Being a Teen is hard. There are the kids who try too hard to fit in, the kids who “aren’t like other kids,” and the kids who truly end up one of a kind. The work put into claiming your status might just push you to do, wear, or talk about things way past the comfort zone. And looking back at it, even years later, can make you and other people who hear your stories cringe hard.
1. Here Comes, Stone Cold, uh, Me
I LOVED WWE growing up. I had a couple of cassettes with some of my favorite wrestlers’ walkout music. If my mom was sitting around with her friends, I would put on a song, usually Stone Cold, Bret Hart or Shawn Michaels, and then proceed to “walk-out,” acting like them standing on a random item and raise my hands to the crowd.
I would take it as far as I could before the embarrassment took over and I would hide in shame.
2. Dinner Dud
At junior prom, I blurted out during dinner to my date, “I’m so bored” and I have NO idea why it came out of my mouth. I’m pretty well-mannered and quiet. I forget how I tried to play it off, but I felt so bad.
3. Whatever, Mom, I’m a PUNK.
When I was younger, I went through a “punk” phase, which largely consisted of listening to Anti-Flag, going to Warped Tour, shopping at Hot Topic, and watching SLC Punk. At one point, I got this heinous leather choker with metal spikes, which my mom couldn’t stand. In an act of misguided “revenge” for my upper-middle-class suburban upbringing, I decided to wear it to my class photo.
Now I’m mortified and for years, my mom paid me back in the most humiliating way possible. She would bring out that photo to show guests what I was like in high school. You win, Mom.
4. I’m Actually a Robot so…
There were a good few years during the ages of 12-15 where I tried to convince everyone, including myself, that I was a robot. I have no idea why. I had all these explanations as to how I grew (pneumatic bones) and how my brain was actually a computer. During truth or dare, my biggest secret was always, “I am actually a robot.” So cringey.
Everyone thought I was trolling, but to be honest I actually believed it myself. Now looking back, I kind of view those times as undiagnosed mental issues that presented in weird ways, but by God, everyone thought I was the weirdest person ever and I don’t even blame them!
5. Out of This World
My worst phase was when I was pretending that I was an alien disguised as an earthling sent to this planet to observe humans through friendship. I don’t know how those who became my friends during that phase stayed friends with me. Also, I’m thankful I don’t remember much of it.
6. But I Did What You Told Me to Do!
So, I had really long curly hair and the one girl I liked said, “You should straighten your hair.” It was the worst mistake of my life. Mind you, I’m so ginger that my hair glows orange. I took her advice, asked my mom in the morning to help me out, and went to school to impress her. Well, people gave me trouble all day, and then it got worse.
I looked like a small and pasty white bootleg version of Fabio. When I finally saw the girl in class, I said, “Hey look, I straightened my hair!” She replied with, “Oh…” and turned around really quick. God, how bad the cringe was made my stomach cramps from the tension.
7. Sister Act
I stole my sister’s boyfriend when I was 16. I’m not proud of it and she’s still mad at me. Also, he was eight years older than me. Should’ve added that.
8. Take the Hint
I had a video game addiction that caused me to miss out on some potentially good memories and fed into my social anxiety. As an example, a cute girl in my Pre-Cal class was like, “Jonah, who are you asking to homecoming? I may just go with friends unless someone asks me.” My response was mind-blowingly dumb. I just said absolutely. Nothing.
9. Pink Floyd Fan Fraud
I had a classic rock/metal phase in early middle school. Back then, I found out my crush who was four years older than me liked Pink Floyd so I thought that letting him know that I listened to them too would get him to notice and talk to me. So, I drew the Dark Side of the Moon album art on an A4 paper with colored pencils, because I wasn’t able to print it and I wasn’t able to buy any merch.
I put it in my binder then just kept walking past him while holding the binder. Spoiler alert: that didn’t work.
