25 Awkwardly Funny Family Photos Weirder Than Yours

Smile! It’s Awkward Family Portrait Time!

Crazy Funny Family Photos


Even at the tender age of 5, Timmy had a profound message for the world.

awkward family boy portrait eat shit shirt


Another afternoon of delight for Eunice at Le Diplomate.

Vintage pic diplomate motel grandma awkward


Never mess with the Dale and his bad ass crew from Shady Acres.

vintage snap grumpy old folks bad ass awkward


“If you ain’t first you’re last”

funny awkward horse jumping rider flying off


Grandpa Carl finally found his honey.

man covered in bees funny awkward family photos


Bobby Martinez. Product Tester: Lowe’s Home Improvement, Allen Park, Michigan

kid pooping on toilet at Lowes awkward family


Welcome to Team Cream.

awkward family monster truck ice cream


Dale Turner on the day he hit the milestone that you officially lose your dignity.

awkward family 65th birthday party balloons


We always made sure the raw hamburger that sat in the fridge passed the “Aunt Ethel Test.

vintage snap putting food in grandma's mouth


Shelly Little on the biggest day of her long, lonely life.

awkward family vintage photo girl accordion nerd


We always knew that Jean would make it in the big city.

vintage 1960s go go big hair blonde


Testosterone was never a shortage with the Gentry brothers quartet.

awkward family brothers on bench


Workplace Cosplay at the Saltine Crackers headquarters, Elmhurst, Illinois.

awkward family woman man parrot suit


awkward family mom with come back with a warrant welcome mat


“With great power comes responsibility”… even if it’s working the photo booth at Sears from 9 to 5.

awkward family boy on spier man's lap


No one had the heart to tell Nadine that critter she found walking the streets was not her childhood dog Sprinkles.

awkward family woman walking capybara on city street


The moment Ted came down and realized he was no longer at Burning Man.

awkward family naked man pringles can over penis city street


Barry Goldman. Living proof that calculus is sexy.

Awkward family math nerd with bikini babes


For Dwayne, it wasn’t the Happiest Place on Earth, but it would do.

awkward family photo man in mickey mouse pajamas sleeping at bus stop bench


After all these years, Derrick finally proved the naysayers wrong. Canaries do kill inside of Target Store restrooms.

awkward family photo man card screaming by parakeet


Grandma Pearl. Cocked, locked and ready to rock.

awkward family grandma with gun


What nightmares are made of.

awkward creepy photo little girl with axe and clown portrait


The Brillos, Frank and Sandy.

awkward family man bad hair lower


The day they finally got a gig outside of Martha’s mom’s basement. Little did they realize that it was at Todd’s mom’s bridge party.

funny awkward 1980s band promo pic big hair


Someone’s not a happy little princess.

awkward family photo little girl giving finger

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