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The Freebie

“My buddy Josh and his older sister and brother when they were little guys. Apparently when the photographer saw all the prints from the photo shoot, he gave this one to his mom for free because it’s just so hilarious. He would hide it from me when I went to his house because I would cry from laughing at it so much.”

(submitted by Eric)

Tiger Twins

“I’m not sure what’s more awkward. The matching tiger print overalls my grandmother made us…or the expressions on my grandma and cousin’s face from all of my protesting over these photos. This is the best we got.”

(submitted by Alex) 

Mammaw Knows Best

“Mammaw insisted that babies liked being held this way.”

(submitted by IG @sarahj.rob)

Stay Golden

“I used to watch The Golden Girls a lot. When we showed up for pics at Glamor Shots, my mama let me pick one of the outfits. Blanche Devereaux would be so proud.”

(submitted by IG

Trunk Stop

“Just me and my dad taking a break from a road trip in the 1970s. Apparently my parents found it convenient to just pop the trunk and prop me in a box while they took a break from driving. I had always heard the story and now I finally have proof.”

(submitted by M.) 

Denim Days

“Every year my mother wanted a nice family photo and this time around she chose our outfits. Matching jean dresses for my sister and I, jean dress for her (with that awesome big hair that she permed) and a jean shirt for my dad. (Plus I don’t know where we are all looking…but it wasn’t at the camera.) This is in honor of my mother who passed in 2015 from Melanoma.”

(submitted by Colleen) 

Cap & Gown & Jorts

“My dad thought it would be perfectly fine to wear cut off jeans and no shirt for my graduation photo.”

(submitted by IG @pwshannon

Lunatic Toons

“5 year old me with an odd-looking Mickey Mouse and Pink Panther on our family vacation in Mar del Plata, Argentina.”

(submitted by IG @angelagravano)

These Are Some Of My Favorite Things

“This was my senior picture in 1998.”

(submitted by IG @kmichel_actor_voiceover_artist)

17 Is The New 40

“This magnificent awkward moment was my high school graduation photo from 1997. I remember thinking to myself ‘don’t fall, don’t fall, don’t fall!’ while precariously balanced on what I can only assume were old books under a wrinkled drop cloth. When the photos were sent to me I was too mortified to give them to anyone; in fact I still have the full sheets of them in a bin in my basement. I’m actually 17 in this photo, and I just recently turned 40. Not everyone gets to experience their 40’s twice in life. I just happened to do it the first time when I was in my teens.”

(submitted by IG @shannon_l_norberg