We’re taking a trip down memory lane as people open up about that one cringe-worthy moment that has been forever etched in their minds. From hilariously awkward encounters to cringe-filled blunders, prepare yourself for a rollercoaster of secondhand embarrassment.
I was driving and had my brother and a friend in the car. I’m in the turn lane waiting to go left. The light turns yellow, so I start to turn. This A-hole decides to blow through without stopping – swerving around me. I honk. The next guy DOES THE SAME THING. Now I’m pissed and lay on my horn. The third car in a row keeps going through the red.
This is when my brother informs me, “Dude, that’s a funeral!” Turns out I’m the a**hole. I had to sit there as at least another 30-40 cars went by; totally obstructing their way. And I couldn’t even back up as there were cars behind me. I always cringe when I think of the looks I got from drivers as they passed me.
A couple of weeks ago. A couple of colleagues and I got lunch together, and as I was leaving, the CEO asked if he could get a ride with me as it’d be a good time to catch up on things. We get back to the office and he holds the door open for me. For some reason, the way he held the door open, I thought he wanted a hug.
So I gave him a hug.
We then proceeded to walk up the stairs together, then through half of the office after our embrace.
Alright so I was with some friends at a bar and I got up to go get another drink, I had already had a few. While standing at the bar, I made eye contact with a beautiful girl sitting in the area of my friends. I got my drink and started to walk to her, and she gave me that look all the way back, we held eye contact. When I got there, I asked if the seat next to her was taken, and she replied no. I proceeded to pick up the chair and take it back to my group of friends. I was too drunk to realize what I had done until later. It was a sad epiphany “Oh sh*t she actually wanted to talk to me!” 🙁
When I was younger (probably around 12) my mum used to take me and my sister swimming to the local pool.
One day, when we arrived, my mum met up with some of her friends, which included a younger lady (about 25). They were all gasbagging about something or other and I just wanted to go and swim, so my mum told me to ask Amy (the 25-year-old, relatively attractive friend) if I could go and swim with her.
I walked up to her and asked:
“Mum told me to ask if it was OK if you will sleep with me”
She looked a combination of shocked and amused, and I then realised my mistake, so I tried to correct myself with:
“Sorry, I really want to go and sleep with you”
She was confused, we went to my mum and Amy told her what I had said, all of the women in the group had a jolly good laugh at my expense, and people then decided I obviously had a thing for Amy.
I often wonder if Amy remembers that, or was as embarrassed as I was.
I saw The Addams Family movie when I was about seven years old. I’ve always had a really morbid sense of humor and basically thought I was Wednesday Addams. At some point in the movie, the family decides to run through the cemetery on their property to play “Wake the Dead.”
My dad had a best friend that killed himself before I was born. He didn’t tell me that he killed himself of course, for years he told me it was an accident while he was cleaning his gun.
One day, my mom told me we were all going to the cemetery to plant flowers on her parent’s graves. I asked my dad if his friend Robin was buried there too. He said he was. I suggested it would be a great idea to go play “Wake the Dead” and find out if Robin would come back as a zombie.
I have never seen my dad look so hurt. He was absolutely forlorn and disappointed. It was the first time he ever raised his voice to me, and I knew I f*cked up really badly. I felt like such a piece of sh*t. I was a daddy’s girl and he was disappointed in me. It took days for him to act normal to me again.
For years, when I couldn’t sleep, this was all I could think about.
I had a humongous crush on an older boy when I was 13-16. I can see now that he just wasn’t interested in me, but every couple of months he’d give me a reason to think he was – he’d call me up and get me to meet him, tell me he loved me but he was worried about the age gap, etc. Then he’d disappear for months, with no contact whatsoever.
Anyway, I used to text him at least a couple of times per day, every single day without fail, telling him what I’d been up to. At least once a week I’d send him an ‘accidental’ text ‘meant for a friend’, usually talking about something provocative, or just about how much I missed hearing from him.
This pattern carried on for a good couple of years. So, yes, essentially I was desperate and shameless enough to send him hundreds (probably thousands) of unreplied-to texts.
