These Awkward Family Photos Should Have Never Seen the Light of Day

Looking at old family photos can do one of two things: trigger nostalgia or make you regret some of your childhood choices. Just ask that sweater you believed was oh-so-stylish when you were twelve. We’ve all been there, and our kids will probably be no different.
 
Self-humor is usually the key that will help you laugh it off and move on with your life. And while we all have some awkward photos stashed in one album or another, we found some family pictures online that were just too hilarious to ignore. Take a look and see for yourself.

The Tree House

Trees are great. They provide shade, oxygen and are generally a hoot to be around. They are also fantastic for nice photo ops. Except there is nothing nice about this photo op.

 

And to think of all the trouble this family went through to take this photo! The matching clothes, climbing, balancing on that branch… Let’s hope they didn’t use it as a Christmas card.

S(pr)ay Cheese!

There are good intentions written all over this picture. The mom obviously got a glam squad for hair and makeup, the whole family is dressed to the nines, and the greenery around couldn’t be more perfect.

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That’s exactly why it’s so sad that the kids are apparently not into photoshoots whatsoever. We feel for the poor kid getting reacquainted with his breakfast and hope that no shoes were harmed in the process.

Lamaze Classes All-Around

Okay, we know what this looks like. But before we start judging this family for their poor choice of photoshoot concept, we have to admire some of the physical abilities displayed here.

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Someone here is obviously paying attention during Pilates. How else would you explain strength and flexibility? We bet this family’s core muscles could crush steel.

Cool Cucumbers

Well, “cool” may not be the first word that jumps to mind. What words do jump? “Mustache” for a start. Next would be an “ill-fitted blazer,” and we best keep the rest of our associations to ourselves.

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Also, is it just us, or does the guy in the middle look exactly like a younger Russel Crowe? It looks like time travel IS real!

Dazed and Confused

Oh god, where do we even begin? How about the galaxy background that must have been designed by someone under the influence of illegal substances?

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Then there are the parents to this furbaby cosplaying as each other. And finally, the poor, poor kitty with its former private parts on display for the world to see. Not much to do but shake our heads.

Meet the Rainbows

We love the commitment of this colorful family, although we do have a complaint to submit. We’d like to give them a perfect ten. We really would. But with all due respect, it seems like they haven’t thought this through.

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If you go through the trouble of dying everyone’s hair and painting everyone’s faces, you could have tried getting some matching shoes (or matching socks at the very least).

The Camera’s up Here

Ahh, puberty. The hormones, the acne, the awkward… everything. We’re happy for this pair of twins to have each other through this difficult time. We do think, however, they need some parental guidance.

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You know, the kind of guidance to teach them that you’re not supposed to wear t-shirts to a wedding or stare at the bride’s cleavage.

Baby-Ball

Millennials nowadays turn everything into an event. This is what brought on the absurdity that is gender-reveal parties. Another event that has become almost too prevalent in recent years is getting pregnancy photoshoots.

 

These two were probably pioneers in the genre as they haven’t thought of the very basics. You know, like including mom’s head in the picture?

All Bark, No Bite

What a sweet family. What nice, friendly kids. What well-mannered dogs. Okay, scratch the dogs’ part. These two are obviously at each other’s throats.

 

Our only question is, what did the poor brother do to deserve being placed right in the middle of this war zone? And why does everyone seem so happy about it?

Just Kidding

Okay, this we can get behind. Yes, this eyesore makes you cringe in every possible way. However, it was done as a joke.

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The parents and kids staged the whole thing to make fun of this kind of past-time family portraits. Good job, guys. We crown you as Cringe Kings of the year.

Mullet Mania

We used to think that growing out your bangs was the most agonizing thing your hair can put you through. We now understand we were wrong. Recovering from a mullet sounds even worse.

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Our hearts go out to the kid. Middle school is enough of a trauma to live through even without this questionable choice of hairstyle.

Goat Milk?

