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The Most Hilariously Awkward Family Photos

The Most Hilariously Awkward Family Photos March 18, 2022Leave a comment

Kids these days would never believe the things our parents put us through. But we're not going to make you feel bad about the cringey clothes your mother made you wear as a kid. No, no. We're here to make you feel better about yourself—or at least, to remind you that there are other people out there who had it worse.

The Tree House

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We can only imagine the planning that had to go into taking this photo– the matching outfits, climbing up there, and balancing on that giant branch. Oof. We’re not sure what they were going for with this family pic, but whatever it was, we hope they didn’t wind up using it as a Christmas card. We can't blame them for trying, though!

Yoga Classes Paid Off

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We're not sure where these folks took their Pilates classes, but their instructor must be proud. They've clearly mastered the art of the "leg extension” and holding a pose for hours (or long enough to take this photo). Either way, we can all agree that this family photo is an impressive display of strength and flexibility.

But we have so many questions. What kind of exercise class is this? Is there anyone behind the camera telling them how to pose or did they just wing it? Whatever the case may be, this family proves that just because you can doesn’t mean you should.   

Epitome of Coolness

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When you're trying to capture a special moment, you don’t want to take the same boring pics everyone else is taking. So it’s important to choose the right outfit. But between the ill-fitting blazers and the crazy '70s mustaches, these besties must’ve hurt their backs running away from good taste. Yikes!

Dazed and Confused

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I mean, everyone gets major brownie points for commitment. But clearly, no one ever told this family that simplicity is the ultimate sophistication. Between the galaxy background, the geeky hairstyles and the poor kitty’s “thing” on display, we have a recipe for a bad family photo.  

The Rainbow Family

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With all due respect, this type of thing is why the divorce rate is so high. While some parents can barely get their kids together for a photo, others like to go the humiliating route. Their outfits scream “fun childhood memory,” but this is likely the picture they’ll use to bully the kids at school.

The Camera's Up Here

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Gosh. Puberty, eh? It's a time of hormones, acne, and SO much confusion. But for some it can be a truly awkward experience. Luckily, these two seem to be breast buddies. But even though they’re twins, they clearly have different interests judging by the way the boy on the left is gawking at the bride’s cleavage.

All Bark, No Bite

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This funny picture from the '90s captures all the classic elements of an awkward family photo, from the matching turtleneck sweaters to the goofy smiles and the dogs’ seething hatred for each other. It must’ve been a cute idea on paper, but the end results of this photoshoot is more disappointing than an unsalted pretzel.

Just Kidding

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For the love of everything that is holy… can anyone explain what is going on here? The bizarre editing in the back is enough to give anyone nightmares. And the awkward hairdos and creepy smiles aren’t helping either. Let’s just hope everyone was on board with this cringefest photoshoot, otherwise we’re calling CPS.

Mullet Creepiness

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Mirrors can’t talk, and luckily for this crazy family, they can’t laugh either. We don’t blame the kiddo for looking like a washed-up rock star from the '80s. He was too young to know better. Top it off with the questionable mullets and mom’s cheesy fringe jacket and we’re not really sure what’s going on. But hey! The family that takes cringey photos together stays together, right?

Bruised Santa

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We didn’t know the mall was open to hiring ex-convicts. How else do you explain Santa’s bruised eye? Maybe he got into a fight with a couple of rowdy kids on his naughty list. But whatever is going on here, we guarantee the kids don’t give a darn and just want their Christmas gifts. 

Telephone love

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We get it. It was a different time back when this photo was taken. There was no social media and people couldn't ask for wedding photoshoot suggestions on Reddit. But what was the creative direction behind this pic? Were these two reciting their vows over the phone? Did she work as a telephone operator? Were they living in two separate states? We have SO many questions!

Everyone’s Included

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Everyone thinks their pet is an important member of the family, so naturally, you want to include them in your family picture, right? Wrong! This giant capybara doesn’t seem to enjoy sitting in front of the camera for hours. So we don’t want to hear any complaints when it finally snaps and starts scratching everyone.

Santa Needs Some Air

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You know that one family member who’s obsessed with all things Christmas? For this family, that’s definitely mom! You can tell how happy she is to meet the big man from the North Pole, but sometimes too much excitement can take your breath away. Just look at poor Santa all smooshed in the middle! We hope he was able to breathe some fresh air after this pic.  

Mr. Evil Bunny

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Nothing to see here except the creepiest bunny costume we’ve ever seen. We can’t tell if this is the backstage of a horror movie from the '80s or just a bad DIY costume. But whatever it is, we’re pretty sure the guy wearing the bunny costume is just as scared as the kids.