In high school, they were announcing the winner of prom queen or homecoming queen or something like that at an assembly prior to the dance in question. They had all the nominees down on a stage in the middle of the gym, and when they announced the name of the winner, one of the non-winners thought they said her name (even though her name sounded NOTHING like the winner’s) and did her whole “OMG I WON” hands shaking, mouth-covering, Miss America impression. She actually started walking towards the announcer before someone finally grabbed her and was like “Hey, you didn’t win. Sorry.” This was in front of the entire school.
It’s been almost 15 years since this happened, and it didn’t even happen to me, but I still have cringe PTSD just from witnessing it.
I was late for a lecture but had not got the e-mail that the room had been changed, So I opened the door only to realize I’d walked into the wrong room, saying “Sorry”, some people started laughing and I got a bit embarrassed. So I go into the next room alone, but I’d forgotten it’s actually another door into the same room, so I interrupt the lecture again and see the same people yet again but from a different angle, cue everyone (lecturer included) pissing themselves laughing.
When Facebook chat was first introduced, I was elated that I could spend time talking to my crush online without asking for his AOL/IM/Skype.
After he would say goodnight and go offline I would send messages like “I love you.”, thinking that once someone went offline, he wouldn’t be able to see any messages I sent.
Nope, still there.
Walking around one of my first parties at college, absent-mindedly flicking matches off a matchbox and watching them flare into life in mid-air.
I walk into a circle of dudes that are talking and drinking and go to flick a match.
One of the guys says: “Don’t do that, it’ll go in someone’s eye”.
I grin my most smart-a**ed, little grin and sneer “As if that would ever even happen” and flick a match.
Straight into that same dude’s eye. Death stares all around. I back out in shame.
The worst.
It has to be the love note I wrote to the girl I had a crush on when I was 13 in middle school. It was so embarrassingly cringe-worthy, with excerpts like “You are an angel floating down from heaven” or “Beauty like the rising sun” or “I’m floating on a cloud of love”.
Then I signed it anonymously by putting my locker number instead of my name. My locker was right next to hers, it’s not like it was hiding my identity at all. I thought I was being so clever, so I slipped it into her locker and waited.
When she found it, she shared it with all of her friends who stood in the front of the classroom passing it around giggling their a**es off and staring straight at me. About a week later I got a note in my locker saying, “Sorry, my mom says I’m not allowed to date until I’m older.”
I still can’t believe I thought it was such a good idea. I cringe every time I think about it.
When I was in sixth grade, I was really good friends with a girl who was kind of a social outcast. I didn’t understand why – there was nothing wrong with her. She was super smart, friendly, gregarious, and cute. She had an adorably gigantic mop of curly brown hair, and glasses perched on a pointed nose. She had big, round brown eyes and an earnest smile. She liked the outdoors, and animals, and liked to wear boots to go trudging through the marshes looking for frogs.
One time, she and I were at a week-long nature camp with our class, and she was dragging me through the swamps in our free time to get closer to some geese. She held me by the hand the whole way. It was nice. But when I went back to the camp to eat, I was stopped by a popular girl I sort of knew.
This popular girl, who was a little older and more developed physically than the rest of us, led me aside and smacked me on the forehead. “What do you think you’re doing? You can’t hang out with Nicole! She’s a lesbian! You’re ruining your reputation for some weird lesbian girl who talks to ducks! Stop holding her hand!”
I didn’t even really understand lesbianism at the time. I didn’t know what to do, but I was scared that people wouldn’t like me. So I found Nicole and interrupted her invitation to eat dinner with her by saying, “I’ve heard some things about you and I just don’t think… I don’t think I can trust you anymore. Or be your friend.”
She looked at me for a minute and said, “Ok. If you don’t think you can be my friend, you don’t have to be.” She turned on her heel and ran. I didn’t try to stop her. The popular girl put a hand on my shoulder and said I’d done the right thing.
That was the second to last week of sixth grade. I didn’t see her the next week. Or ever again after that. Ever.
What I wish I’d understood then was that I liked holding her hand as much as she liked holding mine. I remember what it felt like. It was soft, cool, long, and milky white. I liked walking through the mud with her and watching the geese and frogs. I liked her boots and her big hair. I liked her a lot, really.
We were just kids, but if I’d known then what I know now about myself, I’d have punched that Sabrina girl square in the face and run back to my girl and asked her to be my first girlfriend.
