Being a waiter or a waitress means encountering all different types of people every work day. Sometimes, waiters and waitresses walk up to tables at bad times and hear conversations they weren’t meant to. People share the most uncomfortable conversations they have overheard while serving. Content has been edited for clarity.
Proposal Gone Wrong
“I can’t imagine I would have been the only waitress to have ever overheard this but – the turning down of a marriage proposal.
The guy had informed us beforehand he was going to propose when you make a booking we always ask if there’s a special occasion, so we can do something to make it even more memorable, and he had told us he was going to propose, they’d been together about five years I think, and he decided it was finally time.
Well, when they came in, he looked nervous, as to be expected. I was their waitress so quickly got them seated and got their drinks, after they’d ordered I was putting the food through the system when I heard him start talking, saying how much he loved her, how he wanted to spend the rest of his life with her, etcetera, so I sent a message through to the bar asking them to bring over two glasses of prosecco, which was customary with proposals. Well, when he got down on one knee, she looked really uncomfortable and started shaking her head, telling him not to do this, and then looked up and saw one of the bar staff heading their way with the prosecco, and she bolted.
Quite literally jumped out of her seat and ran for the door. The poor guy was left kneeling on the floor in front of an empty chair looking completely shocked. He got back in his chair and proceeded to sit there for about half an hour, before finally up and leaving – never did find out what happened to them but I imagine they had quite an uncomfortable conversation after.”
Father and Son Feud
“I was 16, and this was my first ever serving job. I was on the Sunday morning breakfast shift at around eight a.m., and this small family came in; a mom, dad, and son. They were not super cheerful or talkative. Not everyone can be a morning person, but I could tell there was some tension in the air.
While I was serving them and pre-bussing, I caught a couple of phrases or words the dad would say to the son. Such as, ‘check your attitude’ or ‘not in my house’ sort of thing.
Fast forward, the family had their check, and they were still talking in quiet, but tense tones. The next thing we knew, the son tackled the father onto the table, breaking it instantly. They started struggling, wrestling, and screaming at each other on this broken table in the middle of a busy restaurant on a packed Sunday morning. All we heard was the son and father fighting since the restaurant went silent once other customers realized what was going on. Stuff was flying everywhere; food and drinks were flying onto other nearby tables. One of my coworkers started yelling for someone to call 911.
The stepfather was sending his stepson to a boot camp for his behavioral issues. I guess the stepson didn’t take the news all too well.”
“I ended up being the manager/bus boy/waiter at the restaurant. There was a week when we had four different couples break up at one of our tables. Two happened at the same table on consecutive days.
The most brutal was when a woman was destroying this guy, laying out everything she had issues with.
She said things like, ‘your car sucks, your appearance is too messy, your clothes look like garbage, your friends are rude, etcetera.’
He just sat there and took it. At some point, I guess he had enough and left. The lady stayed for one more drink, and a lot of texts, and then she left.
A day later, it was reversed.
The guy was breaking up with the girl. He was a little blunter and a little less cruel simply saying, ‘I don’t want to be with you anymore.’
She wanted to know why.
His answer was, ‘I don’t have to justify my feelings.’
A version of this conversation continued for about 30 minutes until they paid and left. I don’t think he successfully broke up with her.”
“I waited tables for a summer job in high school. One weeknight, not too busy, there was a middle-aged, extremely cold couple seated in my section having a very serious, quiet conversation. The woman was on one side of the booth, the man on the other. Very tense.
While pre-bussing I caught a few snippets of the man apologizing for slapping/hitting and/or scaring the woman. I never picked up on the details I just gave them a wide berth after and gave the guy the entire ticket without asking. I surmised it was some kind of attempt by the guy to reconcile.
Her body language was stone-cold, and she wielded her silence like a blunt object.
I told my manager who shook her head and said to nobody, ‘Run far, run fast honey.’
All these years later I can still see both of their faces clear as day.”
Watch What You Say
“After I retired from the military, I got a job as a defense contractor, but I had to wait a while for the security clearance process to do its thing, which takes a while. So I was working several joe-jobs in the meantime to keep the bills paid. One of them was waiting tables.
