A fun activity, for waiters and waitresses, to do to pass the time, is to eavesdrop on couples that appear to be on dates. But sometimes, they hear things that just make for a crazy story to later tell their co-workers and friends.
When Mom Joins You For Your First Date
“I have two stories:
Story 1: One was at this candlelit, white table cloth restaurant. These two older teenagers come in on what looks to be the first date, and his mom walks them in and takes pictures of them at the table. Really awkward. Then the mom leaves and they proceed to have a really smiling/nervous meal together. Fast forward 45 minutes or so, and dude man didn’t have enough money to pay. So we wait on mom, who comes and picks up the tab. The poor girl never lost her nervous smile, but pretty sure she was mortified.”
The Regular At The Bar Broke The News To Her
“So during the summer months, all these dudes come to town to do construction. Well, they come to where I work because it’s the only decent place to eat in my town.
This guy starts hitting on our busser. She’s 17 so we’re a little weirded out but whatever. He gets her number and pretty much stalks her. But there’s a catch he has a girlfriend from back home. The busser ignores him so eventually he just leaves her alone. Out of nowhere, this guy brings in said girlfriend. Everyone at work is just kind of like, ‘what the?’ But here’s the kicker, a regular from the bar is hammered and tells the girl that the guy hits on girls while he’s away. So she gets all upset. And tries to leave. But she can’t because she’s in a town she has no idea around. So he makes her sit through a freaking meal with him.
I could literally feel the anger radiate off of this poor girl until they left. He never came back. But I did get 10 dollars.”
Waiting On The Ex He Wasn’t Over…And She’s On A Date
“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 restaurant 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.”
Leaves A Date Early To Hit On The Waitress
“A girl sits down at my table in the bar and is waiting for her first tinder date. They have a couple drinks and she leaves. I think everything is normal… UNTIL… The dude then hands me his card and says, ‘You’re prettier. Call me.’ And proceeds to head into a meeting in the dining room.
To make matters worse, she calls the restaurant 10 minutes later to ask me if he really had a meeting to go to or if he was blowing her off. …suuuuuper awkward.”
Scary To Think Someone Can Act That Possessive
“It’s been years since I’ve waited tables but I remember this one couple. The guy was very possessive over the girl. Every time I tried to ask her anything he would interrupt and speak for her. I don’t know if it was for my benefit or hers but she obviously wasn’t impressed. She kept giving me this kind of embarrassed/apologetic look.
Well, I felt really bad for her so just a few minutes after I delivered their entrees I returned with a glass of wine and told her it had been sent by a gentlemen from the bar. I’ll never forget the dude’s expression: kind of furious but ultimately defeated. He never really spoke again and I, of course, didn’t get a tip. He kept craning his neck around though; surveying the dudes positioned around the bar. I wasn’t really worried about that because this dude was a shrimp compared to the guys around the bar. Thinking back now, I don’t really think it was as clever as I did then.
Sure, the guy was a total jerk but I didn’t know him and I could’ve easily sparked something that would set him off later. Scary to think about but the girl seemed delighted with the glass of wine. She thanked me and she drank it. Maybe it sparked something in her; like the realization that there were better people out there. Who knows?”
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Do NOT Propose In Front Of Your Coworkers At A Restaurant If You’re Not Pretty Sure Of Her Answer
“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 terrible his night had been.”
She Nearly Stood Him Up…But She Was In The Restaurant All Along
“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.
A 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.”
The Valentine’s Day Date-Ditching Mystery
“First time I was ever a waitress was at this fancy restaurant. You know, folded napkins, two glasses on the table, two forks, all that smush.
Valentine’s Day, this couple somehow decided that the 14th would be a great time for a first date.
Appetizers roll around, they’re chatting about what they do for a living, which was the dead giveaway that they were just getting to know each other. I deliver their main course and these two bozos are pretty much on their phones until dessert.
Man gets up to go to the bathroom, takes his jacket. Woman pays for the meal, which I overheard them discussing beforehand anyway because she didn’t want to take advantage of him and was a bit of a nontraditional gal, from what I caught eavesdropping from my other tables. I noticed her leave on my smoke break cause I didn’t see anyone get in the car with her, which was confirmed when I saw the guy back in the restaurant at his table asking for the check.
They leave in separate cars.
Guy comes back, I thought he had left he was gone for a REALLY long time, and sits down at the table on his phone. Eventually, realizes that the lady’s coat isn’t there and leaves too. Cringed when he asked for the bill and I had to tell him it was already paid for and that the lady wasn’t in the bathroom.
