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.
A good looking dude, fit, clear shaven, kind of looked like Jim Cantori from the weather channel but younger and slimmer, was sitting at the bar and going on about how he had a date with this girl that his best friend was crushing on hard. That his friend just refused to ask her out because she was into him instead. He was really getting into his story when she walks in and he clams up like someone shocked him.
She was by anyone standards drop dead good looking and killing it in a little black dress and high heels. It was really that rip the record kind of moment. She comes up to him, does a little kiss-hug greeting and orders a tequila shot with a lime. He does one with her and they banter about getting that out of the way. Suddenly, out of the blue, this dude whistles at me. I was honestly shocked as the bar is pretty empty. He whistles at me again while I am looking at him trying to figure out if he really just whistled at me like I am a pet dog. “yo man, more shots!”.
Disappointed, as he really kind of seemed like a nice guy, I go to pour him a shot and let him know I am not a dog he doesn’t need to whistle to get a drink. “Sure sure man..no worries just keep and eye out we’re gonna get lit! Yo!”.
I retire to the side bar real quick and one of the other guys working that night starts to talk to him while the girl goes to ladies room. When she gets back he whistles at the other bartender again and shouts “Hey man! Where are my shots! Pronto!”. This guy starts hammering shots. Pretty quickly he is though at least five while the girl only did one and is now sitting there sipping at her Wine.
The dude, we will now call “YO!” starts to get a bit sideways. Nothing big, just loud, laughing at his own jokes, talking over the girl every chance he gets. He then announces that he has to piss on a rock and walks to the back. The girl looks mortified and sad. She is texting away like a mad man. Then I hear him in the back raising some cane and out he comes with a dude under his arm.
They sit down and he starts talking to a different girl at the bar. He is not really piss drunk, but well on his way. He says something out loud to the other girl about gay people and walks outside. His friend follows quickly after and the girl is left at the bar alone.
Five minuets later the friend walks in, sits down, has a drink with the girl. I hear him say that he put him in a uber and sent him home. They walk to go to the place the other dude had reservations for them at. I honestly thought hell ya, good for you dude.
About 30 minutes later “YO” boy walks back in – sober as the day one is born! Sits down, waves me over and apologizes for whistling at me. Give us 20 bucks and buys us a shift drink for when we get off. I was off at this point and sat down to have mine with him. He lets me in on his game.
He did it all for his friend. Got half drunk, played the fools 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 super impressed and was in awe the whole time.
They all came in, the trio of them, about a month later looked all buddy buddy. That “Yo” guy whistled at me again – I admit it was funny.
I work at a fairly nice Italian restaurant which does a lot of business. One night a man who I was not even serving came up to me while I was punching an order on the computer. He 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. Tell me that I have to get home right away. I don’t care what excuse you make up, I just gotta get the myself out of here.”
I thought he was kidding until 2 minutes later the guy who was serving him came up to me to tell how wicked the woman sitting with him 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 never talked to the wicked woman. But from what the server in charge of her table said, she was just overly rude and off-putting.
One of my shining achievements as a server.
It was my first job as waiter.
An attractive young woman and an average-looking man walk in. The guy was wearing plaid sleep pants and an oversized red zip-up Columbia. The woman was better dressed, but it was still casual. All goes well until its time for entres.
This guy orders a ton of ribs (a few full racks) and refuses the girl her original order – a house sirloin, which was only about $6 – less than a fifth of this guy’s order. Then the man orders a four dollar salad and a water for her. The woman stops talking completely while the man talks about some crazy party he went to. The man guzzles a few Strawberry Quencher Iced teas, says “Seeya Friday.” and leaves her with the bill.
She said the guy seemed nice when they talked on Tinder, but it was very uncomfortable with him in real life. She felt afraid to say something. A co-worker and I paid for her meal, and later she and my same co-worker started dating. They are engaged now!
I used to work as a barman in a restaurant bar in Hertfordshire.
So this guy at the bar tells me how he’s meeting his date for the first time, and that she’s also bringing her parents – some arrange marriage tradition he says.
