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Behind The Awkwardness

The Ice Storm

“My grandparents immigrated to the U.S. from Switzerland. On a family trip back to their homeland, they posed for this photo in front of a glacier. Armed with ice picks and standing in the arms of a stranger dressed in a polar bear suit, the photo leaves just one question: What do polar bears have to do with Switzerland?”

(submitted by Tim)

The Monolith

“This is my sister Shannon on vacation in Ireland. My boyfriend saw this at Thanksgiving and commented that this has got to be one of the MOST horrid things ever!”

(submitted by Tara)

Green Steel

“So my Dad’s landlord, who is trying to bring business back to his failing modeling agency (failing probably because he takes photos like this), volunteered to take pictures of my dad and I. He dressed and posed both of us, and this was the result. Oh, his instruction for our facial expression was “Give me stubborn! Give me sassy!”

(submitted by Clarity)

My Mom, The Cougar

“This is a photo of my mom and her new boyfriend. They like to travel and take pictures of themselves. She is very proud to be with him and makes sure to post pictures like this one all over the internet for me and my sister’s friends to see. So not embarrassing.”

(submitted by Hayley)

Down In The Dumps

“This is me, posing for my father on a Sunday morning, shortly after he separated from my mom. He let me wear whatever I wanted and do whatever I wanted with my hair (opportunities that I made the most of). For some reason, he thought it’d be a good idea to take pictures of me standing in front of a dumpster. I have a whole set of these. I guess he was a bit depressed…”

(submitted by Lucia)

The Great Outdoors

“This is a photo of my sister camping in Hana, Hawaii. We lived there during our ‘awkward’ phase of 12-14. Family friends, who didn’t have children of their own, decided it would be a good idea to take 5 girls camping ages 9-13. Notice the lovely Christmas nightshirt my sister thought she should wear camping in July. She also is wearing the same braid that my mother put her hair in 4 days earlier. Jen was so filthy I think my mom burned her nightshirt when we got home.”

(submitted by Shauna)

Beaches

“Mum bravely volunteered to let me practice my face painting skills on her. Let’s face it– who wouldn’t want a beach painted on their face?”

(submitted by Laura from the UK)

Wonder Woman

This was at my family Christmas party when I was about 4. I had just gotten a makeup kit from Santa and wanted to prove to the world that I had the cosmetic fortitude to wear all of it at the same time. That’s my grandfather and a longtime family friend on the left. Both of them were college professors. In my eagerness to have my facial masterpiece captured on film, I managed to pop up during a conversation that most likely consisted of literature or world travels.”

(submitted by Annie)

Tooth Fairy

“Picture of me 5 months old on Halloween. My parents dressed me as the tooth fairy and hung me from the plant holder that hung from the ceiling by the front door.”

(submitted by Megan)

Baby Blues

“Unfortunately, this is one of my first baby pictures. And yes, it is me. And no, I do not still look like this :)”

(submitted by Seth)