Since dinner dates are a staple of the dating scene, servers often get to see dates first hand, including the ones that don't go so well. Though they were undoubtably super uncomfortable and awkward to witness, these unfortunate dates do make for great stories.
You Know The Date’s Bad When The Staff Intervenes
“I worked at a restaurant in college and one time we had to hide a girl in the back of the restaurant from her date.
This girl was on a blind date and had let him pick her up, so she was stuck at his mercy. He brought home videos of his childhood and planned on taking her back to his parents’ house so that they could watch them. When he got up to go to the bathroom, she was freaked out enough by whatever this guy was doing that she asked her waitress for help. She came back into the kitchen and when her date got back, he stormed all around the restaurant looking for her. She called a ride and was able to go out the back door safely.”
They’d Been Fighting All Night, But No One Expected Him To Flip Out Like That
“During a shift once, another waiter had a table with a couple who slowly started getting louder. They just kept having mini outbursts, enough that people knew that there was a fight going on, but not enough that everyone was staring yet. Then, seemingly out of nowhere, shortly after receiving their food the dude flipped the table with food drinks and all onto her. He then walked out of the restaurant, leaving her covered in steak, baked potatoes, and margaritas. She just sat there in shock for a good minute before my manager went over to help her get cleaned up. He then comped their meal and she left with an incredibly embarrassed look on her face; felt immensely bad for her.”
When He Pulled Out The Ring, She Just Said Two Words
“I had man come in for dinner (I work in a four star restaurant) sweating bullets from the time he sat down. He and the lady were obviously a couple and the entire staff guessed what would happen, especially after he ordered a $300 bottle of champagne to start the meal. She looked happy, but worried through the entire meal. When the dessert came, he got down on one knee and I heard her say, ‘Please don’t.’
Those two words stopped MY heart, I cannot imagine what this poor dude was going through. They had a hushed conversation and she ran out, literally ran, while he sat there, still holding an open ring box. He finished the bottle of wine they had ordered during dinner, and pretty wasted, turned to me and asked, ‘Why won’t she let me love her?’ Just like that. Like I was going to give him some kind of answer to explain the complex and painful thing that has just happened. I told him that sometimes we fall in love with the wrong people, and the only people worth anyone’s time are the ones who give back what they get. He finished the bottle, paid his tab and walked slowly to the parking garage. I never saw him again.”
Her Appetite And His Rudeness Weren’t Compatible
“I once waited on a first date where they had met online. It seemed to be going well, they had drinks and ordered their food. When I brought the food, they commented on the large portions (the place I worked was an American style diner/cocktail bar in London, so fair point).
When I came back for their plates, the guy commented that his date ate a lot. I kinda laughed and said something about the food being really good, so I’m not surprised. He goes ‘No, like, this girl [pointing] barely chewed. She inhaled her meal. And some of mine HAHAHA!’ At that point, the girl looked rather annoyed, but still had a polite smile on her face.
I went to check on them a while later and the guy seemed completely oblivious to the fact that his date didn’t like his sense of humor. He ordered himself a beer and commented that while his date seemed to loooove food, she’s not much of a drinker. At that point, the girl looked like she wanted to stab the guy. She told me they’re about ready for the bill. Guy went, ‘Are you really not going to have any pudding? Are you suuuure?’
As they left, I heard the girl tell him that he didn’t have to walk her to her train and he looked utterly confused.”
The Worst Way To Deliver The News
“Last year, a man came into my restaurant around 4 pm alone and asked to have a dinner ‘arranged.’ My manager chose me to be the waitress for this special dinner. The man explained to me that he would be meeting a woman for dinner later that evening, but would not be staying long. He told me he would be excusing himself to the restroom, but not returning. He also instructed me to give her a thickly stuffed white envelope in his absence. Furthermore, I was to inform the woman a cab will be waiting outside.
I agreed to do this charade for the man, but I should have requested a tip up front. While waiting for the couple to arrive, all the waitstaff speculated on what would happen. We tried to read through the envelope but to no avail. They arrived. She seemed happy, he seemed stiff. They ordered one round of strong drinks before he rushed off to the ‘bathroom.’ After he was gone, I checked outside for the cab. Sure enough, there was not only just a cab but what must have been this lady’s every physical possession crammed inside. Crap, here goes nothing.