This mother to be probably woke up thinking, “oh yay, I’m getting my pregnancy photoshoot today!” She then proceeded to look over the list of things she needed for it.

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White dress? Check. Flower crown? Check. Grassy location? Check. Fancy goat model with toilet paper scarves and a smaller flower crown? Check. Good job, girl!

Jumping for Joy

Family photoshoots are more about the parents than the kids. The grown-ups are the only ones interested in making perfectly-framed memories. The kids are usually more interested in getting cereal and watching “Frozen” for the hundredth time.

 

This is obviously the case with these three kiddos in the picture. We hope their parents got the hint.

Um, what?!

It looks like the tradition of making awkward family photos dates further back than we even realized. And boy, do we have questions!

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When did this happen? Why is the guy in the chair facing the back? Whose idea was it to position those people that way? Why is the woman on the left holding a broom, and where can we get a pair of those funky sunglasses?

No Tube Tops, Please

This list contains lots of pictures that are beyond salvation. This one, however, isn’t a major-scale catastrophe.

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Most of the disaster could have been averted if the mom would simply have said cheese when she was asked to. Throw in a shirt that covers the shoulders to avoid the nude illusion, and you’re golden.

The Plunging World Championship

Every school has one kid who’s friends with the janitor. It’s actually kind of cute. This kind of friendship is what brought on “The Queen’s Gambit.”

 

This very well may be the case here. Before we know it, this little girl might be winning the Plunging World Championship!

Turn up the Volume

Big, voluminous hair was all the rage in the 80s. The bigger, the better. Just ask Bonnie Tyler. These two were just keeping up with the trends.

 

Still, we can’t help but wishing someone told them all that volume was just too loud.

Doing His Own Thing

It doesn’t take more than a glimpse of this picture to know what’s the parenting style of this chill mom and dad duo. The white suits can’t fool us. We know they’re hippies at heart.

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Only true hippies would let their kid wear a full-on mask (of… what is it, really?) on Picture Day.

Too Cool

This family is the epitome of cool. I mean, they’re wearing sunglasses, so they must be cool, right? Isn’t that a common law?

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We’ll be right back. We just need to check the world’s rule book if the glasses *must* be paired with an I’m-better-than-you facial expression.

The Floater

One of the most questionable norms in studio-pictures of the past is the floating head. For some reason, there was always one member of the pack who needed to have his/her head blown up and facing a different direction.

 

Now what we’d really like to know is how they decide who that person is. Is it arbitrary? Is there a lottery? A challenge to complete? We bet there’s a reality show involved.  

Don’t Look Her in the Eye

If horror movies have taught us anything, it is to never trust a little blond girl with murder in her eyes.

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While most of the family seems like pretty nice, friendly people, we have a feeling this little girl takes after her big brother. Soon, that student would become his master.

Russian Dolls

When mommy and daddy love each other very much, they go to the store and get a child they could love together. Every once in a while, that child opens up to reveal another, similar-yet-smaller child.

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Here we have a rare example of that Russian-doll situation, where the parents got seven matching kids for the price of one! How extraordinary!

Creepers

Ladies and gentlemen, boys and girls, welcome to Creepland! The land where everything is creepy and designed to give you nightmares!

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Please remain seated and don’t stick your heads or hands through the bus windows, or the demons will get you. We don’t have insurance for that.

Tree-Topper

Everybody gather around, the cameraman is here! Make sure you’re wearing your finest clothes and looking like the most distinguished version of yourselves.

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What’s that? Uncle Joe doesn’t fit in the frame? Just stick him up on the tree or something. That’s better. Now say cheese!

Hello From the 80s

We are so used to gadgets fitting in the palm of our hand we tend to forget that old phones used to be the size of Mount Rushmore.

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We aren’t going to make fun of the old technology, but we are definitely going to laugh at how they thought this was a legitimate concept for a photo shoot. Oh, and for having one of the kids hold *two* phones for some reason.

Beach Day

Someone clicked the camera at the absolute worst moment. Or the absolute best, depending on your sense of humor.