Then he left with his head down, leading me to think they both thought they ditched each other.
Whether they had done this intentionally or unintentionally or had changed their minds halfway, that’s the real mystery.”
Don’t Keep Ordering If You, Or Especially Your SO Can’t Pay
“Worked at a breakfast diner.
A couple came in. I remember almost exactly what they ordered: she had oatmeal and a fresh fruit cup, and he had banana french toast, three eggs, sausage, bacon, hashbrowns, and toast. She got a mimosa, too, and he just had coffee.
Every time I went to check on them, he ordered something else. More bacon, more hashbrowns, etc. The average bill for two people at this restaurant was between $15 and $20.
This dude racked up a $40 bill.
The time came to drop it off, and I went back and he said he forgot his wallet, so she put her card down. I went to the card machine and it got declined. I returned to the table and told her it had been declined. She called her bank and I assume they said ‘tough,’ so then she said she would call her mom for money to be deposited.
The call got heated so she stepped outside. I could see her pacing and crying out front. She came back in tears and said something to the dude. Then she left. I went over and said that he could run home and get his wallet. He looked at me and sighed irritably as if I had inconvenienced him.
Then he reached in his back pocket, threw down some cash, and left. It was a really small town, so this was the topic of discussion for a while with our regular customers.”
Don’t Ever Get To The Point Past Belligerent On A Date
“Oh man, so I actually knew the girl this happened too and she was my table.
She arrived with a guy I knew who has a bad rep of being drunk and just a bad person. Right in front of his date (who is super hot) he tells the host that she doesn’t know him, but he follows her on Instagram. When I’m taking their order, he tells me that he ‘pregamed’ the date at a buddy’s house. Orders a bottle of pinot and tells my friend its only for himself, laughing.
My restaurant has exquisite food, he insults half of it.
He tells my friend that he is a sous chef at a restaurant 200 miles north in a big city and is only in town to visit his parents. This is all untrue, I know that he is a busboy at a local restaurant.
On his second glass of wine, he becomes belligerent, yelling and insulting the girl, when she says she may not go to a bar with him after dinner. He tried to order another bottle of wine but I cut him off.
She ended up paying the whole tab and walking out.”
Snappy Woman Ain’t So Sweet
“Alright, so I had a small table in my section made for 2 people. I had the Hostess sit a young lady at the table by herself. She was early twenties, blonde, pretty black dress, cute heels, etc. I walk over to greet her and in the process of saying ‘Hey my nam- ‘ ‘Water.’ ‘Okay, I’ll go ge-‘ ‘I have a guy meeting me here too.’ ‘Okay Ma’am, no problem!’
So I bring her water to her and she tells me she doesn’t want to have to wait for him and orders a lobster by herself.
Her food comes out about 15 minutes later. Still no guy there. Once she’s about halfway done with her lobster, the guy comes in.
She says she’s upset he didn’t show up early for their date. I can only assume he was on time, and she was 20 mins early.
I go talk to him and he was the sweetest guy. Like gives boots to homeless people kinda sweet. Very handsome as well.
So he orders some food while she’s arms deep in her plate horking down her lobster. I kept overhearing little bits of their conversation while waiting on nearby tables. All I can hear is him trying to be sweet and her just cutting him off, showering him with small bits of crustacean. I felt so bad for the guy.
His food comes out and she’s already done with her food. So she sits there playing on her phone while he tries to talk to her. She keeps responding with small little ‘fine’ ‘K’ ‘not really’ kind of answers. He asked me for a box and asked her if she wanted a desert. She says she wants a slice of cake for herself tonight.
So I go in the back and get it for her to-go. He quietly pays and walks out with his head down, while she’s on her phone. He just seemed like the sweetest guy. I don’t know why she could act like that to someone so sweet.”
The PDA Couple Had To Be Asked To Come Up For Air
“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 decide she’ll eat.’ It’s really annoying because he’ll just cut me off mid sentence and tell his girlfriend 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 freaking food.
PDA is gross.”
The Rich Guy Who Hired His Date
‘Mr. Dudebro’, a very wealthy, very roided-up, American guy in his late 30’s early 40’s who apparently had zero friends decided the only option was to hire an escort to join him for dinner.
When he arrived, the valets were all chatting about who would get to drive the vintage white and gold trim Rolls-Royce that he arrived in. Complete with convertible top and red leather interior.
This is a very expensive restaurant/resort with a reputation for fine dining and romantic views.