Homage to Mr. Doggy

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There are a couple of things in life that are truly, completely irreplaceable. For many people, that's the family pet— and when a pet passes away, it leaves a hole in your life that can never be filled.

This little girl’s dog lived a long and happy life— from 2000 to 2015 to be exact— but the memories and the love they felt for each other will live on forever in this awkwardly cheesy family photo!

Whose Baby is That?

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Some awkward family photos are proof that evolution CAN go in reverse. There is so much going on in this photo that it's hard to know where to start. You can see toys and empty boxes scattered all over the place, and tucked under this guy’s elbow there’s a baby trying to rest. But dad and his friend are too busy playing video games. And it's pretty clear that neither of them have any intention on stopping anytime soon.  

Have An Awful, Awful Birthday

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Ah! Family photos. Is there anyone who doesn’t regret some of the choices they made as a kid? If you think back, there's bound to be a few cringey photos lurking in your basement. But you probably never had to pose next to a nightmare fiend from down below like this one.

Easter Creature

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Wow. There’s just so much to unpack here. The horrifying costume, the evil bunny staring at the camera, the heartfelt tears. It might’ve been a cool idea on paper, but it ended up scaring the bejesus out of these poor kids.

The Dummy

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We love family photos. Most of the time, they're a great way to capture what your family was all about at that time. Which in this case seems to be…ventriloquism? Hey! We’re totally not judging, but if our parents made us get anywhere near that thing, we’d probably ask to be emancipated.

Creepy Bow Ties

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You’ve seen the "everyone must smile at the same time" poses. And the classic, "let's just take this photo with no one's eyes open" that never disappoints. But have you ever seen two shirtless brothers awkwardly flanking their sister? We hope not.

Don't Be Clowning

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It's okay to laugh at those ridiculous speedos that were all the rage in the '80s. It's okay to wonder how many turtlenecks one person can own. It's okay to make the kids wear overalls with ugly Christmas sweaters. But forcing the family to dress up as mimes? Definitely not okay. We love awkward family pics, but this one takes creepiness to a whole new level.   

Got Milk?

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It's no secret that milk is a staple in most households, but we can't help but question the message this family was trying to send to the world. Were they trying to show off their love of milk? Or were they just proud of their calcium levels? Whatever they were trying to prove, we think this photo would make an excellent Christmas card. 

The Winnie Family

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We get it. Winnie the Pooh is adorable to bits. And this could’ve been a cute photo if the family had stuck to dressing up their toddler as Pooh. We’re not sure how we feel about mom and dad’s costumes. But sometimes—and by sometimes, we mean all the time—these “cutesy” family shoots are just plain ridiculous.

Holiday Hot Tub

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There comes a time in every family upbringing when kids should be allowed to say, "I love my family so much… but I definitely don't want to take a picture with them in a hot tub." But it was a different time, so we'll give them that.

Santa is Inspecting the Goods

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We all have an awkward family photo that makes us cringe. But this one gives us the creeps. Did Santa get caught off guard or did someone put him up to it? Either way, the big man from the North Pole is getting the side eye from us.

The Arson Family

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Here’s a family that knows how to stay calm during a crisis. Dad appears to be unfazed by the blaze in the background, and mom? Well, she’s confusingly happy. The kids are too young to know better, but this pic really makes you wonder if they were anticipating their insurance payout.

Don't Go Near This Santa

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You know what they say: "A picture's worth a thousand words." But this one is likely to make you scream in fear. This picture of a family posing with Santa is so unsettling, we can't stop looking at it. We’d be too afraid to go anywhere near that terrifying thing. And judging by the look on these kids' faces, they probably felt the same way.

Pet Possum

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This family looks like they came out of a country music video, so it wasn’t much of a surprise when they showed up with their pet possum to the photo studio. They might not be everyone’s cup of tea, but they're real and authentic, and that's why we love them.

The Stare

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One of the biggest problems with family photos is getting the kiddos on board. Just getting them to make the right pose is a total nightmare. And when they’re not in the mood, they’re not in the mood. Take this family for example. Little bro and big sis are all dressed up and ready for the pic, but little Evil McEvilson decided to stay inside and menacingly stare through the window.

The Family That Smokes Together, Stays Together

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It was a different time back then, but this picture probably breaks a hundred laws. What was going through these parent’s minds? It doesn’t matter when this picture was taken either. We just can’t imagine how anyone could think this would be a good idea.