One Friday afternoon a large group came in, all fairly well dressed, and got a table together. It was obviously an ‘office lunch,’ and I didn’t pay them too much attention since it was the other waiter’s table until I heard the topic of conversation.
I was two tables over when I overheard what they were talking about. I recognized several keywords, which caught my attention. After about three minutes of listening, I could tell exactly which government agency they worked for, had a pretty good idea which office they were in, and could tell who was a contractor. I had also determined their conversation had bumped off the ‘classified’ wall a few times, all while in a restaurant which was owned and operated by foreign nationals, and I know the owner had cameras with audio recording.
I managed to catch one of the customers after he came out of the bathroom and strongly advised him and his colleagues to alter their subject of conversation. When he looked at me funny, I ran down the list of everything I had gleaned from their discussion just by eavesdropping from one table over and watched the color drain from his face.
Three years later I was sitting in a ‘protecting secure information’ seminar, and I heard this exact story told by the guy giving the speech. Apparently, the story of the semi-crazy white waiter in the Korean restaurant had left an impression.”
A Dinner Affair
“All of my experiences were very open and very awkward. I approached two weekly regulars, a man and woman, who came in with another couple. Before I greeted them, the regular guy spoke up. He told me he needed to explain something.
‘I have to explain something,’ he said.
He motioned to the woman sitting across from him, who was not the woman he was normally with.
‘This is my wife.’
He motioned to the woman sitting next to him, who was the woman he was always with.
‘This is the woman I’ve been having an affair with.’
I greeted the woman he had been having an affair with and apologized to the man’s wife. She laughed, but it wasn’t unkind.
‘This is the man my wife has been sleeping with, who is the husband of the woman I’ve been having an affair with.’
My eyes darted around the table. I took a drink list from my apron and handed it to the wife.
‘You’ll be needing the drink list then.’
The table erupted into laughter.”
Well That Was Awkward
“On Valentine’s day, one of the couples I waited on seemed to be on a date not going well. It was likely the first date, too. They barely spoke to each other, and things kind of just felt awkward.
Anyhow, flash forward to the end of their meal. I had given them the bill a few minutes beforehand and was back at the table with the card machine.
As the guy handed his card over, the girl said in the loudest, the rudest voice, ‘You’d better not think just because you’re paying, I would ever love you.’
If I had thought it had been awkward before, I had no idea. And I just had to hang around super uncomfortably while the guy entered in his details. It felt like time was going glacially slow.”
What Is Going On Here
“The table was behind me.
Him: ‘I’ve brought you here today because I have something important to tell you.’
Her: ‘Well start talking before the food gets cold’.
Him: ‘We’ve been together for four years now.’
Her: ‘Three years and 10 months.’
Him: ‘Yeah. And for the last couple of weeks, I’ve been thinking about it. You’re the person I want to spend the rest of my life with.’
John: ‘Let me speak Claudia, please. I know we’ve had our ups and downs, I know your parents don’t approve of me.’
Claudia: ‘Yes about my parents.’
John: ‘Please Claudia, it’s already hard for me. I know I don’t have the biggest house, nor the richest bank account, but I really love you. And I think we can make a great family together, with lots of kids and your brothers and sisters can come to visit.’
Claudia: ‘Speaking of brothers and sisters.’
John: ‘For the love of God Claudia let me finish. I can’t live without you, not even for a moment. We have lots of things in common.’
Claudia: ‘More than you think.’
John: ‘I know baby, which is why I need to ask you this: Claudia will you marry me?’
John was on his knee.
Claudia: ‘John, please get up.’
John: ‘I need an answer.’
Claudia: ‘I’m your sister John.’
John: ‘I know.’
What the heck?
I needed to do something.
Me: ‘Are you okay, guys?’
Claudia: ‘Yeah, we’re fine, we’re just practicing our lines for theater class; today’s our finals.’
Me: ‘What? Are you kidding me?’
Claudia: ‘We were convincing weren’t we?’
Me: ‘Pretty much.'”
So Much For Christmas Spirit
“I am not a waitress, but I am a hostess at Applebee’s. It was December 23rd, 2016, around 9:30 pm. There were three ladies. Let’s call them Mary, Sue, and Jill. Mary had a baby and is sisters with Sue. Sue is a lesbian and just got out of jail. Jill was just a friend.
