Awkwarddd — People Share Their Most Cringeworthy Moments From Their Teenage Years

Nothing stings more than remembering the most cringeworthy moments from those awkward teenage years.

That Really Sucked

Somehow I knew this was going to become a thing. OK. You know those old Electrolux, rolling vacuum cleaners? I discovered that by laying on top with a pillow underneath and sticking my dick just barely in the hole, the vacuum would both suck and vibrate my dick. I wasn’t full grown at the time so it still fit. Actually, my relationship with Electro may have contributed to my present size. Anyway, you can imagine this was a pretty loud thing to do. So I was alone in the house one afternoon and no one was supposed to be home for a couple hours and I figured I’d put on a porno (VCR at the time) and have my way with Electro. Midway, the den door opens and there stands my Mom, little brother, little sister, and my best friends little sister, all staring at me with expressions ranging from horror (Mom) to amusement (sister and friend) to interest (brother). I jumped up with a raging hard-on and ran through the other door and down to my room, leaving the porno running. I don’t remember the scene but it was the super dirty one that was always at the end of the tapes those days. My room had a door to the outside so I put on some clothes and bailed. My step dad tracked me down a few hours later and tried to make me feel better by telling me a story of how he got caught when he was a kid. That just added to the awkward. Eventually I made it home and from everyone’s expression I could tell that they had been lectured to never mention it again. That didn’t happen but luckily, we all went to different schools and no one could believe such a crazy story. At family dinners though, when awkward experiences comes up, you know who’s story is the topper? Not mine. My family is f_cking nuts. (Source)

Smells Like Teen Embarrassment

Playing smells like teen spirit by nirvana in the school talent show On bass. With no accompaniment. (Source)

The Trench Coat Sealed the Deal

Biked to school in a trenchcoat then whipped out my wooden cane and scarf and went about my day…Sophomore year was tough. (Source)

Engage Invisibility Mode

When I was 13, I thought somehow that my window blinds made me invisible. I decided if I turned them a certain way, I could see out, but nobody could see in. We lived in an apartment, and a family with some kids my age moved in next door. They were dorks, but they were the only other kids. One day the family was leaving to go somewhere, and I stood at my window with my blinds tilted to invisibility mode. I suddenly started doing this primal dance that involved vigorously flipping off the family and mooning them, I was really into it – I was throwing some hard middle fingers and ass at them. I look back out and see the whole family stopped, and they’re staring at me; mom, dad, kids, all watching me dancing with my ass out and flipping them off. I can remember the shocked frozen horror on all of their faces. My knees buckled and I fell to the ground, where I hid until I heard them leave. Once I knew it was clear, I ran to their position to confirm my suspicions… They saw everything. (Source)

That’s When I Knew

I wore short-shorts in fourth grade. Also, I’m a guy. See, there was this girl I had a huge crush on in school. She was brilliant and beautiful and just great. So, me being in fourth grade, I took my cues on how to impress girls from television. The problem was, for some reason I never took the cues from the men on TV… I took it from the women. So, I would wear these extremely tight fitting shorts that kept on getting smaller and smaller as I continued to grow. I must have worn these shorts twice a week for six months, thinking this girl was really enjoying my tight butt. Then one day I was walking past the girl and her friends and I could feel their eyes on me. I felt cool and sexy and wanted… only for me to round the corner to hear them burst into laughter. I stopped and listened as they mocked my tight short-shorts. And that’s when I knew that short-shorts weren’t really going to win that girl’s heart. Pfft. No regrets. I looked fabulous, Audrey. You hater. (Source)

I’ll Just White It Out

In middle school, ADIDAS shoes were all the rage (white shoe, three black stripes). I had to settle for the four-stripe knockoffs from Payless. I took it upon myself to white-out the fourth stripe. Middle school kids could be so cruel. (Source)

P_ssy Confusion

I’m an only child raised by a hard working single mother. Im also male. So there’s a lot in life I had to learn on my own growing up. I had overheard my cool older cousin say he “got p_ssy” to another relative during a family party. That stuck with me even though I had no clue what it meant.
So I’m in 4th grade and I was being picked on by a group 6th grader boys. I had enough and thought I had the perfect comeback to shut them up forever. So with complete confidence I yell “Yeah? Well at least I have a p_ssy and you don’t!” It kind of worked because they stopped their insults due to their uncontrollable laughter. I immediately knew having a p_ssy was not something to brag about. I didn’t find out until years later what it meant. Still cringe. They still ask how my pussy is doing every time I run into one of them around town. (Source)

