Grandma Not Included

March 30th, 2015

Grandma Not Included - Awkward Galleries

Here at Awkward Family Photos, Grandmas can do no wrong. So, when 86-year-old Floridian, Yolie Ball, decided to sell her house and get a little creative with her online listing photos, we decided we wanted to help her.

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Penicidal Tendoncies

March 30th, 2015

funny brother photos

When Mom, Beth Woolsey, the author of Five Kids Is A Lot Of Kids asked her twin boys to guest post a blog by picking an important topic, this is what they came back with…

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March 30th, 2015

funny school picture

“This is my brother Bobby’s class picture back in ’97. The red stuff is ketchup.. don’t ask how it got there.”

(submitted by Elizabeth)

Puerto Rico Blues

March 30th, 2015

Puerto Rico Blues - Awkward Galleries

He won a trip to Puerto Rico, his wife couldn’t go, and he had no fun. At least that’s what he wants her to believe.

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17 Head-Scratching Real Estate Photos

March 30th, 2015

17 Head-Scratching Real Estate Photos - Awkward Galleries

A few pics from the hilarious Tumblr blog, proving that some people aren’t that concerned about selling.

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The New Guy

March 30th, 2015

funny standout

“That time my mother thought it would be a great idea to take us to Madam Tussaud’s to meet her new eight foot slash lookalike boyfriend for the first time.”

(submitted by Roxzann in the UK)

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The Wonder Years

March 28th, 2015

funny school photo, 70s


“During the ages of 8 to 11 years old (1972 to 1975) I became trapped in a vortex of awkwardness. And my mom’s taste in clothing really brought it to another level – this stuff was embarrassing even back then. I honestly don’t know how to chose which pictures to send because it seems each one was worse than the last. But here are the two best , age 8 from 1972 and age 10 from 1974.”

(submitted by Brad)

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