The Duality of Life

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Did she have some mind-blowing revelation before the shot? Did the photographer dangle something disgusting in front of her face before he took the pic? If that was the case, then we’re all for this classic troll move. Either way, this picture makes us giggle every time we look at it.

When You See It

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At first glance, the Smith family look so adorable with their matching outfits and all. But you’d never guess that they're crushing poor Aunt Trudy. Whoever came up with the concept gets an A+ in our book. 

The Freaky Fam

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It looks like this family is trying to win the "weirdest family" award! Mom is rocking neon green hair, while the oldest daughter went for a pink shag. Then you’ve got the three pouty demons standing next to her. But the boy with an iguana resting on his shoulder sure looks like he’s got mind-control powers.

No More “Me” Time

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Being a mom is a full time job. You can’t even get a moment to yourself in the bathroom. But at least this momma can say that she always there for her kids when they needed her, even if she was on the toilet. And apparently, the same goes for her dog.

The Secret Grandma Clan

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Reddit user u/iwhisn shared a hilarious picture of their great-grandmother, who got caught in the middle of who knows what. They caption reads, “This old picture of my great-grandmother, far left, makes it look like the cameraman just stumbled into a secret meeting of the grandmas”. They sure look like sweet old grannies, but it really makes you wonder.

Grandma Needs to Take the Edge Off

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We truly believe that the best family photos are the ones that make you feel like you’re getting a sneak peek of a person’s life. A candid shot of your grandma getting drunk at her 65th birthday party? Now that’s something special!

Don’t Fall Asleep, Grandma

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We all know at least one relative who falls asleep in strange places, but this grandma takes the cake! She fell asleep at the beach and then the tide came in. Little did she know that her awkward beach moment would be photographed and immortalized forever. 

The Couch Brothers

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We're not sure exactly what this family's going for, but we’re here for it. According to the site Awkward Family Photos, these guys’ mom made their outfits from leftover fabric that came with their couch. Is this a total '90s moment or what?

The Most Beautiful Family Ever

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It might look like an ad campaign for Calvin Klein, but it’s actually a photo of someone’s mom and their siblings in the '80s. Clearly good genes run in the family. We're guessing they spent their entire childhoods waiting to see who would land a modeling contract first.  

Accidental Haunting

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Have you ever tried to take a photo of your child, only to end up with something that looks like it came straight out of the "Twilight Zone?" No? Just this mom? Okay.

The Baptism of Emily Rose

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Exorcisms are a significant event in someone’s life, but for this young girl, it was a rite of passage she'll never forget. Oh, wait a minute. Scratch that. There is nothing creepy about this picture! Believe it or not, it's actually a little girl being baptized.

Tainted Love

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Meet Uncle Jack. By day, he works in an office and schedules time to play with his nephew. By night, he frequents the club scene and hangs out with his goth friends in the cemetery.

Scratching an Itch

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This is a lovely photo at first glance. The two little girls in the front are clearly ready for their picture, but it seems that the little girl in the back had an itch she couldn’t wait to scratch.

The Rabbit Family

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What do you get when you cross a family that loves matching costumes, a grandfather who’s completely shameless, and little kids who love bunnies? A family photo shoot that’s the trifecta of cuteness.

Have an Awkward Merry Christmas

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You’ve seen the awful horror film, “Human Centipede,” but did you hear about the sequel, “Human Santapede”? All kidding aside, this photo concept is pretty epic and will be the talk of the family for years to come.

Share the Love

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The family was ready to take a holiday photo in front of their tree when they were suddenly photobombed by two dogs… humping each other. It may not be the photo they wanted, but it sure is one they’ll never forget!

Don’t Drop It

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If you thought your family photos were awkward, wait till you see this one! Photographer Liz Hansen was taking photos of a family reunion at the beach when she captured this hilarious (and somewhat scary) image. But don’t worry, they caught the baby right on time.

Toilet Humor

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What's more memorable than that time your whole family went to the toilet together for family photos? We’re not sure what they were going for but the end results are doo-lightful!

Throbbing Bubbles

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So, there they were. These two friends were blowing bubbles and then this happened. The bubble didn't turn out the way they’d planned. But it makes a nice addition to the "Awkward Family Photo" album.

Flexing Mom

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Sometimes you look at family albums and think, "Wow. What the heck were we thinking?" Mom must’ve been seriously into fitness or maybe she’s related to Rocky Balboa. Whatever the case, it seems like she’s never heard of rest day.