From scaring a pregnant lady by saying, "It died," to a guy making a joke about seeing his girlfriend in a bikini in front of her relatives, people share their most cringy "I should not have said that" stories.
(Content has been edited for clarity.)
Should Not Have Asked That
“Once as a kid I asked a girl in another class why she was walking around with her arm up her jumper. She just shrugged and walked away. Later found out it was because she only had one arm. Every so often as I’m lying in bed, the memory of asking her that pops into my head, and I feel like suffocating myself with my own pillow.”
Oh No, It Died!
“I was in my OB-GYN clinical rotation. I had a nervous and overly worried first-time mother in my office. She was in for a routine pregnancy visit. I was performing the fetal heart monitor check with the doppler. Perfect heart sounds for a few seconds then the battery on the doppler machine ran out. I mutter ‘Dang it, it died.’ The mother lets out this shriek. ‘NO, NO, NO – the battery died!’ Needless to say, lots of time spent with me sitting there with the ultrasound showing her the beating heart and taking pictures.”
It Has Nothing To Do With The Movie
“I walked into the break room at work and heard one middle-aged co-worker talking to another. I wasn’t paying too much attention, but I heard her say ‘left side.’ This activated a part of my brain devoted to remembering ‘Remember the Titans,’ a movie I had seen most of once at least five years prior.
So, like any good person would, I half-to-three-quarters-shouted, ‘LEFT SIDE! STRONG SIDE!’
My co-worker looked at me for a full two seconds, then said to her companion, quieter now, ‘Yeah. He’s doing a little better, but that whole side is still paralyzed.’
Her husband had a stroke. It turned out to have nothing to do with ‘Remember the Titans.'”
When Confronted With The Child’s Mother
“I was a cashier at a local grocery store. My boyfriend was a bagger there as well. So was ‘Scabies’ – some poor skinny kid with what I know now is psoriasis. But of course, kids being mean picked on him because of his appearance.
My boyfriend was a bully and was probably one of the worst perpetrators. One evening shift they got into a punching match outside while collecting shopping carts. Both of them got suspended.
Upon their return, they both had to meet with the manager. I was working during their meeting and had a good view of the three of them. I was watching them intently- trying to figure out by lip reading and body language what was happening. Were they going to both lose their job? Or one of them? A transfer of departments to keep them separated?
Suddenly this beautiful woman stepped up to my register with a few items. She was quiet at first, but was friendly and asked me what I was watching.
I said, ‘Oh, see those two guys with the manager?’ Pointing in their direction.
She turned and looked. She nodded. Asked, ‘What’s happening?’
I proceeded to tell her about this, including how we call the skinny kid ‘scabies,’ and I concluded the story with, ‘And the bigger kid is my boyfriend. He punched Scabies in the face a few times.’
And as sweet as can be she leaned in and said, ‘Well, Scabies, as you call him, is my son.’
Oh good lord, did I feel like a jerk? I don’t think I’ve ever felt worse in my life for saying what I said to that poor kid’s mother.”
Unintentionally Insensitive To This Man’s Struggle
“I used to work in optical. One day, a patient came in and handed me his glasses with a broken hinge on the arm. He had come in several times before to have it fixed or adjusted. We typically see this problem when people take their glasses off with one hand and pull them to one side, stretching the hinge.
I took it to the back and realized that this time I can’t fix it. I headed back to the customer and put the glasses in front of him. I looked at him and began saying that in order for this to stop happening, he needs to learn to take his glasses on and off with two hands. And I show him how. The customer looked me dead in the eyes and put a prosthetic hand on the counter. I apologized profusely. Told him I couldn’t believe I didn’t realize and showed him another way to put his glasses on and off.
After that, I explained this time it wasn’t fixable, and I would have to replace the part. We chatted a bit more and I said, ‘Ok, I’ll be right back, I’m going to find you a new arm FOR THE GLASSES,’ and ran to the back. I was so embarrassed I had to let another lady take over while I cried in the back room over how insensitive I was to this mans ‘struggle'”
One Last Laughter
“I had been fixing this old guy’s computer for years and he had told me a bunch of stories about the war and such. I like talking to old people. There’s a lifetime worth of knowledge and experience just waiting for someone to listen.
Anyway, after his wife died, he took a sharp turn. He stopped taking care of himself and ended up in a nursing home. I still fixed his computer there, of course. One day, I got a call from the nursing home (I also fixed their computers regularly) that he was in the hospital and it was serious. They thought I was his grandson or something.
I found some time in my schedule to go shake his hand one last time. We had a pleasant conversation about his wife. Then, he cleared his throat and delivered this incredibly sincere final goodbye. Despite being well into his 90s, he remembered the name of my girlfriend from when we took him and his wife to dinner, and he remembered the name of my dog from a story I told him years ago.
It felt like someone tied my throat into a knot. He ended his goodbye with, ‘I hope when you get to my age you are satisfied with the man you were.’ I had no words. There was a silence as I thought of something to say. ‘Thank you?’ No, too impersonal. ‘I’ve enjoyed knowing you?’ kind of weird.
Guess what I choked out? ‘You too.’
