Working in the service industry, you get to see it all. From the sweet and thoughtful anniversaries, to the awkward first dates that make your skin crawl.
Here, food service workers tell the story of the worst first date they've ever witnessed on the job.
(Comments have been edited for clarity.)
An Ex Spying On The Date
“I lived in a small town where our restaurant was the only one with a full bar in it. There was this lady who was famous, among the waitstaff, for bringing all of her blind dates there. The reason our restaurant was the best for her to use was that her husband wasn’t allowed to go inside our bar. Anyway, on one of her dates her husband literally stood outside the window and just stared at them. We eventually had to ask him to stop loitering but by the time we got around to it, the woman’s date had already split. I always assumed that must have been the worst first date ever for that guy.
On a side note, she sat in our upstairs section every time after that.”
Meddling Boss Ruins First Date
“This is a first date story where the (somewhat awkward) guy was doing pretty good until my boss messed it up for him.
So there was this couple on a first date, seated at a table in the back. At first I didn’t think much of it, wasn’t even aware that it was a first date until the restaurant’s phone rang. A man called to let me know his son was there on his very first date ever (the son was in his late twenties). Obviously this was a big deal to him and he called the restaurant to make sure we would do our best to make sure they have a pleasant evening.
My boss heard and instantly went to the kitchen in order to make sure they would get a ‘special treatment’. What followed was plates with rose petals, red hearts, etc. Way over the top. When serving the plates my boss even mentioned the phone call. To finish it off, the desert came complete with sparklers and all that. The idea was sweet, but obviously this was way too much for a first date between two people who were basically just getting to know each other. As the evening progressed, the girl was visibly put off by my boss trying so hard. Poor guy. Up until then he had been doing quite well, the pair seemed to have a lovely evening. Until my try-hard boss entered the scene.
The girl was polite towards the end of their date, but it was obvious there was not going to be a second date. And it wasn’t even the guy’s fault. Other people ruined it for him. I felt so sorry for that dude.”
Man’s Date Leaves In An Ambulance
“I was working in a small restaurant with two floors. A woman and a man came in and I had a table for them upstairs. It looked like they were on a first date because they were asking those “getting to know each other” questions. After ordering food the woman had to go to the restroom, which was downstairs. As she walked to the stairs, the food arrived. She tried to walk down, tripped and fell all the way to the bottom, knocking her head on the ground. Two colleagues immediately rushed over to her to see how she was doing. She was unconscious and bleeding from her head so they called an ambulance. I went back to her date, and the man had already started eating! I told him his partner (didn’t know how to call her) fell down the stairs and that she was unconscious and that an ambulance was on the way. He walked to the stairs, looked down, and walked back to his table to finish his food. Later the ambulance arrived and I asked him if he wanted to go with hem to the hospital and he declined, while finishing her food as well. It was so awkward… he just sat there for another 45 minutes eating, drinking, paid the bill and left. I still don’t know what kind of relationship they had and whether the woman is okay.”
Spoiled Rich Girl Ditches Date
“I work at a country club that is up to its ears in old money that uses said old money to make more new money. The membership fees cost more than a year at my university. To say money is not an issue there would be an understatement.
Anyway, I was serving a young couple and the power imbalance was phenomenal. She was the daughter of one of the board members and the entire staff knew her father’s club account was major money. And the gent, well he wasn’t a member, and certainly looked like he was just the average broke college student. He was wearing plain but nice clothes and she was dressed to the nines in fashion. The date seemed to go smoothly enough, nothing out of the ordinary. Until she gets up and leaves the table before I’ve brought out the bill. I bring the bill to the counter, knowing it is well over $300 worth of food and drinks. Mind you, it was $300 of things SHE insisted on ordering – 2 bottles from the top shelf, neither finished – two steaks (when he asked for the chicken, she insisted on him eating steak “like a man”). He solemnly goes to pull out his wallet and starts tearing up apologizing that he won’t be able to tip. I mean, I’ve never had a customer cry over not being able to tip. And he explained further that he was a server too and that she didn’t know he wasn’t rich and she left because he had told her about his scholarship. I was flabbergasted. And kindly reminded him that at this country club we do not take credit cards nor cash, we only charge to accounts. And so her father got a hefty bill – rest assured he signed a handsome tip to me in her name. (Club policy is that the registered guests may sign for their host member, given that the members have invited them.) It was entirely satisfying. Last I heard, her father cut her off. I can’t help but smile at all the life lessons she is learning – like actually working to go on dates.”
Disapproving Parent Shows Up To Teen Date
“The worst date I ever saw happened at my bakery maybe six months into our first year. Two boys come in, chatting normally, clearly on their first date. They’re both young, maybe 15 at most, and adorably nervous. They order at the counter and go find a table, sitting close. One of them starts holding the other’s hand, playing with his fingers, just being generally cute.
