July 17, 2020 | Maria Cruz

People Share Their Biggest “I Shouldn’t Have Said That” Moment 

Now, technically we’re in control of what we say. But when we’re smack dab in the middle of an argument, we lose control of our tongues. This phenomenon also happens when we’re just generally awkward people. These quotes are definitely things these people wish they could get redos on.

#1 You Don’t Either

This one time, I was fighting with my mom and she said something about how I didn’t pay for this house. However, since she was and has been a stay-at-home mom at the time, I just shot back with, “I mean, technically you don’t either.” Well, that was the wrong thing to say to her and I knew that I had it in for me.


#2 Foot-in-Mouth Syndrome

My brother and I worked at a fast-food restaurant. The one type of new burger we served took 15 minutes to cook though, so we’d often have to tell customers and suggest they find a table to wait if they were willing. Well, my brother was working cash and this person in a wheelchair decided to wait. My brother was like, “It’ll be a while for it to be done. I'll bring it to your table when it's ready if you just want to take a seat sir — I mean pull up a chair — I mean…” Thankfully, the person had a good sense of human but it was funny watching him put his foot in his mouth repeatedly.


#3 It Wasn’t Easy

I remember one time, back in the day, when I happened to see some dumb 2007 meme. It just said something like, "Hey, man, thanks for not being an addict." This one time, I said it to my youth pastor because I was a dumb teen. He replied, "It wasn't easy getting away from it, that's for sure, but I'm glad I'm here."


#4 Uncle Steve

I went to my uncle's funeral a couple of days ago. As we were about to leave to go to it, we were wondering what family would be there. Without thinking, I said, "I wonder if uncle Steve will be there." Well, that was who the funeral was for. Right away, I couldn’t help but think, “Oh god, no. Why did I say that?”


#5 The Headband

I had on a headband once and a co-worker, who is kind of a tool, but in a loving way, told me I looked like a patient one day. I wore it a few weeks later and I asked a few of my friends, who are all related, if I looked like a patient in it. I then immediately remembered their uncle just shaved his head because of his treatment. Yikes. I sank and later sent out an apology text. They all played it off like they didn’t hear me.


#6 If I Was Blind

A number of years ago now, my wife was complaining about how she thought that she was overweight. In my opinion, she wasn’t overweight at all. In an attempt to comfort her, I put a hand on her shoulder and said, “You’d be perfect if I was blind.” Sadly, the look on her face was not exactly what I had in mind.


#7 Like a Potato

My wife and I were going somewhere and she asked if she looked okay. She was wearing brownish capris, a light colored camisole, and a brownish shirt over it. I tried to come up with something cute and brown, so I said, "Like a potato." She then asked, "Do I look like a potato in this?" This is now the basis for all clothing-related questions, 20-ish years later.


#8 Wrong Answer

I was in high school, working fast food. It was slow in the line, so me and the girl working were talking. She was complaining about her weight, so without really thinking I said, "Oh come on. You're not that fat." I knew how badly I had messed up before finishing the sentence. She stormed off. In my defense, she really wasn't that fat.


#9 Put On Your Seatbelt

I was in the car with my parents and my mom turned around and told me to put my seatbelt on. I responded by saying that I wouldn't and I hoped I would lose my life in a car crash. I don't remember the exact words I used or why I even said it. The whole car went silent as I painfully remembered that my father's first wife and unborn child lost their lives in a car accident on their wedding night some 40 years ago. I’m also her namesake.


#10 Underground Railroad

In my middle school music class, we were studying the Underground Railroad. Our teacher asked us to name famous African Americans from the period. My hand went up. Now, I had the image of Harriet Tubman in my mind. I still have no idea why I said what I was about to. The teacher called on me and I answered, “Martha Stewart.” The class roared with laughter.


#11 On the Spot

When I was in high school, I had a part-time job at a store. One day, probably in April or something, a girl I hadn’t seen for a while came to my register with her mom. As I was ringing them up, I tried to make conversation. “I haven’t seen you at school recently. Have you picked your university yet?” She sort of looked away and mumbled, “I don’t go to school anymore.” Her mom looked pretty embarrassed.

My stupid, sheltered, education-first-and-foremost butt hadn’t even taken into account that some people might not have an answer to that question. I rang them up as quickly as possible and vowed never to ask it again. I didn’t see her after that. She wasn’t in high school anymore and likely hadn’t been for some time. I didn’t see her at graduation, either. I felt pretty badly for putting her on the spot like that.


