'For a winter play... I offered to do the worm across the stage ': 25+ Moments of cringe that keep people awake late at night

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Sep 20, 2023 11:00 AM EDT

We all have at least one moment in our lives that makes us shrivel up with embarrassment (and if we're being honest with ourselves, there's definitely more than one cringey mistake we look back on). 

I used to be way more embarrassed when I made mistakes, but the older I get, the more mistakes I make. I'm getting used to it, I suppose. If you let you of your need to be perfect and impress all your friends, you have a little less cringe to look back on at night wondering, "Why did I ever say that?" At a certain point, you just have to embrace your mishaps, and realize that everyone makes mistakes, and most likely no one else recalls your worst moments except for you. 

Something that gives me second-hand cringe is when people ask me for directions for things that are easy for me to point out. I can count on two hands how many times I have been asked, "Hey, do you know where the Freedom Tower is?" by tourists while living in lower Manhattan. Then I would wordlessly point to the very very tall Freedom Tower, which is easily visible from almost street surrounding it. Then, the tourists laugh at themselves and make their way to the monument. I hope I'm not embarrassing them on purpose, but, well, it is just right there if you're looking upwards. 

Worse, though, is that I know I've given people the wrong directions by accident. I know I sent at least one dude off to the wrong train at Jamaica station when he asked "where the next train to Penn Station was." I directed him to the subways downstairs, when he may have been looking for the LIRR upstairs. I'm so sorry to that man---there are few fates worse than being stranded at Jamaica train station. Please know that I am also embarrassed, and lying awake at night thinking about what I've done. 

Next up, this retail employee was forced to work all night long---because their boss insisted they could never tell customers that the store was closing. 

