Some dates are just destined to go bad from the moment they begin. Servers have seen so many people come into their establishments on first dates, they can almost smell it when things start to sour. These are the worst, most horrific first dates servers have ever seen and there is no embarrassing, despicable detail left unshared.
His Casual Bigotry Did Not Make A Good Impression
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“He made a comment to her about how he’s ‘not Jewy,’ so she should order whatever she wanted. One of the only times she spoke was to respond that she was Jewish. She spent the rest of the evening in silence as he went on about how his ex-girlfriend was anorexic and ‘so annoying about food.’ He was happy to be on a date with a woman who could eat like a normal person. So weird.”
Why Would She Think That Was An Okay Thing To Say?
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“I was working at a Mexican restaurant at the time. I was waiting on a couple and I could tell it was a first date by the questions I heard them asking each other. Anyway, towards the end of their meal, there was this Hispanic girl sweeping next to their table. The woman looks at her, holds out the remains on her plate and says, ‘Would you like to take this home to feed your kids?’ I stood there in complete shock. The girl spoke no English, but she could tell this random woman was completely degrading her. The sad thing is, the woman seemed like she really thought she was doing a good deed. Her date looked so embarrassed.”
They Thought Things Couldn’t Get Worse After She Fell, But They Were Wrong
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“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 had a first date because they were asking those ‘getting to know each other’ questions.
After ordering food, the woman had to go to the toilet, which is downstairs. As she walked to the stairs, the food arrived. She walked down, tripped and fell all the way down, 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 to the man while he already started eating and told him his partner (didn’t know how to call her) fell down the stairs, 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 her to the hospital and he said, ‘No,’ while finishing her food as well. It was so awkward. He just sat there for another 45 minutes eating and drinking before paying the bill and leaving. I still don’t know what kind of relationship they had and whether the woman is okay.”
When The Date Got Bad, He Just Got Out
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“I worked at Applebee’s. This woman was the worst woman I’ve ever waited on. She was needy and slurped down her iced tea like there was a worldwide shortage. He was silent. He didn’t talk once except to order his quesadilla burger, and she just kept going on and on, just prattling. And she was mean too! Talking down about how people were losers to be servers, and how much better it was to work in a shop.
At the end, he went to the bathroom and just never came back. He apparently jetted out the side door where the to-go girls worked and gave them a $20 bill to give to me. The woman was just sitting there and waiting for him to come back. I stood there at the servers station just waiting for her to realize he wasn’t coming back.
So after 10 minutes, she just started crying, pushes her chair over, and flounced out. I didn’t get a tip, but it made my night.”
He Seemed Like A Great Guy…Until He Whistled For The Bartender
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“I have been a bartender and a waiter over the years and have witnessed a couple of really sad ones, a couple crazy ones, and one that was just brutal. This one was the best of them all, I thought.
Good looking dude, fit, clean shaven, kind of looked like Jim Cantore from the weather channel but younger and slimmer. He was sitting at the bar going on about how he had a date with this girl that his best friend was crushing on hard and that his friend just refused to ask her out because she was into him instead. He was really getting into his story when she walked in and he clammed up like someone shocked him. She was by anyone standards drop-dead gorgeous and killing it in a little black dress and high heels. It was really that rip the record kind of moment.
Anyway, she came up and they did the little kissy huggy greeting and she ordered a drink. He had one with her and they bantered about getting that out of the way and moved into a little more intense banter. Out of the blue, this dude whistled at me. I was shocked, honestly, as the bar was pretty empty. He whistled at me again while I am looking at him trying to figure out if he really just whistled at me like a freaking dog. ‘Yo man, more drinks!’
I was disappointed, as he really kind of seemed like a nice guy. I went to pour him another and let him know I am not a dog, he does not need to whistle to get a drink. ‘Sure, sure man, no worries. Just keep an eye out we are gonna get lit yo!’
