June 9, 2023 | Eul Basa

Cringey Memories


From "Why did I say that"? to "I’ll never live this down", we’ve all been haunted by embarrassing moments in the past that we’d prefer to forget. But few among us are brave enough to ever speak them out loud. These people took to Reddit to share their most memorably cringey experiences that are guaranteed to make you laugh and cry at the same time.


1. Boss Move

My first big meeting at my job with all the head honchos...and I had to leave to go to a doctor's appointment. I was so nervous about walking out of the meeting, I actually said to my boss's boss "good night, I'll miss you"! The second the words left my mouth I turned bright red. My boss found it hilarious and told me as I shuffled out the door.

cringey memories

2. Au Naturel

I was working backstage in a production of The Addams Family (the play). I asked the girl playing the old lady if the effects makeup they used to make her teeth look all old and gross had a funny taste. Then she suddenly burst into tears.

They hadn't put any makeup on her teeth.

Cringey MemoriesPexels

3. Radio Silence

I was a big fan of a certain DJ on a station I listened to via the internet. I got to writing regular emails that he would read on air. I was witty! I was funny!

I happened to plan a vacation that involved being in the same city as the DJ. He told me I should stop by the station and meet him.

I did. I never, ever, ever thought in a billion years he would put me ON AIR. And he did. And he asked me to read a promo for another DJ who has a difficult name. And I could not pronounce it. And I was desperately UNFUNNY in the banter he tried to engage me in.

My embarrassment went SO deep that I felt I was almost having an out-of-body experience. "This is not happening. It simply cannot be real life".

I turned maroon, I soaked my clothes in sweat. I was shaking when I stood up to leave.

But I survived.

And oh, I was 40-something when this happened. And yes, he was in his 40s and knew my age.

And bless him... he mentioned me in a nice way in the book he later wrote about his years as a DJ.

Cringey MemoriesPexels

4. Cringey Confession

Back when I was 15, I was leaving Ireland to move to the UK, and I admitted to my friend that I'd been in love (I was not really in love at all, but I thought I was) with this girl in our class. She was all I ever thought about. As I was moving, I knew I would never see her again, but for some reason I wanted her to know how I felt, but I couldn't tell her myself. So I wrote a cringy note and left it in her bag one day. But it gets worse. A few days afterwards, I texted my friend, telling him to tell this girl that I love her and will miss her very much.

He texted back, saying he showed the text to her. Her reaction was apparently not good at all. I felt like a complete loser but then, whatever, I was moving away.

One year later we moved back. I was back in the school, back in her classes. Yeah, I kinda never said a word to her for the next 3 years. I still hate my 15-year-old self.

Cringey MemoriesPexels

5. Shake It Off

I stole a handshake from a guy walking right behind me. Not a wave, not a high five, a literal handshake. I just grabbed his hand and looked at him, then he looked past me. I turned around, and my stomach dropped. There was another guy just standing there perplexed with his hand out. The only thing I could do was walk away without saying a word.

Cringey MemoriesPexels

6. Keep The Change

I was at the grocery store purchasing some cookies for my school very early in the morning at around 7 am.

Being in a rush, I quickly handed him the cash and started bagging my own few items. As I turned to leave he held out his fist. Not sure what he was doing, I decided to fist-bump him.

He kept awkwardly staring at me until he said, "do you want your change"?

Ahh, that still kills me today

Cringey MemoriesPxhere

7. From Hero To Zero

I did a similar thing a little while ago that still haunts me. I went to a friend's for drinks before we were going out and his housemates were there playing beer pong. I'd never been particularly amazing at it, but I joined in and by pure luck sank three shots in a row, which with the rules we were playing meant that I took out all of their cups almost immediately. Everyone was cheering for this random beer pong god that had just walked in and I got a bit caught up in it.

A guy to my left reached his hand out towards me, which in my worked-up state I grabbed and shook. I then realized the guy hadn't been looking at me, and from that and the confused look on his face, I decided to turn around only to see his girlfriend handing him his phone behind me. People saw. They noticed.

It immediately took the wind from my sails and I can't think back on that moment without wanting to punch myself.

