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40+ Most Awkward Family Photos Ever Taken

Hizkiail September 3, 2021

Family photos are taken to cherish the beautiful moments we share together as a family, but they often capture some less desirable – and much more awkward – ones instead. As the saying goes, all happy families are alike – but each awkward family is awkward in its own unique way. And while we all have our fair share of bizarre family photos, none are as strange and funny as this next bunch:

1.Creepy Bunny

This innocent Easter picture turned out more like the stuff that nightmares are made of.

The creepy, black-eyed bunny approaching in the background, surrounded in smoke, the weeping girl, the boy who is still unaware of the impending doom… We hope that their Easter dinner went better than this photoshoot.

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2.He’s Got the Blues

“My dad used to take some of the best pictures of me as a kid”, writes the now-adult man who shared this awesome photo.

Fast forward from when this picture was taken to our current time – and he could totally fit in an alternative emo band.

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3.What Went Wrong

What started out as an innocent birthday party, seemed to have quickly deteriorated into a little rendition of Lord of the Flies.

The boy who’s laughing hysterically on the right-hand side makes the whole scene even more concerning.

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4.Memory Lane

Who says birds don’t have feelings? Look at this sweet photo of a parrot reminiscing about the good old times, in front of a picture of him and his owner.

We also want to have such a loyal companion, especially if it comes with these amazing crest feathers.

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5.The Wedding Crashers

In ancient England, single women used to try and rip pieces of the bride’s dress in order to obtain some of her good luck.

Nowadays, we settle for trying to catch the bride’s bouquet, though we bet this determined bunch would do some serious work on her dress as well, had it been an option.

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6.Baby Farley, that you?

Schuyler Sharp posted his funny baby picture to Reddit – and it naturally went viral, with other Redditors roasting the photo which Sharp had captioned: “The only baby photo I have … wonder why?”.

We actually love this photo of big-headed, double-chinned baby Schuyler, and he himself didn’t mind the comments.”It’s just a silly picture. I knew people on Reddit would destroy it”, he told the Fremont Tribune of his experience as an internet celebrity.

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7.Run for It

We all know this moment in a family meeting (or at least, we did before selfies came into our lives) – the whole family is standing together, and one brave person goes to prepare the camera timer, and then runs back to join the group.

In this photo, however, the woman didn’t make it back in time for the shoot – so we’ve got this glorious photo of her running instead, arms swinging and all.

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8.Face Off

This sweet family photo is perfect in every way: from the fact that every family member is looking in the opposite direction, to the little boy’s whine, to the other kid’s attempt at hiding.

Both parents look tired, and from the little peek we got into their lives – we think we understand why.

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9.Where Were the Authorities

The ‘good old times’ were maybe good, but they definitely weren’t safe.

This photo of a mother and a daughter taking the chairlift *with no safety bar*, and the way the mother is using her arm as a guard, are literally making our hair stand on end.

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10.Who’s the Boss?

This cool pair proves yet again that many dogs look like their owners, and even adopt some of their personality traits.

The guy’s caption makes this sweet picture even better: “My dog showing my girlfriend that I’m his…”. We wonder who will sleep in the doghouse tonight.

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11.Full House

First, we gotta applaud the fact that all thirteen family members managed to all fit into one seemingly small studio.

Second, their expressions are just hilarious, with some looking overly excited, and others – like the family patriarch – look like they cannot wait to get out of there.

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12.Nose Job

This could be such a lovely family photo, if only not for the boy’s bruised nose (though we must say, he looks awfully proud about it).

Note to self: do not go roller skating the day before a photo shoot. Perhaps COVID quarantine is finally good for something.

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13.Caught on Camera

Sing it with us: “It’s the Circle of Lifeeeeee… And it moves us all.”

This unsuspecting girl’s parents took this photo of her during a family trip to the zoo – only to later notice this unexpected sex ed activity in the background.

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14.Food Coma

This kid does what many of us want to do at the end of a good meal: cut the small talk, and get some food-induced sleep instead.

And to be honest, there are probably worse foods to sleep on than mashed potatoes.

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15.Knife Party

Featured hair, assault rifle (with a knife!) and a parrot – they all make just a normal ensemble in our awkward family album.

By the way, pet parrots can be trained to attack on command, so this couple might even be more hardcore than they seem at first glance.

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16.Slam Dunk

Pregnancy photos are often quite cringey, but this one definitely sets the bar high.

But, who knows, the unborn child might still become the next Jordan – his dad seems eager enough to maybe make it happen.

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17.Wedding Surprise

Apparently, humans aren’t the only species who get off on romance.

This happy newlywed couple naturally had their best friend join the wedding photoshoot, but looking at the pictures after the big day, they probably discovered that he was a bit more excited than they thought.

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18.The Naked Truth

We’re not sure how we feel about this naked family group photo. Maybe a bit uncomfortable?

When does family nudity become inappropriate? We’re not sure. Though, to their credit, this happy bunch all looks pretty comfortable in the naked hug.

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19.Naughty or Nice

Everybody likes a good mall Santa, and this Santa, apparently, also likes everyone.

Even though he’s posing with a family, including a husband and a baby, he can’t seem to be able to keep his eyes to himself. Guess this Santa will not get a gift this year.

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20.Outdoor Adventures

“First look at newest horror film written by Stephen King about Maine forest demons, or my toddler refusing to nap on a camping trip. You decide.”

Toddlers, nap time, and camping trips – probably not the best combination in hindsight.

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21.Party Down

When the group that’s getting their picture taken is as big as this one, it’s no surprise if not all participants remain happy throughout.

The toddler in the front is in the midst of throwing a fit, and the contradiction between his anger and the rest of the group’s smiles, makes this photo priceless.

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22.Little Miss Sass

In a world of generic yearbook smiles – be this girl.