All of a sudden this woman comes up and starts berating one of the boys. It was his mother. She had shown up because she wanted to meet the “girl” because her son was being cagey about who he was going on a date with. (I assume he had mentioned where they were going because she wouldn’t let him out if she didn’t know.) She starts screaming and crying about how her son could do this to their family. Doesn’t he know she wants grandkids? His father would be so ashamed if he was still alive. Doesn’t his father’s memory mean anything to him?
She then tells him that if he keeps up with this, don’t bother coming home, and then marches out of our shop. This poor boy is just weeping, while his not-even-really boyfriend is trying to comfort him, completely bewildered with what had happened.”
Date’s Parents Take Offence
“I used to work as a barman in a pub in Hertfordshire.
So this Indian guy is at the bar telling me how he’s meeting his date for the first time, and that she’s also bringing her parents? I start thinking this is possibly some cultural tradition.
Anyway, I’m chatting with him as he’s waiting for the girl and her family to arrive. After about ten minutes or so they do arrive and are all seated on a table nearby the bar.
I notice throughout the evening how much he’s seemingly making the family laugh and they seem to be getting along really well.
Then, the fun begins…
After dessert the mother and father of the girl go get drinks outside, leaving the couple alone. After a moment or two, the man comes up to the bar and, with a cheeky smile on his face, asks to pay the bill. Without hesitation, I process the transaction and congratulate him on how well his date appeared to go.
He returns back to his table and takes a seat. The girl’s parents now return from the garden with glowing smiles and rejoin the table.
I notice again how they all appear to be chatting and laughing until, suddenly, the man brandishes his receipt for the meal.
The mood changed instantly. The glowing smiles replaced with looks of anger and disgust. The girl’s father stands up and shouts, “HOW DARE YOU DISRESPECT MY FAMILY LIKE THIS?!” (Bear in mind this is a small country pub. So this was creating quite a scene.)
The man then sheepishly exclaims his apologies in the deadly silence to the father, to which he replies, “YOU WILL NEVER SEE MY DAUGHTER AGAIN!”
Following this, the father picks up his coat and turns to leave whilst demanding his wife and daughter leave with him. The wife stands up and immediately follows him out of the door.
The girl hesitates, half-rising from the chair, and then decides to remain with the man. She now bursts into tears. The man was clearly so overwhelmed with embarrassment and shock he did not know what to do, or how to react, so he proceeded to pat her on top of her head.
After around half an hour or so of her crying, she eventually stops and decides to call a taxi to go home, explaining how upset she was. She ultimately said, “Sorry, but I have to go with my family.”
The man, clearly downtrodden at this point, reluctantly agreed and called a cab for her.
Now… fast forward about three hours to when I finish my shift (approximately 1 AM). I leave the pub and walk to my car in the parking lot. At this point I notice a dark figure sitting on a bench near my car. Apprehension rising, I am trying to decipher the person sitting before me, and only when I am around 10 meters away do I notice it’s the man from the date.
He was bawling his eyes out. Turns out his date was now locked out of her house for the night as the parents were clearly furious with her, AND when the parents had left, they had slashed the poor guy’s tires so he couldn’t even drive home!
Talk about a date gone wrong… all over him paying the bill!”
When Someone’s Spouse Crashes The Date
“I was waiting on a table that had some plants beside the table. When I came back with their drinks they were seemingly gone. As I rounded the corner, they weren’t gone. Just ducking and hiding low behind some plants near their table. The lady pulls me close and asks, “Is there another way out of here? That’s his wife sitting next to the exit.”
Hilariously, there was a very discreet, other way out, as the restaurant connected to a different restaurant through a hallway in the back. But this was obviously unbeknownst to them. So I said, “Nah. That’s the only way out.” As they tried to leave, the wife saw them. Things were escalating quickly, as I walked to the back with a hidden smile.”
Guy Goes On Date Right After Surgery
“I work in an Italian restaurant. A few years ago I waited on a guy and girl who met for the first time when they arrived at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated.
When I was taking their order, the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough. We don’t have soup, so I explained that the “softest” food on the menu was gnocchi. He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over a three hour period and the girl stuck it out for the whole thing. She looked miserable and I’m pretty sure they never saw each other again.”
Maybe Leave That Out Until The Second Date?
“I once had a guy come sit at my bar who was waiting for his blind date. He orders a couple of drinks to calm his nerves. Well, he probably should have slowed it down to keep his mouth from working faster than his brain. Anyway the woman shows up and is waaaaaay out of his league. She is absolutely beautiful. She orders a drink and they start talking. I come back to check on them and I hear him talking about how much he hates children. He was saying things like how he hopes he never has any, and how he would never want to be stuck taking care of them, and how he wishes that kids couldn’t be taken into public places so that he wouldn’t have to be around them. She looked him dead in the eye and said, “Well I have a daughter, and I love her very much.” She grabbed her purse and walked out on him. The look on his face was absolutely priceless.”