Cringey MemoriesPexels

8. Stalk Around The Block

In sixth grade, I had a crush on this girl and so I followed her around on my bike at the homecoming pep rally, at our town square. I was absolutely conspicuous, and her and her friends even ran away one time when they noticed me once. Then when I was riding around looking for her, I was stopped by a guy and his friends from a different middle school, and he asked if I was following his girlfriend around.

I said no, but he knew I had, and said to stop cause I was creeping her out. He ended up being friends with some friends of mine and told them about it. I didn't live that down for a long time, and it makes me cringe every time I think about how lame I was.

I have a whole list of awfully embarrassing middle school stories.

Cringey MemoriesPexels

9. 60 Minutes Of Shame

One of my best friends had a radio show on our university's station. I liked a guy in one of our classes and my friend and I thought it would be clever for him to interview me (off-air) about my interest in that guy. We put the interview on a disc and gave it to him.

The feeling was not mutual. I graduated five years ago and I'm married now but this still makes me cringe so hard.

Cringey MemoriesFlickr, Ivan Radic

10. Watch Where You’re Going

I had gotten hooked on Rubik's cubes during college, so I carried that thing everywhere, playing with it as I walked to and from class.

So I walk into my dorm building, up the stairs, and to my room, mostly focused on the Rubik's cube. I open the door, walk through the kitchen (they were suite-style dorms), and I notice a girl doing something in the fridge. No biggie, she's probably with one of my roommates. I open the door to my room, and immediately start noticing something strange with the decor, and then I noticed two girls in the room sitting on either bed.

Then it hit me. I started backing out blurting explanations. To this day I still remembered the horrified look on the girl's face as I backed past her. They followed me to the door and slammed it in my face, partially pushing me out with it.

Then the screaming started. To this day I don't know why they started screaming, but they did. I got out of there. I later heard from a friend on that floor that the girls apparently had the RA looking for me.

Cringey MemoriesPexels

11. What’s Down, Doc?

I had a disgusting crush on this 8th grader when I was in 7th grade.

Me being a creep, I found out his dad was a doctor. My stupid brain decided that would finally be how I start a conversation with him. So I go up to him one day after school and I'm like:

"Hey! Your Dad is a doctor right"?

He looks at me strangely and says yes.

And I open my big dumb mouth and say, "He's really great! I go to him a lot"!

He gets this very confused and slightly disgusted look on his face and walks away.

Come to find out, his Dad was a gynecologist. :/

Cringey MemoriesPexels

12. Mardi Gras Faux Pas

I went to a really swanky Mardi Gras event in Louisiana as a guest and didn't know that the buckets of drinks were ordered per table because people were up and dancing. So I grabbed a drink from a table and was sitting nearby and my wife nudges me and says, "That dude at the drink table is seriously mad and he’s looking right at you". I just froze up for some reason, like do I face him or just awkwardly stare in every direction but his the rest of the night. I chose the latter.

I felt bad and just left the drink where I sat, unopened after like 30 min. If I had just gotten up, apologized, and given it back explaining the mistake it would have been no big deal, but as each minute passed it just got worse and worse. I still think about it while I try to go to sleep sometimes and the cringe keeps me awake...

Cringey MemoriesPexels

13. Lesson Learned

When I was 16, I ran into my mom's best friend in the grocery store, and said "Mom didn't tell me you were pregnant! When are you due"?!

"I'm not pregnant, I'm just fat" was her reply.

I've never made that mistake again. I could be in the delivery room with a woman, and see the baby's head crowning, and I'd still ask something like "so, do y'all plan on having children"?

Cringey MemoriesPexels

14. Nice Save

I had a close call with a woman from my old job. We were both clocking in and we said hello, and I asked her "so is it a boy or a girl"? As soon as I said it I recalled how much of a taboo asking about pregnancy is, so when she looked at me with a combination of perplexity and hurt in her eyes and said "...excuse me"? I had just enough time to snap to a flimsy cover: "Oh sorry I uhh... heard your department was getting a new employee. Is it going to be a guy or a lady"? She said they weren't getting an employee and I said it must be maintenance then and I ran away faster than a 250 cp Zubat.

Cringey MemoriesPexels

15. Voice Of Treason

In the 9th grade some older friends asked me to be the keyboard player in their band. My third time playing with them on stage, the lead singer and the guitarist said that they were gonna be late so it was just myself, the bassist, and the drummer and we had to start. After a quick discussion, the drummer and bassist told me that I had to sing, and I begrudgingly accepted it. It was going well until we got to our third song which started with a drum solo. The drummer for some reason couldn't remember how to start so I started playing hoping it would jog his memory. He couldn't figure it out, so I went on to the first verse.