I approached the woman as calm and compassionately as possible. I handed her the envelope, mentioned the cab, and told her if she needed ANYTHING, I was happy to help. There were a thousand emotions flashing through her eyes before I could run away from the table. I continued watching her discreetly. As she opened the envelope and pulled out some paperwork, I realized I had just served her divorce papers. That, and a huge wad of hundreds. After she had emptied the content of the envelope, she shoved all the money in her purse and stormed for the front door. No one had paid for the drinks.
I quickly told my manager that the bill was not paid and I hadn’t the heart to ask her for the money. My manager, being the callous fellow that he was, had no qualms. He proceeded to stop the obviously distraught woman and collect the check. This is when her tears finally started. She was hurt and embarrassed at this point. I worked at a large restaurant and everyone was looking at her, whispering about her.
When she got a few feet from the huge, clear glass front doors, she finally saw the cab with all her stuff jammed in the back, including an adorable chocolate lab dog. This lady lost it. Dropped to her knees and sobbed. It’s not long before she was back on her feet and FURIOUS. ‘How could you all do this to someone?!? What am I going to do now?’ She knocked over a display case, the host’s podium, and dumped a container of root beer barrels all over the place, before finally storming out the door. I guess we know why the dude didn’t want to stick around for the show.”
The Date Felt Off From The Very Beginning
“I work in a sports bar/burger joint. Last week a woman came in and wanted to sit on the patio, which was odd on account of it still being in the high 90s. She sat down and ordered a Long Island iced tea and a water while she waited on one more person. A few minutes later, her significant other showed up and immediately complained it was too hot and wanted to move inside. They picked themselves out a booth and, as he was ordering a beer, the woman slipped me a $20. I brought his beer over and she asked me to take a picture of them and handed me her phone. I noticed her phone was set to video, not picture, so I asked if she wanted me to change it. ‘Just hit the button,’ she said. Once the filming started, she stood up, yelled, ‘Don’t you ever come to my house or talk to me again!’ as she threw both her drinks in his surprised face. I handed her the phone and she walked out the door.”
The Date Soured Before It Even Began
“I once saw a date go straight to hell before it even started.
Guy came into the bar at lunch time, ordered a beer for himself and a glass of wine ‘for my girl, she’s on the way.’ The guy was in his mid-thirties, but he was giddy as a schoolgirl waiting for his girlfriend. Then, all of the sudden, I noticed he had a look of fear and dread smacked all over his face. So I asked him if everything was ok, and he responded, ‘My girlfriend is gonna be here any minute and my wife’s best friend just sat down over there in the dining room.'”
Things Were Going Well, Until They Started Talking About Their Families
“I was waitressing at a sushi place, and it was late and these two people came in, a male and a female who were obviously very intoxicated. They had just met at a club and decided to leave and go get food together because they were so stricken with each other. Well, he’s pulling me to the side, telling me he already knows he’s gonna marry this woman. She’s holding his hand and they’re just smiling and it’s REALLY cute.
Well, I go into the kitchen to grab a plate for another table and by the time I come out, she’s slumped over crying, and he’s just got his head in his hands like he’s made a huge mistake.
She drunkenly stumbles out the door and he picks up the tab and as he’s paying he looks at me and says, ‘We were talking about our families. We were planning to introduce each other to them, but my brother is the one who killed her father,’ and just walks away.”
This Last Woman Broke Him
“Every two weeks, like clockwork, this sleazy guy would frequent the Mexican joint that my brother worked at and he would have a different girl (half his age) with him every time. You probably know the type of guy he was, somewhat wealthy, divorced, totally full of himself dude in his 40’s. He would keep the cheap margaritas flowing in hopes of bringing home these girls as his latest conquest and, if the girl wasn’t responding, he wouldn’t hesitate to hit on the the female staff any chance he got. Since my brother was one of the few dudes on staff, he ended up on ‘creeper duty’ and would often be the one waiting on this guy and his dates.
