These Cringe Moments Are Excruciating

September 30, 2023 | Taylor Medeiros

These Cringe Moments Are Excruciating

Throughout our lifetimes, from adolescence to adulthood, we have plenty of experiences we'd rather forget. Thankfully, people don’t tend to forget the mortifying things they’ve done. From biting a kid’s junk to not being chosen for a dance, follow along as these people reveal the most embarrassing details of their past cringe moments.

1. Another Year, Another Disappointment

I was a rather fat middle schooler on Valentine’s Day when they were handing out "candy grams" which were a piece of candy you could buy at lunch that would be delivered in the homeroom to your significant other on Valentine’s Day. It was a low point every year for me as a kid, as I never got anything and never expected anything. But, in the seventh grade or so, the teacher handed me a candy gram from the hottest, most popular girl in the class.

It was a paragraph love letter. I could not believe it. I was over the moon...then I realized with horror what was happening. The teacher looked at the card and saw that it was TO the most popular girl in the glass FROM someone who happened to have the same first name as myself. I had to hand it to her and return to my seat with nothing. I still think back to that time and want to throw up.


2. Not Following Cultural Customs

I was in the lobby of a guesthouse in Thailand waiting for our car to pick us up. The manager was a tiny lady who was standing with us and she had been so lovely to us during our stay. She spoke very little English, but when the car pulled up, she raised her arms up to me as I stood up and I assumed that she wanted a hug from me so I obliged, even though I recalled it was impolite to hug a Thai person.

As it turns out, she was gesturing for me to pull the cord on the ceiling fan in order to turn the fan on, because she couldn't reach it and I was tall enough. It was so awkward.

Cringe mimentsPexels

3. Messaging Machine Mistakes

This makes me want to die every time I think about it. When I was around six or seven, my best friend lived next door to me. They were the well-to-do type because they had an answering machine, while my family did not. This was circa 1995. So, I never really thought much about how an answering machine worked. I mean, I got the general concept, but I am an idiot.

Anyway, I would call their house before coming over and ask if Michael was home. From time to time, they would be gone to Disneyland or be making pottery or helping disadvantaged children or whatever rich people do with their time and I would leave a message. At first, I’d leave messages like, “Oh, you’re not home, just me calling, call me back.” Click.

After a while, I realized that you could listen to the message back. This is where it gets mortifying. Gradually I would start to leave more messages just to listen to myself talk because I was a little narcissistic jerk. Eventually, I would leave messages that went something like this, “I love Danielle, I want to have intercourse with her, we would have intercourse all the time, Danielle is so hot.”

Mind you, I really had no idea what intercourse even was, but I wanted to do it. And since I was an idiot and didn’t realize you could delete the message, my poor neighbors would arrive home to these gems. Needless to say, they made my parents listen to these messages and they talked to me about it. All I remember from “the talk” was that I wanted to die from shame, and I had no idea what intercourse actually was. WHY COULDN’T YOU JUST DELETE THE MESSAGES!?

Cringe momentsShutterstock

4. He’s Always Watching

I was 13 and at a female friend’s "family friendly party." All the kids were on the second floor. We were all dancing and trying to outdo each other in a comical way. I decided to get on all fours and pretend to smack by butt, wondering why no one was laughing at me, so I tried harder. Everyone gave me a weird look. I turned around—and my stomach dropped.

Her father, who happens to be a Minister, was just standing there looking at me. He didn't say anything, just turned around and went back downstairs. It still haunts me 19 years later.

Cringe momentsUnsplash

5. Same Name, Different Meaning

When I was around 14 years old, I used to play videogames all day. So, my mother made me go to a group therapy for gaming addicted people. So we made our way there and I entered a room full of people at least twice my age. After I stepped inside, the door was locked. This was to have a secure location to talk. That’s when it hit me. The German term for "gaming addiction" can refer to gambling as well.

So, here I was, 14 years old and in a room full of people who have lost their possessions/family over a severe gambling addiction that had ruined their lives and they made me talk about my gaming addiction. Lots of fun!

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6. The Perfect Storm

I was in community college at the time and two of my friends and I were starring in a student run production of The Complete Works of William Shakespeare, Abridged. The whole show is about three goofy guys acting out all the parts in every one of Shakespeare's works, so there's a lot of running around and instant costume changes.