#12 Let’s Go For a Walk

At an old job, I was getting to know my colleagues and there was a really nice girl in a wheelchair that also happened to live near me. We'd end up going on lunch together often. One day, we were bored on the break. I said, "Let's go for a walk" and even motioned walking with my fingers. I will never live that down. She took it well, though, surprisingly.


#13 Make Believe

I made someone cry by accident. A friend of mine told me her grandmother passed away recently and how much she was struggling to cope with that. So, later that day we were discussing a school-related project with some other friends. We weren’t going to finish our project before the deadline, so I jokingly said, "Well, what if we pretend someone's family member passed away and that's why we couldn't focus." Right after saying that, I looked at my friend who began to tear up a bit. I immediately thought, “Oh, that's right. I'm an idiot."


#14 Lusting Devotion

I know that a lot of things can go wrong on a wedding day, and maybe it was because I was nervous, but I made a boo boo during my vows. During the ceremony I said, "with lusting devotion" instead of lasting devotion. I mean, both phrases work. I don't mind having to commit to lusting devotion for the rest of my married life.


#15 Guard Dog

I was a groundskeeper at a school and I was talking to a few students about my dog. Of course, they were asking me all sorts of questions about him. I was trying to dodge all of their questions, but I could only keep it up for so long. I let slip that what the dog is guarding is between professor Dumbledore and Nicholas Flamel.


#16 Having a Party?

I was standing behind a lady checking out at Walmart. She had several 40-50 can packs of Bud Light that she was buying. It looked like she was stocking up for something, so I asked, "Having a party?" She stared at me for a second and said "Nope, just a Tuesday." That was one of the more cringe-worthy episodes I've had with random people.


#17 Talking Back

My boss gave me some really menial work to do when he knew I was too busy for it. He was being lazy and didn't want to do it. I literally grabbed one of his hands and looked hard at it. He took his hand back and asked what I was doing, and I looked him in the face and said, "Your hands look fine." Three other co-workers were there around and tried their hardest to not burst out laughing. Pretty much as I was saying it, I regretted it.


#18 Skype Interview

I once had a business school interview over Skype. They were very interested in a global conference I was helping organize and suddenly asked, “What would you do in the event of a terrorist attack?” I immediately blanked out. The first thing out of my mouth was, “Well, the event’s going to be a bomb.” I didn’t get in.


#19 One Man’s Trash

This one time, my neighbor was telling me the story about how he and his ex-wife had split up. Weeks after their divorce, she got married to his best friend and they moved a few states away. As soon as he said that, I went, "One man’s trash is another man's treasure.” He did not think it was as funny as I did.


#20 Disaster Artist

My professor was trying to remember the name of this artist. He was describing what kind of work he does and asked us if we know the name. I chime in, thinking I’m going to say, “Kim Jung Gi” but instead I blurted out, “It’s Kim Jong Un.” I felt everything go into slow motion when I said that last syllable. Then just about everyone in class looked at me and yelled “No!”

Caritas Secondary School, Port MoresbyFlickr

#21 People Being Awkward

My mom unfortunately passed away this year, but my friends I have definitely started making more “gone mom” jokes than ever. It definitely makes the whole thing a lot easier, but sometimes other people get awkward about it. I have to say, though, there’s nothing more awkward than people being awkward on your behalf.


#22 Offensive Santa

I decided to be an offensive Santa during a family Christmas. I blurted something along the lines of, "This one's for the addict baby," as I held the gift that was for my cousin. My cousin is a legitimate addict baby. I immediately knew it was too far, as did my mom, who smacked me. I got a few people to laugh pretty hard, though, so it was all worth it.


#23 I’m Just Blind

I was at a rehearsal with a blind opera singer, accompanying her as part of a string quartet. The venue was pretty cramped and they didn't bring any stands for the music, so they set them up on chairs. I didn't bring my glasses that day and was squinting a little bit to read the music. The audio technician asked me if the setup was okay.

I replied with, "It's okay, I'm just blind.” The worst part is, everyone gave me a weird look, but I kept on trucking because I didn't even realize. That is until ten minutes later when I realized that I called myself blind in front of an actually blind person. She was very nice about it, but it was still mortifying.


#24 Thanksgiving Plans

My cousin recently received a sentence to one year of house arrest. When asking my cousins (we were all together at the time) what their plans were for Thanksgiving, I turned to my cousin, who is now on house arrest, and said, “Not you, though. We know where you’ll be.” I followed up with “Too soon?” We all had a good laugh.


