Grandpa Was Quite The Stud - Grandpa

Grandpa Was Quite The Stud

“Grandfather died in 1994. Going through his things today, I found his wallet. This was next to his license, military ID, and Medicare card. Clearly important.”

(via source

Chernobyl Claus - Christmas

Chernobyl Claus

“This is a photo taken in 1976 in Pittsburg County, Oklahoma. It looks like Santa’s face is a melting pile of vomit.”

(submitted by Rachel)

Grandpa’s Newest Hobby - Grandpa

Grandpa’s Newest Hobby

“My grandfather and his hobbies…”

(via source

A Holiday Letter From Debbie, Gary, & Lance - Christmas

A Holiday Letter From Debbie, Gary, & Lance

You’ve been pranked. That’s right– introducing the Awkward Family Photos Prank Holiday Card Set.

Each Prank Holiday Card set includes three tear-off cards featuring an Awkward Family Photos brood with their fake yearly summary on the back.

• SEND one in the mail anonymously
• SNEAK one onto wall at a friend’s holiday party
• DISPLAY on your fridge amongst all your real friends.

Whichever you choose, bewilderment will follow – which is what the holidays are all about, right?

Me And My Tooth - School Photos

Me And My Tooth

“My second grade picture. Yes, that is a tooth. Yes, that collar is flight-worthy.”

(submitted by Scot)

Going The Extra Mile - Christmas

Going The Extra Mile

“My parents like to make their own holiday cards and think it’s more personal to include photos of themselves or other family. Last year they were inspired by The Elf on the Shelf and took this little gem. It was sent out to the entire family, their friends and even my boss.” 

(submitted by Catherine)

Slice Of Life - Teens

Slice Of Life

“They told me we were getting pictures taken and I could wear anything I wanted.”

(submitted by Kaylie)

No, It’s Not A Wig - Behind The Awkwardness

No, It’s Not A Wig

“This is what happens when your mother chops off your beautiful, long, thick, Crystal-Gayle-length hair the day before school photos in Grade 2.  She curled it under every morning.  Success was not having to break out the Aloe Vera for the accidental forehead burns from the curling iron. My hair rivals one of the stooges but it’s meticulous, I give her that. She must have forgotten to do laundry in her haste and put me in some costume that would rival Liberace’s stage clothes. And check out the glasses.  Didn’t realize I was cross eyed until this picture surfaced 33 years later.

(submitted by Krista in Canada)

Benjamin Button - Behind The Awkwardness

Benjamin Button

“I don’t know what is worse… the bowl cut, the glasses, the ultra tight pants, the giant belt or the fact that I was off by at least 2 buttons.”

(submitted by Wayne)

Recovering Chocoholic - Recreations

Recovering Chocoholic

“I did some recreation photos for my Mom.”

(via source