Aloha, Hawaiian Shirts
Social media is filled with fun, games, and cat memes, until it occurs to you that it now also doubles as a time capsule for the most cringe-worthy moments of your life. Everyone has that Facebook friend who insists on posting recently discovered gems from years, or even decades ago.
Teenage years are awkward. You’re trying to navigate the pressures of both childhood and adulthood, all while trying to find your identity as a human. As it turns out, that road to self-discovery is paved with a lot of bad style choices, questionable behavior, and cringe-worthy music choices.
If you’d like to feel a little less alone in some of your choices throughout the years, check out some of these people’s hilarious stories of cringe-worthy teenage phases. Fair warning though: you’re likely to relate to more than a few of these stories…
An Emotional Response
I went through a phase where I only wore Hawaiian shirts. The brighter the better was my philosophy. I even had a super bright orange one that was my favorite. Now it’s more like “orange you glad you’re not wearing these shirts every single day anymore?”
But back then I guess I didn’t understand that it wasn’t so cool. I thought it just meant that I liked to party. As the comedian Chris O’Dowd once said, “I’m a Hawaiian shirt guy. I’ve made that life decision.” Yes, he really said that. Reddit user: YLedbetter10
Long Hair, Don’t Care
I was honestly such an intolerable jerk when I was a teenager. I rejected emotion as an option almost completely when I would be responding to things, and when my own mother approached me with an even slightly emotional response, I would cut her off.
I would actually say to her, “That’s an emotional response, let’s talk when we can both speak logically.” That phase lasted a few months before I finally got back on track and understood that emotions are actually a good thing to have. Reddit user: LucJenson
Mother Dearest
A girl I used to go out with had once asked me to grow out my hair very long. I complied and did it. She eventually left me, and I thought, “Hey, this girl likes men with long hair. I’m pretty sure others do as well.” Nope, that in fact wasn’t the case.
I wasn’t successful with women until after I got my hair cut. Thinking back, my hair was quite silly then. Did you really live as a teenager if you don’t have at least a few pictures of yourself with a terrible hairstyle? I think not. Reddit user: _ak
Discover Your Truth
Being extremely disrespectful to my parents and showing no appreciation was my phase. I’m still apologizing to my mother even 20 years later. It’s funny. The teenage years are generally spent hating your parents and venting to your friends.
You tell your friends how they “just don’t understand me at all!” Then you get to your 20s and start to freak out at the idea of adulting. Wait, I have to actually buy my own shampoo and schedule my own doctor’s appointments without help from my mom? What is this? Reddit user: theoneupstairs
The Entire Twilight Saga
That phase during freshman year of college where your eyes are opened to the world and you jump into discussions with the assured certainty that your feelings and opinions are truth. For the record, you should always stand by your feelings and opinions.
But it may get messy at this point in your life. You’re only 18, and had to ask for permission to use the restroom just mere months earlier, and are now expected to figure out your entire future. Who wouldn’t be awkward? Reddit user: ForayIntoFillyloo
Monster Crush
Yes, I had a Twilight phase. Can’t wrap my mind around the idea of why I thought it would have been a good idea to whip out the good ol’ Photoshop CS2, desaturate my skin, overlay yellow over the eyes, and upload that onto Facebook as a profile picture.
I didn’t look anything like a Cullen vampire at all. It was honestly pretty bad. Before there were Kylie Jenner lips and Facetuned features, there were people who tried to look like sparkly vampires. Let that sink in…pun intended. Reddit user: [redacted]
The Force Was With Me
There was a time when I was crushing on Creepypasta characters. It doesn’t really sound too bad without context. It’s perfectly harmless to develop a crush on a fictional character; you may have had a major one on Aladdin or Prince Eric from Disney movies.
But it gets creepier when you remember that Creepypasta is where Slenderman originated, along with many other terrifying monsters. Guess you could make the argument that all your exes are already monsters, but you know…Slenderman. Reddit user: baconeggtomato
A Hairy Situation
The ages of eighteen and nineteen were my big Star Wars/Jedi Knight phase. I went for the hippie-braided hair and beard look, wore a Jedi robe, became a vegetarian, carried a lightsaber, and talked a lot about sensing disturbances in the Force.
The girl I was dating was mostly unaware of Star Wars and thought I was developing schizophrenia. Star Wars is one of the greatest series of all time, but this was probably taking it a bit too far. Stick to the Baby Yoda memes. Reddit user: ThadisJones
Get in The Ring
I guess you could say that I was majorly burnt out during high school. There was a time in my mid-teens where I could grow my sideburns out…but I couldn’t grow any other facial hair to accompany it. I thought the sideburns looked cool on their own.