10. British But for Only Six Months
Oh boy, I was the kid who decided freshman year to talk ONLY in a British accent. I’m American. That lasted a semester. I was almost literally stalking a girl I had a major crush on. At least I was able to take a step back and realize, “This is really weird,” and I started getting over it. God knows what I was thinking at the time, it wasn’t even convincing.
11. Creepy (Inappropriate) Church Crush
I had a crush on a youth leader in my church when I was 16. I actively pursued him while thinking I was being subtle the whole time. I even showed up at his work unannounced and had my friend drop me off there so the guy would have to take me home. I even left a note under his pillow at one point when I was at his house with other people.
Eventually, it came to an utterly embarrassing end. Another youth leader had to sit me down and tell me that I was making him feel very uncomfortable and that I needed to back off. She said it nicely, but it was so awkward that I still hardcore cringe thinking back on that. Clearly, unfinished brain is the correct way to put it.
12. Wannabe Frat Boy
One of my hobbies during middle school in the early 2000s was shooting movies with my dad’s video camera using my Barbie dolls as the actors. I also watched a lot of MTV at the time so I would try to recreate things I saw on there like wild spring break beach parties and scenes from 50 Cent’s music videos because I assumed all the “cool grown-ups” acted like that.
I also remember asking my mom if I could have a frat party theme (I’m a girl) for my 14th birthday party. She, of course, said no.
13. Two Consecutive Cringe Phases
From ages 13-14, I wore anime shirts constantly. I talked about moving to Japan as an adult. I went to Chinatown often, bought posters of anime girls in underwear, and hung them in my room. I also wrote fanfiction. From ages 15-16, I wore a leather jacket constantly, a necklace of a giant silver dragon head, sunglasses indoors, and weird shirts with those draping Victorian sleeves.
I pined over girls and wrote bad poetry, but never had a “nice guy” phase, thank Christ. I also hung out with a Wiccan who brewed his own potions.
14. A Random Wardrobe IS Cool, Okay?
I was in middle school when the pop the collar with a random tie around your neck for no reason phase was super popular. I wore cargo shorts and MN twins T-Shirts, EXCLUSIVELY, at this time. I showed up to school wearing an untucked, button-down shirt, Hollister T-Shirt, American Eagle shoes, and a random tie around my neck. Then, the worst happened.
A girl I had a majro crush on approaches me before I even get to my locker and says, “Looking good Scott!” sarcastically to me. I open my locker, look in my mirror, sigh, and take off the tie. I never wore that outfit ever again. It was a shameful day and it took me a while to get over it, but it’s one that I am still proud of in the end.
15. The New Clint Eastwood
I was really into Westerns and started to talk and act like Clint Eastwood in The Good, the Bad and the Ugly. I even bought a poncho and a cowboy hat. I started smoking cigars because of it too. If I went outside, I toned down the whole poncho thing but I did wear the hat and cowboy boots with the shirt and vest that Clint had.
Good god, I thought I was cool and unique, but looking back now it’s super cringey. I still love Westerns and Clint though!
16. Failing to Hit on My Teacher
YEP. I had a massive crush on a young teacher when I was in high school who I got along very well with. My dramatic teenage brain felt like I would never see him again after I graduated, so I tried to give him my number at the end of senior year. He very politely declined. That’s mortifying just on its own, but it’s even not the worst part.
He’s actually someone I ended up seeing on a very regular basis for years after graduating due to a common interest, and still see now and then 10+ years after graduating. Had I not been insane in the membrane, I would have realized that at the time and could have contented myself with thinking that maybe something might happen down the line.
To be clear, nothing ever happened and he had/has absolutely no interest in me whatsoever and rightly so—we just get along swimmingly on a platonic level. But if I hadn’t been so panicked and dramatic, I wouldn’t have to be a 30-year-old who still occasionally wakes up at 3 AM and remembers that I once tried to give my phone number to a teacher. Ah, youth.