After I fumbled, I did manage to come up with something better. We had one last laugh over that.”
This Morbid Joke
“A friend picked up my husband and me for brunch. She had to use the restroom urgently, being pregnant at the time, so I brought her upstairs to use ours. Our building is old and has a reputation for being haunted. It’s a two-story building. The upper level is apartments, the lower is storefronts.
As we ascended the stairs, my pregnant friend told me a bit more about the history of the building. She told me that the upper level used to be a birthing center in the late 19th Century, and the downstairs was a morgue. I quipped, ‘Well, that explains the chute in the hallway.’ I saw the look of horror on her face and then looked down at her pregnant belly. I realized that she was probably not the person to make morbid jokes about stillbirth to.”
Uncovering The Truth Over A Couple Of Drinks
“I worked at Starbucks for five years. Here’s one of my regrettable customer encounters:
A regular customer and his girlfriend would always come in and order the same thing. One day, as they walked in, I reactively started their usual order. They proceeded to the register. I had a proud grin on my face as I knew their order already. I told them their total and his girlfriend proceeded to tell me that this was not her drink. That’s when I realized the girl was different and I blurted out, ‘Sorry, he’s usually in here with someone else.’ Their faces sank and she left without a word. I had apparently uncovered a long-running affair.”
A Shameful Walk Away
“I was walking the family pug and came across a woman with her toddler daughter in a stroller. She said hello and told me that she had met our dog before when one of my sisters was walking her and that it was quite funny because her daughter and our dog shared the same name; Tilde. So we talked a bit, and suddenly I felt the urge to make a joke, something along the lines of ‘your daughter is certainly the better looking of the two.’ What came out, however, was, ‘Well, at least now your daughter knows someone who is uglier than her.’ I do not think that it hit her at first, but at about the same time as I realized what I just said about this poor woman’s daughter she figured it out too and made this weird face.
I nodded at her awkwardly and walked off even more awkwardly.”
A Serious Illness
“In high school, I sat next to this girl on the cheer squad in our ‘silent reading class’ we would chat before the bell rang, but as soon as it rang no one was allowed to talk.
Anyway, she came in and showed me this bump on her hand and told me the story about how she fell and she is going to the doctor because it won’t go away. She thinks it’s a cyst and that the doctor is just going to drain it.
She came back the next day and her wrist is all black and blue. Turns out it wasn’t a cyst, and as soon as she told me that, I jokingly said, ‘IT’S CANCER!!’ to which she looked at me and said, ‘Yes.’
I just blinked for what seemed like hours, then the bell rang. I just opened my book and started reading.
She ended up losing all her hair and getting the prom queen vote and all of that.”
“I work at a hospital. I was helping an elderly man out of bed, and a lot of the time where I work they need help getting their legs off the bed, due to weakness. I’m about to get him up, and as he throws the covers off, I say, ‘Do you need help getting your legs off the bed?’ I then realize he only has one leg. Immediate embarrassment until he grabs his one leg and says, ‘Sure, I’ll get this one and you get the other one.'”
Not The Right Time And Place For Such Jokes
“I had been dating a girl for about two years through the end of high school and the beginning of college. I was close with her family and was going to spend Thanksgiving at her grandmother’s place with her relatives.
I was at her parents’ house, waiting to leave, and her little sister was putting up a big fuss about having to dress nicely for Thanksgiving dinner. My girlfriend, of course, was not complaining about what she was required to wear, so the sister said to her dad, ‘How come Melissa doesn’t have to wear this dress?’ Her dad, trying to emphasize that Melissa’s attire had nothing to do with the little sister’s, told her, ‘For all I care, Melissa can wear a bikini to dinner tonight.’
Dumb old me, I comment from the other room, ‘Yeah, and then we can all see what I’m thankful for.’ I’ll never forget the look on her dad’s face, the perfect combination of being amused at the joke but being appalled by it at the same time.”
A Lucky Coincidence
“I went to a pub, had one drink too much, went outside for a smoke and saw this Asian looking guy. Being the friendly guy I am, I decided to make a new friend and what’s the better way than making a joke?
‘What’s up, Suzuki?!’
I immediately felt like the biggest jerk in the world while the ‘should not have said that’ meme flashed before my eyes in a violent fashion. But then the Asian guy turns to me and says:
‘Have we met before?’
‘Well, I don’t think so.’
‘Then how do you know my last name?’
The guy was named Suzuki! You can imagine my relief! We smoked one more together, had a pleasant chat and went our ways.
Even though I dodged the bullet on this one, I still feel terrible for blaring out such a thing.”
Babies In Movie Theaters
“A few years back, my brother and his wife were visiting for the weekend. They have two girls who are now 14 and 11 years old. We were talking about movies and bad experiences in movie theaters. I recalled going to see one of the ‘Lord Of The Rings’ movies in the theater. I can’t remember which one, but I remember someone bringing a baby to it. There was a small room in the back of the theater where you could still see the movie through glass and speakers in the room but were secluded. None-the-less the couple with the baby didn’t leave right away to go up to that room, and I remember the baby crying for a while. It was annoying and I was saying I couldn’t believe someone would bring their baby to a movie like that.
