"Two couples were having a lovely dinner and suddenly one of the ladies screamed. Champagne glasses had been delivered to their table, one with a diamond ring in it. As you might have guessed the wrong couple got the ring and the look of horror on both the gentlemen's faces was quite a sight! I happened to be serving the other couple at the time and the only thing that sprung to mind was to drop my tray as distraction. It kinda worked as with the loud clatter all attention suddenly went to me and my colleague managed to quickly apologize for the mix up and rescue something of the situation. Still felt awful for the gents though!"
"Had this couple obviously on their first date and the poor guy was SO visibly nervous he was just sitting there with these wide 'deer in the head lights' eyes, profusely sweating (like drenched) and I think they exchanged a total of three words the whole date. When I took the guy's order his voice cracked making the situation that much worse. Poor guy, hope he's doing alright."
"First date. She's doing all of the talking, but it's ok, because he's totally into it. Every time she changes the subject, he's more infatuated with her. She likes football and guns and trucks, southern style, and he loves it. Then she starts going through the pictures on her phone.
When she finally got around to mention that the three kids in the pictures were hers, I swear I actually heard his junk deflate."
"I was serving a guy who was obviously being stood up, he had reserved in advanced and came in about 10 minutes early, he seems pretty calm but is constantly checking his watch and phone. After about 30 minutes he orders a large pizza, another 20 minutes pass and his pizza arrives and is placed in front of him, at this point I'm feeling really bad but have no idea what to do. He leaves the pizza untouched for about 15 minutes before finally having a couple slices, probably an hour and a half after he originally arrived he decides to leave, he's about to pack up his pizza when one of the other servers decides to take her break and chooses to sit with him.
I quit working there a couple months later but as far as I know they're still dating."
"Had a couple come to dine in, and they had the three-course meal and everything. The guy had mentioned to our host that he was proposing, arranged a bottle of champagne to be delivered to the table once dessert was ordered (that's when he was planning on proposing).
Dessert is ordered, looooong awkward silence at the table. She's tearing up, grabs her purse, apologizes and leaves. Thankfully, we had all been keeping an eye on them (we wanted to see a cute 'Yes!' moment), and the server didn't put through the order for the champagne. We all could see it was a rejection.
Ten minutes later, his parents arrive, and tell the host that they're excited to 'Meet their future daughter-in-law!'
I'll never forget that poor host's face as she led them over to his table. Him alone."
"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 percent tip too, which was nice considering how s--tty his night had been."
"I was not a server but a kitchen manager and head cook who was called to a table one night. It was one of those 'we want to meet the chef' things. I put on a new chef coat and go out to the farthest reaches of the dining room to where earlier in the night we all noticed that the people there had asked to have the lights turned down. As I'm going there one of my server friends says quietly 'buckle up for that.' I get to the table and greet a very well-dressed college kid, probably no older than 20, who is not drinking or eating and is sweating profusely while sitting straight up in his seat like a mannequin. Then I look at his date. She was probably in her 50's or 60's, painfully thin, tan sagging skin, too much neon pink lipstick circling busted up yellow-gray teeth, she's got an empty bottle of wine in front of her and a ton of hoop bracelets. She's grinning at the guy and in a split second I could tell she was using her feet to rub the guy's crotch under the table. I exchanged some pleasantries with them for a minute and the guy asks if he can see the kitchen real quick because he used to work at the same restaurant but in a different city. I say sure, we'll be right back, etc., and as soon as we're out of earshot he says that his friends had set him up on a blind date and that woman is obviously a prostitute. He was f--king terrified, like hostage situation terrified, so I told him I'll let him out the back door through the kitchen. I haven't seen anyone power walk to their car like that in my life and with that, he fled. Funny thing was that the lady he was with paid for both of their meals and left a large tip."
"I once served a blind date. She got up to go to the bathroom and he told me to guess how old she was - turns out about 10 years older than she looked. He wasn't thrilled about it. He told me he was thinking about bailing. Ended up sticking it out. They were the last table in the restaurant and when the busser started cleaning near them he threw a fit and acted like they were getting kicked out, but he probably just wanted an excuse to leave.
He tipped pretty well if I recall correctly."
"I was on the date, but I am a server, so technically it's still my best date gone wrong story. I was fresh out of college (22) and a long-term relationship (five years) and ended up moving to a new city for a fresh start. Went on a date with a cute guy from my new job (I know, rookie mistake) who told me within minutes of getting our drinks that he planned to be married and have at least one child in the next two years. I told him he'd better start looking, it didn't end well. I found out later it was the poor man's birthday."
"I had a couple that looked like something was up, having a long cocktail and dinner type date. I didn't think it was too extraordinary until the lady found me outside the restroom and told me that her husband asked her for a divorce. She hugged me and cried on me and talked for like 10 minutes (not a regular). That is forever in server time, so I was super happy that we weren't busy, I had no food coming up, and my friend tended to my other table. It would have been awful to blow her off. She stayed for dinner and they both got drunk."
"Work at a local restaurant. When they first opened about three years ago we had some guy come in with his girlfriend for dinner. All is going well they're eating drinking when suddenly this guy's REAL longtime girlfriend's sister comes in to eat with one of her friends and decided to stop by and introduce herself. Says I'm 'whatever his name is' girlfriend's sister and the girl he was on the date with flipped out threw her drink at him and storms out, he runs out after her and I'm watching from the window as she's smacking him in the head with her purse (wasn't a small one either) to the car. That's an awkward ride home right? Too bad she didn't drive she could've left him there. Wonder if he was able to keep/save the relationship of either of his girlfriends that night."
