Some dates can be awkward for everyone, but more so for the server that watches the events unfold from start to finish. These servers are here to share the most awkward dates they've unfortunately had to witness. Keep in mind stories were edited for clarity.
"I saw a Tinder date. The guy kept ordering for the girl. Poo, like that is weird anyway, but when you are legitimately having dinner with a stranger, why the heck would you think that's OK?
He ordered her drink, which she corrected to a glass of red. Then, he ordered her some soup, which she stated she didn't want. Then he ordered her meal (shrimp scampi), which she corrected to chicken marsala because she is allergic to shellfish.
She was very sweet and, I assume, was trying to give him the benefit of the doubt, until something took a turn and she poured her drink on his head and stormed out.
The one good thing about him though: he tipped the heck out of me - almost 60% on an already expensive meal.
I would kill to find out what he said to make this seemingly sweet girl pour Cabernet all over him."
"I used to bartend and serve at a pub back in the day. One evening, a guy came in and sat down at a table for two. I asked him if he wanted a drink. He ordered a drink and told me that he was waiting for a girl he was meeting for a date before ordering food.
He waited for a bit and I served him a couple drinks. An hour passed. He was looking at his phone occasionally and drinking. He finally came up to the bar after an hour and a half and told me that he thought he had been stood up.
He ordered a couple of drinks - neat - and pounded them back. He started to look and sound considerably worse for wear at this point. He ordered a couple more drinks and I told him to wait a bit. He convinced me to get them for him by saying he was going to drink them and leave. He downed the drink and got up to leave.
Who should walk in the door as he's turning to go? His date.
She was still wearing scrubs and looked pretty disheveled. She apologized up one side and down the other for being late.
I then got to serve one of the most awkward dates ever. He was inebriated. Like, I probably shouldn't have given him that last drink inebriated. They made some small talk and it was terribly awkward. Then, he got up and went to the bathroom.
Twenty minutes went by and he didn't come back. Finally, one of the male servers walked up and told her that her date was having some trouble in the bathroom. He was sitting on the toilet bawling.
We asked her to get him out of there. We called him a cab and she pretty much shoved him into it and ran."
"I was managing a restaurant at the time and had a lady in her mid-40's come in dressed pretty nicely. She was not an ugly woman by any means, but she wasn't overly attractive either. She was super excited to be going on a blind date and showed up early. She sat, had a glass of red, and chatted up my bartenders, servers, and myself.
We all really liked this woman. She was super sweet and friendly and seemed to really be trying to have a nice time.
Then, her date showed up.
He came in about a half an hour late talking on the phone. He sat next to the woman but continued talking. Finally, he got off the phone and went over to the bar to get a drink (which is also strange since my server would have done that for him), proceeded to order a drink from the bar, drank it, ordered another drink, and then sat back down. The woman tried to have a conversation with him, but he was constantly looking around the room like he was trying to see anything better for him to be doing.
Finally, when my waitress took their order, he asked for his food to go. When his food came out, he grabbed it, got up, and left it. He tried to say something to me about how the woman was not attractive and he had to get out of there, trying to convince me to agree with him. I just eye-rolled him and walked away.
The woman started crying and my entire female staff was over at the table trying to talk to her. I was going to, basically, let her hang out there all night and get whatever she wanted on the house, but she was too upset and left shortly after. That guy was such a turd and she was such a sweetheart. It really angered me how he treated her."
"I work at an ice cream parlor. A couple of years ago, a couple came in, seemingly on their first, or at least one of their first, date. They looked kind of nervous around each other but seemed to go well together.
They looked over the menu before finally deciding what they wanted to order. As they stood at the register, the girl took out her wallet to get ready to order her own. The guy insisted that he would pay and they spent a minute or two going back and forth over this while I waited for them to order. They came to an agreement that he would pay. Thank goodness. It's always awkward standing there while people argue over this and both shove their credit cards at you and expect you to choose who is responsible for the bill.