The Vanishing Man
“I was bartending in New York and watched this couple that had met on tinder have their first date sitting at my bar. The girl was a complete maniac. Kept bringing up the fact that the dude she was with could be a psychopath and could murder her (he had given no indication of this). She even went on tinder while he was still sitting beside her at the bar. She kept telling him he was lucky that she agreed to meet him at all, and she hadn’t thought he’d be this boring. She ordered about 5 or 6 Long Island Teas and several shots, while he literally just had 2 drinks. She made him pay for everything. My favourite part of this disaster was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had vanished from the bar.”
Clearly Not Like Other Guys At All
“I once witnessed a date where the dude talked about how special he was and how his mind wasn’t like other people’s for the entire date. The girl was politely nodding along and every time she tried to get a word in, he’d cut her off. Absolutely brutal.”
Lady’s Date Shows Up Slurring His Words
“My bar has two floors, and on this night I was working upstairs. Couple came up with drinks they already had bought, and sat in my section. I go to introduce myself, girl seems nice, guy says nothing, just stares at his drink.
They eventually get another round, and as I’m dropping off their second drinks, I hear the guy slur out “chank youuu vurry mush.” Uh oh. He’s wasted. It was just one drink anyway – nothing too strong – but it WILL be his last round.
I go about my business for a while. At one point I glance up at their table. The girl is gone, and the guy looks like a total mess. I thought to myself “Whoa, he looks like he’s about to -” and right then, he hurls. Not a lot came out, and he tried to pass it off as a cough. I saw enough pour out of his mouth, onto his chair and the floor.
I grab my barback and a trashcan. Barback gets to work on the vomit, and I put the trashcan in front of the guy. I told him to go to the bathroom, take the can with you on your way, then get the heck out. He says nothing, just stares at his phone for a minute, then gets up and leaves.
I raced around looking for his date. I found her at the bar trying to pay her tab. I tap her on her shoulder and try to tell her about the guy, but when she turned around, her face told me everything. The shame and embarrassment that glazed over her might make one think she was the one who just tossed her cookies. That’s when she told me it was their first date. They had met through a mutual friend, and she really didn’t know him at all.
My bartender and one of our awesome regulars overheard. We paid her tab. She ended up staying at the bar hanging out for a while as the aforementioned regular bought her more drinks. Real nice lady.”
Waiter Gets Asked To Help With Escape Plan
“I work at a fairly nice Italian restaurant, where we do a lot of business. One night a man who I was not even serving came up to me while I was punching in an order on the computer and hands me $20 and a napkin with a phone number on it.
He proceeds to tell me, “I am on the worst date of my life. This woman is horrendous and I have to get out of here. Take this $20 and please go to the nearest phone and call me and explain that I have to get home right away. I don’t care what excuse you make up, I just gotta get the heck out of here.”
Initially I thought he was kidding until 2 minutes later the guy who was serving him came up to me to tell me how wicked this woman was and how he could tell the guy didn’t wanna be there. I promptly called that guy as soon as I had a free second.
One of my shining achievements as a server.
In case you’re wondering what I said on the phone, I told him my car broke down on the side of the road and I desperately needed a lift.
I never spoke to the nasty woman. Consensus from the server in charge of her table was she was extremely rude and very off-putting.”
Can’t Even Finish The Date Without Opening Tinder
“I served a couple a few months ago. Every time I walked over, he would always be the one talking, and she would just be sitting there, clearly not having a good time. At the end I asked if it was one bill or separate and she immediately piped up, “SEPARATE!” I go and take his payment, and as I hand over the debit machine to the girl, I see the guy take his phone out and start swiping through tinder.”
A Real Momma’s Boy
“Young teenager brings his girl on a date. They are young enough that they need his mom to bring them. His mom is cool and offers to go sit at the bar so they can have privacy. He tells her no. He then proceeds to talk only to his mom the whole time they were there.”
Being Obnoxious and Cheap Are Terrible Signs
“Couple is on a first date on Valentine’s Day. I was working at a fine dining Mexican spot in downtown Los Angeles. They come in, have a reservation, and sit down. I felt bad for the guy because he was just clueless as to how much of a jerk he looked like. His outfit just didn’t match and he looked messy. The young lady was a beautiful woman in her late twenties. I approach them and start to talk to both of them. He cuts me off to ask questions like, “What are the specials? Do you have anything special for Valentine’s Day? What’s good here?” It was clear he’d never been to a fine dining restaurant before but, hey, no big deal. I can help the guy, or so I thought.
