Service Industry Workers Share the Worst Dates They’ve Ever Witnessed

We’ve all been there…

I’m talking about being on a date where it just feels all wrong and everything is super uncomfortable.

And it’s even worse when you know that your waiter or waitress is picking up on the vibe too and you know that they’re probably making fun of you in the kitchen in between stops to refill your drink.

BUT, the good news is that we get to hear stories about OTHER people going on bad dates because these service industry folks were nice enough to share their stories with us!

Let’s check out these entertaining stories from AskReddit users.

1. Not a great night.

“I used to work for a restaurant called Houston’s. It’s somewhere in between casual and fancy.

Anyway, a young couple was on date night and I guess the guy checked me out and they were awkwardly fighting the whole night while I kept serving them. I don’t think they realized how much I could hear.

Pretty sure the girl was just being crazy because I wasn’t very flirty or anything. I always knew to be extra nice to the female on date night.

I did not get a good tip.”

2. Rough.

“The couple that came out to eat on Valentine’s Day, dude broke up with her while i was getting them drinks.

He ordered appetizer and a meal, she said she wasn’t hungry. She cried, he ate, they hardly argued much and then left.

Dude barely left me five bucks he was kinda an *sshole.”

3. Shot down.

“I was a waiter at a Kelseys restaurant when some guy decided to propose via cake with “will you marry me?” written in frosting on top.

She turned him down by smearing the frosting with her knife.

They paid and left very quickly.”

4. Gross.

“This happened last Saturday and was recounted to me by my manager at the bar/restaurant I work at.

A couple came in to “celebrate” their 10 year anniversary and sat on our patio next to the table my boss was sitting at (he was off work). The husband began harassing both waitresses who were on the patio at the time, being very loud and obnoxious, constant flirting, stopping them when they would walk by, asking the manager on the floor to let them off work so the girls could drink with him and all the while the wife is quietly drinking her beer and looking dejected.

My manager said it was so uncomfortable and off-putting that he ended up leaving and went to the bar I was at. Unfortunately this type of date happens more than I’d like to think.”

5. The happy couple.

“Husband and wife were sitting at the bar.

I wasn’t even bartending but they still dragged me in for some reason. She was cussing him out for pretty much the entire meal and even outright hitting him a few times. At first I thought it was all in good fun kinda deal but as they had more to drink she quickly got angrier.

At one point she angrily tells him to “shut the f*ck up or I will hit you with the car again!” It was incredibly awkward.”

6. What a jerk.

“There was a middle aged couple that came in at around 7 pm to the Italian restaurant I am a waiter at.

White guy, Hispanic-looking woman. Their “conversation” revolves practically entirely around his recent endeavors trying to work his way up through the ranks of whatever school district he was working in. I don’t know if he was a teacher or just an administrator, or if he even worked at a specific school or for the District.

Anyway, not 10 minutes in to the date he begins to describe how utterly unfair it is that he can’t get a better job because (and I quote) “maybe if I said “yo hablo español” the Mexicans that run the place would promote him. He was loud, obnoxious, and several times throughout the night after making a blatantly racist or xenophobic remark, he would go in for a high five like “yeah, you get it! High five sister!”

To which she would always turn down. Quite funny, but also I felt bad for her. She probably didn’t know what she was getting in to when she agreed to go on a date with him, and I assume he was her ride because she seemed to want to leave but couldn’t.”

7. Brutal.

“I used to be a server at an upscale restaurant and had this lady come in a few hours before her reservation with a cake that had “Will you marry me?” written on it.

She then gave me a bunch of those sparkler candles and asked me to bring the cake out at the end of their dinner and surprise him.

You could tell this lady had the crazy eyes, and all the servers there had never seen a woman propose in our restaurant before so we all were watching as it went down.

Delivered the cake with the firework sh*tstorm and all, and the guy just gets all wide eyed and mutters “uuhh… I… I was going to propose eventually…” and she’s just sitting across from him with this huge smile on her face waiting for him to say yes. He never said yes.

They sliced into it and ate a piece in awkward silence and left shortly after, without the cake.

So cringy.”

8. Crushed.

“Two sat at a table, the dude obviously trying to make a go of a last romance, but she’s sitting beside him rather than across, and staring into space.

They order all night. He’s piling on the drinks, and when she starts asking for water, he starts drinking for the both of them. It becomes clear this is a last ditch effort at saving things.

After about three hours of this, she still hasn’t left, and is patiently putting up with the awkward tension, evidently hoping for a graceful death. He, having consumed a good deal of alcohol, and being more than buzzed, gets cut off. Then, he decides to get into it.