#25 Good Times All Around

Me and my friends were having a group photo session for prom at one of our houses. Everyone's parents were there, taking photos of their daughters or sons with the dates they had. I was going alone and one of the parents asked me who I was going with. I immediately blurted out, "My right hand.” Dads were holding back laughter, moms were standing there shocked. Good times all round.


#26 Meeting Conversation

I was picking up my daughter from my wife who was in a meeting for work. The meeting consisted of a bunch of the managers from the local area and the district manager was doing the meeting. We both work at the same company, so I know who he is and he’s a great guy who’s pretty personable. On my way out of the meeting room, he said, “See ya later, dad.” Just out of pure instinct to say something funny, the words, “That’s daddy to you” slipped out.


#27 Safety Talk

I was once getting a fine for jaywalking. The cop was going on about safety and how it's for my own good. He asked, "Why do you think we're doing this?" as a rhetorical question. Me being me and having a bad habit of answering rhetorical questions, I said, "Revenue raising." The cop, my friend, and I all kind of just had a look on our faces of "Did that just happen?" The cop asked me what I said and I was like, "Oh, nothing.” But he knew exactly what I said and proceeded to go on a rant about it.

Wenatchee Police at Albertsons 1Flickr

#28 Cue Exit

Not me, but my boss and I were riding up the elevator. I was six months pregnant at the time and it was obvious. There was also another pregnant lady standing right next to me, then another lady who appeared pregnant. My boss, who is a very nice lady, said, "Oh, look at you three standing there!" The one on the end said, "Oh, I'm just fat." Cue exit, stage left.


#29 Commemorative Shoes

My co-worker and I were stocking shelves and chatting one day. He asked me if I saw the 9/11 commemorative shoes Nike was releasing. I asked, "What, are they covered in rubble?" I realized as soon as it was coming out that I was surrounded by four customers in a really uptight, older, rich, white community. So, that went over really well. Of course, Karen wanted to see my manager. I didn’t get a write-up, though.


#30 Man on the Moon

I can’t remember exactly where I was, probably school. There was a group of us playing some kind of trivia game. When the group was asked, “Who was the first person to walk on the moon?” without really thinking, I blurted out “Neil Young!” I was immediately aware of the mistake I had committed but the damage was done.


#31 Buy One, Get One Free

When I worked at a supermarket, a guy came through with a small bottle of vodka. I'd spent the afternoon stocking that aisle, so I mentioned that the bigger bottles were “buy one get one free” and only 10% more expensive. The guy gave me a sad look and said, “That sounds great, but whatever I buy I'll end up drinking tonight.” That was the day I learned to never comment on alcohol purchases.


#32 Two Hands

My cousin worked as a cashier back in the day. He asked a customer whether he'd like a bag for his purchase. The guy bought only one item, I forget what it was but it was definitely a situation where you'd think about not wasting a bag. "Yes! Why would you not automatically give me a bag? How else am I supposed to carry this?" My cousin said, "Well, God gave you two hands." He instantly regretted it.


#33 Arm and a Leg

My brother got a twofer when our grandmother had her leg amputated. We went to visit her the day after. During the conversation, we were talking about how expensive the hospital visits can be and without thinking he said to her, “I bet this visit is going to cost you an arm and a leg.” Not even five minutes later, he asked about the recovery time. But, he phrased it like, “How long will it take you to get back on your feet?” Thankfully, my family has a warped sense of humor and we just laughed.


#34 Pregnancy Pants

This was said by my husband, but I could see the look on his face. I was nine months pregnant. We went grocery shopping when we saw another pregnant lady. I said, "Oh, she's wearing the same pregnancy pants as I do!" My husband looked at me in disbelief and answered, "Really? Well, hers must be a way smaller size then!" I think I was mad at him for four days.


#35 Mysterious Bumps

When I was seven, I was hanging out with my sister and her friend. Her friend had really bad acne (they were about 16 years old). I remember looking at her friend and asking, "What are those bumps all over your face?" She walked away crying shortly after. I felt really bad knowing I hurt her feelings, but not knowing how. I had the almost exact same thing happen to me when I was an acne-covered teen. It made me laugh thinking about it.


#36 Joe Mama

I was talking with one of my friends. I don't remember what he said, but I made a "your mom" comment, only to remember that his mom recently passed away. I thought fast and said, in a joking way, "No, wait. That wasn't her. That was [another friend]s mom.” My friend burst out laughing and told me that her mom passed away as well. At least he was a good sport about it.


#37 You Have Friends?

I once said this to a homeschooled 16-year-old co-worker. I overheard her say something about hanging out with friends. "You're homeschooled! How do you have friends?" She and some other co-workers laughed, but I immediately felt bad about it. I apologized a few minutes later. She said it was fine and it sounded genuine, but I still felt really bad about it.