But upon further review, they really did not look very cool in any way. If you think it’s weird when men end up growing a beard without a mustache, just imagine how strange it looked with having just sideburns with no other facial hair. Reddit user: galejprz
The Goth Guy in White
I LOVED WWF (now WWE) wrestling growing up. I had a couple of cassettes that had some of the wrestlers’ entrance music. If my mom was sitting around with her friends, I would put on a song, usually one of the entrance songs for Stone Cold, Bret Hart, or Shawn Michaels.
I then proceed to “walk out” acting like them, standing on a random item, and raising my hands to the crowd for their approval. I would take it as far as I could before the embarrassment took over and I would hide in shame. Reddit user: JustAnotherVoice44
Not Cool, Man
Before there were the emo and scene kids of the 2000s, there were the goths. They were known for being non-conformists by nature, but I took it to a whole new level by dressing in all white, rather than the trademark black attire that most goths wear.
Doesn’t that defeat the purpose? I guess not. It was like the dance-off episode of South Park, where the goth kids refuse to join because it’s conformist, and then the last one joins rather than conform with the other goths. Reddit user: Altogetherguy
One of My Phases
I’m a super white ginger dude who is not cool at all by any means. I used to actually wear a gold chain in high school and actively “studied” on how to be hip. I hate it. I hate thinking about it. And I hate the internet for making me think about it all over again.
I have so much hate thinking about it in retrospect. I guess that studying doesn’t always give you all the answers, especially when it comes to being cool. Just hope that you find your people and don’t have to pretend to be something you’re not. Reddit user: Who-Dey88
Funny Guy
I had about a month-long phase of full-on backwards baseball caps, Cross Colours, and like those T-shirts with Looney Tunes characters in thug gear. Everything was massively oversized, and I was skinny as a rail. This was in high school in the ’90s if you couldn’t tell by clothes.
Thank goodness there are no known pictures of me looking like this. This was one of many “phases.” I shouldn’t be so hard on myself. Anybody who went to high school in the ’90s probably knew at least one guy who dressed like this. Reddit user: poseface
I Wore Cat Ears to School
Everybody knows that one person who will do literally anything in an attempt to make others laugh, even if they have to cry. Of course, most of the time, people would laugh at them rather than with them. I was that guy trying to be as random as possible in an attempt to be funny.
And it’s not even limited to teenage years either though. Plenty of offices have that one guy who will end up eating 10 donuts on a dare or leave pictures of Nicolas Cage’s face in a folder for no reason all. Good times. Reddit user: TimDuncanCanDunk
Brony Up
Cat ears are the go-to Halloween costume for girls who want to look cute without putting in too much extra effort. But you wouldn’t wear them any other day besides Halloween, right? Wrong. Some people wore cat ears to high school every single day.
Yes, they wore them to school EVERY day, just because they felt like it. Today it might be considered quirky or even cute to do something like that, but chances are these people probably got bullied a good amount back in the day. Meow. Reddit user: zalyni
Jersey Girl
Definitely being a Brony. What attached me to My Little Pony so much was that it was such a happy world that I could escape to after having, even 9 years later, the worst part of my life (dealing with my first breakup at age 15, losing my first family member, dealing with my own identity).
It was such a simple fantasy story with very likable characters that I kinda lived vicariously there for a while. The cringy part wasn’t that I enjoyed a cartoon meant for children, but that I thought everyone else would enjoy the stuff I enjoyed for all the same reasons I did.
So I tried to pitch this thing that was very important to me to other people, excessively, not understanding when they said, “No, I don’t want to watch.” I thought they’d enjoy it too, and when they didn’t, I became defensive. Social interactions are difficult when you’re 15. Reddit user: pompousaardvark
I Shut Down My LiveJournal
In high school, I was obsessed with Jersey Shore and tried so hard to look/act like a “guidette.” But I lived in Missouri. And I’m not even the slightest bit Italian. The year 2009 produced a lot of great TV shows like Modern Family and Parks and Recreation.
But it’s safe to say that Jersey Shore was certainly not one of them. If you’re bored at work while reading this, take a second to Google the cast and see what they look like now. They didn’t even look like that in 2009 either. Reddit user: [redacted]
It’s The Climb
Let’s just say I’m glad I finally wised up and shut down my LiveJournal. Oh man. LiveJournal was the ultimate symbol of teen angst where you wrote poetry, quoted song lyrics from your favorite emo bands, and posted about how your crush wouldn’t notice you.
