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30 People Reveal The Funniest, Most Cringeworthy Stories From Their Pasts

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Have you ever struggled to fall asleep only to end up tossing and turning over whatever thoughts are in your head? No matter how much you think you’ve got a handle on your stress, it’s normal to stay awake when you can’t think of anything but the things that have happened—or might happen—in your life.

While we’d all like to think that we can move on from silly, embarrassing things we’ve experienced, sometimes it’s easier said than done!

These 30 Redditors were asked, “What cringy thing you did in the past still keeps you up at night?” Their answers? Hilarious!

1. “Sent like five love confessions to a girl in high school over MySpace, then chickened out and deleted them. Turns out deleting stuff from the sent box doesn’t unsend the message.” As if the fact that we all used MySpace wasn’t embarrassing enough on its own! We’ve all been there, kid.

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2. “There was a brief time in middle school in which I would speak in the manner of Tony ‘Scarface’ Montana. ‘Shot da fock up, you pile o cockaroches!’ So embarrassing.” Hey, at least there were worse things he could have said as Scarface, right?

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3. “I was really sick one day in high school, and my mother thought I was faking it and still made me go. I sneezed so hard I s*** myself. It was everywhere. I called her to ask if she could pick me up from school or at least bring me a change of clothes, she still thought I was lying.”

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“Luckily my gym teacher found me a pair of pants, but I had to deal with my shame for the rest of the school year. I got made fun of a lot for that.”

4. “I was invited to the birthday party of someone I’d only met a couple times but we had a lot of mutual friends. I was sat in the lounge having a drink and the birthday-guy came in, leant over me with his arms outstretched… so I hugged him. He was reaching for something behind me.”

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5. “I was out with my dad at some event. I was maybe 14 or 15. It was an off-roading club and it was his first event to go to. I was tired and we were getting ready to leave. I saw my dad talking to some people, he was like leaning on their car, looking into their window and talking to them. I came up and put my head on his shoulder/chest area and looked into the car for a couple seconds just to hang out and see who he was talking to. It wasn’t my dad.”

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“It just looked like him from behind. All conversation stopped and it didn’t hit me for like 20 seconds. Then I said nothing and walked away.”


6. “I was crawling across the floor of a store to go play with a girl on the other side of the store. (Crawling because my mom said I couldn’t go play so I was very sneakily sneaking away.) An old woman didn’t see me and tripped over me in the middle of the store.”

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7. “When I was in middle school (6th grade) these older kids were making fun of me, so I turned and yelled at them ‘I can’t hear you I have a POTATO IN MY EAR‘ like I was the smartest f***ing person on earth. They proceeded to continue making fun of me and my potato ear.”

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8. “I went to a Blue Jays game (I am from the States) when I was like 7. I thought the U.S. hated Canada and started loudly booing the national anthem. My mom was not happy.” Nothing shows support for a team better than obnoxious nationalism, right?

Feb 26, 2014; Clearwater, FL, USA;The Toronto Blue Jays line up for the national anthem before they play the Philadelphia Phillies in a spring training exhibition game at Bright House Field. Mandatory Credit: David Manning-USA TODAY Sports

9. “Last year on New Year’s Eve I was at a big bar in New York with friends and I got kind of drunk and went outside for a cigarette at one point. I must have actually been outside for the countdown, because when I came back in I looked at my phone and it was like 12:02 and I asked my friend why there wasn’t a countdown done by the DJ. I couldn’t really hear what he said, so I went up to the DJ and asked to use the mic and I did a second countdown.”

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“In front of the entire bar. With hundreds of people. Starting at ’30.’ And no one joined in.”

10. “During my alcohol phase I went on Facebook to search for and pore over pictures of my crush. When I woke up in the morning, I realized that I had actually created an event with her name as the title.” 

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That certainly does sound like an “event!”


11. “In third grade, my mother gave me 30 Valentine’s Day cards to write my classmates’ names and attach a small candy. I instead wrote the name of my third grade crush in [an]other class on all of the cards. ALL OF THEM. I proceeded to leave them by his classroom door while he was at recess.”

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“Sure enough, that boy never talked to me again.”

12. “Farted in karate class. I was like eight but never went back after that.” That’s certainly embarrassing, but who could honestly say that they haven’t been there? Especially when this person was just eight years old, quitting karate may have been just a bit overboard!

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13. “I tried to pick up the teller at a bank… I haven’t been back to that branch in a good five years or so.” That certainly sounds ill-advised. As another Redditor pointed out, “Tough sell. She can see what’s in the bank account.”

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14. “In middle school we had this mean-looking teacher that everyone hated, until our last year of being there, she seemed to lighten up a lot. On our last day of school everyone was hugging her and saying goodbye in the front part of the school, and I decided ‘Why the hell not, she’s pretty cool.’ So as she was walking up the walkway towards me and I put out my arms to hug her, well she walked right past me, and I hear laughter from behind me, and it’s my crush and her friends dying of laughter.”

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“Still kills me to this day.”