I assure him we do have specials and I explain everything as I would to any table. I was good at what I did so these people just had to sit back and relax. I would make sure they enjoyed their meal. The woman is looking at me attentively and trying to get him to let me talk. Every dish had a question, and every ingredient had a question followed by “I’ve never had that. Have you? Is it good? Yuck.” I set them up with the pre-fixed Valentine’s menu and they were set for food. I’m walking by the table between courses and he’s just shooting down everything she’s saying. She went to college, he would talk about how school was dumb, she liked the squash in the appetizer, he would make comments about why we didn’t just use potatoes, she would compliment the ambiance (we had a classical guitar player), he would keep saying, “This place isn’t THAT nice.” (It was.)
So their meal is over and I thank them for coming in. She’s literally about to thank me and he says, “Hey boss, can we get the check? We’re gonna go have some real fun!” I wasn’t shocked but the look in her eyes screamed, “Oh God, I’m so sorry.” I drop off the bill and could see him a bit flustered when he looks at it. There were tiers to the prefixed meals and they got the lowest one and a single round of drinks so his bill was a little over a hundred dollars. Still really good deal for what they got. You can see the lady is trying to pay for some of the bill but he refuses. He gives me his card and I run it. I drop it off and she immediately thanks me profusely. He seems upset with me, I’m assuming over the bill, and says, “Yeah, thanks.” They pass me on their way out and he thanks me again, a bit more genuine this time, and the woman is beelining it for the door. He extends his hand to shake mine and when they meet I feel something in his palm. It was cash. This has only happened to me a couple of times but you close your fist, put it behind your back, and thank them again. I knew what was coming so I walk over to the table. I open the billfold and there’s a 0 on the tip line. I open up my hand and there’s an old, crumpled, folded $5 bill. I’m assuming he folded it up at the table, told her what he was going to do, and she was embarrassed so she left ASAP. I start to laugh, it’s not a big deal. I’m going to make up for it later and even if I don’t, it was a cool story. I start to tidy up the table and a $20 bill falls out of the lady’s napkin. I appreciated it but felt bad for her. I remember thinking, “Dude, you should have caught her when he was in the restroom, empathized with her, and asked her if she wanted to grab a drink after.” She was a really good-looking older lady, not older in general but I was 21 at the time. I doubt there was any fun had that night and that guy still probably tells the story of the stuck up snob that never called him again after he took her to a really fancy dinner.”
Still Being Married Makes It Hard To Date
“I served at Applebee’s. I get way into the whole making-it-a-fun-time for those who seem like they’d be into enjoying their time there. I could tell it was a first date because of how nervous each of them seemed to be. They were probably late 20s/early 30s. Also, the guy showed up before the girl and was on his phone… seemed nervous from the beginning. She got up to go to the bathroom at one point as all seemed well, so I took my chance to snoop. I asked if this was their first date. He happily replied, “Yeah.” And told me how they’d each driven about thirty miles to meet “halfway.” All is well.
Twenty minutes in, he stops me and asks for the check just a few minutes after getting their food. I jokingly asked, “Uh oh. What did you do?” Guess that was the perfect question. They get quiet for a second. I realize my mistake. He says, “Well… it would seem she is not as okay with the fact that I am married as I thought she would be…” Still trying to keep my composure, I’m curious, so I go deeper yet and ask, “Oh… well you’re at least on your way OUT of being married… right?” Even longer pause. He just laughed nervously and said, “I should probably just get my check now… sorry.” “
Swearing and Making A Scene
“I don’t know if it was a first date, but it was hopefully a last date. A week ago I had a couple come in, and the man (thugged out and in his late twenties) began cussing about everything on the menu. “Yo, why’d you pick this lame place?” “Everything on the menu is expensive as heck.” Now this was a mid-priced lunch restaurant. 90% of customers were locals and regulars of the senior variety, for the most part. So this dude continues to cuss and berate his girl, and she doesn’t say anything. I come over and take their order, while he refuses to get anything. She gets some chicken strips, and then he starts in on me about how this is a “snobby old white folk place.” At this point the regulars ARE noticing and being disturbed and one went to the owner to let him know what was going on. He came out, hands on his hips and said, “You have two choices – either stop the profanity and act civilized, or leave my establishment.” The man said, “I don’t gotta do anything, yo.” Meanwhile the girl is now quietly eating her chicken, not saying a word. So the owner goes and calls the cops, because now this guy is getting louder and ruder to his poor date. When the dude sees the cops roll up, he takes off, leaving the girl sitting at the table. Officers intercept him in the parking lot, and at the same time go and question the girl, asking if he’s ever hit her, if she feels safe, etc. Man, I felt so terrible for this girl.”