It’s been twelve years, during which time I’ve dated both men and women and mostly forgiven myself for being a jerk, but I still wish I could tell her I’m sorry.
In late elementary school, Facebook had just come out and all of my friends and I made accounts. I got a friend request from a girl who looked somewhat familiar. For whatever reason, I started telling my friends that she was my girlfriend and the cliche “she goes to another school”.
It turns out, she went to our school. Unbeknownst to me, her last name on Facebook was actually her middle name. Word got around to her and she confronted me about it in front of a bunch of my friends in gym class. I even tried to double down about it saying “No, I swear it’s not you, she goes to a different school!”
At the time she probably thought it was funny if anything, but I still cringe to this day. I actually spoke to her at a birthday party for a mutual friend a couple of weeks ago. That had to be one of the darkest days of my life…I still remember it vividly.
My uncle and his wife married when I was about nine. I had lots of little cousins and assumed I’d have another in a year or two. Almost two years passed with no pregnancy, so I asked if I was going to have another cousin soon and they said, “Not yet.” I kept asking every time I saw them until I realized they probably were going to wait a REALLY LONG TIME before giving me another cousin.
They had two children in the past five years and revealed they had been dealing with infertility. I can’t imagine how much pain I put them through, and how much they probably dreaded any visits where they knew I’d be there. Not only that, but I know now firsthand how annoying it is to have people assume that because you’re married, you’re going to pop out babies ASAP.
I need to sit down with them, confess I remember doing this, and apologize. 🙁
When I was a senior in High School I got out of class first period and was walking to my second period class. There was a weird buzz in the air that I couldn’t really place. A girl I knew but wasn’t exactly close friends with was walking nearby and I asked her what was going on. She told me that two planes had flown into the World Trade Center.
My response? “Cool”.
Got to the second period, and spent the entire class watching CNN, the rest of that day was kind of a blur (our school was a few miles from a major nuclear naval base so at the time there was a lot of confusion and worry about our own safety). Still, I can never get that exact moment out of my head. I didn’t understand the gravity of the situation and it was just an automatic response to something interesting happening to break up the monotony of an average school day, but it still bothers me.
I haven’t spoken to that girl since High School, but we’re friends on Facebook and about a year ago she moved to the same city I now live in, so I see her posts more often than I used to. I often wonder if she sees mine and if when she thinks of me she remembers that moment. For all I know she forgot it 10 minutes later in the stress of everything, but in my mind, I’ll always be the guy who said September 11th was “cool”.
Me and my family are African American. We lived in an all-white neighborhood when I was about 15. That being said all of my friends were white and we had a lot of awkward moments. I never ran into any racism but I did run into stereotypes and things like that. One day I’m at a buddy’s house and he pulls this hot sauce named “Spontaneous Combustion” from his refrigerator that’s inside of a large prescription pill-like bottle so as to keep it away from children. He dares me to put some on my finger and lick it off and of course, I’m not gonna back down so I do it. It was the hottest thing I have ever put in my mouth. It took about an hour for the burn to go away. We go into his room and start playing super smash bros and I completely forget about washing my hands. I get up and go into the kitchen to get a drink and his mom is sitting at the kitchen table reading. Right before I open the fridge door I rub my eyes and all h*ll breaks loose. I’m Screaming and jumping up and down from the pain of my eyes feeling like they are being burned out of my skull. His mom never moves from the table. My buddy hears my screams of death from his room and comes sprinting into the kitchen. Between my cries of pain, I tell him what just happened. He yells at his mom asking why didn’t she get up to help and she yells back….. I THOUGHT HE WAS RAPPING!
I was at a bar a few years ago with some buddies and a group of people were at the table next to us. Me and this girl locked eyes for a brief second, and she grinned. I didn’t really think anything of it. A few beers later, she and a friend go to the dance floor, and after a minute, she looks at me and motions for me to come join her. I immediately think back to when we locked eyes and thought ‘Cool, I like aggressive chicks’. She has her back to me as I walk up and start dancing on her, and as she feels me grinding she whips around in horror and jumps back. She said, ‘Uhh, I was motioning for my boyfriend to come dance.’ I turn around to see her boyfriend giving me the stank eye, 2 feet behind me… All I could do was mutter an apology and walk away ashamed. The worst part, my friends saw the whole thing and I have to go back to a table of 4 other guys sh*tting their pants with laughter. Took a while to live that down, but I’ll never forget the cringe of that moment. I’m an idiot.