Our core costume was velvet shorts, puffy shirts, purple stockings, and Chuck Taylors. We had been doing a lot of dress rehearsals to get used to costume changes and our budget was low so we had opted for the cheap stockings which began to fray at the crotch. About a week before our first show we decided to do a little promo show on the sidewalk in a big downtown open air mall to get people interested.

The show was going great. There was a decent crowd around and we had just finished the bit where we rapped "Othello, the moor of Venice," when I saw them in the very front. Two college age girls are leaning in towards one another and whispering and smiling and pointing at my crotch. I looked down...and wanted to throw up. The end of my Johnson had been out of the front of my shorts for god knows how long.

All the animated movement and the bad panty hose and the loose fly of the shorts had come together to create the perfect storm. I swiftly grabbed a kilt and wrapped it around myself and shuffled away once we took our bow. I made sure to take a needle and thread to those shorts when we got back. My face was so red. Dear god...there were children there.

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7. Definitely Not For You

I was at work on my birthday and saw a man walk in with a HUGE bouquet of flowers. I stopped the haircut I was doing, rushed to the front of the busy salon, all aflutter, and took the flowers from his hands. I didn't realize I was making a mistake until it was too late. Not only were the flowers not for me, the man wasn't even a delivery person. He was my new coworker's husband who'd come to bring her flowers.

He just stared at me while I gushed about what a great boyfriend I had, until he finally said, "I'm so sorry, but could I have those back so I can give them to my wife?"

Cringe momentsShutterstock

8. Middle School Dares

I was tormented by pretty much my entire class in elementary school, and I had a crush on this popular boy who treated me like dirt. On our sixth-grade field trip, we were all sitting around having lunch, and someone dared him to kiss me. He starts coming towards me and everyone is laughing and chanting like this is the most hilarious thing ever.

I grabbed my backpack and ran. My backpack wasn't zipped. All my stuff went flying. I had to turn around and go back to pick up my cassette tapes and walkman and stuff while everyone just laughed.

Cringe momentsShutterstock

9. All By Their Lone Self

I went to visit my grandparents in Delaware when I was 15 and my grandmother drove me out to Jolly Roger's Amusement Park. She didn't go on many of the rides, so I was always going up in line alone. I was last in line for the bumper cars and of course, there were no more cars left when I got to the front. I watched people have fun for 5 minutes and as I waited, nobody else got in line behind me.

Their fun ended and it was finally my turn. The operators let me get in a car and switched the ride on. I was hoping at least one of them would ride around, too, but no...they just watched me sit there. So, I started driving in circles and ramming empty cars. Oh but wait—it gets so much worse. As this was going on, a line started building up again. I saw those people and sat there again for a bit, looking from the line to the people in charge of the ride.

Nothing. I continued to drive in circles for the longest 5 minutes of my life as the line got longer and longer. My timer ends and the cars shut off. I'm sitting there thinking I get another go since that was pretty stupid of them. Nope, they came up to me asking for more tickets. Of course, I had none left and had the saddest, loneliest walk off of one of my favorite amusement park attractions.

Cringe momentsFlickr

10. Taking T-Rex To The Next Level

I was about 10 and going to a daycare, and it was pretty late because my dad tended to not care much about picking me up on time. Me and this kid were two of the last five or so kids to get picked up, and I was really bored and I wanted to play "dinosaurs" or something. So I went t-rex mode and started snarling around and such, but he didn't want to play and I just kept doing it. I don't know why, but I ended up biting him on his...private area.

The kid had to go into the bathroom, one with two doors and three toilets, but it was unisex essentially, and have his junk checked out by this enormous fat lady and another who was probably 60 years old. His balls were apparently red/irritated...because I bit them. The next day, the guy's older sister was berating me. I, like the genius child I was, threatened to do the same to her.

Cringe momentsShutterstock

11. Wandered And Got Lost

I went camping with some friends once and we ate some shrooms. At one point, I had to go to the bathroom, so I went to find the bathroom on the campground, did my business, and went back to our campsite. I grabbed a drink from the cooler and it was Bud Light and I thought that was weird because I don't drink Bud Light and neither do any of my friends, but I just wanted something cold in my mouth so I didn't care.