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This picture only gets better the more you look at it. The tripping surfer is obviously the best part, but when you look at each individual face in this picture, it becomes pure gold.

I Did Not Sign up for This

Most of the pictures on this list weren’t meant to look awkward. That’s exactly what makes them awkward. But this one is great for the opposite reason.

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While everyone was in it for a goofy, twisted picture, one of them remained grouchy and did not even crack a smile. He must be fun at parties.

Flannel Fans

If we didn’t know any better, we’d think these kids are two of the three members of Hanson. That shiny blonde hair almost fooled us.

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But the Hansons weren’t camera shy, and the little kid in the front is obviously very uncomfortable. The poor thing needs a change of clothes and a good hug.

You Can’t Win Them All

The pictures on this list are usually awkward because of the people. The family in this one, however, has nothing wrong about them.

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They are all looking at the camera, no one’s eyes are closed, and there are no awkward hairstyles to regret in the future. Too bad the pooch in the background didn’t get the memo on Picture Day.

Window Shooting

We see what you did there. It’s actually kind of brilliant when you think about it — built-in individual frames! How genius!

 

Still, it seems that some members of this family don’t appreciate the innovation and decided to look like that stalker out your window…

Don’t Forget Rufus!

Oh, Picture Day. Happy times. Remember how we used to plan our outfits for weeks in advance and made sure to wash our hair the day before?

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It was glorious. The whole family would come together, set up a backdrop, say cheese… and realize something’s missing. Oh yeah, Rufus, the family dog in a precarious position in dad’s lap. Perfect.

So Fresh, So Clean

Just like Monica from “Friends,” this family is a big fan of vacuum cleaning.  Their dustbusters are an inseparable part of the family photo.

 

We do wonder, however, why the baby was deprived of a teeny-tiny cleaner of his own. Even a little feather duster would have done the trick.

Ready for Prom

Beautiful girls wearing their beautiful prom dresses with the beautiful forest as background. It sounds like nothing could put a damper on this photoshoot. That’s what everyone thought. And then came the chickens.

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There must be some weird tradition behind this, but that still doesn’t explain why they aren’t looking at the camera. Not even the feathery friends.

Not Enjoying the Tram?

Tram rides are usually quite a hoot. You get to ride in a floating bubble and look over an entire city as if you were a bird. What’s not to like?

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Well, you’ll have to ask the disgruntled-looking sibling on the right. Something must have rubbed him off the wrong way to mess up what would have been a lovely souvenir.

Scary Gary

We can forgive the hair. We can overlook the clothes. We can even get over the prom-date flower brooch. But that hell-sent, antichrist of a dummy is simply inexcusable.

 

It is a well-known fact that all ventriloquist dummies were forged in the bowels of the underworld and put upon this earth to haunt us, humans. We’ll try to forget we’ve ever laid eyes on this picture, but we can’t promise anything.

It Takes a Long Time to Look Like You Just Woke Up

Almost everybody in the family is looking good here. Dad’s ready in his best Mr. Rogers sweater, Mom is pulling her best Enya look, little Johnny has a slick leather vest, and young Abby is proudly showing off her missing tooth.

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Older sister Anna, on the other hand, paid six hundred dollars for someone to make her hair look like a flock of crows, and by golly, she’s not going to change it. The family did their best by having her huddle behind mom, but it still draws the eyes. Still, plenty of good family feelings here.

It’s Difficult to Pick a Favorite

The kid on the far right looks like he’s one sharp squeeze away from painting the floor with his lunch. The baby in the middle can’t take her eyes off of the ceiling, and the kid in the back just wants to go to Dairy Queen.

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The…mother…on the left was not paying attention to the birdie and is likely just happy everyone managed to be in the same photo, and Grandma (maybe) needs to remember that duckface hasn’t been invented yet. It’s amazing this picture wasn’t cast into the fire the moment they got it. No surprise Dad wasn’t interested.