Anyway, I’m chatting with him as he’s waiting for the girl and her family to arrive. After about 10 minutes or so they do arrive and are all seated on a table near the bar.
I notice throughout the evening how much he’s seemingly making the family laugh and seems to be getting along really well.
Now, the fun begins.
After dessert the mother and father of the girl go to the beer garden outside, leaving the couple alone. A moment later 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 was going.
He returns back to his table and takes his seat. The girl’s parents now return from the garden with a glowing smile and rejoin the table.
I notice again how they all appear to be chatting and laughing until, suddenly, the girl’s father picks up the paid 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!’ This is a small country pub/restaurant, the shout definitely grabbed attention of everyone present.
The man then sheepishly exclaims his apologies to the father, in the deadly silent restaurant, to which he replies ‘YOU WILL NEVER SEE MY DAUGHTER AGAIN!’
Following this the father picks up his coat and turns to leave while 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 where she now bursts into tears. The man was clearly overwhelmed with embarrassment and shock. He did not know what to do, or how to react so proceeded to pat her on top of her head.
After around half an hour of her crying she eventually stops and decides to call a taxi to go home explaining how she was really sorry, and should now return to her family.
The man, clearly downtrodden at this point, reluctantly agreed and called a cab for her.
Now. Fast forward about 3 hours to when I finish my shift (around 1am) I leave the pub and walk to my car in the parking lot. At this point I notice a dark figure sat on a bench near my car. With apprehension rising, I try to decipher the person who’s now almost in front of me. Only when I am around 10m away do I notice it’s the man from the date.
He was balling his eyes out. Turns out his date was now locked out of her house for the night as her parents were clearly distraught with her, and when the parents had left they had slashed the poor guy’s tyres so he couldn’t even drive home!
Talk about a date gone wrong. Turns out this was all because he didn’t let them pay the bill by paying in advance.
Continue reading on the next page.
It was 2014 or so, around like 7:30 on a weeknight.
A middle-aged man of sub average attractiveness was sitting alone at a table with a glass of water, insisting that his date would be there any moment “just a few minutes, she must be in traffic”.
At around 9:15 our manager had to come out and let him know that the restaurant would close at 10, and if he’d like to place a food order he should probably do it now. He ordered a bruschetta appetizer and again said his date was on her way and they’d order when she got there.
At 9:45, this BEAUTIFUL woman walks in and awkwardly stands by his table.
The man didn’t say anything, took another bite, then asked for a box for the appetizer and left without her even sitting down.
Once I 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. Every time she tried to get a word in he’d cut her off. Absolutely brutal.
Worst part – Apparently the guy was thinking the date is going really well.
I am not a waiter. But my first date with a girl my brother’s girlfriend set me up with might count. The waiter was awesome.
My brother’s GF set me on a blind date with her friend who is, in her words, “totally into heavy guys.” So I go to pick her up and my alarms go off. While she’s not a 9 she is definitely what most would consider out of my league. I tried to talk to her on the ride, at most I get noncommittal grunts of words in response.
We get to a steakhouse that’s noted in my area for being nice but not super expensive, and get our table. We order our food. I try to talk to her while we wait. Simple things. If she’s from around here, got any hobbies, etc etc. She just taps on her phone and gives me small two word answers for the most part.
Food shows up, she picks up her plate and heads to a whole other table. Tells me her friends showed up. I, apparently, was not invited. Meanwhile, she’s sitting at this other table with a good bit of expensive food. I blink for a bit, then call the waiter over and explain to him what’s up. I want separate checks. He agrees. I go ahead and pay for my food.
She begins ordering drinks. Not just for her, but all of her friends. I just finish what I can of my food. About an hour later she comes back over and says she’s ready to go. I wave the waiter down and tell him she’s ready to go. He brings her a check for well over $100. She just smiles, looks at me and pushes it towards me explaining I was paying. I push it back and tell her I’m not, as I get up and keep smiling at her.
“I’ve had a lovely time tonight. I hope you have good luck in paying your tab and finding a ride home that doesn’t involve a police cruiser.”
Brother’s girlfriend began blowing my phone up an hour later about how could I do that to her friend. I shut her down real fast.