He asks her if she wants to go out again, after this. She says, no. She’s breaking up with him. He is crushed. Crushed. You could see his heart shatter, and the pinprick pieces slip through the pores of his skin. Pure agony. And he starts sobbing.

She hugs him, and tries to comfort him, and that’s when he throws up.

So now, security is on him. They call him a cab, and his now ex-gf tries to usher him into it. But he won’t leave the table, somehow convinced that if the date doesn’t end, he can still save it. He’s clinging to her arm, and she’s apologizing profusely to him, to security, to the people around them.

Finally, he starts getting belligerent enough that security feel compelled to forcibly remove him. And he starts throwing punches. Kicking. Clinging to the walls of the bar. They literally have to give him the bum’s rush onto the street, then haul him bodily into the cab, and send him off.

The girl goes back into the bar to pay up, and finish her water.”

9. Valentine’s Day.

“Any couples out on Valentine’s Day.

I usually get on great with couples and they’re my favorite tables to wait on, but the couples out on Valentine’s Day were so miserable and silent. There was no chatting with them or having a laugh with them.

I just took the order and brought the food. One girl ordered a toasted cheese sandwich for her Valentine’s Day dinner.

I think all the bad couples go out on Valentine’s Day.”

10. This is insane.

“When I was a waitress, we had a couple who would come in for their date night every few months.

The man was overweight, and the woman was obese. I worked at a buffet. They would come in and make sure they got a table next to electrical outlets so they could plug in their phones. Oh, and the woman would come in with three or four rolls of toilet paper that they would then set in the middle of the table.

I’d then watch them, for hours at a time, get plate after plate overflowing with pizza, brownies, ice cream, spaghetti, you name it. The woman would get so worked up eating, she would start profusely sweating, and then would (obviously, right?) use the toilet paper to wipe her sweat from her face, armpits, everywhere.

They’d leave, and they’d leave the toilet paper. Their date nights ended in me picking up piles of totally sweat-drenched toilet paper from a table.”

11. This is depressing.

“When I was in college an older couple would come in every Thursday like clockwork, they were so cute.

We didn’t see them for a few weeks, and then he comes in – alone. She had passed away and he just looked lost.

So sad.”

12. Total disaster.

“Had to wait on couple of kids that were in high school, the entire thing was awkward and they almost said nothing to each other the entire date.

I wanted to give him a list of topic conversations because it was so awkward. At the end of the meal I bring the tab, and he gives me his card. I go run it and it gets declined.

So I have to go back over and hand him a booklet back and I wrote a note in it letting him know. This kid just goes white and hops on his phone to check his statement, and proceeds to tell his date and I that his parents didn’t give him his allowance.

He then asks his date to pay and she responds by telling him she didn’t bring any money cause she thought he would pay for everything. He then hops on the phone with his mom and asks her to bring him money and she agrees.

They sit in silence for another 20 minutes till the mom arrives and pays the tab (doesn’t tip) and storms out and yells at her son to get in her car. Before he goes with his mom he runs up to me and apologizes and asks me if I want a Harkins gift card that he thinks has 5 bucks on it.

I take the card and was relieved that all of that was over….. I check the gift card the next day $50.00 on the gift card. I would rate that tip 5/7.”

13. Sad.

“The worst date I ever watched (or arguably the saddest) was a guy in his 20’s came to my restaurant and said he had a booking for two. I took him to his table and make small talk. Then after 15 minutes and his date still hadn’t turned up I brought him some complimentary food.

Then after 15 more minutes I remember looking over and seeing his head buried in his hands. I was occupied at the time but I remember going over some minutes after that since he signaled me over.

He asked to be moved to another table (right next to a plug socket), he plugged his phone in and waited for his date to arrive.

After 30 more minutes (so he was roughly at the restaurant an hour) he told me he wanted to order food. I took his order and then continued with my duties. I remember giving the guy his food and he just sat there with a flat look on his face, as if he had the 1000 yard stare.

At this point there was only him and another couple at the restaurant. I watched him pick apart his food, leave it mostly untouched. So I went over to talk to him. He never said much and I could tell he didn’t want to either. He stayed for another hour just glued to his phone before asking for a check and getting up to leave.

I felt just so bad for the guy, I couldn’t imagine what it must be like. I can only assume he was stood up.”

Now we want to hear from you!

What’s the worst date you’ve ever witnessed?

Heck, what’s the worst date you’ve ever BEEN ON?

Talk to us in the comments!