31 Hilariously Awkward Family Photos Both Funny & Weird

Awkwardly Funny Family Pics to Warm Your Cockles

And you thought your relatives weird? Get a load of these awkward family photos that prove you’re in a pretty good place. These vintage snaps capture a side of funny family life that shouldn’t be shared with the world. Oops! However, if your kin seems to be a lost cause, may we suggest a good self-help book?

 

Little Toby had it all. Charm, sex appeal and man boobs.
31 Hilariously Awkward Family Photos ~ young boy glamor shot pool silhouette

 

Half-way through the bottle of rum, Tony realized fresh coconut would be a great addition.

31 Hilariously Awkward Family Photos ~ vintage snap Florida old couple climbing palm tree

 

Colleen found her perfect math on eHarmony… except for the questions that mentioned  pee pants.

31 Hilariously Awkward Family Photos ~ portrait husband wife matching outfits pee pants

 

Mere moments before Deborah cast open the fiery Gates of Hell.

31 Hilariously Awkward Family Photos ~ vintage snap girl parade 1950s

 

Entitled: Cock-a-doodle Gingers in Moring Light

31 Funny Awkward Family Photos ~ vintage portrait girl holding chicken

 

Unfortunately for Dorothy and Ray, their ship still hasn’t come in.

31 Funny Awkward Family Photos ~ vintage snap old couple beach bathing suits

 

When you’re 6 going on 60.

31 Hilariously Awkward Family Photos ~ vintage snap glamor shot school pictures girl old lady hair

 

My, someone didn’t enjoy their Happy Meal.

31 Funny Awkward Family Photos ~ sad mad grandma McDonald's ball pit

 

You’re doing it wrong.
31 Funny Awkward Family Photos ~

 

Meet the Skepticks.

31 Funny Awkward Family Photos ~ creepy vintage family portrait

 

Even God had something to say about Martin’s speedo.

31 Funny Awkward Family Photos ~ vintage snap man in speedo posing next to road lightening bolt

 

Jack wasn’t sure what he did to deserve this award, aside from that lost, drunken Tuesday night at the Peoria Holiday Inn.
31 Funny Awkward Family Photos ~ AHDB pork services to sausages phallic trophy

 

Stella McElroy, raising the stock price of Aqua Net one spray at a time.

31 Funny Awkward Family Photos ~ vintage snap woman big hair 1960s

 

The unveiling of the Gladys Pervus portrait – in honor of her selfless philanthropy and contributions to raising the awareness of the attributes of the C-cup.

31 Funny Awkward Family Photos ~ vintage snap unveiling portrait of topless grandma

 

It’s time to play, “Who’s Hiding the Squirrel in Her Hair!”

31 Funny Awkward Family Photos ~ generations women posing big hair 1960s 1968

 

Nothing like a couple of darling princesses to soften the tone of your message.

31 Funny Awkward Family Photos ~ little girl princess dad protest sign wages for sin is death

 

…and then she wondered. Was a free drink really worth hearing another story about how “them bastards denied my insurance claim” again?

31 Funny Awkward Family Photos ~ vintage snap woman in casino de Paris bar

 

3 more Falstaffs and the fun really begins!

31 Funny Awkward Family Photos ~ vintage snap old couple posing in driveway 1950s

 

Whoever it was making the cooked cabbage for dinner, they never stood a chance.

31 Funny Awkward Family Photos ~ vintage snap 1950s family with guns rifles in living room

 

Their bowling skills may be in the gutter, but their fashion sense is truly striking.

31 Funny Awkward Family Photos ~ vintage snap women's bowling team pelican lanes animal print dresses 1960s

 

Gerald and Dusty never missed an airing of Seabiscuit.

31 Funny Awkward Family Photos ~ man with horse watching tv in living room

 

Grandma Estelle. Always the rebel.

31 Funny Awkward Family Photos ~ vintage snap vacation lookout mountain grandma hitchhiking

 

Robert and Denise called the maid in early. Their role-playing was bound to get messy.

31 Funny Awkward Family Photos ~ vintage snap role playing leopard outfits

 

Happy Bar Mitzvah, Irving.

31 Funny Awkward Family Photos ~ vintage snap bar mitzvah 1950s 60s

 

1985. The year Kevin peaked.

31 Funny Awkward Family Photos ~ vintage snap 1980s man big hair leather jacket

 

Ernie’s love for late put a special twist upon every social gathering.

31 Funny Awkward Family Photos ~ vintage snap man balloon animals

 

“Ehhhhhhhhhhhhh…..right?”

31 Funny Awkward Family Photos ~ vintage snap Vito Joe fireplace

 

Ima Jean sure weren’t happy about Uncle Joe “choppin’ his wood” out in the front yard again.

31 Funny Awkward Family Photos ~ vintage snap redneck hillbillies

 

Damn. That drink cost 12 dollars.

31 Funny Awkward Family Photos ~ vintage snap woman spills drink on baby

 

When you have to walk 7 miles to the nearest JC Penny Olan Mills Studio in mid-July to get your family portrait taken.

31 Funny Awkward Family Photos ~ vintage snap portrait unhappy family

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