After they ordered, I went to get their sundaes, rang them up, and, once this guy saw the total (which was probably about $10 or less), he awkwardly stood there for a minute and said to me, 'Can we do them separate?' He then turned to the girl and said, 'You still wanted to pay for your own right?'
She looked at him kind of like The heck?, and slowly got her wallet back out of her bag that she had put away WHEN HE DECIDED HE WOULD PAY.
'Yeah, sure,' she said. 'That's fine...'
They sat in mostly silence for about 15 minutes. She clearly was no longer interested. I didn't know who to feel bad for.
I'm all for splitting the bill. I would never expect a dude to pay for me just because I'm a woman, but after the few minutes they spent debating and he insisted before instantly changing his mind because his date was not worth $5, that was an awkward one, especially because that couple and I were the only people in the shop the whole time."
"The following is the most awkward start of a date I've ever seen:
A dude came up to the bar looking all nervous. I asked him what was up and he told me he was on his first date after a long term relationship had gone south, but he had never seen the girl before. I told him, 'Cool. First drink on the house. Have a seat and we'll wait for her to show up. I've got your back, buddy.'
Some time passed. He had another drink and, suddenly, a girl walked in who matched the description she had given him. He looked to her, to me, back to her, then to my beverage selection, and said, 'Make me a double shot, quick... please.'
I poured it. He downed it. They didn't have a good time."
"I once was a server at a very upscale French restaurant in New York City. One evening, a middle-aged man and a young woman sat in my section, clearly on a date. I could tell this woman was his mistress by the way they interacted with each other. They were high maintenance, but pleasant enough. Right after they had received their entrees, the man looked across the way to another table and lost all the color in his face. His date noticed and turned to see what he was looking at.
The man's wife was at another table, also on a date with her side piece, on the other side of the restaurant. The wife saw him and had the same expression on her face, which very quickly turned to rage.
She briskly walked over to his table and started whisper-yelling at him, pointing her finger right in his face. He started to do the same back at her. This was not a very big restaurant. Therefore, everyone knew what was going on and the atmosphere got icy. The man's date was just staring at her plate, absolutely mortified. The wife's date pretended nothing was happening and continued eating.
Eventually, the wife stormed back over to her table and wolfed down her dinner (no exaggeration. She was practically rage eating). The man sat down and his mistress would not speak to him for the rest of the meal. This was a fine dining restaurant and they ordered multiple courses. Having to clear, crumb, and reset their table two more times was less than fun. He left a very big tip and apologized on the way out."
"We had a middle-aged lady come in with a gentleman. They asked for three menus. I went over to the table to introduce myself and asked if they were waiting for one more. The woman said, 'No, my husband is here.' Then, the two who were physically at the table ordered drinks and a water.
When I came back to drop off the drinks, her 'date' was in the bathroom. The lady explained to me that her husband had died a few years ago and this guy (a friend) kept asking to go out. She said yes, but insisted her DEAD HUSBAND come with them. This is why they had three menus. She instructed me to bring her husband up as often as possible, pretend that I knew him, and make sure that I ask if he's having anything for dinner when I took their dinner order. She would refer to him just as if he was sitting right there. I then heard her tell this guy all night that he tried too hard and he's kind of mean.
I do not miss working in the restaurant industry."
"To preface this story, I work in a restaurant where we make our own ketchup and some people just don't like it. Fine. Whatever. If you're nice, I'll bring you the secret Heinz ketchup as long as you don't tell anyone.
Anyway, a woman was seated at my table looking super excited and told me that she was on a blind date. She ordered a glass of red and waited anxiously. How cute right?
This dude showed up on his phone, ignored my hostess, and eventually found this beautiful woman waiting for him. He continued to talk on his phone for about 15 minutes. When he finally hung up, I went to the table. He tried to order for her, which obviously embarrassed her. For himself, he ordered a well done steak and fries. When I brought it to him he asked for A1 and 'REAL' ketchup. When I informed him that we had neither, he grunted and said he had ketchup packets in his truck.