The moment I started singing, puberty shoved its dongle down my throat and I had the worst voice crack I have ever had to this day. Everybody stopped and looked at me. I panicked and I left the stage. Holy Jesus. Even now, four years later, every time I'm with someone who was in the crowd or with my previous bandmates, it gets brought up and another part of me dies.

Cringey MemoriesPexels

16. Off-Color Joke

This was actually my mom, but unfortunately I was right there. When I was doing a study abroad year in college, my mom came to visit, and we stayed with my French boyfriend's family during the holiday. They were really nice people who ran a program that helped blind people. At the time, my mom didn't know they worked with the blind. They spoke some English, but my mom didn't speak any French at all.

One night at dinner, someone was telling a story, and my mom said, "I guess you could say that's like the blind leading the blind". Silence. Louder this time. "THE BLIND LEADING THE BLIND. GET IT?? HAHAHAAAA"! They just sort of smiled politely.

Cringey MemoriesPexels

17. How (Not) To Comfort A Friend

A close friend had been dumped by her boyfriend and kicked out of her house on the same day. She called me in tears and I invited her round my house for a couple nights just to let her gather her thoughts. Now, I'd never done anything like that before, and I couldn't remember the last time I had anyone around my house, so I had no idea what the heck to do.

When I'd shown her around the house and introduced her to my parents, we went to my room where she ranted about what she was going to do and how it's gonna be hard to get back on her feet etc. I was putting quite a few hours into playing World of Warcraft during that time, and I hadn't logged into it that day, so after she was done, I kinda said "Soo, is it alright if I just play some WoW"?

I'm so bad at this stuff.

Cringey MemoriesPexels

18. Incognito Mode

I was at the cinema with my boyfriend at the time, the theater was pretty empty and we were on our own in the middle of a row. I got up to go to the bathroom and on my return I quickly went and took my seat. I turned to look at my boyfriend, only it wasn't my boyfriend, it was a stranger, and on the other side of him, was his girlfriend who was scooched down in her seat so I hadn't noticed her. Then I spot my boyfriend, two rows in front.

I'll admit I was so mortified that I panicked and as to draw less attention to myself I sat there for a minute before getting up and going to the bathroom again. Where I took off my jacket, put my hair up and did my best to look like a different person. I went back in and sat in the correct seat and proceeded to die inside for the next hour. As soon as we left and reached the safety and anonymity of the carpark I have never laughed so hard in my life. Fourteen years later I still cringe when I think about it.

Cringey MemoriesPexels

19. Low Five

It's Kindergarten, and we're walking off the stage into a small hallway next to the gym. The hallway leads to the school's lobby, and that's where our parents are waiting.

I'm at the head of the line. Behind me are Adam and Ben - they're two particularly talented five year olds, and they just had a duet ("ABC" by the Jackson 5.) They just did their solo, and returned to their spots on my right. I bowed, turned left, walked out the gym, turned right, and headed down the hallway. Adam and Ben are behind me.

Our principal walks towards us. He crouches down, puts up a hand for a high five, and says:

"You two were great"!

I only say that sweet, sweet five, coming at an intercept vector. I leap off the ground, slam that high five, and give a little "Yeah"!!!

I took two more steps before I processed what he said and a deep shame overcame me. I walked to my parents, and took another step towards a life of c o n s t a n t a n x i e t y

Cringey MemoriesFreepik,freepik

20. No Contact

One day I went to visit my optician to purchase some contact lenses. I saw a really cute girl behind the counter, whose job was to introduce me to some contact lenses and showing me how to put them in etc etc.

So I already decided that I was going to flirt with her and try to get her number. She filled in some papers for me and I confidently said "Oh are you writing your phone number for me?"

She giggled and smirked while looking into my eyes, and I suddenly knew that I got this in the bag. THEN are you ready for the cringe? In the middle of her trying to explain to me how to put in the lenses, I pretended to mishear her and said "Wait are you talking about the birds and the bees"? With a cocky smile.