The Orthodontist’s Favorite Family

These kids look like they’re ready to show off their great big smiles for the camera, and they also get to display their chic headwear at the same time. All the kids are at different ages, so it’s kind of amazing that all three of them had the same headgear at the same time.

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Maybe the parents rushed them to the photo as soon as they left the orthodontist’s office. There’s also the heartwarming possibility that one or two of the kids got their own set of wires just to make the other or others feel more confident. Let’s go with that.

Left Side Happy, Right Side Mad

Let’s read this picture like a line of text, from left to right. Gal at the top, a bit tired but doing her darndest to smile. Bro at the bottom just thought of a great joke. Mom has a smile that comes from years of experience with smiling.

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The toe-headed kid at the bottom has some bags under his eyes but he’s at least looking at the camera. Above him, this bowl-cut kid is loving his haircut and bow tie. Dad is the rock of the family and doesn’t find it necessary to smile, though he’s got no good reason to. The girl in the upper right looks like she’s pulled an all-nighter, and the one below her…

A Hands-On Picture

Just…why? The two OLDEST children are clinging to their parents’ legs in poses they certainly didn’t want, and tried their hardest to forget as soon as it was done. The daughter is hanging on to her dad for dear life since she either has a step stool back there or had to jump.

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Dad, for his part, is standing tall even with a fully-grown human on his back. But we’ve certainly seen worse. At least no one here is wearing face paint.

This Pleases the Baby

THE BABY demands pictures! Yes, that’s right, gather the goofy blonde children and pose them for pictures! Each one must pass THE BABY’s inspection, but this one, ah. This is one of THE BABY’s favorites. Those poor fools. They have no idea what THE BABY has in store for them!

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They will be forced to pose until the end of the world! Until the end of eternity! Unless, of course, they take a bad picture and displease…THE BABY. Then what will happen to them? There is nothing like it. Ask yourself—have you ever seen these two children outside of this picture? No.

Oh NO!

Why. Why have you done this? Why would you think this is a good idea. Dad obviously thought this was a good idea. Mom, of all things, seems to think that everything is fine! She’s got a big smile!

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The younger child, the son, doesn’t have any problem with what’s going on. Only the daughter isn’t a fan of what’s happening. No doubt this is one of those pictures the parents keep around just to embarrass her later in life.

Do We Have to Flex?

In this picture, the mom is pretty proud of her hard work in the gym and the tanning salon. The rest of the family, for their part, aren’t unhappy, but this still kind of seems like a picture for Mom.

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Maybe she’s a fitness model, and this was just an extra one they threw in with the kids to have some fun. That little guy with the unfortunate mohawk is having a good time, at least. The older son, who also has an unfortunate haircut, isn’t putting as much effort into it. The daughter has a big bright smile on, however.

That One Wasn’t the Silly One?

You know how at the end of photoshoots, the photographer will tell everyone to do a silly one because it lets all of the subjects let off steam after having to sit still for so long? We really hope this is one of those.

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The older son is strangling his sibling, and if you’re an older brother you’re going to understand that feeling. The daughter looks on unfeeling and uncaring — another emotion you might understand, depending on where you are in the family. Dad is proud of his progeny, no matter what they’re doing when he’s not looking.

Don’t Stand Out

The kids here are posed for a photo in their church directory, but they didn’t want to stand out, no sir. They wanted to blend in, be a face in the crowd, look just like everyone else.

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In actuality, it seems like these two kids are perfectly happy wearing their most vibrant shirts for everyone to find in the directory. Looks like we found Bruno Mars’ style inspiration.

“But He’s Part of the Family!”

So much to inspect here. No doubt the first thing you noticed was the girl on the back of her favorite friend. Somehow they were able to get the horse to stand still long enough to get a good snapshot, but that’s just the icing on this weird cake.

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Grandma has just finished spitting out a wad of chew, and Mom could be hiding everything from compound bug eyes to endless voids behind those sunglasses. The best part, to us, is the girl on the right, who looks like she just remembered she forgot to turn the stove off back in London.

