The Most Awkward Family Photos You Wish Never Happened

As kids most of us dreaded the yearly family photo, often forced to wear matching outfits and required to put on a plastic smile. It is especially embarrassing when your proud parents display this family portrait for all to see often centered in the living room.

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We’ll explore some of the most awkward, embarrassing and downright silly family photos many wish were never taken. As they say, a picture is worth a thousand words; some things are better left unsaid.

Au Naturel

This family took the natural look to a whole level; involving everyone, including the kid! How awkward was this for the photographer?!

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Although mom, dad, and baby accessorized with their best gold bling, they didn’t bother to worry about accessorizing in any other way! We hope they had something to cover up the goods.

Family Heritage

These siblings decided to show off the beautiful blend of nationalities in their family. Sis is rocking the Babushka look representing Russia, while brother Paul is showing his English Roots, (he’s a rockstar at heart!)

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Brother Wyle shows off their grandfather’s Australian side; the shark tooth and all! Little bro Willie wanted to represent America since the father is a proud veteran of the Army. Nice cigar buddy!

Dad’s Big Ego

We all know he’s the man of the house. But sometimes dad can get a little full of himself.

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Mom was always saying he had a big ego, and as children, her kids never understood why. After looking at these pictures 20 years later, now they understand completely.

Purrrfect Duo

They make the purrfect couple. Like mother like daughter, this duo consider themselves proud cat ladies, thrilled to show off their babies. These furry friends are essentially additional members of the family so they must be included in the family photo.

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Mother has decided that since cats are roughly the size of babies, they made a perfect addition to the family. Her daughter is thrilled with her new siblings. They even have cat earrings and shirts to match!

Gone Bananas

This crazy couple chose an alternative route for a family. Adopting a litter of baby monkeys. We all know primates are the closest mammals to humans so this adventurous couple decided to give these cuties a chance at domestic life.

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Mom loves dressing up her babies but there is always one rebel who won’t get dressed. Needless to say, they are trying their best to maintain their broad but they are wild ones! Even leashes don’t stop them from jumping around.

Family Feud

It seems Jacob’s true feelings towards his mother were caught on camera. Jeanie appears also to be having some sinister thoughts but chooses not to act on them.

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Meanwhile, the oblivious father seems to have forgotten his pants and tie! We must say this family portrait seems to have captured the family’s true colors. We can only conclude they are a tad bit dysfunctional.

Taking Their Fandom to Another Level

These die-hard Winnie the Pooh fans take their obsession to a new level. Dressing up for a family photo is the best way to recreate their odd fantasy.

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Of course, the baby was in on it too! Who knew dressing up as a bear, donkey, and tiger was on the agenda for a family portrait! This photo will surely be cringe-worthy when this child becomes a teen!

The White Sheep of the Family

We often hear about the kid that is the black sheep of the family. Here we see quite the opposite scenario. The kid seems to be is the most put together of the bunch, with his button-up vest and tie.

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Dressed prim and proper, likely on his own account, he makes his parents look like the rebels of the family. This little angel won’t let his parents bring him to the dark side.

Good Hair Don’t Care

We must say good hair runs in this family. Mom, dad, and bros got it goin’ on. The eighties were a time when the mullet was all the range and this fam is right on trend!

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Johnny can’t wait until he turns 13 so his mom will finally allow him to use Aqanet hairspray. We predict his future as joining a hair band in the mid-1980s. We are looking forward to it buddy!

Anger Issues

A sweet family photo with all the siblings turned ugly quick. These canine brothers are clearly jealous of their middle bro who seems to get all the love and attention.

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Coordinated in matching colors, and ready to pose for the camera, sometimes it takes a lens to bring out the true colors of how siblings really feel towards one another.

Sorry Kids, This is Closest You’ll Ever Get to Hawaii

When mom took the family shopping to get matching Hawaiian shirts the kids were excited! Maybe they would be going on a vacation?

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Sadly they were told the shirts were the closest they would be getting to visit the island. Now smile for the camera kids, pretend you are on vacation!

Oopsies Poopsies

This growing family is thrilled with their new addition. We wonder why they forgot to dress their newborn son. It seems accidents could happen. Big sis got a little more exposure than she intended.

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Both dad and daughter look a little shocked, as this was not the direction they were expecting the family portrait to go in. Meanwhile, mom, completely oblivious looks like a floating head as she smiles to the camera.

Acid Wash Denim and Big Hair

1987 was an unforgettable year. This family was right in style. Acid wash denim, and big hair styled with Dep and Aquanet.

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This family took pride in representing the late 1980’s hard. We’ll guess they stayed on trend with the years to come, transitioning fads with every decade.

Attitude Much?