When I said that the lights in her eyes went out… and her grin just kind of flattened and she just looked at me from an awkward position, and immediately turned all professional all of a sudden. The session lasted about 30 minutes with me giving apologetic advances, and her just shutting me down .

Sufficient to say the least, I left the optician shop with red ears and a sheepish look. Till this day, I silently cringe everywhere I go, and in random places just shaking my head.

Cringey MemoriesPexels

21. Freudian Slip

A female friend of mine - to whom I was admittedly attracted - had been expressing her reservations about an upcoming vacation with her family. Though it wasn't being overtly presented as such, the trip was meant as a way of re-solidifying her parents' marriage, which had been a touch rocky at the time. They would all be driving from San Francisco to Redding (which is a small town in the middle of absolutely nowhere in Northern California), where they'd stay at a bed-and-breakfast inn for a weekend before continuing northward for some unknown destination.

In keeping with the alleged purpose of this so-called vacation, my friend's parents had booked two rooms at the inn. To her dismay, though, my friend discovered that her mother would be occupying one room, her father would have the other, and that she and her sister would each have to bunk with one of their parents. This was worthy of lament on its own, but it was made unforgivably worse by the verbal diarrhea that I offered in an attempt at providing comfort:

"Aw, it won't be so bad"! I told my friend. "Your father will probably enjoy sleeping with you".

A moment passed before I realized what I had said. Then, with a feeling of growing horror, I tried to explain myself. "Wait, I didn't mean it like that"! I hurriedly said. "I mean, like, he's probably sick of sleeping with your mom. No, wait, I mean... I just mean that he wants to spend some quality time with his daughter".

If I had stopped there, I might have been able to salvage the situation... but as it happened, I decided that the best course of action would be to keep talking. "I can't say that I blame him, really. I'd love to sleep with you".

She and I don't talk much these days.

Cringey MemoriesPexels

22. Sorry, Bro

It really makes me cringe and sick to my stomach when I think about how mean spirited I was towards my little brother growing up. He's a year and a half younger than me. I don’t know why I was so mean spirited. Anytime he wanted to hang out with me and my friends I'd say things like "get your own friends" or call him fatboy and other horrible things to tell your younger brother.

Looking back on it today, I realized he just wanted to hangout with his big brother because he looked up to me in a way. It breaks my heart whenever I think about how mean I was. Our parents would drill into our heads "No matter what, that is your brother and nothing will ever change that". I do my best today to show my brother that I love him but I have a really hard time opening up. It's just awkward for me. But when I'm alone thinking of it I can't help but get teary eyed

Cringey MemoriesPexels

23. Call For Backup

So this is the first time I asked a girl out. This was I guarantee you cringier in person too.

Something you should know is that I was a helpless shy nerdy kid who had had a crush on this girl for at least a year. I was so certain that she liked me back so, so certain. In hindsight this is just because I was desperately hoping she did in fact like me back and my friends had been telling me she did.

It was a long recess that day... "Hey Sarah" "Oh hey there guy" "Sooo there's something I've been meaning to ask". "Oh yeah what"? "Do you like me"? "Of course I do". "I mean do you like like me"? "........No" "Um.... Yes you do". "What?!? No I don't". "Look Sarah I'm pretty sure you do". "No I really don't". "Oh... tears forming". "Stay right here, I’m just going to get my friends". "Oh ok".

I ran away and cried my eyes out for all recess then got bullied for the rest of the year for that.

Cringey MemoriesPexels

24. Awkward Phase

Back in high school, I was really bad at talking to girls I liked. Like, I literally could not talk to any girl I had a crush on in person. I had many awkward encounters because of this, but the worst was when I "fell in love" with a girl I exclusively talked to over AIM and text messaging. I would see her in school, and we would not speak, but I felt safe talking to her behind technology. I think she really just felt bad for me, so she would talk to me this way for hours, but it was pretty creepy of me in all honesty.

Eventually I wrote this long text message to her about how I loved her and couldn't live without her. Little did I know, it was just my hormones. When she rejected me, we didn't talk anymore. It still kind of bugs me to this day that I was just that socially awkward.

Fortunately for me, I eventually found a girl that was just as awkward, actually talked to her in person, and have been with her ever since. In fact, we are getting married next year.

