Say Cheese! 18 Awkwardly Funny Family Photos

Crazy Weird Funny Family Pics & Portraits

funny dog smile photobomb family portrait ~Awkwardly Funny Family Photos

The tortured soul of Tommy Rodriquez.

weird school pic portrait ~Awkwardly Funny Family Photos

Aunt Milly, serving up hot and hearty portions of “Shut up and eat it.”

Vintage color snap of old ladies, moms, grandma's cooking in kitchen, 1950s ~Awkwardly Funny Family Photos

They’re so dang cute at that age, aren’t they?

Girl scratches I Love my Dad in car door withscrew driver, they're so cute at that age ~Awkwardly Funny Family Photos

Agnes Kaskey. Tuesday Night Bingo, VFW Post #10147, Apopka, FLA.

62 confirmed kills. 27 prisoners taken.

Vintage snap of big haired grandma, cat eyed glasses playing bingo ~Awkwardly Funny Family Photos

Some days just scream for a Venti Non-Fat Soy Latte With Caramel Drizzle.

Man at starbucks in Britney Spears shirt, pepperoni pizza pants, holding a hubcap ~Awkwardly Funny Family Photos

Doris has a big surprise for grandpa when she gets home.

Grandma with hatchets ~Awkwardly Funny Family Photos


Eye roll, whatever, 1980s family portrait, Ownen Mills ~Awkwardly Funny Family Photos

Jerry’s here. The party has now officially started.

Chubby kid in spongebob swag t-shirt ~Awkwardly Funny Family Photos

Ja’que. Born and raised in South Detroit. She took the noon time bus going anywhere.

Big hair & nails ghetto momma on bus ~Awkwardly Funny Family Photos

Another satisfied customer.

Baby in I love boobies onesie ~Awkwardly Funny Family Photos

We all thought Boris Nogglekov’s notebook of ideas to improve out public restroom facilities was pure horse cocky… we’ll… until we realized it was actually a divine intervention.

Grandpa divine intervention ~Awkwardly Funny Family Photos

Col. Stanley Stemmer. Lost in Space.

Portrait of astronaut with Scotch bottle ~Awkwardly Funny Family Photos


dad's step mom looks like Mrs. Doubtfire ~Awkwardly Funny Family Photos

Sistas Rule.

Nuns giving the finger ~Awkwardly Funny Family Photos

Welcome to the Spring Hair Ball.

Big Hair, 1980s prom pic ~Awkwardly Funny Family Photos

Evelyn Frakes. Preparing to prowl the 4:00 pm dinner crowd at Picadilly Cafeteria.

Vintage snap of grandma & poodle, putting on lipstick in side view mirror of cadillac ~Awkwardly Funny Family Photos

When Toby said he that wanted to have his birthday party at Chuck E. Cheese, his grand dad swore he said the Strip’n’Tease.

Boy's birthday party at strip club ~Awkwardly Funny Family Photos

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