I retired to the sidebar and one of the other guys working that night started talking to him while the girl goes to the ladies room. When she got back, he whistled at the other bartender again and shouted, ‘Hey man! Where are my drinks? Pronto!’ This guy started just throwing them back. Not crazy, but pretty flipping quick. He got through at least five. The girl only did the one and is sitting there sipping from her glass.
The dude, who we will now call ‘YO,’ started to get a bit sideways. Nothing big, just loud, laughing at his own jokes, talking over the girl every chance he gets. He then announced that he has to take a leak on a rock and walked to the back. The girl looked mortified and sad. She was texting away like a madman. Then I heard him in the back raising cane and out he came with a dude under his arm. They sat down and he started talking to a different girl at the bar. He’s not too far gone, but well on his way. Then he said something out loud to the other girl about homosexuals and walked outside. His friend followed quickly after and the girl was left at the bar alone.
Five minutes later, the friend walked in, sat down, and had a drink with the girl. I heard him say that he put YO in an Uber and sent him home. They decide to walk to the restaurant YO had made reservations for them at. I honestly thought heck yeah, good for you dude.
About 30 minutes later, YO walked back in, sober as the day he was born! He sat down, waved me over, and apologized for whistling at me. Gave us $20 and bought us a shift drink for when we get off. I was off at this point and sat down to have mine with him. He let me in on his game.
He did it all for his friend. Drank too much, played the fool, and called him to come save the day. He honestly said, ‘He is a better man for her than me. She is really just not my type.’ I was stuck between awe and impressed.
They all came in about a month later, looking all buddy buddy, the three of them. That jerk whistled at me again, but I admit it was funny.”
It Only Took 20 Minutes For This Date To Go Sour
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“I used to be a server 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 this was the first date because of how nervous each of them seemed to be. They were probably in their late 20’s or early 30’s. Also, the guy showed up before the girl and was on his phone and seemed nervous for that too. She got up to go to the bathroom at one point and, as all seemed well, I took my chance to snoop. I asked if this was their first date. He happily replied, ‘Yeah!’ He told me how they’d each driven about 30 miles to meet ‘halfway.’ All is well.
Twenty minutes in, he stopped me and asked 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 got quiet for a second and I realized my mistake. He said, ‘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 was curious, so I went deeper yet and asked, ‘Oh, well you’re at least on your way OUT of being married, right?’
Even longer pause, followed by nervous laughter, ‘I should probably just get my check now, sorry.’ Jerk.”
He Got Stood Up, But That’s No Excuse For What He Did Next
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“A guy got stood up. He then drank quite a bit and ate three appetizers out of depression. His date called him and he started cussing her out. He asked for more drinks and then I had to cut him off. So he got up and tried to run out of the restaurant with a bottle he grabbed from a rack. An off-duty cop tackled him in the lobby and then he crapped his pants in front of everyone waiting for a table. He laid there, screaming, with the guy holding him down until the cops arrived and arrested him.
This is my fondest memory of being a bartender at Olive Garden.”
She Should Have Gotten Out WAY Before Things Got To That Point
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“A couple comes in, approximately in their late 40’s or early 50’s. The gentleman (term used loosely) proceeds to tell me they are here on an ‘internet date’ and he didn’t realize his date was going be ‘a big, black woman.’ Needless to say, this was going to be my most awkward table all night. Why the lady (not a term used loosely) didn’t leave immediately, I will never know.
They proceeded to order dinner and the guy makes her order a steak, cooked the way he wanted it, and a drink. He also orders a steak and a drink. He leaves for the restroom as I’m dropping off their drinks and she asks me if I could please call her daughter to pick her up. I give the number to my manager to make the call.
As I bring the salads and place them down, she explains to him that she doesn’t think the date is going well so she has called her daughter to pick her up. He tells her she better treat him right when they leave because he’s buying her steak for dinner. She proceeds to throw her drink in his face. He pulls out a big knife and threatens to stab her and I have to restrain him across the table while the cops are called. Obviously, several other staff (and regular patrons) come to my aid until the police come in and arrest this guy.