Cringey MemoriesPexels

25. Double Face Palm

One time a customer (newspaper sales) had a tractor tire explode in his face, causing damage to the pinky and ring fingers on both hands. When he returned to work, and was recounting the accident I flippantly said "At least it was fingers that you don't use often". I mean, gah.....who says that?!

Sssooooo, a few months later, I'm waiting for him to email me an ad, it's after the deadline and he's the last person that we're waiting on, right? So, I call him "Joseph, I want you to take your gimpy little fingers and email me that ad right now"! Cue radio silence, followed by a very awkward apology from me. I did get the ad, though.

Man, I still think about that all the time and have actually addressed it face to face. He was cool about it, but admitted that he was stunned and hurt. And who could blame him?

Cringey MemoriesShutterstock

26. An Offhand Remark

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.

Because 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. Lines twice as long were sailing through, and I wasn't moving at all.

And then I realized the problem. The cashier was taking his sweet time, swiping groceries through one at a time, using only one hand. He didn't care. He 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, and 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.

Cringey MemoriesPexels

27. Trip Of A Lifetime

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 it and I realized everybody had gone quiet and was staring at me.

First I was like "Why aren't you guys talking"? 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 self down at the fire with a family of 4 (a husband and wife and two kids). 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.

Cringey MemoriesPexels

28. Dating Disaster

I didn't hit puberty until about 16. Needless to say, I was a bit behind in how to deal with the ladies... so I got an internet girlfriend. I got my family to drive 900 miles to visit her for two days. A 48-hour cringe is what that trip was. It was so bad that when I was in the army I could get out of trouble with my drill sergeants by telling tales of my awful dating experience.

Take, for starters, the fact that both of our families were meeting at a pizza place. I walked in, saw her, and ran back out of the restaurant and pretended like I didn't see her, I was so scared. Then I came back in, sat next to her, and was too afraid to make eye contact the entire time. My head was on a 90-degree swivel between my mom straight across from me and the soda machine to the left of me. I wish I was joking.

You can imagine how the rest of this night went if I spent my first hour trying to work up the courage to look in her general direction. Now, this girl, let's call her Schmessa, worked at an ice cream place. Her broworker had been teasing her that I was only traveling all this way to "get some". So we go to her workplace and first we see a guy that I've talked to before who's pretty cool. He says, "Alright nice to meet you" and tries to do a super cool bro handshake. I try to keep up but I mess it up about 4 times before he says "Nevermind, nice to meet you" and goes back to work. You can't imagine how embarrassed and scared I was from that alone. But it wasn't even close to over.

We go into the ice cream place, she orders (because I have to try a malt—turns out it's basically a milkshake, I don't know) and then this guy behind the counter comes over to us and asks me "So did you get some yet"? "Huh"? "Did you get some yet"? "Oh uh no we're good, she just ordered". Idiot. He was asking if I "got some" and here I am thinking he didn't just see us order. He laughs and walks away while she loses what dwindling respect remained for me.

WELL, super. The agenda from here is to go to her house so our families can pow-wow, then we have to check into our hotel room, then Schmessa and I will be going to see a movie—any movie. The family stuff is awkward but I get through it without any major incidents that make me feel like my face is melting off. We go to the hotel room to check in and my mom (probably knowing what an abysmal dork I am) has okayed me to get my own room (score! If I wasn't me, that is). My stepdad was unaware and he was hesitant to let me do that, but reluctantly agreed. As luck would have it, my room is on the other side of the hotel from my parents, THE SKY IS THE LIMIT!

So it's time to unpack our stuff, Schmessa comes with me to my room, and just like any hormonal teenager I... panic and start trying to come up with anything to do. Be funny, be aloof, be random, do something quirky. I'm a mess, I hate to even admit this. All I can come up with is to get really excited about the hair dryer. Jesus Christ, it's been almost 10 years and I still cringe about this. I yell out to her about how great the hair dryer is, she should come look. I'm dumping water on the counter and this amazing stupid hairdryer is drying it up SO fast. I can't possibly relate to you how bad I hate myself for this.

Mission success, I've taken enough time that it's time for us to leave for the movie. Being the inner-neckbeard I am, I brought a sweatshirt along; not because I need it but because if she happens to get cold what a suave hero I'll be when I say "Here take mine". We get to the movies and as if on cue she says "Hmm, I'm kind of chilly". Well it's about this time I notice that I have forgotten the sweatshirt in my parents car. I could have pulled her close to keep her warm or even "Not really, maybe you're just a wimp", would've gone over better than "Shoot, I brought a sweatshirt exactly for this occasion"! "It's fine"! "No, god how dumb I don't even need the sweatshirt. I was going to bring it for you but I left it in my mom's car"!