So whoever that waiter was, he’s the man. Keep the $20 tip.
Continue reading on the next page.
I was a waiter at a country club that is up to its ears in old money. The membership fees cost more than a year’s fee at my university.
Anyway, I was serving a young couple and the power imbalance was phenomenal. The girl was the daughter of one of the board members and the entire staff knew her father’s club account was big money. And the guy, 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 smooth, nothing out of the ordinary. Until she gets up and leaves the table before I bring 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–2 bottles of top shelf wine, neither finished–two steaks, when he asked for the chicken and she insisted on him eating steak “like a man”). The guy solemnly goes to pull out his wallet and starts tearing up, apologizing he won’t be able to tip. 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. He said she left because he told her about his scholarship. I was flabbergasted.
I 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 was getting the 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 satisfying. Last I heard the girl’s father cut her off, I can’t help but smile at all the life lessons she must be learning.
I own a bakery, I see a lot of ugly first coffee dates and weird people in general, but there’s one that will always be the worst for me.
This happened at my bakery about six months into our first year. Two boys come in, chatting normally, clearly on their first date. They’re both young, maybe 16 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 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 it was (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?
She then tells him that if he keeps up with this, he shouldn’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 happened.
I was waiter at a bar and steak place and this woman I’ll be talking about was the worst woman I’ve ever waited.
While the guy was really silent and compost, the girl was really needy. She slurped down her iced tea like there was a world wide shortage. He didn’t talk once except to order his quesadilla burger, and she just kept prattling.
On top of that she was mean too, I heard her talk down about servers. She said how people were losers to be servers, and how much better it was to work in a shop like hers.
At the end the guy 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 twenty to give to me.
The woman was just sitting there and waiting for him to come back. I stood there at the servers station, waiting for her to realize he wasn’t coming back. So after ten minutes she just started crying, pushed her chair over and dashed out. I didn’t get a tip, but it made my night.
I was working at a fine dining Mexican spot in down town Los Angeles, and a couple is on their first date on Valentine’s Day. They come in, get a reservation and sit down. I felt bad for the guy because he was just clueless as to how much of a douche he looked like. His outfit just didn’t match and he looked kinda 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 a special. I was good at what I did so these people just had to sit back and relax and 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, actually, every ingredient had a question followed by a ‘I’ve never had that, have you, is it good? Ewwwww’. I set them up with the pre-fixed Valentine’s menu and soon they were set for food. I’m walking by the table to set up between courses and he’s just shooting down everything she’s saying. She said she went to college, and he would talk about how school was dumb. She said she liked the squash in the appetizer, and he would make comments about why we didn’t just use potatoes. She compliment the ambiance (we had a classical guitar player), and he just kept saying ‘this place isn’t THAT nice’.
The meal’s over and I thank them for coming in. She’s literally about to thank me back and he cuts ‘hey boss can we get the check? We’re gonna go have some real fun now!’ I wasn’t shocked but the look on her eyes screamed ‘IM SO SORRY’. I drop off the bill. 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 a really good deal for what they got. The lady was tries to pay 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, the woman rushes to 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. 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 check book 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 ladies napkin. I appreciated it but feet 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’.
I doubt there was any fun they had that night and hope that guy still tells the story of the stuck up women who never called him back after he took her to a really fancy dinner.
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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 little rough for his mouth. 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 3 hour period and the poor girl stuck out for the whole thing. She looked miserable though. I’m pretty sure they never saw each other again.
I have been waiting only for one year now, and this one has been the funniest couple conversation I’ve on.
This was an obvious first date – The guy pulled chair for the girl, ordered some wine and some salad, the girl was all smiling and giving those flirty looks. Fifteen- twenty minutes into the date, after ordering some steak, the lady asked him, “So how much do you make out of that business?”
“Enough,” he said. I exchanged a funny smile with him, a smirk that said “You dodged that bullet well mate.”
When I came back with the steak the lady was still grilling the guy on how much money he makes. It was awkward serving steak during such in depth interrogation.
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 was definitely a first date, they were asking those “getting to know each other” questions.