I’m telling this story all the while my sister-in-law is not saying a word. Then it hits me. Before I could even say it she chimes in with, ‘Yep, that was us. We were with you and had our daughter with us.'”
Unintentional Correct Guess
“In the third grade, we had this regular substitute teacher who was always trying to be upbeat and chirpy in an obviously fake way. Even a bunch of 8-year-olds could see that.
We walked into class one day and she was there, but she was acting like a normal person (depressed by her standard).
I, the smallest and quietest boy in the class, raised my hand and, I still do not understand where this came from, asked her ‘Hey Mrs. S, what’s your problem? Did someone steal your car and drive it into the river?’
She looked up at me in shock and said, ‘Yes. The police just phoned and told me they’d found it on the riverbank.’
Instead of shutting up, I proceeded to laugh like a gremlin. I wasn’t laughing at her, just at the absolute absurdity of having guessed correctly.
The rest of the class was quiet for quite some time.”
Bad Way Of Pranking Mum
“When I was about 11 years old, my mom asked me to put a letter in the postbox up the hill from our house. There was one moderately busy road with a crossing but she trusted me and allowed me to take my younger sister with me.
On the way back, I came up with a ‘great’ idea for a prank.
When we got back, I told my sister to wait outside, then burst into the house and in my best-panicked voice shouted ‘Mum! somethings happened!’
Mum was standing with her back to me but spun around, completely drained of color and fear painted all over her face. I immediately regretted it and said aloud, ‘I’m so sorry, everything’s fine.’ But I obviously still got in a lot of trouble for that one.”
Just Say Yes And Go With It
“I was at a dance social with a few friends about six months ago. I had just danced with an attractive woman and we were chatting a bit. As we’re walking to the side of the floor, she asked if I’d want to grab a drink with her.
Without hesitation, the first thing I said was, ‘Sure, let me see what my friends are doing!’ I started walking towards them (walking away and in front of her), and after a moment I realized what an idiot I just was and internally facepalmed.
To my fortune, she couldn’t hear what I said after ‘sure!’ because the music was loud. Eventually, she asked me for my number, we went out on some dates, and we’ve been together since. We got a chuckle looking back at that event. She’s amazing, and I’m a lucky guy for sure.”
Social Board Game Turns Awkward
“I was playing one of those social board games, where you shout clues and such to each other.
As far as I can remember, it had cards with stuff on like ‘lives in the sea’ and you’d have to say a bunch of stuff like ‘shark’ and whatever until someone figured out what was on your card.
My card was ‘evil’ or something like that. My family shouted all of the obvious things like murder and kidnap and stuff. I had a sudden image in my 15-year-old mind of the embodiment of evil. Being obsessed with ‘Lord Of The Rings,’ what could be eviler than the cloaked, black ringwraiths? On the same note- dementors! Scream from Scary Movie! They’re all hooded, cloaked in black.
So to generalize, I just said ‘black people,’ to the absolute dismay and outrage of my mother, father, and sister, now convinced they’d raised a closeted racist.
Not my finest moment.”
Co-worker Crush Gone Wrong
“I had been trying to woo a new female co-worker at my retail job (and by woo, I mean make awkward small talk and stumble over jokes that weren’t really that funny in the first place).
Over time, we started to get comfortable with each other, and the conversations started to flow. However, this wasn’t necessarily a good thing. As this was a year before I was diagnosed with adult ADHD, I still had a tendency to say things without thinking; a trait that sometimes got credited by others as ‘dry humor’ when I didn’t say something offensive.
So, we were standing there tying a ton of balloons behind the counter (worked at a party city), just talking about random stuff. Eventually, she said, ‘Yeah, [insert manager name] was annoyed with me yesterday. I was restocking aisle four and accidentally knocked one of the shelves lose. There was candy everywhere; one of the jars shattered.’
‘Well, he should have known better,’ I said with a chuckle, ‘You have a tendency to destroy everything you touch.’
We both laughed. Laughter, yes, that’s what I needed to continue my endeavors.
I decided to continue the joke, without actually considering what I wanted to say.
She coughed awkwardly. I winced and crawled into the deepest, darkest crevasse within my mind, trying to escape the train wreck.
‘Um,’ I finally decided to summon my courage and break the endless silence, ‘Do you ever say things, and as you’re saying them, realize that they are things that should never be said?’
‘Yeah, all the time. Um, I’m going to go help that customer.’
We didn’t talk for the rest of the day.
I ended up dating her for a short time.
That didn’t end well either.”
Pass With The Right Hand
“I was on my high school’s track team preparing for the 4×100-meter relay at my last meet of the season. Before we had to move to our positions, I wanted to ask my teammate which hand he wanted to receive the baton with. As I was about to ask him about the baton pass, I mixed up, ‘What hand will you use for handoff’ and ‘What hand do you want to get the baton with’ and instead said, ‘What hand do you get off with?’ There was a moment of silence in which I thought to myself that he maybe wouldn’t take t the wrong way. Unfortunately, the look of slight disgust was on his face. Afterwards, he said, ‘Pass with your right hand,’ and walked away. I just stood there feeling like an idiot.”