You probably wouldn’t want a prospective employer Googling you and finding that . And don’t even get me started on the ultimate emo headquarters that was MySpace. It was very real, Tom, but we have Instagram and Facebook now. Reddit user: onamonapizza
Hats Off To You
I had a habit of climbing dangerously high buildings and objects attempting self-taught parkour, sometimes with my hood up. I was a big fan of the video game Assassin’s Creed. I cringe because I look at some of the things I climbed up at the age of 12 or 13.
I think to myself, “Wow, you were so stupid, you could have easily died.” I never had any serious injuries, thankfully enough, just the occasional grazed knee or bad bruise. I’m definitely not doing any parkour nowadays though. Reddit user: [redacted]
Game Over
I wore fedoras in high school (mid to late ’00s). Of course, there’s nothing wrong with a good fedora. They can look pretty legit on both men and women, and they tend to go with a lot of different outfits…and some of those outfits aren’t even trench coats.
But high school isn’t the time or place, man. How do you even wear a fedora to high school every day without the teacher telling you to take it off in nearly every class? Or somebody trying to steal it as a prank? Don’t try this at home. Reddit user: [redacted]
Trying Too Hard
My phase was a major video game addiction that caused me to miss out on some potentially good memories and it fed into my social anxiety. As an example, a cute girl in my pre-calculus class straight-up try to get me to ask her out to our homecoming, but I was too oblivious.
She literally said something like, “Jonah, who are you asking to homecoming? I may just go with friends unless someone asks me….” While I’m sitting there thinking about Knights of the Old Republic or something. Basically had lots of games, but no game. Reddit user: jonahvsthewhale
Shock Humor
I was not (and currently am not) attractive. However, I was in middle school when the pop the collar, wear 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. You can see where this is going.
I showed up to school wearing an untucked button-down shirt, Hollister T-shirt, American Eagle shoes, and a random tie around my neck. Girl I had a crush on approached me before I even got to my locker and said, “Lookin’ good Scott!” I opened my locker, looked in my mirror, sighed, and took off the tie. Never wore that stuff again. It was a shameful day, but one that I am still proud of in the end. Reddit user: RudeNation
Self-Righteous
I went through a really big shock humor phase. Most of my jokes were totally dirty and pretty offensive honestly. It made people laugh, but it was also middle school. But I was certainly trying too hard. It’s still a part of my personality.
I just don’t do it as much. Middle school kids are arguably worse than high school kids, am I right? But let’s be real for a second…what comedian doesn’t use dirty, offensive jokes and try too hard these days if we’re being honest? Reddit user: [redacted]
I Was So Insecure
Is self-righteous a phase? I was utterly convinced that because I did volunteer work, I was a really good person. Despite my behavior being generally jerk-like and not particularly nice. It ebbed eventually. Luckily, though, being a jerk doesn’t have as much picture evidence as some of the other phases.
Remember the 2013 film This is the End when James Franco almost gets sent up into the skies for his good deeds before getting dropped back down for being “petty, Tom Petty (RIP),” per Danny McBride? Don’t be like James Franco, guys. Good deeds only count if they’re genuine. Reddit user: ConneryFTW
Black on Black
I used to wear big bulky headphones and Vans hoodies everywhere, even during the summer. To be totally honest, I think it was a result of my insecurities regarding my self-esteem, so I covered everything up so no one would have to see how awful (in my mind) I looked.
I was majorly overreacting to how bad I thought it was. It probably wasn’t that bad in reality. I still have that feeling to this day though, and it’s unfortunate. Sadly, insecurities are one of the few things you don’t usually outgrow from childhood. Reddit user: OwnFall
No Free Hugs
Seriously, did all teenagers in the last 30 years have a phase of wearing nothing but black? It certainly seems like they did. I was a weeb and also a goth. That’s a double whammy. People were constantly asking why I was always wearing black lipstick.
Combine that with the black eyeshadow I wore, it made me look like a recently punched raccoon. Sadly my response when people asked was, “I just want my look to reflect how I feel inside.” Even if I did feel like trash…cringe. Reddit user: seventeenblackbirds
Pink Floyd Poser
Being a scene kid was a bad phase. Walking around town listening to Blood on the Dance Floor with a “free hugs” sign and yelling RAWR at people, telling them I loved them in dinosaur…. I cringe at the thought of it. Like what on Earth could I have been thinking?
