf. She again said no, she wouldn’t eat it. He countered with, 'he could afford it, so why not?!' She left."

- MissHillary

Death Arrives Before Dessert...

"I remember this one time a couple were on their first date, the restaurant was empty, and the guy was a regular, so I made sure that they had a great experience. Hooked them up with a free app and some wine and let the lady play her music on the speakers. When I was bringing them dessert, she got a phone call, and she was told that her father had died. It went from a near-perfect evening to probably the worst night of her life."

- Master_Air_8485

It's a Hard No!

"I’ve witnessed two failed marriage proposals. One was uneventful; the proposal happened, and she quietly said no. They both left looking dejected. As for the other one, he was an obnoxious jerk and she seemed over it. He proposed at dessert, she said no, he tried to argue, and they ended up yelling at each other in the rain outside the restaurant. She was right to turn him down."

- HorrorAvatar

He Bailed

"Had a customer who was meeting a guy for a blind date. I saw a man walk into the room, scan the room, and walk out. After a couple of lonely glasses of wine and constant checking of the phone, it became apparent that he bailed. I asked if she wanted to order a meal, and she declined. I gave her a dessert and told her the bill had been taken care of."

- NillarGorillar

'What Did You Think?!'

"Former waiter here. The sheer number of dates I saw that were just one person going on and on and on about themselves and not asking the other person there a single question was mind-blowing."

"But I think the worst one I ever saw was when a guy asked the person he was with to quickly run lines with him for an audition he wanted to do. I think he thought it was some kind of flex, like he would impress his date by slipping in his amazing acting skills before their food arrived."

"Not surprisingly, perhaps, his acting skills were not so amazing. And then he said, 'What did you think?!' and instead of waiting for the answer, started explaining the brilliance behind some of his acting choices while his date was forced to half-heartedly nod along and praise the performance. It was so painfully awkward."

- Silly_Accident3137

Joaquin Phoenix Thumbs Down GIF Giphy

The Bad Guy

"I saw many good dates, bad dates, and everything in between. The saddest was a couple that seemed like a good match. Lady was so excited but the guy was insecure but successful. Persian dude in his early thirties. He got there early and it was a great date spot. I chatted with him while he nursed a drink to cool the nerves. He was a very down-to-earth guy and I felt like we genuinely connected."

"She shows up and was so excited... until he talked about himself and his career for the next 90 minutes. I wanted to scream at the guy to ask a question but he was trying to impress her and was a totally different guy."

- UknowNothingJohnSno

Painful

"It was these 2 kids that I'd guess were 12-14. The boy's mom drove them to the restaurant. The mom planned on f**king off to the bar so they could enjoy themselves."

"The boy would not let her leave the table no matter how many hints she and the girl tried to throw. I saw that he was physically holding his mother under the table."

"The boy was so nervous that he barely talked to the girl. He mostly talked to his mom... and the girl mostly talked to his mom. It was so painful to watch."

- esoteric_enigma

The Performance

"When I was in college, I was working in a bar where the man left his phone in his jacket and left the jacket on the chair when he went to the bathroom. His girlfriend/wife immediately went for it, and within the minute and 45 seconds he was gone, she apparently found what she was looking for, and as he returned, she started yelling and flipped the high-top table over."

"She ran out with his phone, and he ran after, and we just comped the check because no one was interrupting that."

"I hope it was a scam, they deserved every single bite for free, but they didn’t stay long enough to enjoy the fruits of their performance if so. Also, I watched all the color drain from that man’s face and he looked like a fish swallowed a golf ball, so an epic performance if it was staged."

- drulaps

A deer in headlights

"While working at a little dessert shop, a regular brought her date in. Things seemed fine, but later that week he came in alone and tried to get my number. I, of course, told her as soon as I could, and she was sad but grateful."

"The worst I've ever witnessed I was just another person eating next to a date. I was actually catching up with a friend, and we wound up not talking most of the night and just listening to a woman become increasingly more erratic, explaining how badly she wanted to murder a bunch of different people in her life. Her date just sat there like a deer in headlights."

- jperscrpers

Cuba

"The guy spent like 10 minutes explaining to her how monogamy was a trap, and she was like 'Oh, cool. then let me tell you about this other guy I’m kinda interested in,' and then he proceeded to call her a wh**e and ask how many men she slept with in Cuba. Loudly in my crowded cafe, at like 3 pm. She denied ever visiting Cuba."

- doctor4th

Forlorn

"Not a waiter, but I did once see a woman storm out of a date in a very nice restaurant. The couple was seated at an adjacent table to me. She got up abruptly and left, just before the food was served."

"The waiters seemed to handle it very discreetly: they brought a cover to keep her meal warm in case she returned, and after a generous interval, quietly took her plate away. The guy waited for a while before forlornly eating his own meal and asking for the bill."

- InbhirNis

Sad Season 2 GIF by Friends Giphy

It Was Weird...

"We had this one older lady come in every week. She wore a different wig every time. Should would ask to sit at the same exact table and ask that we act like we’ve never met her before. Then, throughout the day, sometimes the entire day, she would have multiple dates."

"These men would just fawn all over her. If they did not bring her flowers, it was a wrap. She would ask that we help sneak her out of the restaurant until the guy left. Sometimes, it got really awkward. She never paid. She also asked that we only address her as Tiger."

"It was weird."

- vtxlulu

Vibes Off

"Saw this one date at the bistro where the dude was full-on analyzing the menu like he was hunting for typos instead of just picking a meal. Meanwhile, his date's doing the vanishing act, scrolling her phone, probably texting her escape route. Classic case of wrong priorities. Shoulda have gone for simpler vibes!"

- Foreign-Purple-3286

It's about ME!

"This was a lifetime ago, but the guy was being pretentious, condescending, and boring. The girl was eye-f**king me the whole time. I ran into her a week later on campus and found out that was a first date that never got a second. She and I ended up dating for quite some time and had a couple of bonus moments over the years when we both were single at the same time."

- Rob_LeMatic

Nicki Minaj Flirt GIF by BET Awards Giphy

People are wild.

How hard is it to pay attention to your date?

That's like Dating 101.

It's the least of what you have to do.

And I'm starting to think that marriage proposals are better off done in private.

Hearing those rejections is a lot to handle... for the servers.

I forgot how personally stressful serving tables is.

Not missing it.

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