I got hammered one night during my Freshman year of college and my roommate convinced me to call an old High School fling, whom I wasn’t over at the time since we’d be in college for like 2 months, and propose to her. She called me the next day, I tried to laugh it off and she quickly cut contact with me. That was about 6 years ago. I saw her at Church over Thanksgiving weekend last year when visiting my parents and tried to strike up a conversation. You could feel the awkwardness as I went in for what I thought was a run-of-the-mill ‘old friends’ hug. Meh, you win some you lose some.
I was/am a fairly classic nerd. I mostly bombed every time I tried to take a girl on a date but one date in particular still makes me cringe when I think about it.
My high school in particular served as a gifted student center for the best students in the public system across the county. The great part about the gifted program was that I was mostly surrounded by peers who were equally nerdy. During senior year (I was a bit late to the game) I finally developed enough courage to ask out a girl who I really thought was the prettiest and in the top few smartest girls I knew. Inexplicably, she seemed to actually be excited to go with me to dinner and a movie.
I picked her up around 7:30 pm. The plan was to go to an evening movie and then dinner after. It was late fall and by 7:30 pm the sun had already set and it was getting pretty dark outside. I should have worn my glasses but my vision was not terrible and I thought I looked SOOOO much COOLER without them. RETARD. So, I’m driving out of her neighborhood, unfamiliar with the roads and I end up on the wrong side of a median driving into oncoming traffic. 25 MPH speed limit, only 50 yards and I’m clear, all I have to do is finish my turn and go on with my night. It’s not a big deal, right? Yep… No problem I got out of it just fine. AND NOPE
My d*uchebag brain locks in on the mistake and fixates on it for the next several hours. I become a complete zombie. I can’t utter a word, I’m mortified at my stupidity. I normally have a pretty clear memory especially when it comes to visual things like movies. I don’t have a clue what movie I sat and cold sweated my way through because my brain could not do anything but re-live the 10-second screw-up in the car. My date tried to assure me that it was not a big deal. She tried to grab my hand and shake me out of my state of shock.
Nothing pulled me out of it. The movie ended, Dinner Time? Oh heck no, neither of us even mentioned it. We went to the car and without even thinking I drove her home and sent her inside. I was too embarrassed to talk to her for the next month.
The worst part was that I not only screwed up the date but alienated someone that I considered a friend. I have no idea what she must have thought of me. Probably nothing at all after that date. Maybe she just felt relieved that she found out I was such a f*cking spazz early on in the relationship.
Anyways, I never really talked to her again. I left for college and we went our own ways. However, I did go back home to visit probably about 8 years after the “date”. I went out with my family and I saw her at a restaurant. She was drop-dead beautiful…. sitting with her husband……….. and fairly young baby. I was not even able to go say hi. I just cringed and thought about what might have been.
I was thirteen, and round a friend’s house. She and I had eaten earlier and I’d eaten a little too much. I needed a sh*t really badly but didn’t want to go in her house, but I didn’t want to go home because I was trying to get with her. She started tickling me and I shat myself. The smell hit her, we made eye contact for a silent ten seconds, then I just started sprinting out of her house, all the way (2 miles about) home. Left my shorts in a bush in the countryside. Ran through a field to my house. My parents had friends over and I enter the kitchen half-n*ked.
