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Going through old pictures usually brings back all sorts of memories. That means both the beautiful times you feel sentimental about and the top-tier cringe-worthy moments. And even though the latter might make you want to disappear into thin air (or close the photo album, at least), looking back at your young self can often be very amusing as well.

Some of the finest examples that can make you laugh and cry simultaneously can be found on the ‘Blunder Years’ subreddit. Dedicated to, in their exact words, “pictures from a regrettable past”, it covers all sorts of disasters, from questionable hairstyle choices (let me remind you, a side fringe bang covering half of your face was a thing back in the day) to the epitomes of “cool” outfits. Today, we invite you to make yourself comfortable and embark on a journey through time, guided by the beautiful messes in these pictures.

#1

1987, We Loved The Cure, 7seconds, The Decedents, The Smiths, Etc. We Taped 120 Minutes Off Mtv Every Sunday Night From Midnight - 2 Am. I'm On The Far Left. Can Believe We Weren't Blind In One Eye After All The Years With The Lopsided Haircuts

1987, We Loved The Cure, 7seconds, The Decedents, The Smiths, Etc. We Taped 120 Minutes Off Mtv Every Sunday Night From Midnight - 2 Am. I'm On The Far Left. Can Believe We Weren't Blind In One Eye After All The Years With The Lopsided Haircuts

Acctgrrl Report

The teenage years are an exceptional period in most young people’s lives, no matter the generation. They are often accompanied by acts of rebellion, experiments with your looks, and all sorts of exciting experiences. That is why documenting them is a must—it allows you to look back on them years later and, well, let’s be honest, have a good laugh most of the time.

This type of content is what makes the ‘Blunder Years’ subreddit great. Its description encourages people to share their “dusty treasures with the world”, and they sure do, which is why there are already 853k members in the community.

#2

My Mom Wouldn’t Allow Me To Wear This 80s Era Spider-Man Undershirt For Picture Day, But I Snuck It Under My Clothes Anyway

My Mom Wouldn’t Allow Me To Wear This 80s Era Spider-Man Undershirt For Picture Day, But I Snuck It Under My Clothes Anyway

Tack-One Report

#3

2003. I Smiled Like This In Every Picture Because I Thought It Looked "Natural." I Swere I've Never Harmed Any Animals

2003. I Smiled Like This In Every Picture Because I Thought It Looked "Natural." I Swere I've Never Harmed Any Animals

NSMetroid Report

Back in the day—during the film camera era, for instance—taking pictures was more difficult than snapping a quick selfie nowadays. That might be one of the reasons current teenagers will have plenty to look back on in the future. Nowadays, young adults have roughly 10 million photos compiled on their smartphones collectively.

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The good old selfie is likely to be one of the most recurring types of photographs in the future. Statistics reveal that nearly 56% of young people (18-to-24-year-olds, to be exact) take up to four such self-portraits a day; 9% of them take eight or more. 

#4

Sometime Between 05 And 07, I Remember I Got To Choose The Background And Which Weapon I Posed With

Sometime Between 05 And 07, I Remember I Got To Choose The Background And Which Weapon I Posed With

shortlegs99 Report

At one point taking a selfie was nearly impossible without doing the so-called duck face. Even though its golden years seem to be long gone, it was a popular trend once, and teenagers can be quite susceptible to pop culture or similar influences. For example, they might start to dress or behave in a way that people in mass media do, that’s supposed to be representative of teenagers.