17. Sewww Random
The girls at my school went through a tie phase in eighth grade, so I bought a ton of ridiculous ties. I couldn’t tie them so I made my dad tie them for me. I kept wearing them throughout early high school as part of this ensemble: big collared dress shirt under a big T-Shirt with the collar out and with a tie on. I had ties with dice, elephants, Kermit, and a trombone on them.
18. Super Snub
For most of my education, I went to public school. Like most kids, I was socially awkward. For high school, I received an academic scholarship to a private Catholic school. It was a really big deal for my family, but I didn’t know anyone at the new school. Between an odd combination of academics, sports, and the tail-end of puberty, I became very popular in this new school.
I wasn’t used to the attention and it definitely got to my teenage head. Nearly all of my social circles became around the new school and not with my old local friends. I’m in my junior year, I head to a McDonald’s for lunch with a few friends from the new school. Working the counter, I see a girl who I used to go to public school, who I used to have a crush on.
She just lit up when she saw me—and I committed a terribly cruel act.She was so excited, and I…I was an awful teenager and I just ignored her. I pretended I didn’t recognize her. She looked so deflated when I didn’t acknowledge her. Note this was the 90s. My family moved a few times after that. I settled down in a different part of the country after university, and I never made it back to that town.
I’ve relived that moment for years now. Fast forward to one of those nights when I relive that moment, and I decide to look her up on Facebook to apologize. That’s when I made a horrific discovery. I find out she died 10 years ago in an auto accident. Since I found out her fate, I feel even more awful about that moment.
19. Hardcore Parkour
I used to like climbing dangerously high buildings and objects attempting self-taught parkour sometimes with my hood up. I was a big Assassin’s Creed fan. I cringe because I look at some of the things that I climbed at 12/13 thinking holy moly, you were so stupid, you could have easily died. I never had any serious injuries, thankfully, just the odd grazed knee or bruise.
20. Fake Smoker Phase
It was my “smoking” phase. I was a nerdy teen and decided to rebel when I was around 14/15. I used to hang around some cooler kids and pretend to smoke. I didn’t/couldn’t inhale, so I used to blow the smoke out of my nose so that nobody could really tell. I remember having a conversation with one of the really cool kids about how often we smoked and I actually said, “Oh I always need to have one before an exam.” Oh God!!!
21. The Dance of Death
I was around 15 years old and having a complete breakdown in all aspects of life. My mother had died suddenly; I had an untreated mental illness and was self-harming a lot for years and no one was listening; my dad was understandably a wreck; school fell to the wayside. I was barely going and intending on dropping out. I couldn’t do anything, let alone it all.
There was a high school dance. I was desperate to have some fun and pretty much have this be the highlight before I left. Though I failed at communicating this, I really wanted a friend to dance with me and our other friends, but she was awkwardly sitting alone. So I took it way too far. I pushed her too hard and made her cry.
I couldn’t see through my own stuff to see how bad of a position I put her in. All I could see was my world collapsing. We never spoke again. She went from my best friend to nothing in one night. That was 15 years ago, and I still feel awful. Hindsight is always 20/20 as they say.
22. Brand Obsession
I was an early 2000s thug/hypebeast. I forced my parents to buy me all the stupidly expensive clothes by rappers. The brands mattered so much to me and I thought they mattered to others too. I would legitimately count the total number of brands that I owned constantly. I also wore a slanted headband and tucked my cuffs in my socks. I even tried to learn Patois at one point.
23. Teenage Anarchy
I had an anarchist/screw the government phase. This was actually an indirect response to growing up atheist—both my parents are atheists—in a community where a good 85% of people are very religious. I stole spray paint and put up some anarchy signs and later in school we had to read lyrics from songs we liked. So, I picked Anti-Flag’s “Die for Your Government.”
I just read it straight-faced with no commentary or anything. The teacher just said, “WELL OK…, that song has a very strong message. I’m glad to see you identify with something.” Her approval was the beginning of the end of that phase. Man, I was doing that stuff for shock value! I feel like this is where I mention my first career job was…for the government, haha.