My best friend’s mom recently found out her cancer is back with a vengeance. The doctors said there’s really nothing they can do now, so it’s essentially a death sentence. He had been pretty stressed about it so I invited him over to play video games. At one point in the game, he says, “Oh no be careful, you’re gonna die!” And I, in my infinite wisdom, replied, “Your mom’s gonna die!” It was meant to be a harmless “your mom” joke, but I didn’t realize what I was saying until the words were halfway out of my mouth. Feels bad man 🙁
When I FIRST started college, I was still struggling to understand my identity. I had grown up in a VERY small rural town, where the population was very homogenous – the only religions I had really had exposure to were Christianity and Judaism. For a long time, I had become very attached to Christianity because it helped me temporarily find a way to cover the identity I had that I was most scared of – being gay. In college these feelings were coming to a head – I was finally starting to be okay with being gay and was slowly drifting away from my religious views. However, there was a peaking point where I was struggling somewhere in the middle and where I had met someone very religious (Christian). We were wandering around campus and were given copies of the Book of Mormon by some Mormon missionaries. We discussed how “stupid” Mormon faith was, and she suggested we throw the books in the nearby fountain. Unbeknownst to us, the missionaries had looped back and saw us right as we threw them into this huge fountain. One of them ran into the fountain and grabbed it, getting soaking wet, and yelled at us for being disrespectful, asking how we would feel if someone had done that to a Bible.
These days I identify as an atheist and think most religion is frequently problematic. But, I still think that was probably one of the most horribly disrespectful things I’ve ever done. I should never have taken the book in the first place, let alone done something that stupid with it. While I have a lot of regret over the memory, it did teach me about how it feels to be disrespected in that way, and that no one deserves to be treated that way, ever.
Valentine’s Day with my first serious girlfriend (17 years old at the time). I showed up at her house, and it was dark except for a lit candle on the kitchen table. Romantic music playing softly over the stereo. There was a trail of paper hearts leading to said table, each one had a little handwritten note on it. The whole thing was absolutely adorable.
I got her f*cking Saw II on DVD and took her to Taco Bell for dinner. Holy sh*t, dude.
When I was a freshman in college, I broke up with my first boyfriend via e-mail by telling him I thought I was gay and I didn’t think we could see each other anymore (p.s. it was more that I just wasn’t attracted to him, though I was exploring being bi at the time). I had rather severe social anxiety and absolutely no clue when it came to dealing with social situations.
He came to see me, all distraught, to try to talk to me, and I was feeling so awkward and scared of the situation that I refused to get off the computer. His roommate begged me to just please talk to him because he was really upset. Finally, I relented, and we had the most uncomfortable break-up conversation in the world before he left.
Really the worst, and I still can’t believe I actually broke up with someone by e-mail. Yeesh. What made it worse was years later, I ran into this ex at graduate school…while I was with my boyfriend. That, too, was awkward.
About 13 years ago I attended a wedding – it was a double date between myself and my wife (fiancee at the time) along with my younger brother and a young lady he had been seeing for a fairly short time (though their romance was intense). We were all staying at the same house (my in-laws, who were out of town), and I had volunteered to drive us that night.
At some point during the evening, my brother and his date left the wedding; they’d found someone who had coke and they had decided to take their party to the next level. The problem was they hadn’t let us know and there was no answer to his cell phone. Long story short my wife and I ended up waiting at the reception venue for my brother and his date to return, which they did eventually (after the reception was over and the hall closed down).
The following day I drove him to the airport to go back to his home, and I absolutely let him have it. I tore into him about how irresponsible he was, about how he only cared about himself, that he was a selfish a**hole, and that he needed to get his sh*t together. Basically, I had been really scared for his safety the night before, and I didn’t know how to tell him, so I yelled at him instead. He didn’t say a word when we got to the airport or look at me for that matter. Can’t blame him the way I had just lashed out at him.
He got out of the car, grabbed his bag, and started to walk toward the terminal. I was full of resentment and anger, and just took off. He flew home to New Mexico, and a few days later he was killed in a car accident, on May 12th 2000.
I cringe when I think about the last conversation he and I had, and I cringe when I remember that I was so incredibly f*cked up wasted at his funeral that I could barely stand or talk. It took me another 10 years but I finally got sober and got my sh*t together. Time heals, but I still miss my brother very much – I wish he could have met my three children, or stood up for me at my wedding, or come to my 40th birthday in a few weeks.
When I first started dating my wife, she was in college renting an apartment in the… more affordable… area of off-campus housing. There was a rash of small burglaries in the area and eventually, they were hit. Adding to this traumatic experience was the fact that they entered the apartment while the guy was upstairs and listened as he escaped via a second-story window.
Fast forward about two weeks and I’m going to pick her up for a date. I arrive a bit earlier than expected and I hear her and her roommate upstairs. Obviously, I decide the best course of action is to sneak up on them and try to scare them.