As soon as he walked out the door, she asked for her half of the check and her food to-go. I helped her leave out the side door before he came back. It was awkward serving him after that. He used seven ketchup packets.
I get that not everyone loves our ketchup and people eat overcooked meat, but this dude was a SUPER turd. He still tipped 20%. I didn't see that coming."
"I worked at a nice Italian restaurant a couple of years ago. One night, a couple came in and specifically asked to sit in my section. I had no idea who they were, but the host said they looked at me and asked to sit there because they 'vibe with me.'
I started taking their order and talked with them. They were acting very odd, being over-the-top friendly, super touchy-feely with each other, and just kind of moving all weird.
Finally, they told me that tonight was their date night, so they decided to take a psychedelic and come get steak and pasta. I don't really know why they wanted to to do it, but they were nice enough. When they were leaving, they tried to get my number to 'hang out' later."
"I walked into work at 5 pm one evening. The only people in the bar were a couple on a date. A fellow bartender walked out of the restroom shaking his head in disbelief and shock. He immediately started pointing to the guy on the date and told me what happened.
I walked into the men's restroom and before my precious eyes laid a Havana omelet (feces) on the floor and poop smeared all over the restroom wall like a freaking mosaic. I was so livid and dry heaving at this point that a waitress asked if she could say something to the gentleman. I said, 'Sure.'
She walked up to the table and asked the guy if he pooped himself and if he needed a doctor. The woman on the date then turned around to look at the waitress in complete confusion and asked what the waitress said. The waitress then replied, 'He knows what I'm talking about. He pooped all over the men's room.'
The woman shoved her plate and drink into the guy's lap and said, 'Really, Vince? Again!?'
He ran out before we could make him clean it."
"The date I saw started out kind of OK. It was a little awkward, as first dates usually are, but they both decided at the end of the date that they were not a good match. The woman said she would pay for her own meal. The man declined and said that he had every intention of paying since she humored him and gave him a chance. I thought, Aw, that is sweet even if they didn't work out.
The woman thanked the man and left in an Uber as I grabbed the check.
The man's card declined.
The man had to call the woman to ask her to pay the entire bill because he didn't have any money. The woman came back about 10 minutes later, but the man was hiding in the bathroom so he would not have to look her in the eye.
It was sad because the woman wasn't even mad, but she seemed peeved that he hid instead of thanking her."
"I worked at a semi casual restaurant and we would have a decent amount of blind dates. One night, a gentleman arrived for his reservation. I sat him at Table 8. Then, a lady showed up 'looking for her friend.' I asked her if it was the gentleman at Table 8. She thanked me and sat down with him. They start hitting it off great! They ordered drinks, appetizers, the whole thing.
THEN, another guy came in. He said he was waiting for his friend and stood in the lobby texting on his phone. Eventually, we caught on that he was also on a blind date, and that he was supposed to be with the girl at Table 8!
The girl eventually came up after getting a text from him, apologized, and then sat down with BOTH guys to enjoy the apps. But, eventually, she suggested that her date was with the second guy and that the first guy should head out. It turned out the first guy was stood up on his blind date. It was such a mess, and the first guy was royally ticked that he was being kicked away."
"I got to witness a Tinder date.
The guy showed up first and explained to me what was going on. He ordered his drink, sat down, and patiently waited for her. She showed up 40 minutes late. She was already hammered and a hot sloppy mess.
Very soon into their date, she lost interest and started going around and hitting on other guys at the bar, sitting on their laps, and paying no attention to her date.
The last straw was when she lost one of her shoes, walked around without it, and yelled through the bar for someone to buy her a shot. I promptly cut her off, but I'm sure other people had already been buying her shots. I split their bill - I wasn't going to make him pay for hers - and gave the woman her part of the check. She tried to tell me the other guy was paying for it, and I told her, 'No, absolutely not.'
After some fuss from her, the bouncer came over and told her that if she didn't pay her check and leave, we'd have to call the police and send her to detox. She paid for her tab and found some other man to take her home.