I sat down at the fire and started drinking. I realized everybody had gone quiet and was staring at me. First I was like "Why aren't you guys talking? Did I do something?" then "Why are you staring at me like that??" then it clicked "OH MY GOD YOU'RE NOT MY FRIENDS WHERE AM I?" I went to the wrong campsite and just plopped my tripping butt down at the fire with a family of four.

They just looked horrified. I'll never forget the look on their faces. This was years ago so maybe the kids are on Reddit now, if so and you're reading this, I'm sorry for ruining your camping trip.

Cringe moments

12. Couldn’t See It All

Here's one thing I hate about grocery store lines: They're all separate. I would much prefer that everyone wait in a single line and move to the next available cashier, like in customs. We all know how much we hate waiting in line and seeing everyone around us go much, much quicker. Well, I was having a particularly bad day, and I chose a particularly slow line in the grocery store. Ridiculously slow.

The lines that were twice as long were sailing through, and I wasn't moving at all. Then, I realized the problem. A horrible cashier was taking his sweet time, swiping groceries through one at a time, using only one hand. He didn't care. It was some teenager with a scowl on his face, probably forced to work there by his parents. Finally, I'd had enough.

I snapped, "This line is huge! Things would go a lot quicker if you used two hands." The two people in front of me turned and stared with looks of horror and disgust. Finally, the cashier, with a totally blank look on his face, turned toward me as well. His left arm had been amputated at the shoulder.

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13. Keep The Change

I was working at my first job at an ice cream shop. A customer's order came out to $7.50 and he handed me cash. I counted a Lincoln and four Washingtons. Perplexed as to why he'd handed me $9 for $7.50, I asked, "Keep the change?" He looked at me like I had three heads. Then, he got this sympathetic, condescending look on his face as if I was dumb. "Uh... I guess so?" he said.

I looked down again and realized he had handed me $8. I tried to explain that I had miscounted, but he interrupted me by saying, "No, no. That's fine. Keep it—help put you through college." Just the pure condescending tone made me feel like a complete idiot. I still think about it sometimes and cringe.

Cringe momentsUnsplash

14. The Stupidest Man Alive

I had an oral examination board when I was in the Navy during which I just completely froze up and forgot almost everything I knew about what I was getting examined on. I could barely get a coherent string of words out. It was three hours of me just sitting there dumb whilst my Captain and two more of my superior officers just asked me questions I couldn't answer whilst looking at me like I was the stupidest man alive.

It was excruciating and the most spectacular failure of my whole life. I'd spent months preparing and it just looked like I'd done no work for it at all. Suffice to say, my performance was so bad I got carpeted and did not get a second chance. I had no idea what happened to me, I could answer most of the questions now, no sweat. I ended up leaving the Navy very soon after that.

That was about six years ago. I couldn't care less about not being in the Navy anymore, it was the right choice for me and I'm more than happy with what I do now, but hoo boy, just thinking about that interview is enough to make my skin crawl.

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15. Stressed, Stink, And A Social Idiot

When I was 10, my dad had his co-workers over to our house with their families for a Christmas party. My mom was doing the whole hostess thing and had been stressed out. I went to use the bathroom in the middle of the party and it stunk something fierce. Being 10 and a social idiot, I then walked out into the big room with the party going on and yelled while waving my hands in a smelly motion "WHEWW, WHO MADE THE BATHROOM STINK SO BAD?!"

I can still picture my poor horrified and embarrassed mom's face when admitting it was her.

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16. Dad Always Finds Out

I found my dad's illicit VHS tape stash and took one of them around sixth grade....for learning and stuff. Anyway, I dropped it on the hardwood floor and busted the flap off when I went to put it back. I placed it back in the closet anyway. It was gone the next day, and he looked at me funny at the dinner table the next night...I always cringe thinking about this.

Cringe momentsWikimedia.Commons

17. Feeling The Pressure

I was 14 years old and at a basketball game. I had bought a raffle ticket to win the $10,000 half-court shot at halftime. My number was drawn and I remember trying to get my dad to do it for me, but he pressured me into walking down to the court. With thousands of people watching me in the audience, and x amount of people from home, I took the half-court shot...and I air-balled about 10 feet to the left and five feet over the backboard…

It was the longest walk in the world back up the stands and into the seats where my dad was laughing maniacally at me...It was worth adding that my childhood crush of four years was there with me because her dad and my dad worked together...that whole walk back I thought of the people laughing. I knew I'd have to sit another half of the game with her thinking I had no coordination.

