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.

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

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

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

Entitled: Cock-a-doodle Gingers in Moring Light

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

When you’re 6 going on 60.

My, someone didn’t enjoy their Happy Meal.

You’re doing it wrong.

Meet the Skepticks.

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

Jack wasn’t sure what he did to deserve this award, aside from that lost, drunken Tuesday night at the Peoria Holiday Inn.

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

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

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

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

3 more Falstaffs and the fun really begins!

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

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

Gerald and Dusty never missed an airing of Seabiscuit.

Grandma Estelle. Always the rebel.

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

Happy Bar Mitzvah, Irving.

1985. The year Kevin peaked.

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

“Ehhhhhhhhhhhhh…..right?”

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

Damn. That drink cost 12 dollars.

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