Incredibly Awkward Family Portraits That Will Make You Cringe

We might get to choose our friends, but we’re stuck with our families for life. Which isn’t necessarily a bad thing! In fact, when families get together and pose for portraits, the results can be incredibly entertaining. From the hilarious to the painfully awkward, check out this collection of some of the most… unusual family portraits out there.

Do you have any photos like these in your albums?

Nice Dart, Bud!

Look at Mom, though. She’s 100 percent ready for the spontaneous knife fight that’s about to breakout after this photo.

Cledus, Get The Possum

We’ve got a family portrait to take!

I Wonder What They’re Screaming

I bet it’s the chorus of “Kiss From A Rose.”

Dressy Casual

Who didn’t follow protocol? The man in the sweater vest or the man looking into the camera?

Talk To Me

We’re hip, we’re cool.

Sky’s Out, Thighs Out

No better time to strut your stuff than when the family gets together for the annual portrait.


There’s nothing like a well-timed fart joke to get the family smiling, right?

Brady Bunch: Okay Babies Now Let’s Get in Formation

Nothing suggests a forced posed like the casual hands in pockets.

It’s All In The Details

When concert attire varies…

Personally I think the girl on the right looks the most out of place.

Pajama Party

Nobody smile, there is nothing good going on here.

That bottom left kit is making this very Johnny Depp face. I actually think they all grew up to be models. They have the pout down perfectly.

How Were Your Travels?

When Mom and Dad are hanging’ with the wrong crowd.

You know though, young love is not so bad. Sometimes you get carried away and you don’t care who sees. It’s not like they’re harming anyone. Live every day like it is your last. You might die of diabetes II tomorrow, so just kiss the one you’re with!

Head Banger

The top of my head; it’s my good side!

Was anybody in your family this blonde? I am impressed. I wish I could get that tone of blonde from my hair dresser. I always get those unfortunate roots though. Ah, to be born with Swedish genes and hair like corn silk.

Parenting Oops

It’s all fun and games until someone is dropped on their head.

I think the mom is going down with that baby. She’s definitely off balance, herself. Maybe she should practice some yoga or pilates or pi-yo or something. The stronger your core is, the easier it is to stand up straight and not drop a baby on its head. She’s probably distracted by all the other challenges that come with parenting. Oh well. Not every kid makes it to see their 5th birthday. That’s just math.

Big Headed

Patriarchy at its finest.

I have a feeling that a dad like this stomps around saying “You don’t respect me.”

Did you think making your head larger than everybody else would result in somebody showing you respect? Dude, you have to give respect to earn it. When I say “please respect me…” I usually am saying “Hey, treat me like a person.” But when you say it, you mean “Treat me like an authority”


Surround yourself with lots of palm trees, and you’re pretty much at the beach.

Matching hawaiian shirts are cheaper than plane tickets. Too bad this guy wasn’t earning miles on his AMEX. Did Travelocity exist back then? Probably not. Flights from Minneapolis to Honolulu are still sky high.

Something Seems Dummy

No animals were harmed during this photo. Scarred, however, yes.

Gather Round, Gang

This is not the pink dressed monkey’s first photo shoot.

Lazy Pyramid

Where does the denim end and the awkwardness begin?

Wear Your Favorite Color

It’s just a phase

Forced Relaxation

Nothing cozier than a jacuzzi.

Look Away

Don’t look at me

She’s Gonna Be A Star

This looks like the beginning of a “Mom-ager” sort of relationship.

Baby Daddy

Regression at its finest.

Trophy Mom

When wearing white, goes wrong.

Grandma’s House

Milk makes the body good.

Our Little Angel

“Mommmmm, cut it out.”

Smiles Are Overrated

She gets her sassiness from me.

Too Creative

Baby: “Alright, I wanna go back in the tummy.”

Sister Rivalry

One dad, four daughters.

Chickened Out

Groom: “Why are we doing this?” Bride: ” I have no idea!”

Tweeting Trio

He’s my brother, but I get along better with the bird.

Jazz Hands

Mom: “We’ll photoshop clothes on him later.”

I’ll Stay Down Here

Only-child syndrome leads to creativity.

Take Your Pick

We wanted to capture Dad’s two emotions.

Sisters At Their Finest

Why is she still here?

Always A Bridesmaid…

Flower her with love.


Flex so hard.

Kiss Of Death

Aunt Carol, you know you’re kissing a guy wearing a bowtie, right?!!??

Play Nice

Dad looks proud.

Party Of One

Someone had to liven it up!

Who’s Your Daddy?

Eddie Murphy today, whoever we want tomorrow…

A Family And A Stranger.

I don’t need your hugs, I like my own.

Black Sheep

Dad: “I’m just gonna put this here.”


Three generations of cranked necks.

Mom, Can You Come Take This?

Covering my abs would mean I’m cold and weak, which I’m not.

Court Is Now In Session

Glad to see the jester is taking his role seriously…

Downright Creepy

They say you can spot the future serial murderers by looking at family portraits.

Poor Baby Had No Choice

I feel for the kid.

Lick It Up!

A family that rock and rolls together, stays together.

Wow, This Is Bad Ass

Everyone say: “Hiyah!”

Please, No

This pose should be reserved for high school graduations and sorority houses.

Nothing To See Here, Folks

Just a couple of tortoises wrestling each other.

Awkward Family Christmas Portrait Level


Matching Tattoos Are Never Okay

Is that a gang sign?


I like it

Dad’s A Real Dummy

All the kids take after their mother

Get It, Get It

Childhood ruined

They Must Suffer From Chronic Cold Neck Syndrome

How else do you explain the matching turtlenecks?

I Can’t Hold It Anymore

I thought i told you to go before getting in the car?

Merry Chrisstmasss!

From Sssarah, Ssstan, Ssteve and Sssophie