#6

It Was The 80s. I Have No Other Excuse

It Was The 80s. I Have No Other Excuse

owzleee Report

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Somebodys grandmother
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I know the feeling - and the amount of hairproducts... sorry ozon-layer... we didn't know better 🙈

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#7

My Mom Cut My Hair The Day Before Picture Day (Early 90s). For Picture Day We Curled My Very Short Hair Resulting In This Delightfully Puffy Abomination Where I Insisted On Wearing Earrings So “I Didn’t Look Like A Boy” . The Result Is This Delightful Xmas Ornament That I Get To Look At Every Year

My Mom Cut My Hair The Day Before Picture Day (Early 90s). For Picture Day We Curled My Very Short Hair Resulting In This Delightfully Puffy Abomination Where I Insisted On Wearing Earrings So “I Didn’t Look Like A Boy” . The Result Is This Delightful Xmas Ornament That I Get To Look At Every Year

teebee431 Report

#8

Me Circa 2005 Thinking I Was The Absolutely Baddest Thing Around With My Men’s Camo Cargo Short And Corset Combo

Me Circa 2005 Thinking I Was The Absolutely Baddest Thing Around With My Men’s Camo Cargo Short And Corset Combo

Kbeefydubbz Report

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NSS Magazine pointed out that over time, the way young characters were depicted in magazines, movies, or TV shows grew more and more distant from the actual everyday youth. Eventually, the portrait presented in the media became more of a role model rather than a representative, and some teenagers started copying it.

#9

This Pic Won Me “Most Embarrassing” Genx Photo A Few Years Back. Christmas 1989

This Pic Won Me “Most Embarrassing” Genx Photo A Few Years Back. Christmas 1989

reddit.com Report

#10

Family Photo. What A Mood

Family Photo. What A Mood

puffsaddy Report

#11

My Brother And I, Late 90s

My Brother And I, Late 90s

KFCCrocs Report

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Alecto76
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My boyfriend in college had these type of jeans. Tripped and broke his toe

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Copying or idolizing certain popular figures is normal teenage behavior. According to child and adolescent psychiatrist Dr. Alan Ravitz, putting them on a pedestal like that is linked to the teens’ inclination to create fantasies and a developing need for independence.

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In an article for the Child Mind Institute, he pointed out that as they grow, kids develop psychological and emotional independence from their parents. That is why they need someone to look up to that is not mom or dad, and in our culture nowadays, they often choose renowned athletes, movie stars, or other famous people.

The Child Mind Institute shed light on the downsides of obsessing over famous people as well. The latter can set the wrong example when it comes to body image or the materialistic world. In addition to that, excessive obsession over a well-known person can consume the youngster to the extent that they start to isolate themselves from the outside world.

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#15

Thanks To My Sister, I Completely Embraced Goth Culture In 1998

Thanks To My Sister, I Completely Embraced Goth Culture In 1998

clumsychickadee__ Report

#16

I Guess Being Able To See Is Overrated

I Guess Being Able To See Is Overrated

EmpireEmpire Report

#17

High School Art Class

High School Art Class

minthotel Report

Newport Academy also analyzed how celebrities influence teenagers. It pointed out that the youth often compare themselves to famous people, which might create unrealistic standards considering their looks. Surveys revealed that as much as 80% of girls have done exactly that. Luckily, some renowned personas use their influence to spread positive messages about body image or start positive trends.

#18

Recovered This Gem From The "Autobiography" I Wrote When I Was 10

Recovered This Gem From The "Autobiography" I Wrote When I Was 10

Dirty-D Report

#19

Somehow It Took Me Until My Thirties To Figure Out I’m A Dude Despite Going Through High School Looking Like This

Somehow It Took Me Until My Thirties To Figure Out I’m A Dude Despite Going Through High School Looking Like This

maybejolisa Report

#20

1985, I’m Mr.gender Bender Glam Goth And Club Scene Regular. The Whole Time I Secretly Listened To Thrash Music Lol. Will I Ever Live It Down?!

1985, I’m Mr.gender Bender Glam Goth And Club Scene Regular. The Whole Time I Secretly Listened To Thrash Music Lol. Will I Ever Live It Down?!

Seanessey Report

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A very significant trend—just look at how many representatives it has on this list alone—was the emo phase, popular in the early 2000s. Its origins came from the post-hardcore music genre, known as emocore. The latter started gaining popularity around the 1980s, way before the emo look became a somewhat mainstream style choice for teenagers around the world.