Advertisement
  • 01
    Font - What cringey moment in your life still keeps you up at night when you randomly remember it?
    via u/monkeypdg
  • 02
    Font - Youfokinwatm8 So I was at Noah's Ark in WI and at the time was in contact with my dad. At the time he was bald, but he had hair prior. I wasn't used to this change and accidentally walked up to a complete stranger (also bald) slapped him full force on the head, then kissed it better. (I was like 5 at the time) I look to the right and see my dad waving at me from three chairs down. The guys face still haunts me to this day.
    via u/Youfokinwatm8
  • 03
    Font - trixy_treat When I was 15 I was trying to get a weekend job in a pet store, the owner asked me if I was flexible, my reply was "yes, of course, I've done yoga for years" It's been 13 years and I still think about it, my brains way of embarrassing me at random moments 'hey, remember that time you were a total idiot?!' ....
    via u/trixy_treat
  • 04
    Font - Beartow I remember interviewing at a fruit stall on my local high street. I turned up in a full suit, and when asked why I wanted to apply the only thing I could think of was "I like how the apples smell" and then we both sat in silence for a few moments until he asked me to leave and said he'd be in touch. Your comment just brought that eleven year old memory back.
    via u/Beartow
  • 05
    Font - deviety Kindergarten, winter time. Come in from recess, take off toque, mitts, coat, snow boots, snow pants, pants... It's my very first school memory. And plays in full HD, with surround sound.
    via u/deviety
  • 06
    Font - Co TooOldForACleverName. I was an extremely unattractive teen. Bad overbite, bad hair, huge classes, baby fat - not a good look for a 13-year- old girl. Anyhow, our school had a poetry contest, where people stood up and read their favorite poems. I couldn't find a poem I like, so I wrote one about falling in love with a beautiful boy. God help me, I can even remember the beginning:
    via u/TooOldForACleverName
  • 07
    Font - The world is filled with beautiful sounds, The rain falling, leaves falling to the ground. Then comes love, that beautiful joy, The moment you meet that wonderful boy. It's been almost 40 years. I can't remember where I put my car keys last night, but I can remember the ded poem that I read out loud while my classmates laughed at me.
    via u/TooOldForACleverName
  • 08
    Font - sketchmcarthur I was like 6 and in this real fancy hotel playing with some other kids my age, including this one girl that was really cute and I had one of those kid crushes, you know the ones. When it was time to go my parents called me over and instead of saying goodbye to the girl like a normal human being I grabbed her by the waist and whispered in her ear "hasta la vista baby" and ran to my parents.
    via u/sketchmcarthur
  • 09
    Font - loveadumb I went to an audition for a renaissance fair. I didn't even want to but my mom pressured me. She told me that you had to be in costume. The audition was at a country club. I showed up in full f cheap costume and couldn't find the audition. I walked around the entire country club looking for the audition literally with people laughing at me. I got there and they were trying so hard not to laugh at me. They told
    via u/loveadumb
  • 10
    Font - me to fill out some paper in the other room and the guy gave me a really nice pen. He specifically told me not to lose the pen because it was expensive. I peaced the f out with the guy's pen. So, in some ways that day, I won?
    via u/loveadumb
  • 11
    Font - [deleted] the time I worked in retail, and I was looking for an empty dressing room to put a customer in. I walked up to the door, knock on it, no answer. so, I unlock the door and open it to reveal a man with his pants half way down, clearly he is trying them on and I've just interrupted him. we both just stare at each other for a second and I say, "they look great!" and I abruptly closed the door.
    via u/deleted
  • 12
    Font - When I was 9, my friend and I knocked at our 16- year-old neighbours' house to see if we could play his NES. My friend said that we didn't want to make it too obvious so we should knock and ask if he wanted to play Gameboy with us (we all had Gameboys at the time). So we knock on the door and my friend goes "Hey, we were wondering if you'd like to play Gameboy with us." I, thinking this was far too subtle, chimed in with "Or as I like to call them... NINTENDO DEVICES."
    via r/AskReddit
  • 13
    Font - They both stared at me for a second and my friend made a "WF" face at me, then the older dude laughed and asked if we'd like to play his NES. I had one go on Mario and was killed by that first f Goomba. I wasn't really paying attention as I was too busy thinking about how much of a d I'd made of myself. To this day, I can't play the first level of Mario without cringing.
    via r/AskReddit
  • 14
    Font - Cyasomeday In highschool I crushed all over this girl who was cute, smart and very nice. She was always easy to approach and talk to, and over two years I never acted on my liking of her. I sort of just assumed like in movies and tv shows that it'd just take one action to make her go "wow" and she'd want to go out with me. Boy was I wrong! On Valentine's Day I sent her a rose and a poem I wrote. I thought it was a great idea to spell out my name through the start of each line...
    via u/Cyasomeday
  • 15
    Font - She figured it out immediately (duh) and told a lot of people about my confession of love. I only recently found out that apparently some of her friends were poking fun of her for it too. It made the next few years of my life very awkward around her, and even during my first year of university, we'd catch the train and bus in due to the same starting times, and I always felt so reserved talking to her.
    via u/Cyasomeday
  • 16
    Font - Endulos I was like seven years old and out trick or treating. I went up a house and a girl, only slightly older than I was came to the door with 2 bags of chips (One a package of Lays potato chips, the other a bag of Hawkin's Cheezies). She tossed the bag of chip into my bag and held the cheezie bag.
    via u/Endulos
  • 17
    Font - I assumed both were for me and she was teasing me. So I held my bag out and shaked it a couple times and she's like "That's it. That's all you're getting." Then she took a cheezie out of the bag and ate it and I slinked away. That was like 25 years ago and I still think of that moment and cringe.
    via u/Endulos
  • 18
    Font - littleh flames When I was like 5 or 6 I took part in a kiddie race at the community games. I was off in my own little world as we lined up to run. There was a signal to go, and once I heard it I just took off running. Ran the whole race without anyone even coming near me, I thought I was so cool! Couldn't understand why nobody clapped or cheered for me. Even the people giving out prizes weren't clapping. Needless to say I was both confused and indignant.