I ended up buying that guy most of his drinks for the night because I felt bad for him. He seemed really excited about the date. It was definitely one of the more awkward dates I've seen, as he just sat quietly and politely at the bar while she grinded on other men."
"I had a table at which the girl showed up first, and then the man. She was super quiet and so was he, until at about 30 minutes, in he started screaming at her and she went to the bathroom.
My table next to them were shocked. After they said nothing to him at all, he said, 'What the heck are you looking at? You think I'm going to beat her? I'm not going to freaking beat her!'
They had obviously broken up during the meal. I told two off-duty bouncers what was happening and they found the girl as she was leaving the bathroom and said they'd walk her home, not to worry about the tab, etc. She left with them and the guy said nothing about the event. Nothing. He asked for their check, left me almost 100% tip, and left.
Then, the girls at the next table spoke up about it to me. They were young college girls, so I had to explain to them that if they ever saw this sort of thing going on or if it was happening to them they should let their server or another server know discreetly and we would make sure they would get a ride or walk home. They were totally shocked that restaurant staff would do that for them. I hope they told their friends they could use that, too."
"I used to be the head waiter (or Maitre'd) of a high-end restaurant. We had a three-month waiting list average and served mostly A-List celebrities and royalty.
We had a fellow come in to discuss some special requirements for a table he wanted to book for the following Saturday night. He said that his girlfriend thought that this would be a normal date, but he intended to propose. He pre-selected two bottles of Dom Perignon rosé from '85 and '92, which were their birth years. He handed me the engagement ring for it to be given to them at dessert with 'Will you marry me' written in white chocolate on the plate under a silver cloche.
When the evening came, the gentleman arrived early to double check if all was OK and waited at the table for her. The lady arrived with a strikingly beautiful dress, jewels and hair. She was excited and surprised at the bubbly in a silver ice bucket at the table.
The lady proceeded to neck her glass and the next glass. When the sommelier didn't top her off, she took her bottle out and drank half of it before they chose their courses. She said that she wanted to ensure that she ate something expensive and that her boyfriend was allowed to have a salad and whatever she didn't eat for her main course. She insisted she wanted the beverages that we kept off the books and then asked me to recommend the most expensive ones to match her food, all while the gentleman quietly looked at the floor.
Once the food was ordered, she continued to neck the rest of her bottle of bubbly and then his glass and bottle. We stopped serving either of them, due to how smashed she was getting, and packaged their bottles to take with them when they would leave.
After the main courses were cleared, I presented them both with the dessert menu. I tried to catch the gentleman's eye and quietly asked him if he would still like to go through with the proposal. She screamed at me, saying that whatever I wanted say to her boyfriend, I could say to both of them, as she doesn't allow secrets between them. I diverted to the menu, asking for preferences. The man just gave me a little nod and took the dessert order.
One of my waiters served the desserts while I carried the plate with the writing and ring box in the middle under the cloche. The waiter cleared some space for the plate. The lady began shouting at me, saying she didn't order anything else and she wouldn't be paying for it and ordered us to take it away.
The gentleman lifted the cloche to show the writing and the ring. The lady started to tear up and took the ring put it on herself before tucking into her dessert.
The gentleman got up to go to the restroom. He pulled me to one side and said he wanted to go pay right away. We settled the bill and he walked off toward the exit.
When the lady finished her dessert, she got up and walked into the men's restroom and started screaming for the man and shouting at another guest in there, 'Where is my fiance?!' She ran out shouting MINE and her fiance's name. Then, she went into the kitchen and into the pastry section, shouting that she had lost her fiance and couldn't find him. She began interrogating the chef, who barely spoke English, asking where he was. She, hysterical and wasted, was ushered out of the kitchen and into the restaurant reception to take her coat and get a cab to where she needed to go. We eventually got her on her way with the bottles.
One of the hostesses beckoned me from behind the counter to show me, behind the curtain in the coat room, the gentlemen curled up in a ball, sobbing away under a rack of coats. We got him booked into a hotel nearby."
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