This six-year-old girl already has the attitude and mentality of a teenage girl. She is well aware her father is not thrilled to be in the staged family photo, he’s just going along with the motions.

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She can’t help to notice the face he is fronting and isn’t buying his act. “Nice try dad!”

1980’s Pride

Another family photo stuck in the 1980s. Complete with acid wash galore, fan bangs, lace mullets, and a Tom Selleck stash; this photo doesn’t need to contain a date for reference.

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This happy dad looks as if he is radiating from the purple background! We’re sure he is proud of his girls for looking so radical.

Who Let the Hen Out?

This quirky family brought all their hobbies to the family portrait. Joey likes to show off his love of the accordion while Sammy wishes he was a cowboy.

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And how can we not mention mom and her hen! Cradling her pet bird with joy. She admits she’d be lost without her bundle of feathers. We can tell dad’s embarrassed over the whole situation.

Head of the Family

This dad takes the head of the family to a new level. We’re curious to know how these kids feel having to pose for such a cringe-worthy photo, that is sure to sit on the mantlepiece for years to come.

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We can guess these girls feel a little awkward, especially showing this photo to anyone in the present day. This strange technique went out of fashion decades ago! Sorry to age you, Carol!

Candy Striped Fam

This family came to the mall dressed in matching striped pj’s to pose for Christmas photos at the closest JCPennys. They are dressed like festive candy canes, and the parents even brought cookies and milk to add to the Christmas theme!

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We know they didn’t lose each other walking through the mall as a family. And we know for certain the kids were rewarded with the cookies for taking such a cheesy photo.

At Your Own Risk

Some habits are taught at a young age and often, as a result, of ones’ upbringing. Clearly, this family didn’t get the surgeon general’s warning about the effects of smoking.

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While the elder members of the family act as if they are so cool smoking cigarettes, poor little Jimmy also looks like he had one too many puffs and is about to pass out!

An Uninvited Guest

Toby, the family horse was a little disappointed he wasn’t invited to the family portrait session. Tom and Tina were ready to pose with their other babies and Toby felt a little left out.

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He tried to barge right into the photo but caught his family off guard. Well, mission accomplished, the horse got his picture taken with the fam!

Tough Girl

When it comes time to pose for the camera, this little girl shows no fear. She is not afraid to look head-on into the lens with confidence and strength.

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She must have inherited her confidence from her daddy, who also bears a stoic stare. Just don’t look at her family the wrong way because she’ll give you the stink eye.

A Very Meowy Christmas

This mom and cat daddy dressed up in pj’s for their yearly X mas card. Plaids and stripes and cats galore! This family surely is in the holiday spirit.

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They even have a backdrop with presents and a tree to complete the holiday look! Sarah also included red and green festive cat ears to top it off! We love the cat sweaters!

Daddy Dress Up

Little girls love playing dress up and what fun it would be if daddy could play along?! This vulnerable father was trusting with his daughters when he allowed them to apply makeup.

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Unfortunately, the result turned out horribly wrong leaving an awkward photograph as evidence. While he’s an outstanding father we can’t say he looks all that fabulous made up.

Say It Don’t Spray It

This sweet family was posed and ready for their annual family photo dressed to the highest degree. They almost got this photo just right until little Johnny got itchy and let it all out. Maybe a little too much for the camera.

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This achoo was caught on camera for all to see. If he only had the nerve to ask mommy for a tissue beforehand it could have saved him embarrassment for years to come.

Meows the Time

Cat couple Jerry and Sherry were excited for their first photos as a family. They brought their baby Fluffy and accessorized with a galactic background. Fluffy was a little camera shy, to say the least.

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And Sherry made the cat much more vulnerable flashing some areas Fluffy was rather not comfortable with. Nevertheless, all three faced the camera with eyes forward, mission accomplished.

Share the Hairspray

There’s no shortage of Aquanet in this family’s household! These sisters take pride in helping tease each other’s hair. The bigger, the better as the oldest sisters have the biggest hair.

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Becca, the littlest sis has the most to learn, these fan bangs are only the start of her big hair days!

Clowning Around

This family took the let’s dress up for a family photo concept a little too far. Mom and dad went all out with the facepaint while it seems the kids were not ready to take the clown theme to that level.

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The older child seems well aware that this photo will bring up some embarrassment in later years. Mom and dad don’t seem bothered by that fact though and the baby of the family is having a great time as well.

Takin’ Care of Business

Like father like son. Benny wants to be a Wall Street stockbroker just like dad; he started dressing this way at a young age. Suspenders and ties are a regular thing.

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Mom also joined the fashion trend, thinking it would help the family look more professional.