Well, eventually, my brother noticed he was bringing the same woman in for a few consecutive visits. He seemed to mellow out a little and actually seemed to really be into this new woman.
Then one night, it all hit the fan. My brother was bringing out their drinks when he noticed they seemed to be having an argument. The night got worse and eventually, the woman got up mid enchilada, went out for a smoke, made some calls and waited out front until someone came and picked her up.
Sleaze guy spent the next half hour sitting in front of his plate of tacos, desperately on the phone, looking progressively more depressed. As my brother was collecting the money for the meal, the guy said something along the lines of, ‘Don’t even bother with women, kid. They’ll just break you.’ That was the last time they saw him.”
The Milk Guy Was Super Weird
“I was working for a little mom and pop type Italian restaurant, and it was going to close in about 30 minutes, so I was the only server left in the shop. This couple ambles on in, heading straight for the back room, and right away I can tell that something is weird. The guy is asking me to turn down the lights to make it more ‘romantic,’ and when I take their drink orders, she orders a glass of wine and he orders a glass of milk. I had been there for about 5 months, and we had milk for people to put in their coffee if they asked for it, but I had never had a single customer, child or adult, ask me for a glass of milk. I bring them out their drinks and take their orders, and when I return to bring them their dinner salads, the guy asked for another glass of milk. It’s not exactly important to the story, but it was one of the clues to why he was so weird. Anyway, I bring him his milk and eventually bring out their entrees. The guy was going on and on about how he wanted this to be romantic because they hadn’t seen each other in ages, and how he works at Hooters and this place is way more romantic, blah blah blah, so I leave them alone, although in the back of my mind I was REALLY hoping they weren’t going to have sex in the restaurant.
So I’m in the front room rolling silverware when suddenly I hear glass shattering and the woman storms out. I ran back to the room to see the guy standing their looking pissed, but whatever, now I have to clean up the wine glass that got smashed. He proceeds to tell me that he thought everything was going really well, but when he told her what he had been up to in the past few years, she yelled, ‘I don’t wanna know who you’ve slept with!’ threw the glass on the ground, and ran out. To be fair, as a lady, this is not something I would really care to hear, either. I finish cleaning up the broken glass and tell the guy his total (it was around $40), and watch him throw cash on the table including my $2 tip (seriously, 5% after all of the trouble you’ve caused) and THEN he goes, ‘Hey, you seem like a cool chick and you’re pretty. You wanna go out sometime? I’m Justin, the drummer from Sevendust.’
You just told me that you work at HOOTERS.
You left me a 5% tip.
You just bombed this date and I watched.
The drummer for Sevendust is Morgan Rose.
‘Um, no thanks.’
Their Engagement Party Was Going Well, Until Another Party Showed Up
“My friend, who is a general manager at a very fancy steakhouse in New York City, told me this story. One Friday evening, there were two reservations. One for a family dinner celebrating an engagement and another reservation for an office promotion celebration. The first party arrived, and it’s husband and wife-to-be with their family and few friends. They popped multiple champagne bottles, were having a great time.
20 minutes later, the second group, the one that’s celebrating someone’s promotion, came in. The lady who was promoted immediately noticed the engagement party and stormed over. She started slapping the guy on the face over and over again.
Apparently, the guy ‘came out’ and broke up with the promoted lady a few weeks prior. But in reality, she was the mistress and he was getting married to his original girlfriend, the one he was celebrating the engagement with.”
Her Surprise Didn’t Turn Out The Way She Thought It Would
“Years ago, I worked at a Chinese restaurant and waited on a couple, probably in their early 20s. It was a busy night and they seemed like they were enjoying being there together, but nothing stood out to me until the woman found me and asked me to do her a favor. She was smiling, said she was pregnant and wanted me to switch out the paper in his fortune cookie for one that she had pre-printed, which said something to the effect of him being a soon-to-be-dad.