Cringe momentsPexels

18. It's Not About You

A few years ago, I was good friends with the lead singer of an internationally renowned indie band. We had a falling out. A few months later, their next album came out, with a very suspicious song on it that ripped lines from emails this singer sent me and seemed to make fun of me. After two years of not speaking and stewing about this awful song, I sent them an email while intoxicated, vehemently accusing them of writing such a nasty song about me.

Their reply made me want to crawl into a hole. "That was about my ex-girlfriend. I have no idea how you'd think it was about you." I was so mortified I didn't reply and never told anyone.

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19. Hidden And Never Noticed

This was during hide and seek during a family party. 12-year-old me decided to hide in the bathtub. I pulled the shower doors closed and waited. Nobody found me, but within two or three minutes, my aunt came in to take a leak. She didn't notice me, I kept quiet for too long. I had to commit! The sound of her pee trickle still haunts me. Oh god, why…

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20. Lessons Were Learned

When I was in middle school, I had just started getting my period. Unfortunately, at the time, I didn't know that I had very heavy and long periods, which would later cause me to get anemia. One day, before I go to school, my period comes and I have absolutely no pads. So, my dumb middle school self decides to just stuff some toilet paper in my underwear to line it and I should be fine.

Yeah, well, I was wrong so, so wrong. Not even the first class passes and I'm leaking. Bad. Oblivious me doesn't really realize this until I get up from my seat and see a giant red stain. I ran out of that classroom so fast and called my mom to come pick me up. I cried for about the rest of the day as my mom tried to console me. Ugh, even thinking of it now sucks.

Cringe momentsShutterstock

21. Kept On Crying

I went away on a school trip with a bunch of people to participate in an art competition. It was a week long, and I looked forward to it quite a bit. I need to preface this story with the fact that I'm someone who rarely cries. I’m just not usually very emotional about trivial things. I arrived at the place, and I suddenly found that I wanted to go home.

I wasn't interested in what we were doing, the accommodation sucked, etc. To my unending embarrassment, I started crying one day. And...I. Could. Not. Stop. I remember being bewildered by my sudden onset of tears, and not being able to stop it. The one teacher was incredibly concerned, she was convinced something terrible had happened that I was keeping to myself. The stupid, lame reason was that I simply didn't want to be there. Somehow, years of not really crying hard at anything burst forth...and I cried periodically for two days.

My mom called me, and something she said just made me stop. After that, I had fun. I'm still kind of stumped at what all that was about, and I cringe every time I remember it. On the ominous side, that incident was the last time I cried that I can remember. Even more embarrassingly, I was 15 when all that happened, not ten as you might think.

I'm 20 now...I shudder to think what random incident might prompt my next tear festival.

Cringe momentsPexels

22. Good Intentions, Bad Execution

I was introduced to a Russian musician as "This is Rachmaninov, haha," and I said, "You're a lot shorter in real life!" because Rachmaninov was famed for being about 6'6', this guy was about 5'4. We all knew he was offended, but my intention was to make a conversational tidbit about Rachmaninov and not just rip on this guy for being short. I couldn't do anything to salvage that lead balloon!

Cringe momentsWikimedia.Commons

23. Breaking Bad Dancer

I was at a party when a girl wanted to dance with me and I didn't know what to do because: a) I'm a bad dancer, and b) I really liked her. She was really good and I had no idea what to do. Everyone was crowding around and watching us and a kid mimed to me "break dance." So, I got down on my knees and started swinging my legs around under my arms and did a handstand. It was heaps of fun and everyone was laughing at me, not with me.

Cringe momentsPexels

24. Cutting Cute Off

When I was in high school, I was sitting with my ex-girlfriend before class started. I was building a motorcycle in auto shop and brought a large chrome-plated castle nut to school with me to finish attaching the wheel to the frame...Well, we were goofing around and I thought it would be cute if I slid the lug nut onto her ring finger. Then, after the novelty wore off, it quickly dawned upon me that this won't slide off.