#21

Found These Pics After Losing My Mom In April. Today, I’m Ready To Share These With The World. I’m 44 Years Old Now, So Please Know That The 80’s Were Not A Forgiving Time

Found These Pics After Losing My Mom In April. Today, I’m Ready To Share These With The World. I’m 44 Years Old Now, So Please Know That The 80’s Were Not A Forgiving Time

reddit.com Report

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Mi So
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

As a 43 yo, I see nothing cringe or embarrassing about this picture. I have several dozen that look basically the same, just with more harvest gold in the upholstery.

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#23

That Weird Al Early 00s Look

That Weird Al Early 00s Look

timconnery Report

As a matter of fact, some style choices that were popular two decades ago are making a comeback. Fashionistas are wearing certain pieces again that might cause you flashbacks. Just to give you an example, remember the tiny shoulder bag that you can barely put your arm through? Or the bucket hat that resembles something students wear on a field trip? That’s what I’m talking about.

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#24

My Hair Was Teased So Much It Had To Be Homeschooled. Wish I Knew Why The Photographer Wanted To Hide My Legs And Feet

My Hair Was Teased So Much It Had To Be Homeschooled. Wish I Knew Why The Photographer Wanted To Hide My Legs And Feet

artisticatrophy Report

#25

(Oc) I Was Not A Fan Of That Easter Bunny!

(Oc) I Was Not A Fan Of That Easter Bunny!

kennethdpedersen Report

#27

My Bedroom 11 Years Ago When I Was 14, Be Careful You Don't Hurt Yourself On All The Edge

My Bedroom 11 Years Ago When I Was 14, Be Careful You Don't Hurt Yourself On All The Edge

XLNerd Report

#28

My “Date” To The Eighth Grade Dance

My “Date” To The Eighth Grade Dance

tamenesh Report

#29

Y’all I Thought I Was Cool Taking These Photos For A Anti Bullying Campaign 😂 I Did Get In A Magazine Thought (It Was A Contest To Submit Photos For Their Stop Think Feel Initiative)

Y’all I Thought I Was Cool Taking These Photos For A Anti Bullying Campaign 😂 I Did Get In A Magazine Thought (It Was A Contest To Submit Photos For Their Stop Think Feel Initiative)

Infinitestripes95 Report

#30

Me Circa 1995. I Think I Thought I Was Grunge Or Something

Me Circa 1995. I Think I Thought I Was Grunge Or Something

hoggytime613 Report

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#31

Mom Was Mad But Admittedly Almost Peed Herself Laughing At The Results

Mom Was Mad But Admittedly Almost Peed Herself Laughing At The Results

NavyNUCa Report

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#32

It Was Not A Good Eyeliner Day, And I Was Trying To Make “Hippie Bands” My Thing. Rip To My Emo Era

It Was Not A Good Eyeliner Day, And I Was Trying To Make “Hippie Bands” My Thing. Rip To My Emo Era

Gothblessyou Report

#33

Did Anyone Else Have These Weird Hairy Tops? I Thought They Were The S**t

Did Anyone Else Have These Weird Hairy Tops? I Thought They Were The S**t

tootyfruitysummerluv Report

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duckie
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I bet the leaves are still stuck to that top to this day

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#34

In My Bedroom, 2006. My Sister Was The One Who Wrote ‘Butt’ All Over The Walls

In My Bedroom, 2006. My Sister Was The One Who Wrote ‘Butt’ All Over The Walls

alexanfaye Report

#36

Senior Picture; Gamecube Not Pictured

Senior Picture; Gamecube Not Pictured

ryly_shane Report

#37

1997 And My Little Tomboy Heart Hated Everything About This Glamour Shot Look

1997 And My Little Tomboy Heart Hated Everything About This Glamour Shot Look

luckymama1990 Report

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Fraxinus excelsior
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I feel your pain, hated being made up to look girlified by my mom, she just didn't get it. I liked boys clothes, haircuts, football, climbing trees, motorcycles. I just wanted to be me, and I was eventually.