24. The Good Ol’ Prank Call
I was a gullible idiot and there was this guy who used to bother me a lot. I was 12/13, I think, and he was the typical guy going, “you are smelly, stupid” etc. and me insulting him back. Well one day, he goes, “my friend from another school likes you.” And I was like oh yeah really, how does he even know me. This was just the beginning of a cruel plot.
The guy goes, “he saw you a few times and thinks you’re pretty. Here, I’ll send a picture of you to him.” I kind of fell for it so I let him. And I saw a picture of the kid too. Apparently, the kid thought I was beautiful and wanted to marry me. Anyway, because I’m gullible I ended up giving my home number away at some point.
The whole time I’m thinking, “oooh this guy likes me.” Cue this kid calling me and declaring his undying love for me. He kept calling and my dad picked up a few times to this guy going, “I want to marry your daughter,” and my dad goes, “Really, huh, I’ll find out your location in a few seconds and speak to your parents.”
The kid got scared off, pretty much. Not long later me and some friends have the brilliant idea of pranking him in return. The guy that I didn’t like had given me the kid’s number too. So, I called anonymously and pretended to be some random girl going, “Hey, did you know I’m pregnant with your child?” His mum picked up, told me to shut up, and hung up. That was so stupidly cringey.
25. The Emo Kid
I went through an emo phase in high school. I was jamming to “Stick Stickly” by Attack Attack every single day. I thought I was capable of murder while also being too socially awkward to ask for extra ketchup at a restaurant. I looked androgynous and basically hate every photo of myself prior to the last year of high school when I became self-aware.
I’m happy to say I no longer look anything like I did back then so I don’t think anyone who knew me back then will recognize me.
26. Teenage Love Knows No Bounds
When I was 15, I wrote my boyfriend a letter begging him not to break up with me. Then I took it to the next level. I smeared my tears on it and even pricked my finger so I would leave blood and said, “Look how much I love you. I bleed for you.”
27. Bargain Bin Eminem
I saw a dude on MTV’s Road Rules vs Real World with frosted tips. Mind you, this is like 1998/99. I thought he looked really cool. My barber did not do this. So, I shaved my head, let it grow out a bit, and then dyed my hair blonde. Then I let it grow out some more. I thought it looked cool at the time but I saw a picture like 10 years later and holy moly, it was horrible.
It also didn’t help that Eminem was getting popular at the time so people thought I was just trying to do the Eminem thing.
28. Inexperienced Teen, Steamy Harry Potter and Green Day Fan Fiction
I was very, very emo. I was obsessed with a lot of things, especially Harry Potter and Green Day. I’m not mad about the Harry Potter part, but I used to write TONS of awkward, cringey fan fiction about both. It included sex scenes—I was also a virgin so you can imagine how uncomfortable it was. Then one day, my worst nightmare came true.
My mom found it and read it. Being very conservative and religious, she was absolutely horrified. I was grounded from using the computer for three out of four years of high school as a result. In general, my entire existence from ages 13-20 was a long and painful cringe-fest that I’m not sure I will ever live down.
29. What Do You Mean You Don’t Know Annie Leibovitz?!
I thought I was so cool and artistic because I had a digital camera. I used to take bad photos of random meaningless stuff like old fruit or the sky or piano keys and upload it to Facebook with cryptic captions to look artsy. I remember at my 14th birthday party me and my friends were playing this game where you had to describe a famous person and everyone had to guess who it was.
The rule was to pick people that most people would have heard of. Because I was an embarrassing freak, I insisted on choosing Annie Leibovitz. I remember acting SO shocked and surprised when everyone didn’t know who she was, even though I knew they wouldn’t know. “She’s this AMAZING photographer, gosh you haven’t heard of her?” God, I was so pretentious.