The threads of the nut were tearing her skin every time we pulled, like a sadistic Chinese finger trap. So first, I went to my shop teacher and we tried to use motor oil to get it off...a painful and un-fruitful venture which only led to me being insulted by my favorite teacher. So, I had to go with her to the principal's office and explain what happened.

Then, she went to the hospital. I went with her and watched as the fire department cut this super hard lug nut off her hand while all the firefighters laughed and insulted me. The nut kept heating up and burning the skin because metal gets very hot when being cut so this lasted quite a while.

Cringe momentsShutterstock

25. Swinging At The Party

A couple years ago, I threw a party at my home. One couple that I invited had just gotten into the swinging/polyamorous lifestyle, but hadn't really figured out the "do's and don'ts" of bringing it up in conversation. Instead, they were pitching it and themselves to everyone like they were selling Amway. They were insanely explicit, and they kept trying to get people to skinny dip in the middle of the day. It was painful to watch. Oh, and if anyone is curious, they just filed for divorce.


26. Keeping It Strictly Personal

I was exiting class and got a text saying, "Please help, campus center." I make my way over there, about a one minute walk. I see my friend "Mini" and there's what I assume to be Lord Neckbeard complete with sandals, white socks, cargo shorts, black wolf t-shirt, trench coat, fedora, and "beard," hitting on my friend. I approach, say hello and, "remind" my friend we have to leave. He introduces himself and says, "Well hello, how long do you last in bed?"

Cringe momentsShutterstock

27. Second-Hand Embarrassment

At my work Christmas party last month, five of my colleagues sang "Happy Xmas" while a sixth accompanied them on guitar. The guitarist was fantastic, the group as a whole sounded passable, but then one of them soloed on the "war is over / if you want it" part. She did it very loudly, way above her vocal range. We're talking falsetto territory here, with her eyes closed and emoting all the way.

It was just... excruciating. To make matters even worse, afterward, she kind of hung around the stage area smiling at people, like she was waiting for everyone to rush up to her and tell her what an accomplished singer she was. Most of us rushed to the door.

Young people are having a dinner party and making a toast.standret, Freepik

28. How Not To Make Friends

One of my high school friends is a bit interesting, to say the least. He wanted to make friends and was quite an avid anime watcher. I remember him going up to a girl in high school doing the whole "bowing" with a love letter behind the school gym kinda cliche. He walks up to her bows and at the top of his lungs says, "Will you please be my friend?"

The girl turns around and pulls out her headphones. She's confused and stunned. "Why is this boy bowing?" He then runs away.

Cringe momentsShutterstock

29. Left It All Behind

I was about 15, getting intoxicated with some friends outdoors and I went to pee behind a bush. I lowered my pants and crouched down, but mid-pee I noticed that I was peeing on my jeans. They were soaking wet, and of course, I didn't have any other clothes with me. My adolescent, intoxicated brain decided it was best just to go back home without telling anyone, leave all my things behind and walk for more than half an hour smelling of urine. I really don't remember what explanation I gave my friends afterward.


Cringe momentsShutterstock

30. It’s Clearly Mine Now

My significant other and I were meeting some old friends of hers who were in town for a day or two. I say "in town," but they were about an hour and change south of us. We met at a restaurant after a bit of a drive. Now, it was a hot day and my air conditioning was on the fritz, so it makes sense that I was thirsty. What doesn't make sense is that at some point after we got there, I just started drinking this dude's coke like it was mine.

It was kind of in front of me, I guess, but I hadn't ordered a soda. I had no reason to assume it was mine. They'd never met me, so it's not like I knew the

m and I knew it was cool. Nobody said a word the whole time. I realized I had been doing it when the waitress came around and asked for our drink orders. Best first impression ever.

Cringe momentsUnsplash

31. Impress Chicks, Ask For Pics

So when I was in my “impress chicks in awesome ways” stage, I thought it would be cool to memorize the opening lyrics to the show Crank Yankers, because I thought it was a cool intro. Fast forward to me on AIM chatting up the hottest girls at my school and copy/pasting that to everyone. At the same time, I was also in a chat room looking for some sweet bare-all pics to trade with random strangers.

