27 Awkwardly Funny Family Photos ~ Weird, Wacky, & Wonderful

Say Cheese or Cheesy!

Hilariously Funny Family Pics

For the Love of Relatives

 

Not quite the beach vacation Maggie dreamed of, but hey, it’s New Jersey.

Not quite the beach vacation Maggie dreamed of, but it would do. ~ Awkwardly funny family photos

 

We’re just happy Toby found a friend.

We're just happy Toby found a friend. ~.~.~ Awkwardly funny family portrait boy vacuum cleaner

 

Pvt. Meldon learned the hard way. There is an expiration date on K-Rations.

Pvt. Meldon learned the hard way. There is an expiration date on K-Rations. ~.~.~ Awkwardly funny family photos

 

Calvin so desperately wanted to form the first Monkees cover band. Go for it, Cal. I’m a believer.

Calvin so desperately wanted to form the first Monkees cover band. Go for it, Cal. I'm a believer... `.`.`.~ Awkwardly funny family photos vintage snap 1960s boy bass guitar

 

Was the Dummy the only one who thought this was a bad idea?

Was the Dummy the only one who thought this was a bad idea? ~.~ Awkwardly funny family portrait

 

This Trek-E Club shot was taken in 1994. These boys would now be in their thirties. Which one do you think still lives in his mom’s basement?

This Trek-E Club shot was taken in 1994. These boys would now be in their thirties. Which one do you think still lives in his mom's basement?

 

While playing a long, Aunt Helen recalled a time when “Gangbanger” had an entirely different meaning.

While playing a long, Aunt Helen recalled a time when "Gangbanger" had an entirely different meaning.

 

Got mom all packed up. Close the trunk. Time to go.

Got mom all packed up. Close the trunk. Time to go.

 

God bless the U. S. of A.

God Bless the U.S. of A.... ~ Awkwardly funny family photos American flag shaved in chest hair

 

The Board of Directors of Miller Family Realty – William, Bill, jr., Donald, and Mittens.

The Board of Directors of Miller Family Realty – William, Bill, jr., Donald, and Mittens.

 

After the passing of Millies, Franklin swore he’d never marry again. But that was before Weeki Wachee.

 

Timing is everything. So are having a neck brace at the ready.

Timing is everything...... ~.~ Awkwardly funny family photos girl dropped on head photobomb

 

How a camel fills its hump. Now you know. Say thank you.

How a camel fills it's hump. Now you know. ~.~ Awkwardly funny family photo boob

 

I LOVE this photo. Ya think their sisters?

I LOVE this photo. Ya think their sisters? .~.~.~ Awkwardly funny family photos vintage color snap country wester trio

 

Nobody can out tricks Grandma & Grandpa when it comes to a Bigflip.

Nobody can out tricks Grandma & Grandpa when it comes to a Bigflip. ~.~ Awkwardly funny family photos skateboarders finger

 

Ring with the Nelsons was always an exotic adventure.

Ring with the Nelsons was always an exotic adventure. ~.~ Awkwardly funny family portrait emu baby monkey

 

Aunt Nancy’s career as a spoon model may have been short-lived, but she’s still got it!

Aunt Betty's career as a spoon model may have been short-lived, but she's still got it! ... ~ Awkwardly funny family photos vintage color snaps

 

Never under estimate the dastardly intentions of Natalie.

cute, sly girl with fake mustache ~.~ Awkwardly funny family photos

 

Betty and Jean in their never ending fight against soap scum.

Betty and Jean in their never ending fight against soap scum ~.~ Awkwardly funny family portrait vintage snap shot

 

It would take years to realize, but the warning signs were there from an early age.

It would take years to realize, but the warning signs were there from an early age.

 

Tennis ace Tony Marguchi, suspended for improper uniform violations.

Tennis ace Tony Marguchi, suspended for improper uniform violations.

 

George was always up for a gastronomical challenge.

Vintage color snap, 1963, All you can eat chicken with bigs bunny holding sign.
Daddy always loved that varmint best.

awkward family portrait with raccoon.

 

Leave it to Cindy to find a way to combine her love for dancing and towel racks.

Leave it to Cindy to find a way to combine her love for dancing and towel racks.

 

Though it would be another 60-years before Tindr was invented, all that ran through Becky’s mind was “Swipe left! Swipe left!
vintage kodachrome color snap couple on a date burlesque show

 

Scorned by fellow art student Hillary Johnson, Derek poured all his frustration into his lasted masterpiece, The Snatch of Destruction.

Vintage snapshot art student 1970s/180s ~.~ Awkwardly funny family photos

 

The day Kevin lost both his modesty and his fertility.

How Kevin lost both his modesty and his fertility.

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