The fact that I wasn't struck by lightning at that moment is proof that God is not merciful. As we're nearing the ticket counter I realize that I have no idea how to buy a movie ticket. I've done it before but I never thought about it and now that I'm thinking about it, I have no idea what I normally do. "Two for Ocean's [Number], please" sounds right but is it too cliche? Do people actually say that or is that just on Happy Days? What else would you say? Time's up, we're there, I have to use the only phrase I can think of. It actually goes really well, my message gets across and the guy gives us our tickets without any weird looks. Thank God she didn't want snacks, that would've been impossible to get through.

I don't think I have enough space to get into what disgusting mess happened inside the theater right now, or the awkward body pretzel I invented to avoid kissing her the next day at the zoo, but trust me that it doesn't get much better from here. The fact that I remember this so vividly after 10 years is testament to just how catastrophic this trip was.

But thankfully, things have gotten much better since this experience. I learned from it that girls aren't fabled mystical creatures and if she's into me I can just be myself and if she's not into me then who cares what I act like anyway? Being honest, Schmessa and I would've never worked out. We had drastically different views on just about everything but being young I figured that none of those things mattered, the only thing that mattered was that we were "in love". Since, I've had enough positive encounters with women and no other experience ever came close to being this awful, thank God - no one deserves that twice. I now have a beautiful wife and 2 kids and actually interpersonal skills are a big part of the work I do now.

Cringey MemoriesPexels

29. Big Stink

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"?!

My poor horrified and embarrassed mom's face when admitting it was her.

Cringey MemoriesPexels

30. Ring Of Fire

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 thing just wouldn’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 and 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....

Cringey MemoriesFreepik, cookie_studio

31. Willy Shakespeare

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" (awesome show. you can find the whole original cast production on youtube)

The whole show is 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 see 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 realized that my junk 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.

Cringey MemoriesFlickr, Garry Knight

32. Don’t Depend On It

When I was in my final grade of elementary school (about 12 years old), I got overly self aware of the fact that my privates "leak" (i.e. pee droplets in 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 had 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 in the front row 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... but I couldn't shake the feeling that they were looking at me somewhat weirdly. 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 turn 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 lied 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.

Cringey MemoriesFreepik,freepik

33. Gamers Anonymous

When I was around 14 years old I used to play videogames all day..actually a certain MMORPG which is not WoW. 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 and after the door was locked (to have a secure location to talk) it hit me. The German term for "Gaming addiction" can refer to gambling as well - so here I was, 14 years old in a room full of people who have lost their possessions/family over a severe gambling addiction that has ruined their lives and they make me talk about my gaming addiction. Lots of fun!

Cringey MemoriesPexels

34. Drew A Blank

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 3 hours of me just sitting there like a moron 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, 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. 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 6 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.

Cringey MemoriesPexels

35. Smooth Ride

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. 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 sat there thinking I’d 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 (previously) favorite amusement park attractions.

Cringey MemoriesWikimedia Commons, FoxLad

36. Dino Sore

I was about 9 or 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 2 of the last 5 or so kids (of the same age) 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 the crotch.

The kid had to go into the bathroom (two doors and three toilets, but it was unisex essentially) and have his junk checked out by this fat-hundred pound lady (fat-hundred pounds, not fat hundred-pounds) and another who was probably 60 years old. His balls were apparently red/irritated (because I literally bit them). And like 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.

Cringey MemoriesPexels

37. Blue Valentine

I was a rather fat middle schooler on valentines 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 valentines day. It was a low point in every year for me as a kid, since I never got anything or even expected to.

But in 7th 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 elated.. until the teacher realized 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.

Cringey MemoriesPexels

38. Not A Fan

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. 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. So. Fricking. Awkward.

Cringey MemoriesFreepik, benzoix

39. I Wanna Dance With Somebody

When I was in 1st grade, we used to have square dance lessons (this is in like 1981, in Kansas - don't judge me!)

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.

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.

Cringey MemoriesPexels

40. Shoot Your Shot

I was 14 years old and at a basketball game and 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 5 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...

