“Had To Fight The Ladies Off With A Stick”: 80 Hilariously Awkward Childhood Photos

Jason Sargent Friday, December 19, 2025

- - “Had To Fight The Ladies Off With A Stick”: 80 Hilariously Awkward Childhood Photos

Rokas LaurinavičiusDecember 19, 2025 at 11:01 PM

The period is called blunder years, and it hits us either in childhood or adolescence. Basically, it's a time when we think we're cooler than others find us to be. And later, no matter how much we would like to forget our cringey past, there's usually a photo or two to remind us of it. Some are sitting in family albums, some are scattered across our friends' hard drives, and while many try to ignore them, a few decide to spread their embarrassing moments even wider by sharing them on the internet, taking ownership of their previous silly hairstyles and questionable clothing choices.

#1 My Uncle Being Embarrassed Of Me Trying To Sip Some Soda In Public

This was at a Hardy’s in Michigan right after we finished a 10-mile bike ride.

#2 Here I Am Winning The “Little Miss Piggy” Award At A Mud Volleyball Tournament In 1998

I was sprayed down with a fire hose afterward and wound up with hypothermia.

#3 Looking Back To My Iconic Fashion Choices

Year of the last warped tour, earlobe blowouts, Myspace, and getting bullied by the older scene kids.

#4 Apparently This Was The Best Photo They Could Get For My First Christmas

#5 I Wanted Dreadlocks In Highschool. Mom Gave Me Braids

#6 I Was 10 When I Realized People With No Bangs Had Grown Them Out, Not Cut Them Off

#7 I Recently Visited My Sister Who Shared Her Favorite Childhood Photo Of Me - The Time I Married My Giant Stuffed Pikachu, Ricky

#8 My Friend Has The Best Awkward Childhood Photo Ever

#9 I Blame My Mom For This One. My Sweater Wasn't Stained, The Photo Is Just Old

#10 My 9th Grade "Graduation" In 2002. 3 Months Later I Was In Military School In Texas

I was obsessed with Linkin Park, but yes.

#11 2004. Trying To Take A Myspace Photo While No One Was At Home

#12 School Photo Looking Like A 60-Year-Old Librarian With My Cardigan, Turtleneck, And Thick Glasses. Date And Age Unknown

Was born in ‘89 if that helps.

#13 My Family Dubbed Me "Fivehead"

My friends said, "Can you do a brainblast for us?" and "Looks like you have a lot on your mind" when they first saw it.

#14 Glad My Wife Changed Hairstyles Since Then

#15 My Husband At 14 Years Old

#16 In 7th Grade, I Didn't Have A Date To The Dance, So I Cut Out A Picture Of Brendan Fraser And Taped It To A Stick And Brought It With Me. For Real

I thought my peers would celebrate my ingenuity and hilarity! They...uh...did not.

#17 2005, College Freshmen, Full Of Rebellion

#18 Glamour Photo From 1994. I Was 8 Years Old (Going On 45 In This Pic)

#19 My Dad Always Thought This Haircut Looked Incredible On Me. My Mom Thought The Shirt Was Incredible. I'm A Female

#20 Apparently I Didn't Know How To Smile In First Grade

#21 I Show My Boyfriend One Picture From My Childhood And Suddenly Reproducing With Me Is Off The Table

#22 Embarrassingly Enough, This Is Not The Only Photo I Have Of Myself With Balloons Stuck Up Under My Shirt

#23 2007 Photoshoot In My Grandparents' Bedroom. Not Sure What The Inspo For This Photoshoot Was Or What Emotion I Was Trying To Convey

#24 All Decked Out In Eyeliner And Angst, About To Go To The Local Emo Concert (2006)

#25 Didn’t Realize Whole Body Photo

The hair was a result of poor brushing during summer swim team, and I had to cut it off. Remember getting dressed that day thinking it was a top half photo, and I’d take the sweater off after the picture, hence the biker shorts. No idea about the gumball machine.

#26 It's 2013, 14-Year-Old Me Liked Photoshop, Fedoras, And Space

It was probably the only image of "space fedora" on Google images. I hadn't figured out how to flip images in Photoshop at that point.

#27 My Friend Was 12 Going On 45

#28 When I Met My Childhood Crush, Jonathan Taylor Thomas, My Face Was Painted Like A Clown

#29 My Childhood Picture

#30 I Used To Think It Was "Cute" To Dress Up Like My Doll

#31 1994, Age 7, First Grade. My Stepdad Says I Wanted My Hair Cut That Way

#32 I Had Liberal Parents And Tried To Rebel With This Haircut. It Backfired

#33 My Original 3rd Grade School Photo (Left). Mom Demanded A Retake (Right) With The Instructions "Smile! Show Some Teeth!" Note Which One Got Framed

#34 I See Your Friend's "Awkward Childhood" Photo, And Raise You Mine. Man, I Was A Looker

#35 Describe Your Childhood With A Picture. This Is Not The Worst

#36 I Present To You This Very Caucasian Girl Who Dressed As A Rapper For Halloween

When I was 12 and decided to go trick-or-treating as "Bob Marley" or whatever this is.