I would literally punch someone in the face if someone did that to me now. The funniest part? The scene kids of the mid-2000s to early 2010s have become the hipsters and Instagram models of today. It makes sense; remember all the scene kid selfies? Reddit user: megasaurus420
“Today’s Music Sucks”
I had a classic rock/metal phase in early middle school. Back then was right when I found out that the guy I had a crush on, who was 4 years older than me, liked the band 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 A4 paper with colored pencils (because I wasn’t able to buy any merch) and put it in my binder. Then I just kept walking past him while holding the binder. Spoiler alert: that didn’t work. Reddit user: [redacted]
Bad Boots, Matey
The “I was born in the wrong generation because today’s music sucks” phase in high school. Also known as a major and super obnoxious superiority complex. Liking older music isn’t the problem, it’s when you feel that it makes you superior to everyone else and you’re obnoxious about it that it becomes a problem.
But honestly, this happens to everybody in every generation. Imagine what it’s like now. It’s the year 2050, and high school kids are reminiscing about Travis Scott, Kanye West, Bastille, and all the music from the good ol’ days! Reddit user: NyanHotDogParty
Sk8r Boi
I had a Lord Of The Rings and Pirates of the Caribbean phase that lasted way too long for anyone’s own good. I wore these horrible brown boots every day for at least something like two or three months. That was until my mom told me to get rid of them.
My friends still think I have a thing for fantasy. But today I find myself a lot more interested in the paranormal and true crime stuff. What are the kind of boots that go along with paranormal and true crime these days? Thankfully I wouldn’t know anymore. Reddit user: aliveinjoburg2
Popularity Contest
I look back on my skater phase. Looking ‘cool’ holding a skateboard wasn’t worth the wrist, shin, elbow, and knee pain it generated. Enjoyed some of the music though. And I guess the clothes were comfortable. Although they came in far too many drab colors.
Olive green, brown, tan, and dark yellow were the main colors I wore…it got boring after a while. “Sk8r Boi” wasn’t just an immensely popular song by Avril Lavigne, an artist that’s likely another treasure of your teenage years, but also a way of life. Reddit user: hazbaz1984
One of Those Girls
I was so desperately trying to be popular. I begged my parents to buy me expensive clothes. I spoke really loudly, had a new crush every week, acted stupidly despite being at the top of the class, and was just overall a very obnoxious person to be around.
I just wanted to be liked, but I wasn’t even close to being true to myself. I was such a brat, to be honest. Everybody wants to be liked, whether it’s in the classroom or the new office. Do we ever really leave high school? Reddit user: lavender_photos
Too Metal For My Own Good
I’ve literally gone through, like, all the cringe girl phases at one point or another. I’ve had the ‘I’m not like other girls’ phase. I’ve also had the ‘Haha I’m so random’ phase. Then there was the ‘I only wear black because I’m edgy’ phase I went through.
Though I still wear black now because it’s super easy and stylish, ya know? I’ve also gone through the ‘I’m a cat meow’ phase. For 6 years, I was a horse girl. I’m the full package, baby. You want some of this action going on over here? Reddit user: Nazail
Jammies For Days
I was a metalhead loner. I had hair down to my shoulders (I’m a dude, by the way) and listened exclusively to the likes of bands like Metallica, Megadeth, and Lamb of God, just to name a few. I made the assumption that all other music was total garbage.
I only really started to appreciate other music when I went to university and made friends. One of the most common themes in cringy teenage phases is being cocky about your musical tastes and arrogantly thinking that yours is better than everybody else’s. Reddit user: Connor92
Ginger Afro
Wearing pajamas in public was my phase. I’d wear them anywhere and everywhere. In my defense though, plenty of the things people wear in public these days are basically the equivalent of pajamas. Leggings, tracksuits, and silky dresses, just to name a few.
If you just want to run out and grab your pizza for a day of Netflix, do it in your PJs. Life is short, why not be cozy? There are tons of memes on social media about wearing PJs in public, so that means it’s socially acceptable now…right? Right? Reddit user: thehomelesscow
Goodbye, Government
For a brief period during the late ’90s, I had this lopsided afro (all-natural, carrot red…think Little Orphan Annie but just way bigger) and wore MuuMuus. I also put on old lady house dresses with 10-hole Doc Martens. I can’t even really justify it.
I can’t even say that it was done ironically or anything like that, or that other kids were doing the same thing that I was. As the kids these days would say, it was definitely “a look” of some kind. Maybe I kept some pictures. Reddit user: MiladyBanana
I had an anarchist/very against the government phase. I stole some spray paint and put up some anarchy signs, and later in school that day, we had to read lyrics from different songs that we liked. So I picked Anti-Flag’s song “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 for shock value. Reddit user: [redacted]