    via u/littleh***flames
  • 19
    Font - Turns out they were just doing a test signal so all the kids would know when to go. I took off like Usain Bolt and claimed a stunning victory before the race even started. The other kids were ped and I experienced my first taste of crippling embarrassment. A great day had by all.
    via u/littleh***flames
  • 20
    Font - cynicaldotes once when I was playing football they told me do the count off at the end were I would have to say "1, 2, 3" and then everyone would say the team name. 7th grade me didn't understand this at the time and I just kind of sat there in the middle of the huddle for 15 seconds until one of the older players did it for me. Didn't realize until my dad told me what I did. I felt so stupid lol.
    via u/cynicaldotes
  • 21
    Font - Nakita-pita Ugh...so many. The summer between my freshman and sophomore year in high school I sent out a bunch of letters to random guys I had crushes on. I looked up their addresses in the phone book (1990's). Thankfully none of these guys ever mentioned it to me or talked about them at school. I don't even remember what I wrote, but I can only imagine how psycho that
    via u/Nakita-pita
  • 22
    Font - must've looked since I was this really quiet loner girl in school! A few years later I was kind of obsessed with an older guy I worked with and after he quit working there (he actually got fired for stealing), I found where he lived and where his new job was and would drive by whenever I could. I left a note on his car about wanting him to call me. I didn't know what to say when he actually did call me and it was a super awkward phone call. I quit the weird letters and stalking after that
    via u/Nakita-pita
  • 23
    Font - ivorella When I was in elementary school (probably grade 2?) the school said we could wear our Halloween *costumes to school. But apparently they changed their mind and called all the parents. Well, my family never got the memo and I showed up as a fting fairy princess. Only person in costume. FML. Luckily I didnt live too far from school and they let me walk home and change, and then come back.
    via u/ivorella
  • 24
    Font - Maverick G On my way to work walked for 15 mins with a torn trouser. When I saw my trousers I realized my undies was completely visible from the back.
    via u/Maverick_G
  • 25
    Font - pk421 Girl in 10th grade asks me to movie for Friday night. Totally perpetually clueless male friend of mine calls me up Friday night and wants to hang. "Can I come with you guys?" Uh sure. I sucked at saying no back then. I'm so sorry 10th grade girl that obviously liked me back then. I liked you too.
    via u/pk421
  • 26
    Font - wishmynamewasbetter I met my celebrity crush and had the chance to have a full on, twenty minute conversation with the guy. I used that 20 minutes to be a cringy fangirl, instead of, ya know, having a genuine conversation. To this day I'm embarrassed, but I can't really blame myself too much.
    via u/wishmynamewasbetter
  • 27
    Font - AudioBoss For a winter play in the 5th grade, I offered to do the worm across the stage during the "rock solo" portion of the song because the teacher asked for people who can dance. She let me. 2nd performance I knocked over props, 3rd performance I kicked a kid in the mouth who was pretending to do a recorder solo whilst trying to do the worm. I got laughed at a lot, my neighbors went to both performances.
    via u/AudioBoss
  • 28
    Font - gaydotaer The time I pointed to my new boss's belly and said "congratulations!" with a huge smile on my face. Turned out she was fat, not pregnant.
    via u/gaydotaer
  • 29
    Font - Chonays I'm awkward but there is a guy at my work that is super awkward and his awkwardness intensifies mine. I can normally pull myself together when I talk to people at work. I don't have to interact with this guy much but one day he had to ask my address to update everyone's work contact info and I couldn't remember my address. it stretched out into the most uncomfortable 5 minutes of my life. The more I sat and tried to think if it, I could feel his awkward stare on me and I was just
    via u/Chonays
  • 30
    Font - He had my address in the computer in front of him but he wasn't throwing me a single bone. Nope just 5 full minutes of h before I finally asked what address was on file and verified that was still my address. Every time I see him at work I feel like he's thinking about how I don't even know where I live.
    via u/Chonays
  • 31
    Font - demonhuntergirl Once I asked a professor to quickly explain a specific concept as I had forgotten what it was about. His answer: ".... well it's what the whole class is about?" Man, I cringed so bad and I still do. I thought I knew what was going on, apparently not.
    via u/demonhuntergirl
  • 32
    Font - burgerkingqueen2 when i worked at starbucks 2 years ago a regular came in and i handed her her coffee. i excitedly and enthusiastically said "i love you!" instead of "have a nice day" :)
    via u/burgerkingqueen2
  • 33
    Font - samuraipolice Was boarding a plane and the guy that checks the tickets reaches out his hand to take my ticket. Instead of giving it to him I shake his hand. I thought he wanted to shake my hand.
    via u/samuraipolice
  • 34
    Font - gt35r Working retail, was finishing ringing this lady up who had 3 of the large paper shopping bags we offered. Clearly too much for her to carry alone, so I said (completely innocently, I was 17). "Do you want me to follow you to your car?" That one still stings like it just happened because she goes "no I don't want you to follow me to my car." All I had to say was do you need any help carrying that? Christ....
    via u/gt35r
  • 35
    Font - Skorne13 I was driving home after work one day. I stopped off at the shops, and then got back in the car and put my phone on the passenger seat. I put on the radio and Jose Feliciano's version of Light My Fire was on, so I started singing along to it. I started belting it out toward the end.
    via u/Skorne13
  • 36
    Font - When I got to a set of traffic lights, I checked my phone for messages, and saw that I had accidentally dialled a Water Authority inspector that I occasionally do inspections with, and had been madly serenading him over the phone. I promptly hung up, drove home and lay in bed thinking about it for about an hour.
    via u/Skorne13
  • 37
    Font - TheGreenGuyFromDBZ. I was at my locker at school and a girl dropped her books and had already bent down to pick them up when I kinda spontaneously swooped in and picked them up and gave them to her awkwardly and said 'there you go' or something. My mate saw from a distance and was ping himself.
    via u/TheGreenGuyFromDBZ

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

ask reddit cringey school work stories embarassed funny stories students embarrassing work cringe askreddit sad cringe workplace cringeworthy
Scroll Down For The Next Article