The Rebel

This lovely family has one clear rebel, and he was not willing to hide this fact in front of the camera. The rest of the family seem happy to let him express himself, although they tried to convince him to take at least one photo without the mask.

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Billy refused to participate in the family photo if he could not dress as his alter ego. “Monster Man” fit right in and this is a decision we know he will never forget. Lucky, he got over this phase quite quickly.

Silent Night

“Happy Holidays kids! now let’s have a silent night or you won’t be getting any presents.” Mom and dad are in pure bliss as they enjoy coffee by the fireplace.

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The kids have no choice but to be silent. They know if they get through the night without a peep, they will be rewarded! Guess that means no Christmas caroling kids!

Piled High

This family has no boundaries and is very comfortable getting close to one another. The Warners also enjoy dressing alike in denim representing the cowboy tuxedo; full denim with a belt to match.

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The fam seems to feel no shame tumbling over one another and making a family pile aka “doggy pile.” This brings a whole new definition to carrying the family weight on your shoulders ..Ouch!

Tough Love

Dads can show their love in the most awkward ways. It’s especially embarrassing when its caught on camera. This proud papa basically has the entire family in a chokehold.

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I guess they call it tough love for a reason, although it is playful, little Jeremy looks as if he can barely breathe. The rebel, “Mr. Mohawk” Eric seems to enjoy being the center of attention, aka his dad’s biggest pain.

May the Force Be With You

This family had a strange guest join their family photo. It was Luke’s father! And dad was stoked. Lizzy seems a little weirded out by the situation, but she doesn’t have any siblings so it makes for a nice fantasy family.

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We can definitely notice he’s the black sheep but he’s doing his best to fit in. Mom’s pretty excited to have a supervillain in the family!

Family Fiasco

This family is full of diverse personalities. When you have a brood this big, it’s hard to keep everyone in line. There are the serious ones, the goofballs and the ones who just don’t care.

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And big bros gotta keep them in line. Little Sammy gets a face pinch for not settling down. We hope he learns his lesson. Because for years to come he’s going to have a reputation as being the bratty one.

Not Giving A…

This happy fam is all smiles while little Sarah clearly doesn’t give a …She’s got some real feelings and she’s happy to show off her true colors.

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Mom and Dad are in their own world, and Little David is showing pride. We’ll guess Sarah got a talk after this photo was developed. They’ll have to censor this family portrait before adding to the collection in the living room.

Ginger in the Country

This redheaded brood is channeling their inner Little House on the Prairie vibes for the day. With matching countryside attire they are reading to pose in style.

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With that beautiful country backdrop setting the scene, we can only imagine them skipping through the meadow in their matching attire, singing a happy song in unison.


Like mother like daughter. This duo are dead ringers for one another. This mother holds her pride and joy in the highest standard. The standards of her own.

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Dressing her daughter from head to toe as her doppelg√§nger to show the apple doesn’t fall far from the tree. We bet she grew up to be a mirror image of her mama.

No Please!

These kids are acting as if posing for the camera is complete torture. Jared reaches his hand as if he is blocking the paparazzi from snapping that shot.

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Kara throws her arms up in surrender, “Fine I’ll do it, let’s just get it over with! I am not capable of walking away from this anyway, I just want a cookie after this photoshoot is over.”

Generations of Weirdness

We are not quite sure what is going on here. We do know that grandma, mom, son, and baby all fall from the same tree. This tradition of a finger in the month is mind-boggling.

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And we’re guessing dad’s look is a costume yet he’s the only one dressed. I’m sure he’s been explaining the scenario of this photo for years. We hope he has a good excuse for this awkwardness.

My Favorite Things

We only think of the Van Trapp girls from Sound of Music when we see these matching sisters. With Bavarian style attire and matching hair alike. We are ready to hear their sweet voices.

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Dad and brother are dressed ready to make a business deal. We love the Buzz cut Billy!

Life on the Wild Side

Cheryl and Eddy like living life on the wild side. With their favorite props in hand, this couple is ready for any adventure that comes there way.

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For their family portrait, they brought along their baby Polly, who they have taught to say “hello pretty bird!”

Concerned Mother

There is no shortage of creativity and individuality in this family. Mom lets her kids express their unique interests. Although she does seem a little concerned.

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She can tell she isn’t ‘thrilled with her daughter’s choice in artistic hairstyles: but she sure is a fan of A Flock of Seagulls. We imagine “I Ran” playing in the background. We’re certain her youngest wants to run away from this photo.

Pink is My Favorite Color

We wonder who made this choice for one of the most flattering colors on just about anyone (sarcastic.) Looking like a school of salmon, this family accessorized with the trendy pants of the 1980s.

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We’re certain they regretted this fashion decision years later.