The woman’s daughter came to pick her up. My co-workers and I bought her and her daughter dinner to-go.
This is why I have not tried online dating.”
Little Miss Country Club Thought She Was Too Good For Her Date
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“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 (read: 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 have brought out the bill.
I bring the bill to the counter (knowing it is well over $300 worth of food and drinks, all things SHE insisted on ordering: two bottles of the nicest stuff, neither finished, and two steaks, when he asked for the chicken and she insisted on him eating steak ‘like a man’) and 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 further explained 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 or 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 working to go on dates.”
It Took Him HOW LONG To Eat?!
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“I work in an Italian restaurant. A few years ago, I waited on a guy and girl who met for the first time upon arriving 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.”
No One Likes To Be Treated Like That On A Date, Lady!
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“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. She 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.
Then she 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 didn’t think he’d be this boring. She ordered about five or six drinks and he literally just had two drinks. She made him pay for everything.
My favorite part of this show 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. I straight up thought he had vanished out of the bar.”
Pro Tip: Don’t Get Wasted On First Dates
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“My bar has two floors, and on this night I was working upstairs. A couple came up with drinks they already had bought and sat in my section. I go to introduce myself and girl seems nice but the guy says nothing, just stares at his drink.
They eventually get another round, and as I’m dropping off their drinks, I hear the guy slur out, ‘Chank youuu vurry mush.’ Crap. He’s wasted. It was just a 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 he’s in bad shape. I thought to myself, ‘Shoot, 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, but 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 trash 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 race around looking for his date. I find her at the bar trying to pay her tab. I tap her on her shoulder and try to tell her about her date, but when she turns around, her face tells me everything. The shame and embarrassment that glaze over her might make one think she was the one who just tossed her cookies. That’s when she tells 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 overhear her. We pay her tab. She ends up staying at the bar hanging out for a while as the aforementioned regular bought her more drinks. Real nice lady.”
He Really Put His Foot In His Mouth With That One
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“I once had a guy come sit at my bar while he was waiting for his blind date. He ordered 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. Anywho, she showed up and was way out of his league. She was absolutely beautiful. She ordered a drink and they started talking. I came back to check on them and I heard him talking about how much he hates children. He was saying things like how he hopes he never has any, and that he will never 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 Date Was Going Well, And The Whole Restaurant Could See Just HOW Well
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“I work at a Japanese restaurant and one couple comes to mind. It was the ‘worst’ for everyone else involved. We offered ‘private’ rooms that have sliding doors, and this couple clearly was hitting off very well…to the point that after a few drinks, she had moved to his side of the table and they just went at each other’s faces and bodies for about two hours. They could have done all that with the doors closed and it would have been less cringy, but still cringy nonetheless. But no, the sliding doors were wide open for all the patrons to see. Kids, big groups of people, waitstaff, runners, etc.
If I remember correctly, they tipped pretty bad too, so it was not a fun time.”
His Persistence Got Them On The Date, But Couldn’t Keep Them There
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“I used to work at a little crappy diner place, definitely not the type of place to bring a first date. There was this guy who’d come in every Friday with a different girl. He was a very good looking dude, was always super polite and very nice to me, but he was super awkward. The girls would look kind of skeptical as they walked in (probably because of the crappy diner scene). Every week, about halfway through the meal, like clockwork, the girls would develop these ‘get me the heck outta here’ faces. That’s when I would bring the check. They always boxed up their food and left right away.
I had the chance to talk to one of them while he was in the restroom. Apparently, he wasn’t harmful, there was just something off about him that the girls didn’t like. His persistence is on point though.”
He Was So Desperate For An Escape, He Bribed The Staff
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“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 an order in 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 tell me that I have to get home right away. I don’t care what excuse you make up I just gotta get out of here.’
Initially, I thought he was kidding until two 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 minute.
I called him and told him my car broke down on the side of the road and needed a lift.
I never talked to the wicked woman. The consensus from the server in charge of her table was she was just overly rude and off-putting. One of my shining achievements as a server.”
