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Behind The Awkwardness

Lawnmower Mullet

“What you get when you ask your mother to give you the ‘layered’ look.”

(submitted by Erin)

Pretty in Pink

“When I was 9, my teeth were so messed up that I had to wear “headgear” to create more space for my overcrowded mouth. The only say I had in the matter was choosing the color; either clear plastic or pink, which I hated. I asked them if there was any way possible that they could make it electric green, because apparently, that would make me look “cool.” The dental assistant shook her head and looked at the ground. I sighed and chose clear. Apparently, she checked the wrong box on the order form because when it was time to pick up the contraption, it came out of the box hot pink. Mortified, I begged my mom not to make me wear the pink thing to school. Fortunately for me, I had a very understanding mother. So, I only wore it at home and on car trips to see my grandparents.”

(submitted by Caitlin)

Lone Star

“My dad owned a restaurant in Austin and they had the bear from the Paul Newman film The Life and Times of Judge Roy Bean come to a party. This is the 1970’s so a loose bear drinking Lone Star and being fed tootsie rolls from little kids mouths was okay… right?”

(submitted by Alysa)

Special Occasion

“My 16 yr old son had to get the ‘exam nobody likes’.  I thought it best to twist the (cake) knife since I’m definitely Dad of the year.”

(submitted by Joel)

Udder Nonsense

“My wife and I took our 2 girls to the University of MO’s College of Vet Medicine’s open house in 2002. We took lots of pictures and this gem was discovered by my mom when we were showing her the pictures a few weeks later. Even with sophomoric minds, my wife and I hadn’t noticed the great placement of the cow’s udder in relation to me standing there.”

(submitted by Scott)

Run To The Hills

“This picture was taken circa 1985. I grew up the only Chinese kid in a very small town. I went through a heavy metal phase after being introduced to Iron Maiden from the cool older kids on my block. In an attempt to fit in, I pierced my ear and got a mullet.”

(submitted by Josh)

Blink

“In 5th grade I was worried I would blink and mess up my yearbook photo.”

(via source)

Meow Factor

“Cat Vest. Throwback to a time when I just wanted to dress like my teachers.”

(via merrymushroom)

Dazed And Confused

“This was my wedding day September of 2000. Someone got a shot of us looking dazed and confused! I’m the bride and my two sisters are on each end looking totally puzzled. Not really sure what’s going on there on the right!? This is what happens when you have a large family with many photo shoots! This picture has been a classic for almost 15 yrs now.”

(submitted by Gina)

Deep V

“My 2 year old son’s preschool recently did school photos and I sent him in a cute sweater. I’m not sure if his teachers and the photographer completely failed to look at him, but it seems pretty obvious that the intention of this sweater was to have the zipper partially zipped. The unzipped sweater coupled with his lack of smile and messy hair made for a memorable first school photo.”

(submitted by Vicki)