Restaurant Workers Shared Stories Of The Worst Dates They’ve Ever Seen And Now I Weep For Humanity

A bunch of restaurant workers shared stories of the worst dates that they’ve ever seen and I’m beginning to wonder if humanity has lost complete respect for the food service industry. A restaurant is not your frat house. You do not have free reign to do whatever the hell you choose in a restaurant, but that doesn’t seem to stop anyone if these stories are to be believed.

This collection of stories comes to us by way of AskReddit, and I’ve gone ahead and pulled the best/worst stories from that thread so that you don’t have to wade through all the bullshit. If you want to read all of the responses you can feel free to click through on any of the links below. Now let’s get to the worst dates ever witnessed in restaurants. As always, if you have a story that can top these I want you to CLICK HERE to send us your worst by filling out our anonymous tip line.


A guy made a reservation saying he was going to propose. He asked for a special table and for dessert to come with a sparkler candle and, “will you marry me?” written on it. I bring out the cake, the manager follows me with two glasses of champagne, my co-workers are cheering. We set everything down and walk away. They end up having a serious, quiet discussion and it is very obvious that she is rejecting the proposal. Then three of their friends show up and sit at the table, all excited thinking their friends just got engaged. But it quickly became apparent to them that it was not the case. It’s very quiet and awkward at the table. The woman who was being proposed to left, and the reject and his friends got wasted. He gave me a 20% tip too, which was nice considering how shitty his night had been.


I had a regular sitting at my bar in a chain restaurant about two weeks ago. He sits there for an hour, leaves for 20 minutes or so, then comes back complaining that he’d been stood up. The date was supposed to have arrived an hour before he mentioned anything. Poor guy.
All of a sudden this woman appears, apparently his date. Nothing out of the ordinary except for the fact that she was an hour late, so I continue making drinks for the restaurant.
Couple of minutes later and a waitress comes up asking if the woman was on a date with the guy at the bar. I respond yes and ask how she knew. She told me that the woman had just left her (the waitresses’) section and had been on a date with another man.


this guy takes his wife out just to outline to her the details of how he found out she’d been cheating on him, as he’s telling her, his lawyer serves her with divorce papers
and he leaves
she was rekt, probably deserved to feel like shit, but still, to do it that way
i mean i was pouring her wine when he dropped the bombshell, like he wanted me to be part of it, he wanted her to be humiliated in front of someone
edit: wow… umm, i told another poster yesterday that i’m new to reddit, didn’t know the story of zach and jenny. i’ve also never been upvoted so much… and for a pretty stupid story too. not sure about you reddit.
couple things, first, i’m a guy. and yeah i felt a little sympathy for the girl. i’ve been cheated on, i know it sucks. but i didn’t appreciate being made to part of that, because i wasn’t, i don’t know you and i’m only doing my job being polite.
dude seemed like an asshole, assholes get cheated on. cry me a river about the injustice i guess.
yes, he paid for the dinner on his way out, 15% tip. left her sitting there looking lost. i comped her a slice of cheesecake drizzled in caramel, asked if i could call her a cab. she ended up calling a friend to come and get her. last i ever saw of either of them.


I once ended up waiting on my ex-girlfriend, who I was not over, and her boyfriend. After some extremely awkward small talk I went to grab her drinks and noticed her boyfriend was not there when I came back. Then, one of my co-workers told me he was outside the restaraunt crying because apparently they fought a lot and he was a crier. It was both satisfying and sad to see. Eventually, they made up but the whole experience was just a bucket of uncomfortable.


Couple comes in on Valentines Day – no reservation. They get seated at the bar, order some drinks and apps, and are sitting there chatting and laughing. Seems pretty normal.
After finishing their apps, the guy drops to one knee, and pulls out a ring. Girl immediately shuts him down. He didn’t so much as get a word out, before she’s saying, “Nope. Nope. Nope.” Grabs her coat off the back of her chair, and is putting it on, still saying “Nope” over and over. Practically RUNS out of the place, does not look back.
He looks gutted. Pays the bill, walks out, staring at the floor the whole time.


I’m gonna hit this from the opposite perspective. Me and my wife were on a date in a loud pizza parlor. We were both kind of annoyed of the place we had chosen, not knowing it would host a bad musician after 8. The waiter essentially “picked” up on us being on a bad first date and he treated us as such. Me and my very happily married wife who basically just wanted to get our food as quickly as possible at that point asked for a box the second the food was delivered. As he layed down the box, he said “Sometimes people just aren’t as interesting as you think huh?”
That was the only time I have ever left nothing for a tip. Fuck you guy. Don’t make assumptions, sometimes your avenue is not what people thought it would be.


There is this couple that comes in about once every week or two into my restaurant and the guy is a complete tool. He won’t let his girlfriend order what she wants and cuts her off saying “She’ll eat what I decides she’ll eat.” It’s really annoying because he’ll just cut me off mid sentence and tell his gf to stop talking. They also sit on the same side and suck each others faces the whole time. Last time i served them i was standing in front of their table with their food and they wouldn’t stop making out so i had to ask them to come up for air so i could give them their fucking food. PDA is gross.


Alright so I had a 2 top table with a very handsome young guy and a super attractive young woman (early 20s I think). Anyways I proceed to go over and greet them and discuss the specials for the night. They seemed nice and it looked like it was their first or second date. I asked for their drink order and the guy gets an ice-tea while the woman orders a glass of wine. She then proceeds to tell the guy in the highest pitched voice to order alcohol because she will feel, “so naughty if she is the only one drinking, and she doesn’t want to be a naughty girl”. This goes on for a few minutes until the guy gives up and awkwardly just orders a vodka soda. That was the first weird exchange. Next I bring them bread and they devour that shit fast. I ask if they would like some more and the woman says oh yes she would love some but she doesn’t want to be a naughty girl again. She described herself as naughty again for another few minutes until I just left. They place their orders and she goes to order a steak with fries as her side. She again repeats how she is so so naughty for getting carbs as her side. The guy just looks so drained by the end of the night because this woman would not fucking stop saying the word naughty. I could tell he was just pushing through because she was wicked hot and apparently a “naughty girl”, but god damn there is a point where the whole “high” pitched fake “I’m a naughty girl” shit gets so annoying.

So basically these are all lessons on how to be a dick, or if you do the opposite of what happened in most of these situations then you can learn how not to be a dick. I guess being a dick is in the eye of the beholder…or dickholder…I really don’t know.

Anyways, if you’ve got a story that can top these CLICK HERE to send us your best/worst by filling out our anonymous tip line!