The Longest Squat

At school, about 14, having an assembly, a giant one with about 500 students. We all had chairs, my chair is placed next to the aisle-gap in the middle.. We stand up when the headmaster (uk school) walks in. During this brief period of standing, the bastard behind me takes my chair and passes it behind him, that bastard does the same and soon my chair is at the very back of the hall. All 500 people sit down, I at least notice and don’t fall on my arse but I am left with a predicament. I was a massive unpopular bag of awkward and anxiety at school, I decided the best solution was to hover. Pretend I have a chair. This worked for about five minutes before I wobbled and the headmaster boomed “[surname], where is your bloody chair?”. I was terrified of speaking so just pointed to the back of the hall. All the other kids were laughing and he made me go and get it. That was the longest walk ever. My toes curl jus thinking of it. (Source)

The Trumpet Heard Round the School

One time in middle school social studies, I’m taking a test and feel a quiet fart brewing inside me. Just a tiny little guy, nobody will even hear it.
It goes off like a trumpet, everyone looks up from their tests at me and just starts laughing. It wasn’t THAT traumatic though, I mostly just laughed it off and dealt with the sh_t talking. (Source)

I’ll Just Walk It Off

I was obsessed with trying to be “manly” when I was 13. One day at gym, a kid accidentally hit me in the face with a basketball, hard enough to knock me down. Well, the fall split the back of my head open (bone was fine, just the skin) and the basketball to the face implanted my braces inside of my front lip. So I stand up, blood leaking down the back of my shirt and out of my mouth, and tears streaming down my face. And I try to convince every one staring at me that I’m fine, and no I’m not crying. Then I tried to swagger out of the gym, panicked when the teacher tried to stop me, and ran out with the portly gym teacher chasing after me. Out of everything, the attempted swagger is what makes me cringe. (Source)

Hateful Art

When I was growing up, my dad grounded me and I spent over an hour making an elaborate drawing with markers that said “I HATE YOU.” He actually found it hilarious and kept it. He then presented it to me when I was 24 and pregnant with my first child. (Source)

iPod Porn Lesson

When I was around 16, I had just received an iPod touch (3rd generation I think, the first retinas) for my birthday and was showing it off to my friend at his place when his mom came it and was curious too. So I start explaining to her all it can do and open the web browser to show her how the browser looked like. This iPod was the first portable internet device I owned (didn’t have a phone or laptop), so, being the horny teenager that I was, I had locked myself in my room the night before and searched for porn all night. I didn’t know at the time that the browser on iPods/iPhone keep the tabs opened even if you close the app. So, right in front of my friend and his mom a milf porn site starts loading. I closed it quickly, was super red and like “yeaaah sooo that’s the iPod”. Dinner was right after, I couldn’t look at his mom. (Source)

He’s Really a Nice Guy

Dating the guy I did in high school. The weird kid who tried to pierce his own lip at school with a safety pin. The guy who thought getting a blow job on the bus from a 13 year old was OK. The guy who thought that shoving his hands down a girls pants in the school cafeteria was acceptable. The guy who told a girl (his ex who thought she was pregnant with his kid) who tried to commit suicide that she didn’t try hard enough. Looking back at myself trying to convince my parents that he was a good guy. Now that is cringe worthy. Shivers. (Source)

Stop Rescuing Me Please!

Finally, my time to shine. I was at boy scout camp. 13 years old. About ten of us were standing in the shallow end of the pool. The adult instructor was standing at the edge and was attempting to show us a technique to lift someone in distress out of the pool by holding on to their wrists and bouncing them off the bottom to pull them out. He made me be a volunteer to demonstrate the technique to everyone else. So the instructor, while standing outside the pool, was to bounce me off the bottom to pull me out. When he pulled me up the down force was so strong it pulled my bathing suit down. All the way, around my ankles. I don’t think the instructor realized because he was was just holding me in the air for about 5-10 seconds. So there I was, hanging me air, full frontal to EVERYONE in the pool. Everybody died laughing. I was screaming and wriggling so hard to fall back into the pool but I wasn’t strong and couldn’t break the instructors grip. I think there may be a plaque up somewhere about the incident.
(Source)

