#1 Got Dumped A Week Before Prom, But My Mom Insisted I Go Take The Pictures She Paid For, So I Made A Sock Puppet To Bring As My Date. I Regret Nothing
Image source: Reverend_Deek_Lovin
#2 My Parents Kindly Supported My Peak Edgelord Phase :)
Image source: SpacePenguin69
#3 Had A “Photoshoot” With My Mom And Thought That Being “The Weird Kid” Made Me Cool And Mysterious. Good Thing I Dont Live In The States Cause I Had Some Serious School Shooter Vibes ;)
Image source: Dinkelburger123
#4 Tried To Smile, Channeled Jim Carrey Instead. Allllllllrighty Then
Image source: 8bitcity
#5 I Thought I Was The Coolest Cat There Ever Was
Image source: fromsky610
#6 Give Me The Sassy Grandma Look
Image source: dumbolddoor
#7 One Of My Best Friends And I In Early 2012. We Were 8, And Had Our Own Band
Image source: PiggyGamesALot
#8 Me In The 80s. Sadly, The Coolest I Ever Looked
Image source: JohnnyPolite
#9 My Friend’s Baby Pictures Look Like Mrs. Doubtfire
Image source: elpintogrande
#10 1996, Olan Mills Calls My Roommate Offering A Free Family Sitting. His Family Lived Two States Away, So We Went In To Mess With Them. I’m The Guy On The Right
Image source: reddit.com
#11 For My 2nd Grade Photo I Vouched For The Satan’s-Child-Lawyer Look
Image source: 17UglyBoobies
#12 I Was Evidently The Reference Model For The Kid From Up! ~ Circa 1985
Image source: charliethegeek
#13 I Had Embraced My Nerdy Outcast Status And Went To School Like This, Sadly The Trench Coat Was Soon Banned After ’99
Image source: WhacksOnAnonOff
#14 When Someone Asks How Your Life Is Going…
Image source: laureli48
#15 In 5th Grade I Was Worried I Would Blink And Mess Up My Year Book Photo
Image source: wholebunchofbees
#16 Family Photo. What A Mood
Image source: puffsaddy
#17 It Was “Opposite Day” At School In 2005, Most People Wore Black And White Or Something.. I Decide To Dress As A Girl.. I Lived In A Small Town In Idaho. It Didn’t Go Over Well
Image source: awashbu12
#18 Anytime My Wife Sees This She Burst Out Laughing… I Thought I Looked Cool
Image source: Meowimpersian
#19 Late 70’s. No Idea What I Was Thinking. Made The Suit Myself
Image source: xxSpeedsterxx
#20 My Mother Said I Would Regret This Photo… No Regrets Mom! Circa 2002
Image source: Made_lion
#21 After Explaining What R/Blunderyears Is All About, A Friend Of Mine Gave Me Permission To Post This Gem. Circa Early-90s
Image source: Sgt_Pepsi
#22 Setting Trends At About 10 Years Old, Rural England!
Image source: seafog
#23 My Poor Parents…being Nice To Me Back In 1987 During My Billy Idol Skateboarding Phase
Image source: MrArms69
#24 6th Grade Going On 60
Image source: RICHB0YWINST0N
#25 My Parents Weren’t Surprised When I Came Out
Image source: BoxBopChallenge
#26 Glamour Shot Blunder (7 Years Old)
Image source: denovosibi
#27 Just A Girl On A Spring Communist Demonstration In Lviv, Ukraine, 1968
Image source: xerurg
#28 My Sisters And I Wanted Those Glamour Photos From The 90s, But We Were Too Young So Mum Had Us Do A Homemade One Instead
Image source: emmattack
#29 In Honor Of My Husband’s 37th Birthday, I Present To You His Senior Prom Photo From 2000
Image source: Loocylooo
#30 When You Look Over 40 But You’re Actually 12
Image source: ThatSquareChick
#31 2006 Senior Picture
Image source: Super_Rosie
#32 ‘How Did You Know I Was Gay?’ Said The Posing Seven Year Old Boy In Make Up, A Perm, And Black Sequinned Jellicle Cats Dance Costume
Image source: DefinitelyNotADeer
#33 I Looked Like A Middle Aged Man When I Was A Child
Image source: Strid3r21
#34 Me In 1998 And My Wife In 2000
Image source: camiam85
#35 Ten Years And One Transition Later: Some Things Never Change
Image source: reddit.com
#36 When It’s Your First Day Of Kindergarten And Also Your First Day As Head Of The Pta
Image source: DragonfireEsq
#37 This Surpasses Even The Fivehead
Image source: proffllama
#38 2006 And I Was 17. The Cure Was My Life
Image source: Hollybums
#39 I Give You One 15 Yo Goth With Her Eyebrows Shaved Off. My Step Dad Nicknamed Me “Sunshine” ?
Image source: m4RLA5INGER
#40 That Time I Went To My High School Prom And Looked Like A 45 Year Old Woman
Image source: Clairdassian