After ordering food the woman had to go to the toilet, which was downstairs. The food arrived. She said she’ll be back in a minute, got up and walked to the stairs. As she stepped on the stairs, she 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, who already had started eating, and told him his partner fell down the stairs and that she was unconscious and 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 them to the hospital. He said no while finishing her food as well. It was so awkward. He just sat there for another 45 minutes – ate, drank, paid the bill and left.
I still don’t know what kind of relationship they had and whether the woman is okay. His reaction seems so funny now.
Continue reading on the next page.
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, to which he said, “Yes, why not. You can never tell who’s who.”
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 5 or 6 LITs and several shots, he literally just had 2 pints. He was paying throughout, for everything.
My favourite part was when guy excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. There was only one official entrance and exit. The girl went searching for him and straight up thought he had disappeared using his black magic.
I have seen everything from crying to drinks been being thrown at face. The only obvious first date that really confused me is as follows.
Above average looking guy sits down and says he is waiting on his blind date to show up. I tell him I’ll keep my fingers crossed.
The girl shows up half hour late and she is, well, not attractive. She was probably 120 pounds heavier than what he could have looked for and her face looked more mature than his.
I got an “oh well” look from the guy when she was in the bathroom. He didn’t say anything to me though, just had his dinner. Every time I refilled their glasses, there was intense conversation with both people smiling. At the end of the meal he paid the whole tab and tipped me well.
After they said their goodbye I went to chat with the guy. I had finished all my tables and wanted to know if he was seriously ok with being set up with someone so obviously not in his dating demographic.
I asked how was his meal and date, and then asked if there would be a second date. He laughed and said not likely. I told him that’s what I thought but they seemed to be having a good time.
He told me the best thing I’ve heard from a guy in a long time, “that girl probably hasn’t been on three dates where the guy actually paid and was genuinely nice. Why wouldn’t I be a gentleman? My friends are disgraceful, but she did nothing wrong and deserves to be treated like a beauty every now and then.”
Never forgetting that one.
I definitely have seen a lot of awkward first and last dates.
I used to work at a very small neighbourhood restaurant. Everyone that came in was a regular. Most were couples in their 40’s-50’s out for a quiet dinner, but there was this one man, also a regular here, who stood-out.
A VERY handsome man in his early 30’s would come in, it seems, only to break up with women. About twice a month he would come in with a beautiful woman. Partway through their meal she would be crying. I always tried to clean the tables near them for as long as possible but I never heard much of his speech.
He always tipped well and was super nice to me and my coworkers, it was just brutal seeing him bring in a new lady every two weeks and knowing what she was about to go through.
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I served coffee at fairs on random occasions as a young teen.
A 22-ish year old from another fair booth came over and asked if she could trade fruit roll-ups for coffee. I said thanks for the offer but no.
She proceeded to ask every day of the fair and get rejected. On the last day of the fair, this dude comes over and tells me how rude I’ve been to his girlfriend and demands 12 coffees in exchange for fruit roll ups! I say no, of course, and then his girlfriend appears throwing a tantrum about how this is “the worst first date ever”. What?
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 shouldn’t have.
She shows up. An absolutely beautiful women, way out of his league. She orders a drink and they start talking. I come to check on them and I think he should slow his drinking down to keep his mouth from working faster than his brain. he is talking about how much he hates children. He was saying things like how he hopes he never has any, and that he could never be stuck taking care of them, and how he wishes that kids shouldn’t be allowed 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.” Then she grabbed her purse and walked out on him.
The look on his almost recovering to sence face was absolutely priceless.
I was working at a Mexican restaurant at the time.
While serving this nice middle age couple I heard some of the questions they were asking each other. I could tell it was their first date.
I think everything was going good until towards the end of their meal until this happened. There was a Hispanic girl sweeping next to the couple’s table. Suddenly the woman looks at her, holds out her plate with remains on it and says, “would you like to take this home to feed your kids?” I stood there in complete shock. The sweeper woman spoke no English, but she could tell this random woman was completely degrading her. The sad part is the women seemed like she really thought she was doing a good deed here. Her date felt embarrassed, paid and left.
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