This Is My Real Voice

I remember I went thru a time where I was concerned that my voice wasn’t going to change or something; so I purposely lowered my voice every time I was at school. Like made it ridiculously Barry white style deep. I had a Spanish class with some upper classmates and they would joke around and say me amo Pablo…” (my Spanish class name) in deep voices. Haha oh man and I was in my glasses/braces phase. So awkward!!! (Source)

Scorned Lover

Oh my god. Even the memory of this physically pains me. So, love of my life when I was 13 is this amazing, funny, popular guy. I am queen of painfully awkward and oblivious. He starts talking to me at a party. Oh god. This is it. How we met! It’s going to be our story! I’m already naming our future children and trying desperately to keep up so he thinks I’m cool. More people join us and he starts talking to another girl. Then straight up hitting on her. I was crushed. I needed to make him feel bad for betraying our love! I tried to cry, but lack the ability to fake cry. So I tried to look as forlorn as possible hoping someone would notice and ask what was wrong. No one did. Finally, in a grand effort to bring attention to my plight of heartbroken sadness, I decided to be so upset I would vomit! Which I couldn’t do either. I ran to the bathroom and shoved my hand down my throat to try to get something started. All this accomplished was me salivating all over my shirt sleeve and my face and eyes turning red. I gave up and rejoined the party. No one witnessed the crazy, but I’ll always know. (Source)

Behind Blue Eyes

When I was 13, we had to do a presentation in front of the class, which included choosing a song and explaining why it could be related to your life. Most people picked songs that talked about a specific trait, I can’t remember any particular ones, but basically it was like “I’m a funny person” or “I’m a happy person” and the like. But no, not me. I was going through my emo stage, as I’m sure many of us did, and decided to find a way to portray myself in a way that talked about how upset I was with my life and the world. So I chose Behind Blue Eyes by The Who. So I get up to do the presentation, play a bit of the song and explain in front of the whole class and teacher about how my life sucks and nobody likes me and basically that I don’t deserve to live. Then my teacher says “oh Tyler we don’t feel that way about you” and then I burst into tears still standing in front of the class. As if that’s not bad enough, my teacher is worried about me (rightfully so) and she calls my parents and then I have to not only live it, but then explain what happened to my parents. I can’t think about it without cringing. (Source)

Bad Ass Pirouettes

Late teenage years, 18 to be exact. Some friends and I had all agreed to rent out a house together, 3 story place, 6 bedrooms so one each and a large communal room downstairs that we used as a garage for our motorbikes. Yep, all rufty tufty bikers, long tatty hair, the beginnings of my now magnificent (and greying) beard. Hard as nails, us lot, was the image we were projecting… So, I’m hoovering up in my room. It’s earlyish in the morning and I put the radio on. A few minutes in, the Pet Shop Boys – Left To My Own Devices came on.
Dunno why it affected me like so at the time, but I went through a full on song and dance routine to this with the hoover, pirouetteing, crouches, OTT vocals, the lot. A hairy bearded diva, right there with the vacuum cleaner. I never realized the door to my room was open, lost in the bewitching dream of camp pop stardom as I was. I finished my housework and only then noticed a couple of my housemates practically dying with laughter. They had been watching me for the entire performance. Going 25 years later I still get the piss ripped out of me for that. Don’t care. Pet Shop Boys are my not-so secret guilty pleasure.Don’t Mess With Mama Hulk’s Baby (Source)

Don’t Mess With Mama Hulk’s Baby

My mom walked in on my boyfriend & I having sex. That’s not the mortifying part. The embarrassing, I still haven’t lived this down part was she fully transformed into SHEHulk! She seriously lunged at my boyfriend, threw him on the floor & literally chased him out of the house without his clothes. Before this moment my mother absolutely adored my boyfriend thinking he was a “good Christian boy with wonderful morals”… After this she still refers to him as “the liar who stole her baby’s precious virginity”… I was 17 & he was not my first (Source)

Debbie, Can You Hear Me?