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#38

My Teenage Years Are The Gift That Keeps On Giving

My Teenage Years Are The Gift That Keeps On Giving

Toshhba Report

#39

Frosted Tips, Resident Evil Toys, A Jenny Mccarthy Poster Aka Welcome To 1999

Frosted Tips, Resident Evil Toys, A Jenny Mccarthy Poster Aka Welcome To 1999

thomASSpynchon Report

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#40

1999 Tony Hawk Phase (Yes, Those Are Shorts…)

1999 Tony Hawk Phase (Yes, Those Are Shorts…)

zephsoph Report

#41

1999 - I Told Dad “I Need Your Clothes, Your Boots, And Your Motorcycle”. Only Got The Clothes

1999 - I Told Dad “I Need Your Clothes, Your Boots, And Your Motorcycle”. Only Got The Clothes

TheZone92 Report

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Candice Gardner
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Yes, but was it in The Arnold's voice? If not, that may be why he didn't take you seriously;)

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#43

1998. That Was A Knock-Off Fubu Shirt That I Bought From A Gas Station

1998. That Was A Knock-Off Fubu Shirt That I Bought From A Gas Station

roqthecasbah Report

#44

1991 Obsessed With Michael Jordan

1991 Obsessed With Michael Jordan

foshi22le Report

#45

Me When I Was 12 Years Old Buying My First Cd’s

Me When I Was 12 Years Old Buying My First Cd’s

thetinycatt Report

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A girl
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I was 25 when I bought my first CD. It was Dark Side of the Moon. 1985 was a looong time ago.

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#46

You May Not Like It, But This Is Peak 1998. Korn Poster And Shortys Shirt Says It All!

You May Not Like It, But This Is Peak 1998. Korn Poster And Shortys Shirt Says It All!

tshaff138 Report

#47

'98 Or '99, Around 16 Years Old. The Coppery Bleached Hair Was Not My Best Decision

'98 Or '99, Around 16 Years Old. The Coppery Bleached Hair Was Not My Best Decision

bailey_1138 Report

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#48

My Senior Yearbook Photo. I Thought That Quote Was So Funny

My Senior Yearbook Photo. I Thought That Quote Was So Funny

7fingersphil Report

#49

Lion King Sisters 1994 I Was 8 Years Old And Lil Sis 4 . 1st Day School 3rd Grade And Kindergarten

Lion King Sisters 1994 I Was 8 Years Old And Lil Sis 4 . 1st Day School 3rd Grade And Kindergarten

Seaepona Report

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Mia Black
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Don't hate me but my first thoughts were "this is like kids should look like" because when my teen year younger cousins were in this age they already looked so damn more adult with the clothes and make-up, I was a little confused how old they were... On the other hand: my parents looked so much older my age.... Time and humans are confusing....

hesse böös
Community Member
1 year ago

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Zoey Rayne
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Aww! I went through a Lion King phase from ages 3 to 8. Loved it when my relatives gave me Simba and Nala gifts at Christmas.

StitchIsCuteAndFluffy
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Still love the Lion King. And all things Disney. Favorite movie is Lilo and Stitch tho.

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MacToast
Community Member
1 year ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'm a bit jealous of the lion king outfits tbh. Especially that skirt, I need one in adult size!

Freelove
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'm pretty sure I also owned that Simba shirt on the left! This picture just unlocked some really good nostalgic feelings of being a kid in the 90s! ❤️

Douglas Gilanyi
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Can anyone else "smell" that first day of school from just the photo? Would have been fifth or sixth grade for me.

CORGI QUEEN
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

your in your thirtys aren't you.... makes ppl like my mom feel old

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#50

2009, Black Eye Liner & Lime Green Everything. 13 Years Old, Very Questionable Pose With Dads Webcam

2009, Black Eye Liner & Lime Green Everything. 13 Years Old, Very Questionable Pose With Dads Webcam

symbolicthoughts Report

Note: this post originally had 95 images. It’s been shortened to the top 50 images based on user votes.