I try to sneak up the steps but the boards creak — They hear it and run into a bedroom. I make it to the door and I can hear them anxiously whispering to each other
“Are you sure you heard something??”.
“No, No, It’s probably nothing.”
-I make it to the door-
“WHAT WAS THAT?”
I, thinking this is the perfect time to up the ante, start pounding on the door and jiggling the door knob. They start screaming and I can feel them pulling on the door and trying to lock it with the chain.
Eventually, I get the door cracked a little and they see it’s me. They are in tears. The roommate is holding a pair of scissors and my wife is wielding a pen like a knife. They start yelling at me and beating me.
At first, I’m surprised they are so angry. Then I have the sudden realization that maybe this wasn’t the best timing for a sneak and scare.
The moment I found out I’d been cheated on. It’s the type of cringe that shakes me pretty hard and takes me a few minutes to shake it off and push it to the back of my mind again. It used to ruin my whole day if the memories came flooding back, but with time the pain has faded. That one sharp moment still does it for me though. We’d been together for about 2 years at the time. He was hands down the only man I’ve felt true love for. He loved me and my son from a previous abusive relationship that lasted way longer than it should have. For a couple of months, I realized slowly that things were changing. He was hiding his phone, becoming distant, less affectionate/ physical etc. One day I snooped through his “text history”. He didn’t even know he had that feature lucky for me. It was all there. Several different women from his work. Flirting, sexual advances and suggestions, plans to get to know them better, pictures of his d*ck sent. There were at least 3 women.
This was not the moment that hurts me though. We talked about this after I confronted him and he was embarrassed and apologetic and promised to stop. He didn’t stop though. It kept on for a couple of months until I finally just let him go. A few months passed, and we couldn’t forget each other or move on no matter how hard we tried. He was filled with regret and called me often apologizing and trying to get me back. I stupidly took him back, but things were good. Really good and I believed he had changed and was serious about our relationship this time. Then one day we decided I needed a girl’s night, he needed a boy’s night and we would meet in the morning for breakfast. He dropped me off at my friend’s house that night and told me he was going to a friend of his for a BBQ and he’d pick me up in the morning… he never came back. I drove to his house after my friend took me home, at 5 pm the next day after speaking to him and giving me some b*llsh*t excuse about having to help his mom with something unexpected and not feeling well. I got there, he let me in, and immediately I knew by the look on his face he had done something he regretted. He couldn’t even look me in the eyes. I asked him to see his phone and he said no. I asked him “You slept with her, didn’t you?” …and he started to cry. That’s the moment. The moment that I sat on the floor right where I was standing and just fell apart as I realized that the only person I had ever really loved had hurt me so badly, that I would never really recover. That I was so stupid and blinded by love and the fear of loneliness that I had made myself vulnerable again to him and he broke me.
I had to go to work on a day off to have an impromptu meeting with my manager about a nasty coworker situation that had just erupted. My department manager shared an office with someone, so we went to the HR manager’s office to discuss the situation (the HR manager wasn’t working that day). I was on my period that day (which made me cry even more!), and after the 2.5-hour conversation we had, I got up to leave. The light green fabric of the chair I had been sitting on now had a giant dark red spot. I noticed it right as the manager stepped out of the office and turned off the light, and everything happened so quickly that I didn’t say anything.
I had the next day off, but the following day when I came in the chair was parked near the computer stations with only a wet spot and a sign on it that said “WET. DO NOT USE.” I’m assuming the HR manager had to scrub my dried period blood out of her office chair. It sat there for like a week before it made it’s way back into an office.
Cringed every time I passed it.
I accidentally set the yard of my church on fire while we were selling Christmas trees to make money for mission trips. The fire almost got to the trees, which would have been extremely bad, when we stomped it out. I was screaming and cursing the entire time while stomping like a maniac, and everybody was just staring at me. I still go there, and I’m known as “fire boy,” and I shudder every time I think about it.
My divorce. I know, what a weird thing to cringe about. Actually not just the divorce. The whole marriage. The relationship leading up to the marriage. The work I put into it, the expectations I had, the times I sacrificed, and the day we said vows to each other. Criiiinnnnge I want my life back