We love the rock-n-roll attitude, and if this is what she is like in pre-K, well we can’t wait to see what’s coming next – she’s got a bright future.

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23.Inappropriate Much?

Many touristy areas offer ‘old-time photoshoot’ studios, and tourists, being tourists, often jump at the chance.

However, this pair of mother and daughter, probably regretted their spontaneity once they were back home and looking at this, shall we call it questionable, picture with fresh eyes.

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24.Just Rolling

This girl’s eye roll is so epic, it could replace the eye-rolling emoji.

The difference between her sassy attitude and her parents’ wholesome look, and the fact that she’s dressed in black while they’re wearing light colors, only make this picture more perfect.

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25.Squats & Shots

Everybody loves a good sorority squat, but maybe some more judgement should be used before going for one.

We have a feeling this family wasn’t too happy about the outcome of their photoshoot (though we must say, they seemed pretty chuffed at the moment).

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26.Forever Engraved

We assume this was supposed to be a romantic wedding photo, depicting the way the new husband is ‘engraved’ in his bride’s mind.

We think Can’t Get You Out Of My Head could be this couple’s perfect wedding song.

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27.All Over the Place

We never knew that one photograph can include so many different angles and expressions. But we are happy to be enlightened.

More than a photo, it looks like a movie poster – with different scenes and highlights from a feel-good, though sometimes emotional, family drama.

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28.Dream or Nightmare

This style of photographs was big in the ’80s, but has luckily disappeared since. However, while it lasted, it created some photography gold.

The girl in this picture is probably meant to look like she’s gazing happily into the future, but her reflection looks so shocked and disgusted, that the contradiction is just hilarious.

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29.The Unrequested Promotion

His sign says “promoted to big brother”, but his sad face gives him away.

“‘I didn’t ask for this,’ said our very stubborn 2.5-year-old”, wrote mum who shared this sweet pic. “He had the same expression in every photo from the session.”

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30.D.R.A.M.A.

We just love this family’s dramatic style, and we want to join their tribe.

From the youngest daughter perfect style, to the brother’s over-the-eye hairdo, to the matriarch’s strong posture – we thing it’s too bad that family reality shows didn’t yet exist in the ’80s.

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31.Toga Party

It’s unclear whether the women (mums? sisters? mom and daughter?) and their son are all wearing matching dresses, or if they’re all covering themselves under the same sheet.

The concept is unclear, but the result is awkwardly glorious.

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32.Snowed In

Blazer and a baseball cap on a ski slope? And what about the elegant handbag?

“I am the Pink Panther and the Michelin man’s hybrid in the middle,” wrote the woman who shared this photo of her and her parents in the ’90s. “I still wonder if that visit to the ski resort was a last-minute decision, because that’s the only explanation I can find for our outfits.”

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33.Ride of Horror

Poor grandma, came to visit the grandkids in California, and ended up almost getting a heart attack on Splash Mountain.

Luckily, she was not alone on the ride, and grandpa was there to hold her. Now this is what we call true love.

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34.Crying Fest

No one looks happy in this photo, not even Elmo.

On a second look, the girl on the left looks pretty pleased – and we suddenly suspect that the cryfest perhaps started with her snatching of the pacifier from the – now evidently upset – baby, and the brother seems to feel her pain.

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35.Thumbs Up

Before the invention of the selfie stick, if you wanted a good photo of yourself while travelling, you would have no other choice but to ask a friendly stranger to take your picture.

This photo is so hilarious because it caught the exact moment in which this couple tried to alert their volunteer photographer to the finger blocking the camera.

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36.The Furby Made Me Do It

The sinister look, the oddly-cut bangs, and the placement of the Furby, all make this photo just incredibly funny and just a little creepy.

We’re sure this little girl is all nice and grown-up, and we’re happy to let her know that if she has her doll, Furbies are actually sold for a few thousand bucks these days.

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37.Sinking Feeling

We love everything about this picture of this cute, chubby baby taking a ‘sink bath’.

Since he looks so snug inside, we do however wonder how he was put inside of it – and how exactly will he get out.

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38.Foul Story

Maybe it’s time to get the baby from the clearly-marked ‘biological hazard’ bin?

Luckily, even though he looks like a newborn, his insticts (or sense of smell) are evidently already strong enough to make him protect himself from the danger.

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39.Ahoy Sailor!

Matching mother and daughter outfits? Cute. Matching mother, daughter and doll outfits? Less of a common sight.

“My mom thought it would be a great idea to dress me, her, and my American Girl doll Samantha in matching nautical themed outfits”, wrote this photo-sharer. “Hard to say why we are all staring wistfully in different directions.”

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40.Car Seat

Why is this kid inside the Chevy? How did he get there? And why, oh why, was this picture taken?

So many questions, so little consideration for safety. Oh, the good old times.

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41.Double Trouble

For this special photoshoot, each of the four sisters got a (creepy) lookalike doll, that looked exactly like her.

Notice the attention to details in the haircuts and fashion. The reason for this strange ensemble remains unclear, but the fimal result is impressive.

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42.Feeling Crabby?

This family took the birth announcement photo to a whole other level.

The parents and the older siblings are dressed as red crabs, while the new baby girl is the pearl, which they seemingly just dug from the sea. And they didn’t forget to pay attention to details – check out the pile of wet seaweed placed under the ‘oyster’.

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43.Santa’s Little Helper

Just an ordinary Christmas morning – opening the presents under the tree, and ‘borrowing’ everybody else’s best presents.

To be honest, we still haven’t met a family that doesn’t have at least one fight during the holidays.

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44.Jump!

“This is my little brother’s fourth-grade class photo. Our elementary school decided to change things up a bit for picture day that yearâ€¦ and well, this was the result.”