30. Can’t Buy Me Love
A girl my buddy had given my number to wouldn’t leave me alone. Calls at all hours, follows me in the halls, tries to sit with me at lunch, all of that. I blocked her number and avoided her at all costs. One day at lunch she sees me, beams at me, and makes a beeline right for me. I’m with all my buddies, and she stands there looking at me and waiting for me to ask her to sit down.
Instead, the first thing to pop into my head was to grab a quarter in my pocket, stand up, show it to her, and at the top of my voice yell, “HERE’S A QUARTER, GO BUY YOURSELF SOME FRIENDS!” I then bounce it off the table at her and it hits her square in the forehead, and all she does is stand there while the entire lunchroom explodes in laughter.
She runs out with tears streaming down her face. I calmly sit down and continue eating. It was so out of character for me (skinny, introverted band nerd) that it was the talk of the school for weeks about how brutal that was. I still think about it and it’s been 25 years, and I feel totally ashamed about it all now.
31. Studying at Twilight Academy
My cringey obsession was with the Twilight series. Yes, people are obsessed, but I took it to horrific levels. My best friend and I even decided to “replace” all of our class subjects with Twilight-themed ones. So, music would be “Twilusic” and this was devoted to playing Edward’s lullaby. “Twi-history” was on the history of vampires. Kill me now.
32. 6’2 Marilyn Manson Clone
I was an extremely edgy goth kid. I had black hair, black clothes, black nail polish, black EVERYTHING. Yet, I came from an upper-middle-class home with very supportive parents. I really worry that my poor mom was incredibly embarrassed to be seen in public with me. My sweet mother, with her typically yuppie mom attire, standing next to a 6’2” tall clone of Marilyn Manson.
33. Everything But the Girl
Mine was definitely the whole emo/scene thing. Although I was largely just trying to get laid, the girls I was into at that time were into it and seemed to only be into guys that were also into it. So, I made myself like that. Luckily, I never did anything life-altering like gauging out my ears or getting a band tattoo. But I definitely dressed like an idiot and listened to some pretty terrible music.
The worst part is that it didn’t even work. I think they could sense that I wasn’t really that way and was just sort of hanging out and trying to be accepted, which, in hindsight, was a blessing in disguise. A few of those girls that I was like obsessed with turned out to be absolute train wrecks in adulthood, so dodged a bullet there.
34. The Internet Exists So I Can Lie
Oh god, there are so many things I look back on and just cringe about. I was the kid whose girlfriend “went to another school.” I was also the kid who posted on Facebook with a lot of fake wit. I tried to impress people by exaggerating stories or making them up altogether. I wish I would have figured out way sooner that people like who I really am, not who I pretended to be.
35. Whatever the Opposite of “Smooth” Is
I was working at the movie theater and was off of work. My friend said I should go ask this girl out. I had zero game and confidence, but I try my luck. I went up to the girl and told her my name and said I thought that she’s pretty. She replied with, “thanks…,” and went into her movie. My friend then gave me the worst advice ever.
He told me I should go in there, find her, and try again. I go into the movie and it’s dark, but I find her. I go sit next to her and her friend. They both look at me. I say “Would you be interested in going out with me?” She replies that she has a boyfriend. Complete awkward silence. I literally sat there for at least 30 seconds looking at the screen and telling myself to leave.
Then she says: “You should go.” So, I get up and leave. My friend laughed hysterically at my failure.
36. Weeb, But Make it Innocent
From 14-17, I was obsessed with anime. I spouted random Japanese words, wanted to live in Japan, and thought I was some kind of expert on all things Japanese. I wanted to date Japanese guys. I would only watch anime. I constantly talked about anime to people who couldn’t have cared less about it. Luckily, since my mom was pretty strict, I didn’t have free reign of the internet.
Because of that, I did not discover things like role-playing, fan fiction, fan art, or fandoms in general until after my teen phase.
37. Acrostic Poems Are Love Poems
My cringe-filled phase was in high school where I’d write acrostics to girls that I had crushes on. Their names would be the source of the acrostic. The first time I pulled it off, I put the poem on the girl’s desk before one class we had together. She came in, picked it up, read it, and started talking excitedly to her best friend about it.