Mary: While holding the baby while talking to Sue, ‘While your stupid self was in jail, your girlfriend was hooking up with this other girl.’
Sue: ‘Well, I am going to pound them both into the ground.’
Mary: ‘And go back to jail? This is what got you in there in the first place. You can’t control your freaking temper.’ She handed the baby to Jill.
Both Mary and Sue began to argue and stormed out of the restaurant. The baby was crying, and my manager came running over. Jill explained the situation, and the manager said she would have to pay the bill since they ran off.
Jill: ‘Oh, they are coming back. This is not my baby, but I am sorry for what happened.’
At this point the baby was crying so much she puked. The manager had me clean it up, and I did so promptly. As I was kneeling down cleaning the puke, they returned, still yelling at each other. Sue grabbed her drink and threw it at Mary, and it also landed in my hair. I got away as fast as possible.
I do not know what happened after, but they were kicked out. Five minutes later, the manager let me go home for the night. So much for the Christmas spirit.”
“A lady came in by herself, kind of short with me, but not too bad. She said she was waiting on one more, so I let her be until he showed up. They both just had cokes, and we had complimentary chips and salsa, so they were good for a while. I kept swinging by to check on them or see if they wanted to order anything, but they didn’t want anything. They were getting progressively ruder with each trip by, but I had to keep coming by because it’s a freaking restaurant. It was my job to serve them. They were sat over an hour ago, and I hadn’t checked on them in like 10-15 minutes.
I was doing a quick drive-by, and the lady started yelling at me saying ‘we’re getting a freaking divorce, can’t you just leave us alone?’
Why the heck would you go to a sit-down family restaurant to sign divorce papers? If you don’t want to be bothered, but still be in a public place, go to a freaking coffee shop or anywhere else. She ended up storming off to the bar and downed a couple of drinks and told the drink waitress to charge it to her husband’s tab.”
He Brought What On The Plane?
“There were five people at this one table in the back corner.
Person One: ‘So my friend got arrested in the airport the other day. Trying to smuggle ‘grass’ into the plane.’
Me: Wow. Wild.
Person Two: ‘Ah, busted by the ol’ canine. One time, I had to bring a half-pound of powder and about 40 unprescribed medicines through customs. Man, I was sweating.’
I was thinking to myself, ‘Who are these people? This guy is cooler than my GTA character.’
Person Three: ‘Man, how the heck do you do that?’
Person Four: ‘I have my ways, it was a long time ago, though.’
Person One: ‘It better have been. You are crazy.’
I was thinking to myself, ‘facts.’
Person Four: ‘Actually though, I’m curious now. How do you bring ‘grass’ on an airplane?’
Person Five: ‘Oh, easy. My go-to for bud was always cocoa butter. Dig some out, put the baggie of trees in, and cover it up. Creates a seal for the smell. Slide it in a bag of food, and you’re good to go.’
I smiled and turned around. I was stunned. Not one person at the table was younger than 55-60. These older people were wild.”
“I’ve been in restaurants off and on since 1991 and have worked in every imaginable job you can have in this business. I have a couple of innate gifts which work well in this industry; the best of which is I can cold read people almost perfectly and then pull any info I need from them and conversely, lead folks to where I want them to go dining-wise I almost always won contests when I served. Folks feel at ease with me and my confidence makes many think I’m a manager instead of just their waiter.
I currently run a kitchen, but in the place prior to this one, I did literally everything. I especially enjoyed serving and bartending there. This location had been there for 25 years, and the concept itself was in its late 40s. How many chain restaurants make it almost 50 years) because of the diverse and multi-generational customers who came in; a virtual plethora of minds, experiences, expectations, and opinions to manipulate. One weekend night, I had a late table of four: mom, dad, and two daughters. They gave me the impression of locals who hadn’t been to this restaurant in a while.
Right from the greeting, I felt it was going to be a good experience, and things would go well. Not so much. As I waited for their food to be made, I worked on cleaning up and getting the front ready to close. I believe it was a comment by one of the daughters I overheard which allowed me to engage them in further small talk. My read had been correct: fairly local people who hadn’t been to any of our restaurants in a while. Of course, being ever aware of opportunities to increase my tips/obtain new regular customers, I asked what would be the downfall question: why hadn’t they been in to see us for so long.