When I greeted the table ‘Mr. Dudebro’ was very gruff and barked orders sitting down in his white suit and mostly ignoring his date. When I asked what she might like to drink, as she started to answer ‘Mr. Dudebro’ cut her off and said she’d have champagne. I detected her Russian accent and started to ask her about her entree in what little Russian I knew. This made her smile and light up for the first time, probably, all night.
When she began to answer, he shouted at her, ‘You’re not here to talk!’, and that beautiful smile went away. ‘She’ll have a salad,’ ‘Mr. Dudebro’ barked. I shrugged and put in their orders for her salad and his marrow toast and bolognese.
The rest of the meal either involved total silence, or ‘Mr. Dudebro’ yelling for his escort to do things, like smile more and sit up straight. Now, sadly ‘Mr. Dudebro’ had ruined his appetite after all the verbal abuse he was putting out and Dbol he was taking in so he asked for his leftover bolognese be put in a box to go, which I provided. Sadly, I can’t say our to-go boxes are the best, but it’s possible someone may not have secured this one closed as well as they could have….
The next day ‘Mr. Dudebro’ returned by himself to complain that the bolognese and sauce had spilled all over his red leather backseat and his white coat causing thousands of dollars in damage. Luckily my FOH manager was wise to what happened and had been made aware of ‘Mr. Dudebro’ who was immediately informed he would be receiving no compensation for the damage and he was welcome back when his behavior and treatment of his guests was appropriate for the establishment. And ‘Mr. Dudebro’ rode off into the sunset, in his white car that was probably worth more than I made in several years pay, completely alone and classless. But I’m sure he’s still out there… somewhere… being
And ‘Mr. Dudebro’ rode off into the sunset, in his white car that was probably worth more than I made in several years pay, completely alone and classless. But I’m sure he’s still out there…somewhere…being a jerk…”
The Sweet Guy With Good Intentions Gets Tossed A Rejection, And A Bill He Can’t Pay
“I had a middle-aged gentleman come into the restaurant. This place is fine dining, white chairs and tablecloths and silver service. He was trying, but was noticeably out of place and uncomfortable. He was extremely awkward, kind of chubby and not at all attractive and spoke with a lisp. But he was super sweet and friendly.
His date walked in and I knew right away this was an internet or blind date.
She sat at the table and just about immediately turned her nose up at him. She ordered a very expensive bottle of wine, and I saw him do the mental panic thing a lot of our less financially well off customers do when they see the prices on our menu.
I served the bottle, feeling pretty bad for the guy at this point because man, he was giving this date his all and she was seriously acting like he wasn’t there.
Then before the apps came out she went to use the restroom and never came back.
He sat there alone for over an hour and finally asked for the check. He handed me three different cards and asked to split it between them and let me know if any one of them declined. I talked to my manager and explained what I witnessed and she agreed to discount everything down to cost (so he ended up paying only about 30% of the bill).
The poor guy started bawling when I brought the check back to him and spilled the entire story. Apparently, this lady was a friend of a friend he had been attracted to for a long time and when their mutual friend set up the date he really wanted to impress her by taking her to the nicest place in town but didn’t realize how expensive we were.
Then the girl saddled him with the cost of one of our most expensive bottles of wine and ran out. I felt so bad for the poor guy. I mean, I understand that the date obviously wasn’t what she expected. But that was a terribly awful thing she did.
Because of the nature of that restaurant, I’ve got tons of great hilarious awkward date stories (prom season was always full of great times!), but this one actually angered me, quite a bit.”
The Manipulative Girl With The High-Pitched ‘Fake’ Voice
“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 bread so 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 stop saying the word naughty. I could tell he was just pushing through because she was wicked hot and apparently a ‘naughty girl,’ but gosh there is a point where the whole ‘high’ pitched fake ‘I’m a naughty girl’ gets so annoying.”
He Couldn’t Even Put Down The Phone For His Wife
“Kind of middle-aged married couple that came for lunch on the patio.
The guy starts talking on his phone the second he sits down. It sounded like he was talking business for work on a Saturday afternoon, and he didn’t hang up the entire time it took for the food to come out (at least 30 minutes). The wife was just sitting there quietly waiting for him to come sit.
When I brought their entrees out I was so relieved to see him with the phone hung up, but not 30 seconds later he’s back at it, and he kept finishing and starting new calls all through lunch, dessert and paying the cheque. I don’t think I heard the wife say a single word the entire meal.