Debbie, with spray-on jeans and pouting lips. I didn’t stand a chance, and I did what any smitten teen would do – I made her a mixtape on a C90 cassette. Overtaken by hormones and the fiery desires of my loins, I decided to put in a short – and, in retrospect, decidedly sad spoken interlude halfway through side two. The gist of it was this: “Debbie, I want to see you with very few clothes on.” I gave her a few days to let the message – mixed together with my irresistible choice of 80’s New Rom standards – sink in, before giving her a call: “Hey Debbie, did you listen to that tape I made you?” “I didn’t have time. I gave it to my brother… He’s in the RAF Regiment. I thought it would be nice to give him something to listen to in his barrack room.” Meanwhile, at RAF Uxbridge, a battered ghetto blaster plays. Perched on top of the machine is a cassette box, bearing the words “Debbie’s Mix Tape Vol. 1”. Half a dozen finely-creased and frighteningly muscular young men – some of whom are openly displaying wispy pencil moustaches – sit open-mouthed, hanging on to every last, pathetic word, their fingers tightening over a variety of semi-automatic weapons. “…and Debbie, as the band plays on, we can make sweet, sweet music of our own…” “CUUUUUUUUUUUUUUUUUUUUUUUUN……” I never spoke to her again. (Source)

Spoiler: You All Die

When I was in middle school I wrote a story and read it out loud to the class, It was an Edgar Allen Poe story and I killed all my classmates, broken beer bottles, skinning, eating eyeballs, decapitation via train, ripping out a heart Indiana Jones style, bashing in with rocks. Pretty sure everyone thought I’d shoot up the school, one friend still jokes saying that he always knew he’d be safe because he saved me from being beat up with lacrosse sticks. In freshmen year I was talking to a girl (crush on at the time, friends to this day) and in the middle of her talking I sneezed, the snot shot out of my nose and right into her mouth. She ran out of the room screaming ew, interesting day. (Source)

Secondhand Fight Club

I bought a second hand red leather jacket and used to wear it with an Hawaiian shirt thinking I looked like brad Pitt in fight club. I got scabies from it! (Source)

Sorry! Gotta Go

I was trying to apologize to my girlfriends stepmom for being a dick, and I had a panic attack instead. We were in the car, and I said sorry, then promptly ripped open the door, fell out, slammed the door, started sprinting into my house, tripped, and then dashed inside. (Source)

I Want My Mom

It was the 6th grade, we just finished a football game. At this time we didn’t have a bus so kids drove home with their parents. This was an away game in rural North Dakota. Well after the game I was freezing and I wanted to get warm as soon as possible, so I’m scanning for my mom’s car, and I see it, I run to it and hop in, she wasn’t in the car so I decided to wait for her. I know she doesn’t like me having football stuff on in her car so I start taking it all off, I’m down to my underwear, about to put on my shorts when some lady catches my eye, she’s staring straight at me, I’m obviously embarrassed, but I just wait for her to look away, she doesn’t. This lady is staring me down hard, coming straight for me. Before I knew it she flung open the door and started yelling at me asking what the hell I was doing, I have a absolute panic attack and begin crying, sitting in the car seat in my whitey tighties, just screaming bloody murder. I take all my stuff and run out, once again, I had nothing on but underwear and I stand there crying looking for my mom for like 5 minutes. I had gotten in the wrong f_cking car. To this day, just writing this, I flare up with embarrassment. (Source)

Always Come Prepared

i was at a house party and someone asked me to pitch in money for drinks. I had that typical teenage mindset to try to get laid for the first time (though I was a little overweight and awkward so chances were pretty much zero). I pull out my wallet and out comes flying the “just-in-case” condom and lands in the middle of party. Everyone stops what they’re doing, I freeze as I feel all eyes fix on me and the condom, and an eruption of laughter follows a split second after. I’m instantly on the verge of breakdown and am about to leave when one my friends goes, picks it up, and puts it away in her pocket. She plays it off with something like, “I’ll hold this for you” and the party resumed. (Source)

He’s Got Moves

In like 7th grade I was walking down the hallway from lunch. A hot girl walks around the corner right in front of me and instead of just walking around her, I did a f_cking spin move off of her like she was a linebacker. Still to this day don’t know why I did it. (Source)

Suddenly Single

I had a girlfriend, but heard that another girl might like me. I asked current girlfriend if she would still be my girlfriend if other girl didn’t actually want to be my girlfriend. PRESTO no girlfriends at all! What a f_cking idiot I was…. (Source)

That Run Isn’t Working

When I was 12, I thought I’d run faster and look cool if I ran with both of my arms behind me (kind of like a dragon ball z character or Sonic the hedgehog). I stopped doing it when my gym teacher advised me to stop running like an idiot in front of the whole class. (Source)

What Rhymes With Fajita?

I put a poem in a cheerleaders locker in Jr high that I had a huge crush on. Can’t really remember how I got it in there or what it said, but I do remember I rhymed something about a cheetah with ewwww fajita. Everyone knew about that f_cking poem (Source)