The method to acquire said pics was copy/pasting a message about being a chick who wanted to trade pics for other girl pics. As you can probably already guess, I forgot what I had copied and totally sent the chat room message to one of my biggest crushes. Don't worry, I saved it with a good ol’ "my brother did it," then promptly signed off never to mac on girls on AIM again.

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32. And...Scene

In grade eight, I wanted to look "scene"...But I had thick, curly hair. The solution? Only straighten my bangs, of course! The problem was, I wasn't ready to fully commit to the look, so I wore polos, cargo shorts, and running shoes...whilst wearing my blonde half-Afro with straightened bangs. It was a sight to behold, to say the least.

Cringe momentsUnsplash

33. Phantom And The Parents

When I was younger, I was obsessed with the "Phantom of the Opera" and decided to re-enact it, with my parents as the supporting actors. I made a mask out of a white paper plate, wore a cape, and tried to perform the musical numbers as my mom filmed. College was a strange time…

Cringe momentsWikimedia.Commons

34. Spooked The Wrong Victim

There was once a technician at our house to fix a water heater about two years ago. I was walking by the bathroom when I heard the toilet flush, so I decided to lean flat against the wall by the door in order to scare my brother. Boy, did I give him a fright...But as you may have guessed, it wasn't my brother. I was 21 at the time, so yeah, it was super awkward and cringe embarrassing.

Thinking back now, the look on that guy's face was priceless when I yelled in his face the moment he opened the door.

Cringe momentsShutterstock

35. SchoolYard Pick Gone Wrong

When I was in the first grade, we used to have square dance lessons. Anyways, the teacher used to pick a random person to allow them to choose whatever partner they wanted from the class. I had a massive crush on this girl named Ashley and this particular time, the teacher picked me as the first person to pick a partner. I was FINALLY going to be able to dance with Ashley! I was pumped—but it turned into a nightmare.

As I began to look at the girls standing across the room, I made eye contact with Ashley. She was staring at me too. Unfortunately, she was staring at me so that she could make direct eye contact and mouth out the word "NO" while shaking her head no as well. I was already walking toward her and started saying her name by the time I realized she wanted nothing to do with me.

At this point, I am standing in the middle of the floor by myself, having said the word "Ashl..." And the rest of the girls, about 25 of them start to do the same thing she was doing, shaking their heads no. Literally no one wanted me to choose them. So instead of choosing, I told the teacher someone else could pick first. When she insisted I pick first, I picked the ugliest girl there so that no one else there would have to dance with me. So that sucked.

Cringe momentsShutterstock

36. Misfire and Miscalculation

I bought an airsoft when I was about 14 or 15 years old. It was a gas-powered one, so you could shoot "empty" rounds with it doing the gas cockback thing. I had the great idea to scare a friend by firing an empty round in his face. However, I had forgotten that simply removing the cartridge did not disarm it, and it automatically placed a pellet in the barrel after each shot.

Basically, there was still a bullet in there. So, I pointed it at his face and fired. His lip started bleeding, and a wave of adrenaline took my body, immediately realizing what happened. I remember the sadness and confusion on his face. I started apologizing profusely, trying to explain what had happened. Not knowing what else to do, I reached in my pockets and gave him 10 dollars...

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37. The Cringe Continues On

One Saturday night three and a half years ago, I went out to play cards with some friends. I was pretty tired and after only about an hour or so, I decided to call it quits and go home. When I got home, I noticed the car of one of my wife's co-workers was in the driveway. You can already see where this is going. I walked in and no one was in the living room but two empty drink glasses.

I walked to the back of the house to the bedroom, where the door was closed but not locked, and opened it up to see... well you pretty much know what. I divorced her three years ago. I'm single and I live alone now but I still get a tinge of anxiety whenever I come home from a night out as I approach the door to my apartment. It sucks, but I can feel my heartbeat in my neck as I unlock the door.

It passes after a few seconds after I get a grip. I wish myself or no man to ever experience this in person.

Cringe momentsPexels

38. Nothing But Fake Friends

A couple of years ago, I was really depressed and I ate my feelings often. So, one day, I went to the grocery store—but I didn't realize I was there at prime time rush hour for families coming home from work. Anyways, I filled up a basket with a bunch of bread and donuts and ice cream and candy and stuff. I felt really embarrassed about all the stuff I got so I "talked on my phone" and made it look like I was bringing home stuff for a bunch of other people.