Here’s where you throw up in the back of your throat.
They have a third child, a son, not dining with them. He loved this restaurant. Loved the burgers and always has to get the sundae bar. Turns out they came in that night not to celebrate an occasion but to honor their son. Immediately, my mind went to dark places and things to say to comfort and steer this back in a positive direction from the head-on collision I just created. Sweet Mary, it only got worse.
Their nine-year-old son had been missing for three years. If they told me the how’s and why’s and where’s I can’t remember. I’m a parent and hearing of a child taken, makes you wanna cry out and hug these people. So now I was involved. I was no longer their waiter; I was a sympathetic ear picturing life if something had happened to my kids. Buckle up Dorothy, it got worse.
They had finally, the same day, received word their son was alive. I allowed myself a sigh of relief. But it sounded odd as they talked about finding out he was alive. Which was when mom said they would talk further with the Interpol detective the next day. Interpol? Did he pirate DVDs and was snatched black bag style? No. It seemed I couldn’t have been more wrong. Their boy, who loved this restaurant, whom they hadn’t seen or talked to or gotten any news about for almost three years, was discovered in one of the Baltic States of Europe to have been a victim of human trafficking.
Thankfully, their dinner arrived. I tried to be sincere and even more accommodating than I normally am. I believe they had a good meal and went away satisfied? No. Happy? No. I don’t know. I comped their dinners. They insisted on paying.
When I finally flat refused to give them a bill, I had to walk away to compose myself and end the goofy dispute on them paying. I planned on catching them as they left and thanking them and hoping for the best. When I finally made it back to their table, I found they had way over tipped me and much like me to them over the bill, refused to take their tip back when I went to them as they got in their car.
The mom looked at me and her last words were, ‘When we get him back, I’m sure he’ll have to come here.’
She said she would make sure to bring him to see me so I could take the same good care I had given them.
I kinda rushed explaining the end of the experience but honestly, I was so absolutely shell-shocked I don’t remember much. I was seeing another one of the servers at the time and she happened to be the other closer. I relayed the family’s story to her. I introduced her to the table and who she was to me and they accepted her just like they had me and continued the conversation, openly talking about the situation. In a weird way, I’m thankful my partner was there or I honestly would think I dreamt it all because of how crazy it was.
So, I found out sometimes, you can disarm people too well and end up finding out things which make you rethink life, Parenthood, and how lucky you are to be able to go home and hug your kids.”
“I had one table at this Steakhouse I worked had come in for the last dinner with one of their elderly relatives. The man must have been late 90’s – early 100’s. I guess he was going into the hospital or hospice the next morning where he was only going to have a day or two left to live. So, they came to the restaurant for their last meal.
They were all pretty stressed and tense for a while. I remember the woman who I assumed was the man’s daughter was being very picky and complicated with everything. Had I not known the situation, I’d have been annoyed. Once they had eaten and had some drinks, you could tell they were loosening up and having the dinner they wanted to. I tried to interrupt as little as I could, and every time I did, I was very aware I was distracting from their time with a loved one. Everyone left seemingly pleased.
For a while, I couldn’t get my head around why they wouldn’t want to have a home-cooked meal. It confused me until a bit ago. I realized I wouldn’t want to waste my time cooking a delicious meal either if I was in a situation like this. It would be much better to just spend the time with the person.”
Discussing Their Futures
“A colleague of mine was waiting for a group of two couples in their late teens/the early twenties. They were talking about who would turn on to have kids first. They were discussing the details of each relationship to determine the answer, including their ‘love’ lives.
They also starting talked about another couple in their friend group who wasn’t there, but they concluded they were probably the first ones in the group to get pregnant since they’ve been together for a steady two years and didn’t seem to have many problems in the bedroom either.
This was not a very comfortable conversation to overhear in general, but things got even more awkward when it turned out the guy from the absent couple was one of our colleagues they were talking about.
Apparently, they knew he was working at the place but still proceeded to thoroughly discuss the likelihood of him and his girlfriend getting pregnant, with his co-workers around.”