The worst part was that the patio is overlooking a scenic lake, and he would not sit down, just kept wandering around close to the railing and talking. I know the manager got a few complaints from other patrons. Felt terrible for the wife, looked like she was used to it, and he made a comment about how much he liked spoiling her while paying the cheque.
Still talking on the phone as they walked out of the restaurant. On top of all that, he would snap his fingers at me if he needed something.”
Faking An Allergy To Get Out Of A Bill
“I work at a nice- but not fancy- restaurant. A lot of people dress California casual.
A young couple comes in one night, and the gentleman is dressed in slacks and a button-down. Pretty quiet, but seemed like a nice guy. The young lady dressed how I would imagine a promiscuous woman would dress for a funeral — ridiculously low top straining against her ample bosoms, fishnet stockings, short skirt. She was a beefy girl wrapped up in a small black dress like a plump sausage. It looked pretty indecent, but I try not to judge.
She ordered a salad and asked if there were peanuts in it. A red flag went up. I told her no and asked if she had a nut allergy because the salad did have walnuts. She insisted that she was only allergic to peanuts and that she wanted the walnuts. I told her I would just put the walnuts on the side just in case.
Well, of course, the kitchen forgot to put the walnuts on the side, and someone ran the plate before I could correct it. I check on them, and the girl is claiming she’s having an allergic reaction in between stilted, heaving breaths.
She points a vengeful finger at me, ‘You hid peanuts underneath all the greens!’ I assured her that the only nuts in the salad were walnuts. We didn’t even have peanuts in the building.
She said she would try to struggle through the rest of dinner, but each time I checked on them she became more and more histrionic. ‘I thought I was only allergic to peanuts, but I guess I’m allergic to cashews too.’ Tears are streaming down her puffy cheeks. She insists I look at the rash developing on her arm. It was decorated in thin streaks of red, slightly raised, as if she had been scratching it with her fingernails.
The bill comes. I had comped her salad just to make her happy, but they still had to pay for two flat iron steaks and their drinks. Her voice becomes comically pinched as she claims her throat is closing up. She tells me that she has to go to the hospital right this minute, and she can’t stay to pay the bill.
She also expresses a disinterest in paying for it, lamenting over and over again, ‘It was supposed to be a special night. Now it’s ruined. I didn’t know I was allergic to almonds.'”
Double-Date Turns Into Possible Domestic Danger At Bennigans
“Many years ago I was a 16-year-old hostess at Bennigans. Two couples came in for a what looks to be a double date. It’s a quiet night and they’re seated near me, so I people watch a bit while taking care of other things. The guys sat across from each other on the inside, the ladies on the outer edge in the bar booths. The bar booths at our location were elevated around 8 inches, so there was a step up into the booth making it quite high.
The men loudly drank and smoked and talked while the ladies talked fairly quietly, one seeming to work hard to pry the other into talking a bit.
After the appetizers and just before their entree quiet lady comes out of her shell a bit.
She says something and nudges her date in the ribs a bit chuckling. Everyone is smiling for a brief moment before her date turns red in the face, stands up, backhands her out of the booth, and starts dragging her out of the restaurant by her hair while screaming curses at her. She’s crying and begging for him to let go, apologizing the whole way out.
A lot of us were frozen in place – then everyone’s moving. Servers were running out of the restaurant and I’m on the phone with the police.
He throws his date into his SUV and the other couple gets in the same car quickly. Dude hauls out, nearly running over a server as he backs out. We gave the vehicle description and plates to the police – it was obviously a dine and dash on top of him beating up on his wife/girlfriend. I never heard if anything came of it.
This was nearly 15 years ago and I still think about her, I wonder if she’s ok and ever got away from him. I hope she did.”
The Boy Has Got Some Bieber Fever Going On
“Former waiter here. There was this one date that comes to mind… at first, it seemed like it was going ok but then I noticed the girl was starting to look uncomfortable. I decided to pay more attention to their conversation and the guy was talking about how he likes to use moisturizing lotions and hair volumizing spray and if she ever stays over at his place he’s got her covered for hair products.
Then he started talking about how he thinks Justin Bieber gets a lot of undeserved hate and how talented Bieber is. This guy tried to hold her hands across the table and she withdrew hers immediately.
I could tell she just wanted to leave asap and this dude could too. Then he brought up how rich his dad is and how his dad buys him anything he wants. Then he starts bragging about how he always gets what he wants and she’s just cringing the whole time. I wasn’t able to catch what happened next but later I saw her storming out of the restaurant with this dude just skulking about at his table.