"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"
"I Don't Know If I'm More Embarrassed By How Many Hours It Took Teen Me To Make This, Or That I Actually Tagged My Crush When I Posted It"
"My Mom Dressed Me Like This So I Was Easy To Spot When She Picked Me Up..."
"2008, Senior Friend Asked Me To Prom When I Was A Freshman. My Parents Didn't Want Me To Go But Also Didn't Want To Forbid Me, So They Didn't Give Me Money For A Dress Thinking That Would Stop Us. We Made Both Of Our Outfits Entirely Out Of Duct Tape For Like $30"
"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"
"My Mom Told Me Not To Blink During My 2nd Grade Class Picture"
"My Siblings And I Were Forced Into A ‘Pet Look Alike’ Competition. It Still Haunts Us"
"My Dad Always Thought This Haircut Looked Incredible On Me. My Mom Thought The Shirt Was Incredible. Looking Back At 2nd Grade Me Is Incredible. I'm A Female"
"In Honor Of My Husband’s 37th Birthday, I Present To You His Senior Prom Photo From 2000"
"Ten Years And One Transition Later: Some Things Never Change"
"10m, And Looking Like A Middle Age Mom Who’s Deciding To Grace You With A Smile, While Still Judging You Just A Little"
"My Mother Said I Would Regret This Photo... No Regrets Mom! Circa 2002"
"Tried To Smile, Channeled Jim Carrey Instead. Allllllllrighty Then"
"‘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"
"Husband? Dead. Emotion? Devastated. Insurance Money? Cashed. Eyebrows? Don’t Need Them"
"My Boyfriend's 10th Grade Picture Is Pure Rebellion. According To Him, His Mom Cried When She Received The Pictures Back"
"Found My High School ID This Morning"
"Had A "Photoshoot" With My Mom And Thought That Being "The Weird Kid" Made Me Cool And Mysterious"
"It’s Amazing What Growing A Beard, Growing Up, Changing Your Style And Leaving A Cult Can Do For You! (2011 vs. 2020)"
"School Photo Looking Like 60-Year Old Librarian With My Cardigan, Turtleneck And Thick Glasses Date And Age Unknown
"My Mother Found This Photo Of My Church Friend (Ryan Gosling) And I. We Had Some Awful 90s Hairs Cuts"
"My All-Time Favorite Picture Of My Husband. He Was 20 In This Picture. Posting With His Reluctant Permission"
"12 Years Ago. Teenage Pregnancy. Our First Family Photo"
"My Family Looking Like An Ll Bean Catalog Submission, And Then There's 15 Year Old Me"
"In High School I Went Through A Belt Phase. For Some Reason, I Thought The More Belts I Had On, The Cooler I Looked. I Later Discovered... That Was A Lie"
"When I Was 14 I Was Dating A Girl From Another High School. I Decided To Surprise Her On Her Birthday By Dressing Up As A Clown And Busting Into Her Classroom Singing “Happy Birthday”. She Was Mortified! When The Dust Settled She Thankfully Realized The Thoughtfulness That Went Into The Gesture"
"I Was That Girl"
"Growing Up In Detroit When Eminem Came Out Yeaaaaaah..."
"Me At 17(2010) Living It Up In Vegas"
"8th Grade Me Thought I Was The [Coolest], Went Like This To A Christian Concert Event"
"Me, On My 8th Birthday, Getting The DS I Raved About"
"They Seem To Bring A Smile To Your Face. Hope This Makes Your Day A Little Better. I Present, Me As A Kid"
"Me At Age 15, Channeling My Inner 30something Business Woman"
"14 Year Old Me Photoshopping Out My Dad For Britney Spears. This Is Just So Toxic"
"As Most People Thought My Fiancé Last Photo Was Not A Blunder, I Present To You Her College Library Card - 2003"
"Freshman College, ‘94: Control Yourselves, Ladies"
"My Outfit During A Snowfall In May 2004"
"Hawaii Wasn’t Ready For My Ice Cold Sister And I In 2003"
"I’m Glad My Looks Didn’t Peak At Age 13. (Not A Costume. God Help Me, I Really Dressed Like That)"
"Well I'm 34 Now. Still Into Model Rockets Though"
"My Childhood Was Destined To Be A Rough One..."
"I Was In An Early 2000's Transitional Phase Between Awkward And Total Embarrassment"
"Dwight Schrute Glasses? Check. Braces? Check. Turtle And Cat As Only Friends? Check. Braided Rat Tail With Beads? Zoom In..."
"2002, Age 14. I Have No Idea What I Was Rebelling Against But I Was Going At It Hard"
"Mom Found This Recently, Me At 18, My Reaction When She Showed Me Was "God Damn What Is That Creature""
"My Parents On Their Second Date!"
"My Junior Year Yearbook Picture"
"Every Time My Friend Moves, She Rediscovers This Gem From Middle School"
"I Was A Cute Little Girl, Except For The Fact That I'm A Guy"
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