"I worked at a popular chain restaurant as my first job. On Tuesdays we would have trivia night where each table who wanted to participate could make a team name and answer the questions asked over the loud speaker. There was a table with these two people on a date but the guy constantly was on his phone. Walking passed a few times you could tell he was texting someone else while on this date. Needless to say the woman wasn't to pleased. She decided to try and have a good time anyway and joined in on trivia. When it was time to announce the team names over the speaker she chose the name 'No sex for him tonight.' The entire restaurant got a good laugh, but the poor guy didn't even notice he was too busy with his phone."
"I work at a bar and there was a couple that would come in fairly often. One day they were sitting at the end of the bar and I had just taken their order when I overhear him say something to the effect of 'I just feel like we're just going through the motions, you know?'
He dumped her while they were waiting for their food. So after a few awkward minutes of talking and her crying, he asks if we can make the food to go. The whole thing made the entire bar pretty uncomfortable."
"I'm a bartender. Witnessed a Tinder date at the bar top. Convo started somewhere with 'I have seven panther tattoos. I just feel I really identify with the Panther.'
Somewhere after that he spotted my tattoo of some molecular structures and asked what they were. I explained and he said 'I'm more of an anatomy man myself. WINK'
Heard a snippet of 'All my past infidelities were never my fault. All the girls seduced me. I'm a man that just can't say no.'
Then it ended when he asked the woman what she would do if she broke her leg while mowing the lawn. The poor lady just looked at me and said 'We're ready for the check.' with the most defeated look on her face."
"Alright not a date but a couple brought in their very cute little daughter (probably like 6) into our restaurant and I'm outside by their table when I hear 'Mommy and daddy just don't love each other anymore.' WHO THE F--K BRINGS A KID TO LUNCH TO TELL THEM ABOUT A DIVORCE? Poor kid probably hates Greek food now."
"I once served an old friend's dad on a date with his girlfriend. I was unaware that he and my friend's mom had split up, so on my break I text her my condolences. Long story short, her parents were not split up but because I jumped to conclusions, they are now."
"I worked at a coffee shop in a college town with seating right up near the espresso bars, and people loved those seats. If you sat there, all of us baristas could hear whatever you were saying, which was usually just boring coffee shop talk. However, this one day a couple comes in and they're sitting there seemingly having a good time...when the guy starts in with a 'I'm not looking for a relationship right now' kind of talk. The girl is near hysterical and the guy just keeps telling her 'I told you this from the beginning, it was just physical' etc, and the girl is like 'well I thought you changed your mind.'
At this point we're about to close, so I have to be over there cleaning stuff and it is sooooo awkward. They stayed past closing, I had to ask them to leave, and even then they stayed about 10 minutes after that. They sat in the parking lot for another 30 minutes and were still out there (the girl still crying) when my team and I left. It was super sad and awkward. Those things should never be done in public."
"I waited tables in a small town when I was in college. We were one of the only restaraunts in town. I had an early 20's couple come in one Saturday night and it was obvious that they were on a first date. The guy was trying to impress the girl by being a real douche to me by ordering me around and belittling me. I can handle that, just kill 'em with kindness. So every time he was condescending or sh-tty to me I just gave a nice 'yes sir' or 'right away sir' and did my job. He was so bad that other servers noticed. When he barked at me for his check, I promptly provided it for him. As he took his wallet out of his pocket, he dropped a condom on the ground. I picked it up and put it in on the table between both of them and said 'Sir, you dropped this.' He denied that it was his and I said 'Yes it is, I just saw it fall out of your pocket.' His date was furious. She immediately asked 'What's that for? What did you think was going to happen tonight. We just met!' He tried to play it off but she got up and exclaimed 'Pay the bill and take me home now!' She then turned to me and said 'I'm sorry' and walked away. I gave him his change right there and he said 'Thanks Bro,' and I told him 'Any time!' I didn't get a tip, but another table next to them saw the whole thing and became some of my regulars."
"My wife was a server at an upscale restaurant and I'll never forget this story she told me.
It's Valentine's Day so the place is booked for the entire night and this guy shows up looking to get a table without an reservation. The hostess tells him that they are booked solid and unless there was a cancellation he wouldn't be able to get a table soon. Guy seems to accept this ok and goes to the bar to have a drink and wait for his date. Girl shows up and this guy is on his third gin and tonic and getting loud. She meets him at the bar and looks disappointed about the table. As they are discussing what to do next things go sideways as the guy drunkenly screams about 'How that dumb hostess lost his reservation that he made a week ago and he isn't leaving until they've got a table blah blah blah.' The poor hostess is a basket case and trying not to break down as the the guys date goes as pale as a ghost. Manager obviously comes out to see what the problem is and the guy repeats his loud a--hole-ish tirade against the 17-year-old hostess. Luckily, the manager had a spine and told the man to immediately leave before he calls the police. He refuses so the manager calls the cops and the guy decides he has made his point and tries to run neglecting to pay for his drinks. Manager runs out gets his plate number and almost gets hit but the drunken jacka-- as he is trying to flee. He gets pulled over by the cops, fails a sobriety test, manager presses charges for assault and theft. This guy's poor date is now comforting the hostess who by all accounts did her job and got lambasted for it."