Well, the rest of the waitstaff found out when they saw me trying to do this without breaking the cookie. All the waitresses were giddy and thought it was so cute. I dropped off the check with the two fortune cookies. We all inconspicuously watched with bated breath as she gave him the cookie and saw his face instantly turn sour. He looked ticked. That’s when I couldn’t watch anymore. They had a very brief, lively looking conversation. When I picked up the check, it was very uncomfortable and they were quiet. She gave me a sad look. He stormed out first and she followed. I still think about them and wonder if it turned out alright.”
She Had No Idea She Was Part Of A Scam
“There was a super hot chick and a pretty good looking guy. They ordered tons of drinks, several appetizers, two steak dinners, a lobster, and then dessert. At this point, the guy excused himself to go to the bathroom. The dessert showed up and the girl waited for him to come back from the bathroom. Ten minutes went by and she asked one of the busboys to check the restroom. The guy had bailed on her and left the check for her, which all of that was about $150. She started crying, it was awful. The girl did pay part of the tab, I don’t remember how much exactly, but most of the waitstaff tossed in to cover the bill and one of the waitresses gave her a ride home. The guy was banned from the place and we got to toss him out 2 times trying to come back with other dates.”
Their Match Definitely Wasn’t Made In Heaven
“I used to work at a high end restaurant where dinner for two could easily cost over $100. One Sunday night, a upper-middle class couple come in, the woman reminded me of Dennis and Dee’s mom from It’s Always Sunny In PA, very snooty and articulate. The guy though was completely disheveled, in dirty clothes, unshaven, like he completely let himself go.
From what I got from their bickering was that the guy was having an affair with someone half his age. The entire time, they were hurling insults and barbs at each other and anytime I was there, they would use me as a middleman to insult the other one. The guy would things to me like, ‘She’s a total witch isn’t she? You wouldn’t put up with her crap, would you?’
Or the woman would say to me, ‘The waiter thinks I’m attractive, you’d have sex with me, right?’
This went on through the entire course of the meal. The highlight was near the end of the meal, the guy was texting his new lover and the woman snatched the phone from across the table and snapped his flip phone in half, then the guy stormed off into the bathroom.
Up until this point, this whole event was terribly awkward, weird, and uncomfortably almost funny, then she was left alone at the table. Once the guy was gone, she had a moment where she couldn’t hide her feelings anymore and was crying alone at the table. She saved face when the guy came back from the bathroom, but at that point, I genuinely felt sad for her.”
“She Got This Sassy Look On Her Face And Asked, ‘Is That A Problem?'”
“I used to waitress at this Thai restaurant and we were a date hotspot. One night, this guy and gal come in (mid 30s) and sit down at a booth on the same side. Cute. I come over, take their orders. Throughout the night, they’re completely flirty and it’s clear this was only their second, maybe third date from the questions they’re asking each other. Anyway, towards the end of their meal, I heard him say in a much louder voice than he had been using all night, ‘What do you mean you’re waiting till marriage?!’ He took his arm from around the girl as he said it.
She got this sassy look on her face that was just priceless and said, ‘Is that a problem?’ He literally spent the rest of the night trying to convince her in this pleading/informative tone why having sex before getting married is normal and healthy. She would have none of it. They ended up paying separately and left through different doors.”
Pro-Tip: Don’t Be A Jerk To Waiters While On A Date
“I was waiting on a couple once, had to be a first date. The guy was constantly a jerk to me, and the girl was very apologetic. He asked for a well done filet mignon and when I started to advise him that it would be burnt as such and to ask if he’d like it butterflied instead, he flipped all the way out, yelling ‘You don’t tell me how I like my steak!’
She got up, pulled out a $20, handed it to me, and walked out without a word. He shouted after her to come back, didn’t even get up until she was out the front door though. What a douchenozzle.”
Phone Etiquette Is Important On Dates
“I don’t wait tables anymore, but I still work in a restaurant and have a good view of the dining room most of the time. I saw a teenage couple come in on what I assume was their first date one night and the girl would NOT speak to the guy. She was attached to her cell phone the whole time. He just looked so bored. When they paid out, he had a look like he’d been deflated, and she was on her phone. I felt really bad for him, poor kid.”