15. “I once wrote a letter in second grade to my best friend’s older sister that was in fourth grade, it was gushy and gooey and romantic. He passed it on and I sort of forgot about it until one day several weeks later when I asked him ‘Oh by the way what did she say?’ and he responded ‘She kind of just laughed.'”

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“I still cringe when she brings it up and we’re now in our 20s.”


16. “I get a girl’s number (I have known her for like a day or two). I walk two blocks and I send the longest love confession text message of my life.” It’s difficult not to get excited when you get the phone number of someone you like, but this is a little overboard!

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17. “Waited in line at a gas station bathroom. I went in and took a gigantic s*** and clogged the toilet. I tried to plunge it, but nothing worked. So I walked out with about three guys staring at me waiting to go in. I quickly drove off, only to find out I left my phone in the bathroom.”

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“Had to turn around and ask for my phone while everyone just stared at me.”


18. “Guess it’s not as cringy now considering I was a kid when it first happened, but back in first grade we were writing a test or something and I had to go to the washroom BADLY, but the teacher refused to let me go until the tests were finished so I pissed all over my chair. There was a huge puddle all over the floor.”

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“The girl next to me asked me what was all over my seat and I said it must have been water, she dipped her fingers in it and licked it up and said ‘yep it’s just water.’ No one ended up finding out I pissed myself so that’s always good.”

19. “Every single thing I posted on Facebook before 2013. Aaagh!” The TimeHop app may be a fun source of positive memories for some people, but for a lot of folks, it is, as one Redditor put it, “a daily exercise in humility…”

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20. “I once referred to a friend as having ‘an electric personality.’ At his funeral. Five days after he had been electrocuted. The words kind of just hung in the air at the funeral home swirling around the group of eight or nine of us that were reminiscing.”

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“One of the guys looked at me and winced. A girl rolled her eyes and turned her back toward me. I swear it was innocent but I have never, before or since, so badly wanted to be swallowed by the floor.”


21. “My coworker and I were taking the stairs to get to my office to be healthy. He mentioned my skirt was on crooked so I readjusted it as we stepped out… and a bunch of the bosses were there, staring at two people coming out of the emergency staircase all flushed and sweaty, and one of them readjusting her skirt.”

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“The raised eyebrows were bad enough, the smirk from this really pervy boss was the worst.”

22. “My crush came to my house to do a high school project. It involved the internet and while she sat next to me she tried to navigate to Google on my computer. Unfortunately, the address bar auto-filled and took her to my last Google search… page two of results for her name.”

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“Every link had been clicked. We both just sat in silence.”


23. “At one point during middle school I found out a girl liked me through a friend and proceeded to ignore her for the entirety of middle school… Even though I liked her back.” What a missed opportunity! Hopefully this person found somebody else special eventually.

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24. “After a girl forgave me for I don’t even remember what, I said, ‘Where’s my hug?’ Oh God the flashbacks.” As a general rule, it’s probably never the best course of action to request any sort of physical show of affection after somebody has just been angry with you.

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25. “I went to a surprise birthday party for a friend of mine that I had a crush on in middle school and my mom dropped me off at her driveway which was quite long. I walked into the house and everyone yelled surprise! They thought I was her. I was so embarrassed. I was a loner guy just trying to fit in.”

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“So everyone is upset at me and making fun of me and in walks the birthday girl. So I messed up her surprise. Later on, there is some music playing and people are dancing together and I finally get to dance with her and literally mid-dance she runs off to talk to her friend and left me. That whole night sends cringes up my spine.”


26. “Oh middle school… tried to date basically every girl in my grade without the slightest realization of self-awareness or the fact that girls talk to each other. I thought I had a solid chance with every single one of them. Cringe.”

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27. “When I was 12 I was attending a friend’s party. I had been telling some jokes, and had a small group laughing along. Being young and inattentive and foolish, I started telling some amputee jokes (they were popular at the time), being completely unaware of the fact that the young lady sitting directly to my left on the couch was missing her left arm from the elbow down.”

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28. “As a young kid, I was obsessed with horses. I walked around everywhere bobbing my head (to simulate wind blowing through my non-existent horse hair.) I did this for like a year until my mom asked me what I was doing and then proceeded to tell me I looked like a pigeon.”

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29. “When I was like 16, I had a huge crush on this girl. I also had a bad acne problem. So one day, I guess I popped a pimple or something, but I had some blood on my face. I greeted her (we were close friends so we did that “cheek kiss” that is just actually cheek to cheek contact) and… I stained her face with my pimple blood.”

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“Her friend started laughing hysterically. RIP my self esteem.”

30. “My first basketball game in first grade or so, my teammate threw the ball to me but I really sucked at basketball and didn’t know what to do with the thing so I just threw it to the other team. Everyone laughed at me. It was kind of funny, but I still don’t like thinking about it. Don’t know why.”

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As painful as these stories are, hopefully these Redditors can look back with a better sense of humor. It’s no use dwelling on so much on the cringe-worthy things you did in the past! Just, you know… don’t make those mistakes again!

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