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

I am not a waiter but a bartender, but this particular moment is something I never forget.

My shift began at 7pm and when I arrived at the bar at 6, my manager told me there's a guy who wanted to propose to his girlfriend at this bar and he wanted me to help him with it. I said 'Sweet, no probs.' so the manager gave me a ring and told me to put it on top of her drink.

Fast forward to the date, the girl was wearing normal thing you would see at the bar, low cut top, black skirt and heels and s**t. The bar was pretty busy. She ordered a Long Island (f**k you Laura), so I put the ring on the straw and hand it to him. She had the 'What the f**k mate?' look and then he dropped on his knees. Our manager put on some romantic songs. To my surprise she threw the drink at the poor bloke and ran out of the bar.

Later I came to know that it was their second date.

A guy proposed to his girlfriend at the booth across from my friends and me...at Olive Garden.
When he got down on one knee and opened the box, she was shaking her head and then just stared silently. It must've been a whole 30 seconds of pure silence, but it felt like an eternity.
Then, the guy proceeded to describe the ring, how much it cost, the different aspects of it, etc. Finally, the girl just went, "Nooooooo" and the guy just sat back down and they tried to finish their dinner. I caught eyes with our server and he made the most perfect "holy hell that was bad" face. Geeze that was awkward.

Edit: I still picture him saying "My love for you is like these breadsticks...Unlimited

They came in and the first thing I notice is that the woman was noticably older than the man but I don't really judge about that kind of thing and I also don't assume people are on dates. maybe she is his aunt? or they are just friends?



So I went to go ask about drinks and do the usual peppy greeting and she is super chatty. Bascially talks for him and answers questions that were straight for him. Okay, I think, maybe that's just how they are. whatever. She proceeds to order them both hard alcohol straight..at 10 am.. I figure "eh maybe they are on a vacation together". You never know.



It finally hit me that something wasn't right was when she wouldn't stop making sexual comments about the two (which is how I knew it was kind of a date). I am talking straight up things like "I am 53 but with the amount of work I have had done to my downstairs, he won't be able to tell tonight if I am actually 23" I am watching the mans face and he looks pained.



I watch the table from afar. I realize it kind of looks like a date gone wrong, but they seemed to know each other so I am not really sure what is going on (and servers always chat and theorize about their customers in their free-time) when the man gets up and comes over to me and asks me to chat with him around the corner really discretely. So I do. He looks as me and is talking super fast as he explains that this is his boss and he has to meet with her quarterly and she just has to sign a single form to approve what he has been doing and she insists on going out for a meal and drinking and then trying to sleep with him. Every time. I was horrified for him-- he looked that panicked. He said that he usually gets her to sign it before they leave the restaurant and then makes an excuse to ditch her. We made a code sign (him patting the back of his head three times) so that I could intervene when she would get far too inappropriate but honestly she didn't change much when I would come. He also asked me to bring him fake alcoholic beverages, said I could charge him for the alcohol but to make them water or just soda.



I still think about him sometimes and wish I had gotten his name or something so I could check in and encourage him to report her, but in all honesty she probably owned the comany he worked for or something the way she spent money and looked like.

We had an older lady come in on a Saturday morning. She happily informed the server that she was waiting for a date, and ordered a mimosa to drink. About three mimosas and forty-five minutes later, we start to think maybe her date is a no show. The waitress sits down and starts talking with the lady, trying to assess the situation, see if she still wants to order and what not.

That's when it gets strange. The lady says that her date was going to pay for the meal so she didn't have any money, and she wanted a fourth mimosa. Meanwhile she's cheerily looking out the window for her date, obviously nervous / excited to meet him, and very talkative. The server asks the manager what to do, so he sits down at the booth with the lady to talk with her.

Turns out, her date was Lynyrd Skynyrd and she had dementia :(

I worked at a Subway a long time ago. My regular doctor came in with one of the medical assistants (not his wife). They were sitting side by side and she kept rubbing his leg.

Dude, you're a doctor. Use that brain of yours. If you are going to be a d**k and cheat on your wife, at least go on dates in another town where people won't recognize you.

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.

When I was bartending this guy came into the bar on a week night, 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.

I worked at a place famous for their cheesecake, and I remember right around Christmas a little old lady coming in dressed to the nines, happier than I've ever seen anyone. I was only hosting at the time, so it wasn't my table, but she told us she had a blind date and she was so so excited. Kept asking us girls if she looked ok, nervously talking to us, looking around expectantly. A half hour passes, an hour passes.... And you just see her deflate. She was stood up on her date and it was just heartbreaking. My friend begged our manager to cut him so he could to sit and have dinner with her, but it was busy so they couldn't do that. They did comp her bill and gave her some cheesecake for free, and when she left she was still just as sweet, but I don't know if I've ever seen someone look so dejected. It was really really sad.

There was a couple sitting at the bar together - seemed like it was a 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.

Idk if this counts, but when I was a waitress at Olive Garden, one of my tables was going over their divorce paperwork. When I greeted the table I asked how everyone was and the woman said, “Terrible! We are getting a divorce.” Like wtf do I say to that?

This was just before Tinder and dating apps were a thing. It was a blind date, guy and girl. Guy shows up first and is excited, until he sees his date. She had their mutual friend show him an old photo of her because she had since gained significant weight. You can tell he was let down, but decided to make the most of it. They order drinks and appetizers. We didnt even get appetizers out before the guy noped out of the date. He sat at the bar asking us to bring the appetizers to him there. Her weight wasn't the only thing he was lied to about. Her personality and his clashed so hard the date didnt last ten minutes. He hung out well after she left. We (the bar and wait staff) invited him to hang out with us at a bar after work. Ended up being a cool guy.