No, No, Look Straight Ahead

This blurry photo has plenty of styles to make fun of — Mom has a hairdo that is trying to grow its way into the Guinness Book of World Records, and Dad looks like he’s smuggling a real spare tire under his coat — but the biggest question here is why everyone seems to be looking off to the left of the camera.

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While all three of the sons and both parents have thick glasses that make it a little hard to see, every single one of them isn’t looking at the camera, which is a pretty standard piece of photo advice.

One of Mom’s Favorites

This picture has a few kids, a pair of grandparents, and Dad. And if there is a more “Dad from the seventies” photo out there, we haven’t seen it. He isn’t paying attention, his legs are shaved, and he has those hot pants to show them off.

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While the kids and the grandparents are perfectly aware there’s a picture being taken, it caught Dad unaware. Was he having a bad hair day, and decided that his good side was where the sun usually doesn’t shine? We wonder if this one ever got hung up on the wall.

HaPpy BiRtHDaY!

The biggest surprise in this picture is that none of the kids look like their lives are flashing before their eyes, but for kids, that does go pretty quickly. Their expressions range from happy smiles to confused stares at the camera, which seems to ignore the thing hovering behind them.

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It’s possible that they don’t know it’s there. Perhaps it only appears right at the moment of the flash — and the people in the photo only see it when they get the pictures developed. We wonder if the mother has just finished laughing or crying.

Which One Plays the Bass?

These four siblings are ready to rock. They wear their sixties style loud and proud, and every single one of them probably looks back on this picture with a mixture of groans and laughs.

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If this boy band ever made it to the stage, then they probably didn’t push past the mid-sixties. Yes, this picture comes from that wonderful time of wood paneling, blond afros, and slide projectors, which we’re sure you came to understand as soon as you took your first look. But, we can’t pick too many nits here — these guys have big smiles, and they take a groovy picture.

You’ll Have a Merry Christmas and Like It

This picture comes to us from Poland in the nineties, back when style was still in flux, and Santa Clauses apparently had to wear a big beet-like nose. It also kind of looks like the child is wearing a pair of rabbit ears, which raises quite a few questions.

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The child also has the kind of face that children in the nineties got used to fast – the kind that says “Why are you making me do this?” She’s got her little bag of goodies, and she wants to get off of this weirdo’s lap and get back to the Christmas cookies.

Some Things Take Priority

It wouldn’t be too far of a stretch to say that many of us have a similar picture hiding somewhere in our photo albums. Dad is supposed to be taking care of the baby, but his friend has brought over a new Super Nintendo (as the information tells us, even though that doesn’t look much like an SNES from where we’re standing).

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Down in the basement, toys scattered around, an old beer box that is probably used to carry kindling from when they turn on the fireplace. The kind of carpet that will give you burns just by looking at it, and plenty of fun to be had.

Gotta Go Fast…Back to the Barber

The person who sent this photo in says that it is her boyfriend, and she is oh-so glad that she didn’t know him back when he was a teenager, mostly due to this photo.

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Sonic the Boyfriend is probably super glad that his significant other didn’t know him, either, since he probably wouldn’t have had much of a chance to woo her when she was running in fear and/or laughing at him behind his back. Children can be so cruel, but sometimes it’s for a good reason. Hopefully, this guy realized this isn’t a style for the record books.

Which One’s the Dummy?

The kid featured in this picture had a ventriloquist act in the first grade and decided it would be a good idea to take a school photo with it. Or the parents did, at the very least.

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Apparently, the kid was so scared of it that he couldn’t sleep in the same room as the dummy. And, yeah, we get it. Oh boy, do we get it. The dummy looks like he’s trying not to suck in a soul, and the kid has the thin-lipped smile of someone who is trying really, really hard.

Who’s Next for Pony Rides?

A few kids take a ride with the ponies, which was undoubtedly a good time, but the real star of this show is the handler. We don’t know if he hiked up his shirt to show off his sweet six-pack just for the picture, but it looks just as natural as a Hollywood starlet.