When I got to the checkout line, the lady behind me was staring at me like I'm disgusting with all the stuff I was buying. So, I very loudly talk into my phone about why I have all this food, and I start putting my stuff on the conveyor belt and my phone rings, like REALLY loudly while I'm supposedly talking into it. The cashier started laughing, everyone in line behind me started laughing. I wanted to die.

The bag boy asked if my friends would prefer paper or plastic. I turned really red and almost started crying and then just paid for my food and left. It was probably the worst moment of my life so far.

Cringe momentsShutterstock

39. Not Educated Enough It Seems

When I was young, I overheard my mom telling my dad how she was going to be on her period next week. They were also going on some kind of vacation that same week. It was their second honeymoon. I asked what a period meant, and she stuttered a bit and told me some things about how it means "honeymoon."

Well, a few weeks later, I overheard some girls of a higher grade than me talking about their first period. Being as obviously well-educated on the matter as I was, I wanted to impress some older Bettys, so I proudly announced how my mom just went on her second period last week. They laughed. It was years before I understood why.

Cringe momentsShutterstock

40. Right To The Bone

I work in medicine and I have to give patients injections. No problem, I've given injections hundreds of times. This one time, I was giving a vitamin B12 injection, which goes in the upper deltoid. I prepared the shot, checked the muscle, cleaned the area, and I like to just go in fast so the patient doesn't even realize it is happening. This particular time, I didn't really account for how thin my patient was and the fact that the needle, which is normally 3/8", was 1" long.

I poked him and it went so deep into his skinny arm I am absolutely positive I hit his bone. I felt the tip hit something hard and abruptly stop. I could almost feel the end of the needle bending against the solid mass. I cringed and looked at the patient, but apparently he didn't notice. I pulled out a bit and finished the injection.

I could feel his bone for a full three weeks afterward and can still recall it vividly. I always make sure to use shorter needles on thin people now.

Cringe momentsShutterstock

41. Those Dang Holiday Reps

I was a lot younger, maybe nine, and we were on holiday in Spain. There was a resort close to us that had some Swedish people helping out, kind of like holiday reps for kids. They encouraged me and my sister to sing karaoke the coming night. At first we were scared, we had never sung in front of people before, but we figured why not.

Hours before we walked on stage, we decided on our song. Of course, this was the time when Busted was still big, so everyone knew the lyrics to "Year 3000" As we walked out on stage, ready to belt out the tear-inducing tones of "Year 3000," they didn't give us microphones. It was a dance show. Yep, a dance show.

We proceeded to perform the most awkward dance translation of the lyrics of “Year 3000” I have ever been part of or witnessed. After the awkwardness was over, I bolted off stage, and back to my bedroom. I hate those holiday reps.

Cringe momentsShutterstock

42. Flipped Them The Bird

I was, for the most part, alone on a playground across the street from where my mom was in a meeting with her club. I was on the tire swing, trying to make it spin as fast as I could. I got it going pretty good, and as the rest of the playground whipped past my vision over and over I saw two girls roughly my age walk up to me. "Hey, can we use the tire swing? You've been on it for a while."

For some reason, centrifugal blood loss to my brain I guess, my response is to flip them the bird. Or in this case, spin them the bird. "What's he doing?" "He's giving us the finger." But, it was the way she said it. Not hurt, not impressed, not even surprised. Her tone was like ice, and it made me feel like a subhuman piece of garbage.

I immediately stopped my spin, slunk out of the tire swing, and ran, albeit clumsily and sort've sideways, across the street to my mommy. When I stuck my head in the door I had tears running down my face, and she urgently came out to see what was wrong. "I..(cry)..GAVE A..(cry)..GIRL..(cry)..THE..(cry)..FINGEeeRrR!"

Cringe momentsPexels

43. Run And Never Look Back

I'd love to say this happened a while ago, but it didn't. It happened a year and a half ago. I was going to the gym, and I was on my period. I ran out of pads, so I decided to stuff my shorts with toilet paper as a last resort. No biggie, used to do it all the time. So I'm on the treadmill at the gym. The gym is fairly crowded, with the lunch-break crowd.