#37 10th Grade Me. My Fashion Sense Dictated T-Shirts And Flannels With Sleeves Cut Off

#38 I Went To See The Easter Bunny While Sick With The Flu. Can You Tell Which One I Am?

#39 My Entire Life Is A Kesha Phase

#40 Everyone, Meet My Alter Ego, Kyle

#41 This Is What "Rizz" Looked Like In The 90's

#42 Bringing This One Back. My 9th Grade Picture In 2013. Thanks I Hate It

#43 This Is My Wife's Favorite Photo Of Me

#44 1995-1997 My Dear Grandpa Showed This To My Fiance The Night Before Our Holy Matrimony

#45 In Honor Of National Emo Day, I Thought I’d Share My Favorite Myspace Looks

#46 My 9-Year-Old Official Photo For A Tap Dancing Routine Set To "My Boyfriend's Back". Yes, That Is My Real Forehead. Yes, I Have Bangs Now For A Reason

#47 My Graduation Outfit Was A Polyester Kimono I Spent All My Travel Money On At Disney World

This was before going off to study Japanese at university. To be fair, though, encountering some of the people in that department was what started bringing me back to reality.

#48 Favorite Picture Of My Husband

My husband gave me permission to share this gem of a photo of him. He believes he was in 3rd or 4th grade, 1986 or 1987.

#49 Permission Has Finally Been Granted To Share My Wife's Glorious Childhood Perm/Greatest Soccer Pic Of All Time

#50 My Boyfriend's Senior Picture

I swear this picture watches me sleep...

#51 I Raise You All, My Sister's And My Most Embarrassing Childhood Photo. I'm The Unfortunate Soul On The Right

#52 Aparently I Wouldn’t Stop Licking My Lips

#53 This Is My Wife Circa 1989, Bless Her Heart

#54 “Thriller” Dance Routine My Sister And I Put On For Our Parents, Where Being A Zombie Meant You Had Hairbrushes Stuck In Your Hair

#55 My Dad Sent Me This Picture The Other Day. I Was 17

#56 My Sister Asked Me To Post This For Her. She Asked The Babysitter To Make Her Look Like Ernie. She Loved Ernie

#57 Corduroy Cat Vest, 1994

#58 My Boyfriend And His Mom In 1992

#59 6th Grade Was A Rough Year

#60 Me, Age 13, For 8th Grade Valentine’s Dance

#61 Yes That Is My Real Head, No This Photo Was Not Edited

The hairstyle is not helping me at all.

#62 This Is How I Smiled Because I Had No Top Teeth

#63 This Was Me At 16... I’m A Dude

#64 Right Before A Brutal Transfer From Homeschool To Public School. Circa 2007

#65 My Wife And I Apparently Shared A Common Love For Ladders, Denim, And Bangs. Our Senior Years In The Late 90s

We actually met about five years after that. We grew up about an hour apart and she graduated a year before me, proving that this theme was universal.

#66 My Wife Gave Me Permission To Share This Picture Of Her From The Early 90s

#67 My Wife Was Every Generic 90’s Advertisement In Picture

Every generic ’90s advertisement in one picture.

#68 2004 - It Was "Clown Day" At School. I Was The Only One In Costume. Aside From The Clown At The Assembly. Thanks Mom

#69 Childhood Me Thought This Would Look Awesome. I Can't Believe They Let Me Take It

#70 Our Most Embarrassing Photo

#71 Today I Completed My Master's Degree. To Celebrate My Future, I've Decided To Start By Embracing My Past. I Present My Single Most Embarrassing Photo

#72 My Super Fun Aunt Used To Work At A Photography Center At Sears

#73 Had To Fight The Ladies Off With A Stick In 8th Grade

#74 My Mom Just Sent This To Me, And I Guess Now Everyone Else Has To See It Too

#75 Me In The 90s, Absolutely Thrilled To Be Wearing This Chipmunk Onesie

My mom made me wear this to meet Chip and Dale in Disneyland Paris, in the sweltering heat. It’s a miracle I survived. Also, I truly miss having a TV so big that it can fit a photo frame, a haunted porcelain doll, and a giant lamp on it. The good old days.

#76 Me And My Sibling Crossdressing As A "Present" To Our Mom For Mother's Day (2004)

I'm the one on the left. I really couldn't tell you why, but we decided that we could swap wardrobes and present ourselves to our mom as a gift for Mother's Day. Apparently Pringles are for boys. That was intentional. I padded the dress with bars of soap.