'[We] dressed like we were in the Matrix': 25+ People share the cringiest phases they ever went through as teens

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Mar 29, 2023 3:00 PM EDT

These brave souls told us all about their cringiest teen phases, from bleaching the tips of their hair to unironically rocking fedoras. 

Going through phases in life is only natural. After all, as you grow from a child to a teen to an adult, you need to learn about who you are and who you want to be. There's a lot of trial and error as you make new friends or enter new classes. Suddenly, something you loved last week is now unbearably cringe. That's the gift of hindsight! 

Looking back on their youth, these folks shared the funny and sweet phases they went through. Most are based around fashion trends of the time, like shopping at the 'edgy' stores in the mall, or rocking fedoras or fingerless gloves. But other people expounded upon their interesting personality changes through the years, and those are some wild tales. 

Next up, this person really wanted to hide her three dogs from her HOA, but it seems like a nosy neighbor might rat them out…

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  • 01
    Plant - 'I went through a bucket hat phase' 'Wearing gloves all the time for no reason' 'Bleached tips'
    via Melissa Askew
  • 02
    Font - r/AskReddit Posted by u/Melting_Point77 What 'phase' did you go through that makes you cringe?
    via u/Melting_Point77
  • 03
    Font - Bodie1550 Old guy here - 67. When the Beatles came to America in 1964 I was was a big fan. My mom had an old shower cap and I found some black yarn. So with some scissors and elmers glue I made myself a beatles wig that I wore around the house and even to the local market. Wish I had some pictures.
    via u/Bodie1550
  • 04
    Font - Spiral_Vortex Had a pocket watch phase where I would carry a pocket watch on a chain at pretty much all times at about 17-18. I wasn't dressing up fancy, or going for some Victorian Gentleman look, I still dressed like a lazy highschooler with t-shirt and crap jeans, I just liked the cheap pocket watches that I'd bought from some local market
    via u/Spiral_Vortex
  • 05
    Rectangle - PM_ME_YR_PUFFY I went through a bucket hat phase. Not even going to lie, it was funny as h.
    via r/AskReddit
  • 06
    Font - Roivas7 The "WuffleShuffle" phase. I would put a pillow on my face and pretend to be a creature called a "WuffleShuffle". I also kept saying "WuffleShuffle" like some sort of Pokemon. Then it evolved to other things: TruffleShuffles, JacketShuffles, MattressShuffles, SeatbeltShuffles... It was a pretty embarrassing phase.
    via u/Roivas7
  • 07
    Font - Rav99 Italian American here. My "guido phase" in high school. Edit: this was the early 90s. Think Goodfellas not Jersey Shore. Gold chains, Camaros, acting tough. My favorite 'f you' was "Go getyer shine box!"
    via u/Rav99
  • 08
    Human body - csonny2 Hopefully you've been able to fugettabout it
    via u/csonny2
  • 09
    Font - ElToberino In junior high, I used to draw stuff on my arms with a pen that I thought looked badas like skulls and fire and swords and sh. Said I was going to get full sleeves when I turned 18. Now I'm a 29 year old with zero tattoos
    via u/ElToberino
  • 10
    Font - ThatGuyWorking I had an "I'm too edgy to hang out with the normal people" phase. I shiver at the memory of it.
    via u/ThatGuyWorking
  • 11
    Font - Middle_Stall_Pper There was a brief period of time where my best friend and I dressed like we were in the Matrix. I remember going all dressed in black to Target, of all places thinking we looked sooooo cool.
    via u/Middle_Stall_P**per
  • 12
    Font - Because_Justice When I was in elementary school, maybe 3rd or 4th grade, my older sister was really into Hillary Duff. So, of course, she played it constantly in every car ride we took. Apparently, the music grew on me, and I knew every word of some of the songs (or at least I thought I did...) So my friends and I would play this role playing game where we would create characters for ourselves with "special powers" and fought imaginary monsters around the playground. And, of course, I pic
    via u/Because_Justice
  • 13
    Font - I distinctly remember when it was my turn to "attack" a monster, so I somehow thought it would be a good idea to sing an entire Hillary Duff song. I also remember my friends trying to stop me several times, but I insisted that I had to sing the whole thing so that it "actually feel asleep." Yeah, my friends stopped playing that game after that.
    via u/Because_Justice
  • 14
    Font - Just MeAndMySnail I used to HATE going to thrift shops with my mother when I was a teenager. I would wear a blonde wig and sunglasses and make her call me "Maria" (not my real name). Looking back, my mother was just trying to support 3 kids on my dad's salary, and thrift shops allowed her to buy me name-brand (albeit used) clothing that otherwise we wouldn't have been able to afford. What a d I was. ...and for the record, I LOVE thrift shops now!!
    via u/JustMeAndMySnail
  • 15
    Font - [deleted] I did the whole "emo" phase in middle and high school. The thing was, I wasn't able to acquire the resources that my other emo friends had. I wasn't able to dye my hair and my hair type didn't work with those straightened/fringe styles. I barely had access to cosmetics so I couldn't often paint my nails or wear eyeliner, when I did I looked like an idiot. basically I like to refer to that time of my life as "Kroger-brand emo". I looked emo, but not enough to be legit. EDIT: Woah