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He’s got a cig dangling from his lip, a pair of thick sunglasses, and a big trucker hat to keep the sun away. Leading kids around a pair of ponies would be fun for a few hours, but if it’s your job day-in, day-out, you’ll probably do everything you can to make things fun, too.

The Middle Child

We’ve all had a picture like this. Back when you couldn’t just delete a picture at the touch of a button and take another one, getting kids — and adults, on occasion — into the right mood just wasn’t going to happen.

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While Grandmas are usually fonts of good cheer, the lass on the right isn’t having any of it. She’s staring down the camera as if she’s got a knife in her pocket and she’s ready to use it. If Grandma is worth her salt, the next picture has that middle child on her lap and laughing thanks to some sweet words and tender tickles.

Love Through the Screen

We’re not about to say this picture is bad — in fact, it’s great. But we’d be remiss not to include this cornball wedding photo. Husband and wife are eyeing each other through the screen of their delightful seventies TV? Fantastic!

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We can’t help but love it. The bride is beautiful in a shimmering white dress, the groom is handsome (look at those sideburns!), and they’re locking eyes like they’re meant for one another. This is the kind of picture you proudly hang on the wall until the end of their happy lives, and every year look back on it and laugh — despite the corny look.

Presenting – Us!

A pair of brothers give their best jazz hands to the camera. The picture is from the final tap dance duet they did together, and hopefully, they’re still speaking — though after one brother posted this online, it’s likely the other brother won’t be happy with it.

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We hope the dance went better than the picture turned out, though people in motion almost always look better than standing still. Long, red mullets aren’t the kind of look that has a lot of staying power, but at least tan slacks are always in.

Including the Pet

This gal’s lovable family dog lasted a good long time — from 2000 to 2015 — and the memories of the pooch are helped by this delightfully awkward picture. Both girl and girl’s best friend went through their strange phases, with the girl giving her best gap-toothed smile and palms pressed together in an angelic pose, while the dog joins wearing the cone of shame.

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It turns out the dog’s name was Angel, which makes the floating-over-the-shoulder look perfect. All dogs go to Heaven, they say, which means this Angel is still looking down.

Santa Needs More Breathing Room

This entire family is having a good time meeting the big man from the North Pole, but one person, in particular, is jazzed to make sure he knows what present to bring. Yes, out of the five people pictured, Mom is the one who is most excited about the idea of a Christmas photo.

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That isn’t to say the kids aren’t happy — in fact, this is one of the happier photos on the list. Yet it’s Mom who is cuddling in close with the jolly old elf. Maybe that’s Dad under all that hair. These kids might soon see mommy kissing Santa Claus.

They Went for Timeless

The kid in this photo, apparently raised enough schlepping for his sixth-grade choir that he won glamour shots with him, and his mom. Great!

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This family is big on timeless trends, hence the hairdos, the makeup, and the single-color backdrop. The star-spangled attire, however, might be a little too much for our taste.

Bunny Breaks Bad

Four kids and one Easter Bunny, the classic elements of a bad family photo. For some odd reason, pictures with Easter Bunnies just do not turn out well. The costumes are always so bad, which is why, like in this picture, he’s huddled behind the children.

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And SPEAKING of the children, why do all four of them look like they had no sleep in a week? Little babies having a droopy look passes without a problem, but the oldest son in the back needs a good night’s sleep. And maybe some tea.

He’s Miami-Ready

This finely-dressed family is here to celebrate the youngest member of the family’s first communion, and they’re decked out in their eighties best. Dad’s mustache is fluffed out, mom’s dress-and-jacket combo is pretty in pink, and the sister’s ready to stun in a blue turtleneck.

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The man of the hour has his best pair of suspenders on. The hero here is the middle child, who has a suit and shirt straight out of “Miami Vice.” Don Johnson would be proud. We hope that style icon continued to find his own look.