#1 My Nickname Was “Ronald” In School
Image source: DannyDublin1975
#2 It Was The 80s. I Have No Other Excuse
Image source: owzleee
#3 My Brother And I, Late 90s
Image source: KFCCrocs
#4 I Guess Being Able To See Is Overrated
Image source: EmpireEmpire
#5 Somehow It Took Me Until My Thirties To Figure Out I’m A Dude Despite Going Through High School Looking Like This
Image source: maybejolisa
#6 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
Image source: Acctgrrl
#7 Thanks To My Sister, I Completely Embraced Goth Culture In 1998
Image source: clumsychickadee__
#8 Oh College. I’ll Never Be This Cool Again
Image source: TrondroKely
#9 Me Circa 2005 Thinking I Was The Absolutely Baddest Thing Around With My Men’s Camo Cargo Short And Corset Combo
Image source: Kbeefydubbz
#10 Did Anyone Else Have These Weird Hairy Tops? I Thought They Were The S**t
Image source: tootyfruitysummerluv
#11 This Is So Long Ago And Yes I Worked At Hot Topic
Image source: dinosaurpixie
#12 My Teenage Years Are The Gift That Keeps On Giving
Image source: Toshhba
#13 Frosted Tips, Resident Evil Toys, A Jenny Mccarthy Poster Aka Welcome To 1999
Image source: thomASSpynchon
#14 1991 Obsessed With Michael Jordan
Image source: foshi22le
#15 Leave Some Ladies For The Rest Of Us
Image source: youruineverything
#16 My Senior Yearbook Photo. I Thought That Quote Was So Funny
Image source: 7fingersphil
#17 That Weird Al Early 00s Look
Image source: timconnery
#18 This Pic Won Me “Most Embarrassing” Genx Photo A Few Years Back. Christmas 1989
Image source: reddit.com
#19 Mom, It’s Not A Phase
Image source: inkmaster916
#20 2009, Black Eye Liner & Lime Green Everything. 13 Years Old, Very Questionable Pose With Dads Webcam
Image source: symbolicthoughts
#21 You May Not Like It, But This Is Peak 1998. Korn Poster And Shortys Shirt Says It All!
Image source: tshaff138
#22 1997 And My Little Tomboy Heart Hated Everything About This Glamour Shot Look
Image source: luckymama1990
#23 In My Bedroom, 2006. My Sister Was The One Who Wrote ‘Butt’ All Over The Walls
Image source: alexanfaye
#24 1999 Tony Hawk Phase (Yes, Those Are Shorts…)
Image source: zephsoph
#25 2003. I Smiled Like This In Every Picture Because I Thought It Looked “Natural.” I Swere I’ve Never Harmed Any Animals
Image source: NSMetroid
#26 My Hair Was Teased So Much It Had To Be Homeschooled. Wish I Knew Why The Photographer Wanted To Hide My Legs And Feet
Image source: artisticatrophy
#27 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)
Image source: Infinitestripes95
#28 My “Date” To The Eighth Grade Dance
Image source: tamenesh
#29 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?!
Image source: Seanessey
#30 High School Art Class
Image source: minthotel
title: “30 Of The Funniest Pictures From A Regrettable Past Shared By People Of Their Cool Teenage Years” ShowToc: true date: “2024-08-29” author: “Chester Benson”
#1 My Nickname Was “Ronald” In School
Image source: DannyDublin1975
#2 It Was The 80s. I Have No Other Excuse
Image source: owzleee
#3 My Brother And I, Late 90s
Image source: KFCCrocs
#4 I Guess Being Able To See Is Overrated
Image source: EmpireEmpire
#5 Somehow It Took Me Until My Thirties To Figure Out I’m A Dude Despite Going Through High School Looking Like This
Image source: maybejolisa
#6 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
Image source: Acctgrrl
#7 Thanks To My Sister, I Completely Embraced Goth Culture In 1998
Image source: clumsychickadee__
#8 Oh College. I’ll Never Be This Cool Again
Image source: TrondroKely
#9 Me Circa 2005 Thinking I Was The Absolutely Baddest Thing Around With My Men’s Camo Cargo Short And Corset Combo
Image source: Kbeefydubbz
#10 Did Anyone Else Have These Weird Hairy Tops? I Thought They Were The S**t
Image source: tootyfruitysummerluv
#11 This Is So Long Ago And Yes I Worked At Hot Topic
Image source: dinosaurpixie
#12 My Teenage Years Are The Gift That Keeps On Giving
Image source: Toshhba
#13 Frosted Tips, Resident Evil Toys, A Jenny Mccarthy Poster Aka Welcome To 1999
Image source: thomASSpynchon
#14 1991 Obsessed With Michael Jordan
Image source: foshi22le
#15 Leave Some Ladies For The Rest Of Us
Image source: youruineverything
#16 My Senior Yearbook Photo. I Thought That Quote Was So Funny
Image source: 7fingersphil
#17 That Weird Al Early 00s Look
Image source: timconnery
#18 This Pic Won Me “Most Embarrassing” Genx Photo A Few Years Back. Christmas 1989
Image source: reddit.com
#19 Mom, It’s Not A Phase
Image source: inkmaster916
#20 2009, Black Eye Liner & Lime Green Everything. 13 Years Old, Very Questionable Pose With Dads Webcam
Image source: symbolicthoughts
#21 You May Not Like It, But This Is Peak 1998. Korn Poster And Shortys Shirt Says It All!