    via u/deleted
  • 16
    Font - PrincessIceheart When I first joined the army in 2006 I went through this ridiculous phase where I would use overly motivated army phrases in casual conversation with my friends and family who were never in the military. I talked down to them and acted as if I was the biggest hero just for joining the military and being a medic. This was before I even went anywhere. All I had done at that point was graduate basic and medic training. By the time I came home from Iraq that attitude was comp
    via u/PrincessIceheart
  • 17
    Font - danielstover In the mid-2000's I was a Ska kid. Dressed in a suit, wore a fedora, suspenders, checkerboard everything - Took all my fashion cues from older Ska Bands like the English Beat and The Specials. Skanked to songs that weren't even ska at HS dances -_- There were a few others in my HS that liked Ska music, but didn't take it as far as me. 6.9k PLKnight Share You may have abandoned that phase but who knows? Maybe one day you'll again pick it up pick it up pick it up pick it up!
    via u/danielstover
  • 18
    Font - [deleted] "OMFGuhhh I'm s0o0o0 random! Moo! Rawr! lulzers all of my usernames have some variation of xXsP0rKXx! Ah lurve anime n pocky n biting things!!!!!! >w<" 5.2k . Share Freaky713 Even though it is super cringe, I do kind of miss the internet from 5+ years back. It was so innocent and naive, just like I was at the time. S like Invader Zim and "RAWR XD means I love you in dinosaur!" is stuff that I'll miss purely because it reminds me of my younger years. But that might just be my nos
    via u/deleted
  • 19
    Font - TheComingOfTheGeeks I-am-such-a-smart-nerd phase. I would consider others inferior to my smartness, and paste wikipedia articles when talking about physics online. Sheldon Cooper was my hombre. I was the model r/iamverysmart kid. Obviously, even then I knew I was kinda stupid - so I outgrew the phase in two years. I am happy that I did not find Quora then.
    via u/TheComingOfTheGeeks
  • 20
    Font - bennett93ish Wearing gloves all the time for no reason. Going to see some friends in summer? Gloves School day? Gloves Swimming? Gloves After a while, I upgraded to fingerless gloves. I have no idea what I was thinking. 12-14 year old me was an idiot.
    via u/bennett93ish
  • 21
    Font - MyNSFWside When I was in college, I spent a couple of months mesmerized by matches. I would light one and watch it burn down, and if someone came by, I'd say (in my best documentary voice) something like "Since time began, man has been fascinated by fire." Glad I got through that phase without actually becoming a pyro.
    via r/AskReddit
  • 22
    Font - xoshawnabear Tearaway pants. People constantly coming up to you at school and ripping your pants open. It's all fun and games until you forget to wear shorts underneath.
    via u/xoshawnabear
  • 23
    Font - rahyveshachr Random misused hair accessories. I would wear pigtails and put plastic spoons in my hair, or those chopsticks. Problem was, I put them right up against my scalp which was quite painful after a few hours. I had NO IDEA that chopsticks are used to tie hair into a bun. I just shoved em right behind the hair band of my ponytail. I also wore sunglasses on my head as a headband for a week. I wear glasses. Yes, I had both on my head. Looked absolutely ridiculous. Yes I was so proud
    via u/rahyveshachr
  • 24
    Font - DrWhatNoName I went through a phase that I was a great explorer and a survival expert. Went wondering some time with a plan to build a treehouse and live there. during the night I ate some poisonous berries and ended up bedridden in a hospital for a week. Update: Thank you who ever gave me Reddit Gold. I am appreciative of your generous gift! Update 2: I did a search for what berry it was I ate and it is called Yew tree [Taxus baccata]
    via u/DrWhatNoName
  • 25
    Font - nottooashamed I truly believed for three years that I was going to Hogwarts someday. I even asked the mailman every day and looked at the sky for owls. I was already 10. Three. Years.
    via u/nottooashamed
  • 26
    Font - kjata I used to wear a fedora. 4.3k Polelek m'phase Share
    via u/kjata
  • 27
    Font - RedPatAtsoc Bleached tips. Saw all the boy bands doing it and thought, "yeah, I'll def look just as good". I didn't.
    via u/RedPatAtsoc
  • 28
    Font - Toastedsars I had a angsty teen phase. Unfortunately, my parents wouldn't let me go into the "angry store" (hottopic), so I couldn't buy the black spikey things I wanted. Safety pins were also banned. Being a crafty young lady, I decided to use paperclips to decorate my clothing. I also made ugly paperclips necklaces and chain things. It wasn't cute It wasn't angsty It looked like I got into a fight with office supplies and lost.
    via u/Toastedsars
  • 29
    Font - ArsenicBaseball I went through a phase in my senior year of HS where I only wore Hawaiian shirts and I would wear a big sun hat as well. I'm not even mad about that phase. That s was tight.
    via u/ArsenicBaseball

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Tags

teens immature middle school teenagers cringe nostalgia friends high school funny
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