I really thought I had a chance, but then I made a horrible realization. She’d thought her boyfriend had written the poem.
38. It Was Cool in The Matrix Movies!
Black. Leather. Trench coats. They were big back in the 90s. Spyke, Blade, Neo—these guys were genuinely cool and I wanted to be them. Even better, I lived in a tiny little country town where most people wore plaid and wide belt buckles. This was a great way to define myself as being unique, but also cool. I shopped around for a while.
When I finally found one that I liked, I dropped a few hundred on it. I’ll never forget it! It was mid-April 1999. I got to wear it for all of a week before the entire nation decided it was unanimously uncool for the edge lord teenage outsider who gets bullied a lot to also wear a trench coat.
39. Puberty Made Me Goth
I was so awkward as a teen that I guess you could say I went through a semi-goth phase until graduating high school in 2003, and part of the way through college. I had bad social anxiety even back then and suffered from then-undiagnosed paranoia. I only wore black or dark red. From seventh to eighth grade over summer, I jumped from a B-cup to a D-cup, then eventually a DD in ninth grade.
I wore very baggy shirts and the black pants that were huge, long, and had lots of pockets/zippers/chains—I think they were Tripps Gothic men’s pants). I wore Doc Marten boots as well. I did my best to cover up that I had an adult type body and just ended up looking like an awkward “goth.” It worked though, guys stopped leering at me and I was left to read and write in the AV room during lunch in peace.
Now I still wear mostly black, but I’m resigned to the girls being there and my clothing is kind of form-fitting. I’m still reserved and awkward though and I miss my Doc Martens.
40. Everybody Needs a Hobby
I wanted a hobby/something to collect. My brother was collecting Wheaties Boxes and like NFL figurines or something. I decided to get into something super weird. Lighthouses. I got a giant lighthouse rug that was then hung on a wall in my room. Maybe it was more oceanic collection. I had a ship on my bookshelf too.
41. Kara-Oh No
Between sophomore and junior year in high school, I went on a summer study program. I was an awkward teen (who wasn’t?) but I thought at the time I was the only awkward one of the bunch. There was a “competition” and I wanted to sing in it. I can’t sing. I chose a song to sing that was a classic, but the version they put on was a remix.
I couldn’t keep the timing or anything. So on stage, I made a signal to cut the music and walked off stage after performing poorly, right in the middle of the song.
42. Extreme Crush Obsession
When I was in middle school, I noticed this guy Tommy. He had the same teachers as me but at opposite times, and we shared our elective classes together because he was in the band playing the same instrument as me. Words cannot adequately describe the utter obsession I had for this guy. I’d never had a crush like that before and certainly never since.
I was absolutely convinced that I’d have a crush on him for the rest of my life. I never want to remember the stupid things I did around him. Someone in my keyboarding class was like, “Tommy farted during English today,” and I immediately was like, “ME TOO!” super excitedly. Thankfully I did not share this class with him.
I was so obsessed that I looked in the phone book and found the possibilities for his parents, address, and phone number. I discovered which one it was somehow. I still remember his phone number. I also got someone to find out his middle name for me, which I also still remember. I’d stare at him and get really nervous when he did anything.
I finally gave him a note telling him I was in love with him and blushed furiously. His response was crushing. He told his friend he thought I was butt ugly. Ouch, but I kept going. I tried to get my friend to try and get us to become friends. Yeah no, that didn’t happen. Towards the end of the school year, I finally came down from that awful high.
I started panicking when I realized I “had doubts about our relationship.” Good riddance.
43. The Truffle Shuffle of Shame
When I was a teen, some girl was wearing a Goonies shirt. I had no idea what it was, but it looked like a punk band or something and she was preppy, so my emo self tried to act offended and said, “Do you even listen to the Goonies?”