Image source: tshaff138
#22 1997 And My Little Tomboy Heart Hated Everything About This Glamour Shot Look
Image source: luckymama1990
#23 In My Bedroom, 2006. My Sister Was The One Who Wrote ‘Butt’ All Over The Walls
Image source: alexanfaye
#24 1999 Tony Hawk Phase (Yes, Those Are Shorts…)
Image source: zephsoph
#25 2003. I Smiled Like This In Every Picture Because I Thought It Looked “Natural.” I Swere I’ve Never Harmed Any Animals
Image source: NSMetroid
#26 My Hair Was Teased So Much It Had To Be Homeschooled. Wish I Knew Why The Photographer Wanted To Hide My Legs And Feet
Image source: artisticatrophy
#27 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)
Image source: Infinitestripes95
#28 My “Date” To The Eighth Grade Dance
Image source: tamenesh
#29 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?!
Image source: Seanessey
#30 High School Art Class
Image source: minthotel
title: “30 Of The Funniest Pictures From A Regrettable Past Shared By People Of Their Cool Teenage Years” ShowToc: true date: “2024-10-10” author: “Lindsay Bowman”
#1 My Nickname Was “Ronald” In School
Image source: DannyDublin1975
#2 It Was The 80s. I Have No Other Excuse
Image source: owzleee
#3 My Brother And I, Late 90s
Image source: KFCCrocs
#4 I Guess Being Able To See Is Overrated
Image source: EmpireEmpire
#5 Somehow It Took Me Until My Thirties To Figure Out I’m A Dude Despite Going Through High School Looking Like This
Image source: maybejolisa
#6 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
Image source: Acctgrrl
#7 Thanks To My Sister, I Completely Embraced Goth Culture In 1998
Image source: clumsychickadee__
#8 Oh College. I’ll Never Be This Cool Again
Image source: TrondroKely
#9 Me Circa 2005 Thinking I Was The Absolutely Baddest Thing Around With My Men’s Camo Cargo Short And Corset Combo
Image source: Kbeefydubbz
#10 Did Anyone Else Have These Weird Hairy Tops? I Thought They Were The S**t
Image source: tootyfruitysummerluv
#11 This Is So Long Ago And Yes I Worked At Hot Topic
Image source: dinosaurpixie
#12 My Teenage Years Are The Gift That Keeps On Giving
Image source: Toshhba
#13 Frosted Tips, Resident Evil Toys, A Jenny Mccarthy Poster Aka Welcome To 1999
Image source: thomASSpynchon
#14 1991 Obsessed With Michael Jordan
Image source: foshi22le
#15 Leave Some Ladies For The Rest Of Us
Image source: youruineverything
#16 My Senior Yearbook Photo. I Thought That Quote Was So Funny
Image source: 7fingersphil
#17 That Weird Al Early 00s Look
Image source: timconnery
#18 This Pic Won Me “Most Embarrassing” Genx Photo A Few Years Back. Christmas 1989
Image source: reddit.com
#19 Mom, It’s Not A Phase
Image source: inkmaster916
#20 2009, Black Eye Liner & Lime Green Everything. 13 Years Old, Very Questionable Pose With Dads Webcam
Image source: symbolicthoughts
#21 You May Not Like It, But This Is Peak 1998. Korn Poster And Shortys Shirt Says It All!
Image source: tshaff138
#22 1997 And My Little Tomboy Heart Hated Everything About This Glamour Shot Look
Image source: luckymama1990
#23 In My Bedroom, 2006. My Sister Was The One Who Wrote ‘Butt’ All Over The Walls
Image source: alexanfaye
#24 1999 Tony Hawk Phase (Yes, Those Are Shorts…)
Image source: zephsoph
#25 2003. I Smiled Like This In Every Picture Because I Thought It Looked “Natural.” I Swere I’ve Never Harmed Any Animals
Image source: NSMetroid
#26 My Hair Was Teased So Much It Had To Be Homeschooled. Wish I Knew Why The Photographer Wanted To Hide My Legs And Feet
Image source: artisticatrophy
#27 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)
Image source: Infinitestripes95
#28 My “Date” To The Eighth Grade Dance
Image source: tamenesh
#29 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?!
Image source: Seanessey
#30 High School Art Class
Image source: minthotel
