Bored Panda
"Maybe If You Hadn't Boned Our Son’s Girlfriend": 45 Crazy Stories Servers Overheard
Funny,FailsSEP 11, 2025

"Maybe If You Hadn't Boned Our Son’s Girlfriend": 45 Crazy Stories Servers Overheard

38
1
Dating, particularly first dates, are commonly a bit stressful. Imagine trying to manage small talk with a stranger, all while trying to leave a good impression of yourself and evaluate your counterpart at the same time. So it’s no surprise that sometimes things just don’t go as planned.
We’ve gathered stories of awkward and unhinged date moments as shared by restaurant workers from across the internet. So get comfortable as you scroll through, upvote your favorite and if you’ve overheard or sat next to a date gone wrong, feel free to detail the story in the comments down below.

#41

Another story! This is the tale of how I accidentally become someone's closet hanger.

So about a year into my current job, a young woman about my age starts coming in with one of her (also female) friends. She's very beautiful--blonde, fantastic body, extremely sweet and bubbly. The second or third time they come in, they're dressed to the nines--girls' night out! They order a round of very strong drinks a few times and they chat me up a while. I guess also being a young woman, I'm disarming? Idk I try to be social but I'm awkward as hell.

After a while, they get drunk--and the blonde girl starts laying it on me thick. I'm kind of lost, I get flirted with somewhat regularly (alcohol + food + relaxed people = s*x? idk), but I've never been flirted with by another woman. They leave eventually and the blonde girl departs with a blown kiss and a wink. I've never been so flustered and bisexual in my life.

She comes in every so often after that, progressively more sober and progressively more flirtatious. She's touching my arm, batting her lashes, the whole nines. My male coworkers (at the time, I was the only woman working there) are insanely absorbed in this and constantly ask me for updates. She keeps flirting and I keep not knowing what to do except weakly go "oh yeah hahaha I've got a boyfriend." She's never deterred.

But then! It happens!

She comes in a few months after this all started--WITH A GUY. And she does not look happy. I was working a shift that I usually didn't cover on an odd day, so she was shocked and visibly displeased when I waited on them. The guy with her is totally oblivious and a very chipper dude. I introduce myself, say "oh yeah (woman's name) is one of our regulars!" The guy goes "oh yeah, my financee never stops talking about this place! I totally thought we should come!"

Oh no. I put all the pieces together-- I'm her gay crush, but she's engaged to a man. I have never seen a human being redder in my life as she was. I quickly take my leave to get their food. Throughout the night, he gets up to leave to go to the bathroom/order more drinks/whatever, she's adjusting her hair and touching up her lipstick. It's a disaster. I'm dying inside.

They come in a couple more times, until she suddenly announces (without looking at me) that she's been accepted to medical school, so they're moving. And I've never seen her since.
20points

#42

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.
Report
20points

#43

Three restaurant customers reading menus while sitting at a wooden table in a casual dining setting with servers nearby.
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.
19points

#44

I've worked in several restaurants over the past 25 years. The awkward dates, at least in my experience, are always the ones where the girl (girls in these instances = 16-25) is pretending that she doesn't eat, usually first dates. At Burger King, in high school, she orders an order of fries and either gets water or a diet drink. When I worked for Pizza Hut, girls would always order the salad bar, and "Maybe I'll have a slice when it comes". A chicken wing joint I worked for: a side salad.

The guy would always stare at the girl like she's lost her mind.
Report
18points

#45

Not exactly a date- but 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 our their forks or refill drinks while they were so emotionally charged.
14points
38
1