I'm on a machine that's in the front row of three rows of treadmills, doing a steady jog for about 45 minutes, then I'm ready to get off. So I turn off the machine, and turn around. That's when I saw it. There was bloody toilet paper. All. Over. All over the treadmill, all over the floor. Somehow, I didn't realize that my shorts were too loose and the toilet paper would fall out. No one told me. I haven't been back to that gym. And needless to say I was never unprepared again.

Cringe momentsUnsplash

44. So Not Slick

My first date with a girl was at a theater. I went to put my arm around her, but I couldn't get it behind her head...So, I just kind of sat there for a couple seconds with my arm on her head. Then, when she gave an awkward giggle and leaned forward, I actually said, "Give me a break, I'm nervous." I’ve only been on one date since then. I have flashbacks to that moment whenever I'm about to ask out a girl.

Cringe momentsShutterstock

45. The Weird Awakening

I was about six or seven when I realized that rubbing myself on one of those giant exercise balls felt really good. I told my cousin and he tried it, but said it didn't feel good and that I was a liar. Later that year I remember we were play fighting and then somehow I ended up rubbing up on him in the same fashion. Our parents pulled us apart. I hope with everything in me that he does not remember this. Also, I am female. Ugh.

Cringe momentsShutterstock

46. Scarred For Life

In the seventh grade, a couple of friends and I go to friend X's house to play Super Smash Bros Melee. After playing for a bit, friend X decides to go to the bathroom. Being a horrible seventh grader, I got the idea to go on his computer and look inside his trash bin because, "I bet he deleted illicit photos before we got here LOLOLOLOL, right guys?!"

We go on his computer, and lo and behold, there are pictures of a middle-aged Asian lady getting undressed for a dude on a webcam. After X comes back, we ask him about the pictures. He seems genuinely confused. We showed him, and he just started screaming. It turns out the pictures were his mom getting undressed for a random guy on a webcam…

I never realized how potentially scarring that moment was until a year ago. X and I went to different high schools, and we kind of stopped talking, but we go to the same university now. Even though we still don't really talk, I will never forget him.

Cringe momentsShutterstock

47. Not Self Aware Enough

When I was in my final grade of elementary school and around 12 years old, I got overly self aware of the fact that I "leak." It was basically pee droplets in my boxers due to not shaking enough. So, I figured one summer day that the thing that my mother kept next to the toilet must be to prevent this. So the brilliant 12 yo me took a menstrual pad and put it in my boxers, happy that my problem has been solved.

Later that day I was in a hurry to catch a bus, so I ran, getting pretty sweaty during this. But, lucky me, I caught the bus and even found a seat in the front row with my math teacher and her daughter, who was in my class. Also, I happened to have a crush on her, which doesn't help this story at all. I paid the driver for the ride and said hello while passing them. I couldn't shake the feeling that they were looking at me somewhat weirdly. Something was definitely wrong—but it was so much worse than I'd imagined.

I was walking to my seat when I heard the voice of an old lady who stood behind me in line. "Young man, I believe you have dropped something." I turned around. Everyone, including the driver, my teacher, my crush and the old lady who was in the line behind me were staring at me. I was mortified when I saw the reason: The menstrual pad had slipped from my sweaty boxers, through my shorts, and fallen in the middle of the passage in its sweaty, crumpled, peed glory.

So yeah. The rest of the school year didn't go well. Neither did my love interest with the crush. I had no idea back then that you are supposed to use a sticker to make the menstrual pad stay in your pants. So, I guess, that's one lesson learned. And yes, I'm male.

Cringe momentsShutterstock

48. Picture Frames And Printers

I had a crush on a girl in high school for about two years. On Valentine's Day, I went to Michael's craft store, got a picture frame and crafts, and painted her a pastel-colored picture frame with her name on it. It looked okay. I gave it to her, she was excited and hugged me. Then she got up, left for a minute, came back, and put it on her nightstand with a picture in it.

Before I looked, I confessed my love without making eye contact or breaking a whisper level. Then, I looked the picture of her and her new boyfriend she just got. Then, she noticed I was close to crying. Then, her mom came into the room and was having problems with her printer. So, I stayed for the longest 30 minutes of my life holding back tears trying to fix her mom's printer while I waited for my mom to come pick me up. Oh my God, worst flashback ever.

Cringe momentsShutterstock

Sources: ,

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