My childhood crush of 4 years was there with me because her dad and my dad worked together...that whole walk back with people laughing I knew I'd have to sit another half of the game with her thinking I have 0 coordination.

Cringey MemoriesPxfuel

41. Phone a Friend

A couple of years ago I was really depressed and I ate my feelings often, so one day I went to the grocery store at, which I didn't know at the time, 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 get to the checkout line and a lady behind me is staring at me like I'm disgusting with all the junk i'm 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, 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.

Probably the worst moment of my life so far.

Cringey MemoriesFreepik, tonodiaz

42. Don’t Mind If I Do

I've said this before once, but the SO and I were meeting some old friends of hers that were in town for a day or two. I say "in town", they were like 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 them 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.

Cringey MemoriesShutterstock

43. Based On A True Story

I went to see my ex's play a little while ago. It was a series of shortish scenes and one of the little vignettes was just pretty much a word-for-word retelling of my breakup with her with the names changed. The acting was terrible, and the whole thing made me want to tear off my arm and beat myself to death with it, but the cringiest moment came after the show when she asked me if I enjoyed that particular part.

Cringey MemoriesPexels

44. Math Genius

Was working at my first job at an ice cream shop. 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 stupid. "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.

Cringey MemoriesPexels

45. The Whomping Willow

I had a major crush on a guy in high school. I went to his house for a bonfire with the rest of my friends. Afterwards, I hugged him goodbye, turned to leave and after taking two steps I smacked my head on a tree branch and fell down.

I'm so awkward.

Cringey MemoriesPexels

46. You’re So Vain

A few years ago I was good friends with the lead singer of an internationally renowned indie band (not saying who as I don't want them to find this). 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 angry email vehemently bashing them for writing such a nasty song about me. Their reply? "That was about my ex-girlfriend O_0 I have no idea how you'd think it was about you". I was so mortified I didn't reply and never told anyone.

Cringey MemoriesPexels

47. The Last Straw

I was once in a movie theater that was mostly empty. It was me and a few buddies in the third row and a few other people sitting together in the front row.

Well, one of the guys in the front row is sipping on ice and is at the end of it where the slurps are really loud and annoying.

This seems to be going on for 5 minutes straight so getting annoyed and trying to be a show-off I make a really obnoxious slurping sound. To my horror, two of the three turn to look at me with disgust and then I can clearly see it is not a guy drinking a slurpee, but a quadriplegic boy with a tube and his elderly parents taking care of him. It's even more obvious in hindsight that they were sitting in the disabled spots.

I was so mortified and embarrassed that I could barely utter "I'm so sorry", before I bolted out and switched to a different showing.

Cringey MemoriesPexels

48. Hide And Leak

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 2-3 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 trickle still haunts me. Oh god why...

Cringey MemoriesPexels

49. 0 Stars

A few months ago, my car broke down and I had to get it towed. It ended up getting towed to this place with HORRIBLE reviews, plenty talking about the mean old lady who is the receptionist.

Since my car was towed there in the middle of the night, I only talked to the boss man over the phone. When my car was done, my mom and I went to go pick it up. I'd told her all about the reviews and she made an off handed comment about wanting to see just how mean this lady was.

We get inside, there's no lady at the desk, just a young-ish guy. We start paperwork and payment and my mom goes "We read all the views about the horrid old cow who works here. Where's she at today"?

And the guy takes a deep breath, raises his eyebrows and replies "That's my mother".

Cringey MemoriesFreepik,senivpetro

50. Come Out Of The Closet

Okay funny/really depressing story. I really liked this girl back in middle school. And so as a crazy teen I thought it would be smart to write letters to her. Here's the thing, the letters were encoded with the Caesar cipher. Meaning she had to decode it in order to read my message. I kept giving her more letters and letters until one day one of her friends came up to me and said, "Stop giving xxxx letters, she thinks that is incredibly creepy".

I stopped writing letters to my crush, but I was depressed on the bus ride home. It even started raining as I was crying. A few days later a rumor was started up by a friend of mine that was basically I go into xxxx's closets and watch her while she sleeps. It got so bad whenever my crush was having a sleepover her friends would check all the closets in her house with her. So that's how I got my username.

Cringey MemoriesPexels

 

Sources: , 


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