In law school I always worked the Sunday morning shift at the restaurant in town and it was always soooo 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 s*x 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.

Bartender at the time, not a waiter, but they were righ in front of the bar.

attractive woman comes in with a very loud dude who never took off his rollerblades, humblebrags badly (mostly just bragd he clearly thought sounded humble) loud enough for me to hear in a bar for about an hour, thanks her and leaves.

he thought it was a date, apparently she was doing sociological research on people who use tinder.

i was relieved.

Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears. She whips out a pen and starts writing paragraph after paragraph angrily. It was awkward because i kept having to come back to the table since they ordered multiple courses and he was just eating and signing while she was hunched over the table writing away while crying. When they finally left they tipped me pretty well though so I guess it wasn’t too bad?

Eastern European couple walks in. She looked like she had been crying, but they ordered and seemed nice enough. A few minutes later, I heard a commotion going on in my section. I got there in time to see this man reach over and slap the woman hard enough that the whole lounge heard the sound. He looked like he was gearing up to hit her again, so I instinctively stepped in (I was and am a small, petite woman with no martial arts training or anything) and told him to back off and leave or the cops would be waking him out. Surprisingly, he just left without a fight. What was disturbing is that the woman very quickly composed herself and by the time I went over to check on her (seconds later) she was brushing it off like it was an everyday event. I guess it was for her.



I told her I would feel better if she stayed in the lounge for a bit, so we could be sure the man was gone. She agreed and I got her a few drinks on the house. Once she was a little more opened up from the drinks, she told me her story, about how this man brought her to the US and that she was afraid if she left him, she would end up being forced to go back home. She also warned me never to date an Eastern European man and that most of them were like that. I wanted to take her to the police or to a women's shelter, but she refused and wandered out into the night. I never saw her again, but I hope she is okay and away from that man.

Saw a really young couple, likely 13 or 14, come in and not say anything to each other. Neither could look each other in the eye they were so shy, and ordered their food barely above a whisper. Occasional cringe faces made at the food they were staring at. They were having a very awkward time and it was painful for them as well as me.

No joke, had a woman bring in a candle and put it in on the table. Not a little candle but a big, giant one. I told the woman her and her date could NOT have that on the table and she literally said "Y'all tryna get hit?"

This was in a mall in a pretty big town at a chain restaurant. I just couldn't believe it. Thank God managers exist.

I was at one of these fancy speakeasy type bars they've started opening up installing a new invoice printer for their Point of Sale system. Waiting for the printer firmware and driver to install can take 30 or 40 minutes on slower computers, so I'm people watching.

As I'm standing there watching bars fill up, I notice a gorgeous blonde in her late 20s is sitting with a very well-manicured looking guy in his mid 40s. He's dressed like he just left a high dollar law firm, and she looks like she's going to a fancy professional cocktail party after their date. He is polite, talkative, and super into her, but you can tell that she isn't reciprocating the feelings. To be honest, by the look on her face, she's anywhere but in that bar at the moment.

The guy goes to the bathroom and she quickly picks up her phone and frantically calls someone and begs for pickup ASAP. The gist of the call was the guy was her mother's coworker and her mother had set the date up, and our girl really wasn't feeling it. About fifteen minutes later, a guy around her age comes in, throws some cash on the table and excuses them. She cites some vague emergency and is escorted out.

The older guy continues drinking ($140 tab, note that I'm standing at their main cash register) and starts flirting with the waitress, fails to get her number, pays in exact change without tipping, and leaves.

Was a cocktail waitress at a bar in a high-end restaurant a couple years ago. This couple comes in right around peak hours, guy looks annoyed, girl looks really excited. The whole time the girl is trying to talk to this guy and he's completely ignoring her. He gets a call and talks on the phone for a good 10 minutes, hangs up and starts talking to anyone around him but her. He's getting more and more drunk and starts hitting on the female bartender and eventually the cocktail waitresses (myself included) telling us he could get us all much better jobs in Atlanta. The girl he's on a date with has started crying at this point and once he actually notices he yells at the bartender because it was obviously restaurant's fault for her being upset. She yells at him to stop yelling at the bartender because he's been such an awful date and he goes off, tells her he didn't even want to eat here, she should've picked a better place, and he isn't paying for her food and drinks. He then tells her that she didn't look fat in her picture and he wouldn't have asked her out if he'd known she was that big (probably met online kind of thing). She retreats to the bathroom and the guy continues to make a scene. Another girl at the bar and I go to check on her while the bartenders and manager try to deal with him. The girl is super upset and I tell her there's a back door she can leave through and I can get her tab from the bartender. I go back out and the guy had already stormed out and refused to pay, leaving his date with a nearly $200 check. She didn't have the money to pay so a couple of the bar regulars covered it. Made the whole night super awkward and stressful. Definitely one of the more memorable experiences of that place.

Not a waiter but I was working as a supervisor in a restaurant. And there was a drama lasted for a couple of months.

There was a couple that came to lunch every day. And everyday they went to toilet together for like 20-30 minutes. So you can guess they had s*x. It was inappropriate but we could nothing with that.

But one day she came to the restaurant with another man. And he was her husband. And that was a pretty awkward moment. So she started to come to the restaurant with her husband in weekends.

But one day, as usually, she came to us with her lover. They were arguing and as I've understood they broke up. She was crying an so on. After that fight I've never seen any of them.