#38 Missing Button

The shirt of a girl in my class had a button open by accident and you could see her bra. I didn't want to tell her that it was open because that would have meant I looked. Later she noticed it and said out loud, "What? How long has my shirt been open like that?" I, as a genius, then unintentionally said, "too long.”


#39 Uptight and Bald

My boss used to make fun of my long hair (I'm a metal guy). I once gave that speech from Withnail & I about "hair are your aerials. They transmit information from the cosmos directly to your brain. This is the reason bald-headed men are uptight!" My boss was a little uptight bald man. I swear he was almost going to chew me out.


#40 Hot for Teacher

Two teachers in the staff room were talking about a pretty hot female member of support staff. One said, "Yeah, she was getting smashed by this trainee teacher for a bit. Then he dumped her and she kept pestering him afterwards, right bunny boiler apparently.” I just stared at him, wide-eyed, until he noticed the senior staff member who is the mother of said support staff sat right next to us. He looked like he was going to pass out.


#41 Just in Case

One of my best friends accidentally ended her puppy’s life by stepping on it. She was obviously crushed. Months later, I asked if she wanted to give the pet-owning another shot, but maybe take a bigger dog… just in case. I shouldn't have said that. She was heartbroken and didn't talk to me for months. I felt so bad.


#42 Spread Out

I used to work in a restaurant. I was seating a very attractive gentleman in a large booth because all of our smaller tables were full. He commented on how much space there was, so I said, “Just get on in there and spread your legs!” Immediately I thought, “Stretch, you idiot. Stretch your legs,” but didn’t correct myself. He left me a generous tip, so maybe he was into it?


#43 Negative Attitude

My ex-boss once called us into a meeting. She said that she noticed that our morale was low and was wondering why. Everyone exchanged looks, but no one wanted to say it. She pressed us, and finally I said, "Because you're so negative all the time." I could tell by the looks of my co-workers that I'd said something bad. It was the truth, though. Moral: bosses don't like being told the truth. She blamed me for some mistake that her husband did and fired me very shortly after that.


#44 Divorce Process

My dad's new girlfriend was telling me about the progress in her divorce case. I casually asked if my dad was getting divorced too, now that they were together. She gave me a funny look and said, "Honey, he is divorced." No, he wasn't. My parents had been separated for years and had a fully legal separation agreement, but never finished the paperwork to end their marriage. The girlfriend was not happy that she found out about it from me.


#45 Boss of Me

When I was six, my grandmother used to watch me after school until my parents got home. Apparently, I was annoyed by this. One night, she stayed for dinner and told me to put my napkin in my lap halfway through the meal. I screamed, “You’re not the boss of me anymore!” I then immediately burst into tears because I didn’t even know why I was angry with her and knew I had just made a huge mistake. My first, and last, spanking as a child.


#46 Wine and Flowers

Me and a couple of friends had been partying and were in the supermarket grabbing some bottles for the journey home. The guy in front of us was buying some wine and some flowers. Being a little tipsy, I was nudging the guy and said something like, "Looks like someone is in for a good night tonight, little romance.” The guy looked at the flowers and said no, they were for his parents’ grave. I didn't know whether to laugh or cry at that point.


#47 Brain Surgery

When I first joined my school, I told a kid who had major brain surgery that he looked like a stroke victim. One side of his face was a little bit lower than the other. It's all good now, though, we became best friends a year later. He was the first person in Ireland to have the surgery. There was a chance he would pass away during the surgery as well.


#48 Complicated Order

I was working a busy shift in the drive-thru of my work and I had just finished taking a semi-complicated order. From a combination of stress and the order, I proceeded to let out an audible sigh and said, “Oh my gosh...” I then realized I hadn’t turned my headset off! I felt so awkward when the customer got to the window and started apologizing for their “complicated” order.


#49 Huge Insect

I was with my parents having dinner and we were talking about random stuff. Then my mother started talking about an insect she found in the morning in her room and she said, "it was huge.” I still don't know why but I said, "just like my member.” I started laughing nervously while I wanted to bury my face in the rice.


#50 Don’t Lose Your Hair

A black co-worker of mine usually has a long wig, but one day she came in with a bob. I said "Wow, no way that's real!" But what I meant was, "No way you actually cut your hair that short.” I know she has a wig, but I just forgot and freudian slipped, saying her hair wasn't real. She's a really good sport and knows I'm not that ignorant, so we laughed it off. But, my face went so red. Never call a woman out on her wig.




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