In the good old days you would banish embarrassing family photos to dusty photo albums. However, we’ve managed to discover some hilarious, awkward pics that you must see. We’ll see freaky babies, punks, goths, human reindeer, angry bulls charging brides and grooms. Also, a truly terrifying Bert, Ernie, and Big Bird to haunt your nightmares. If only you’d sit back and relax for just a moment, ready yourselves to feel genuine pity for these poor folk.
Ugly Christmas Sweaters
Well, to tell the truth, we have no idea what’s going on when this couple was showing off their best ugly Christmas sweaters. We’ve got two theories. The second is that she sat on something she shouldn’t have sat on, like a rogue Christmas Brussels sprout.
The second theory is that she saw it in the 10th of a second of the camera shutter snapping that she had made a mistake in marrying her husband and living those last 20 years with him, and she was running to the nearest lawyer’s office to file for divorce.
BaseBrawl
This proud family wanted to photograph an important baby moment but ended up with more than they bargained for. They explained, “While taking some touching photos of my baby sitting up for the first time, his brother and cousin decided to join the photo.”
Bro and cuz are having a right old backyard scrap in the background. In fact, you could say the two boys are having a base brawl! Since the baby is being introduced to baseball, we’re gonna go ahead and call him Babe Ruth.
I Want Daddy
At first glance, this photo seems to suggest that the little kid just doesn’t like his mom. But putting our Sherlock Holmes deerstalker hat on, we think we’ve worked out why he doesn’t want his mother anywhere near him, and the reason is pretty distressing.
Mom took her son to her local salon and asked the hairdresser to give him the same haircut as hers. No wonder he looks so unhappy. You’d be, too… if it happened to you!
Baby Sitter
When this family placed an advertisement for a babysitter in the local newspaper, they were surprised when this small fluffy dog showed up at the door. But everything soon made sense when the dog proceeded to sit on their baby.
There’s also a baby’s eye view of this incident, but we thought it better not to show that angle. In an ironic role reversal, when the same family advertised for a dog sitter later in the year, a baby showed up at the door. True story!
One Hand in My Pocket
When the photographer at their local shopping mall asked, this trio of ladies couldn’t think of a theme for their family portrait. But since they had been listening to Alanis Morrisette’s new album, 1995’s Jagged Little Pill, in the car, they decided upon “One Hand in My Pocket”.
Along the way, there was some confusion about whose hand belonged in whose pocket, and this was the result. Isn’t it ironic… don’t ya think? You ought to know!
Odd One Out
Most of this family loved to watch Little House on the Prairie every Sunday. But one family member wanted to listen to The Ramones, watch Class of Nuke’ Em High, and fight for the right to party like the Beastie Boys.
The best thing about this snap is how blasé the rest of the family is. And before you say that the Beastie Boys were rappers, they started out as punk rockers in the 1980s.
Miami Vice
This picture sums up the 1980s. The OP added the caption, “Palm City, FL 1984 with my Dad. I grew up watching Miami Vice and thought I looked awesome-just like Crockett.” Now, if you don’t remember Miami Vice, it was the coolest detective show and featured Don Johnson as Florida’s finest Ferarri-driving, yacht-living, alligator-keeping, pastel-colored sports-casual blazer-wearing Detective Sonny Crockett.
The only thing this boy is missing is Sonny Crockett’s espadrilles. And the Ferarri. And the alligator. And a partner… unless Dad’s name is Ricardo “Rico” Tubbs.
It Wasn’t Me!
It happens to us when we’re young. It happens to us when we’re old. Hey, it even happens to superheroes! If you remember, Ant-Man peed his pants when he traveled through time in Avengers: End Game and came back as a baby.
This photo must be perfectly timed, as the incident in question must have just occurred seconds before the camera shutter snapped. The poor girl must be mortified that mom posted this on the internet!
The Denim Family
This family loves three things – denim, hats, and procreating. But not necessarily in that order. The original poster explained in a caption, “This is my family. We all decided to wear hats and denim. Awesomeness.”
Fedora-wearing Indiana Jones is lying down at the bottom while his wife has glued her poodle’s hair onto her hat. Two kids became rappers, the other a science nerd. Uncle Jonah is in the “GO” baseball cap because he looks like he really needs to go… to the restroom.
Double Denim
Now, if there’s one family that loves denim like no other, it’s these girls. They’ve doubled down by wearing double denim. The original poster explained, “There was a coupon for a free session at Glamor Shots in 1991, and me, my sisters, and my mom took full advantage of it.”
Where did they get their love of denim from, Mom? As for their claim that this was the 1990s, well… the mid-1980s just called, and they want their denim shirts and hairstyles back!
Isn’t He Lovely?
You know when proud parents of ugly babies land you between a rock and a hard place by asking if you think their baby is cute? Well, imagine what it’s like for friends of this family! While mom and dad both look fine, this baby has either just hatched from an egg or has just arrived from another planet.
Either that or he’s just filling his diapers. And not just halfway, but full to the brim, judging by the poor little guy’s expression.
Mom’s Special Day
Mom and her new boyfriend’s wedding went without a hitch. She made it to the ceremony on time, and his hapless best man remembered the rings. Mother-in-law didn’t have a migraine, and none of the bridesmaids had morning sickness.
Both sides of the family had a lovely time, but there was just one more thing to take care of – the wedding photos. At this point, little Jonny decided to stage a lie-down protest to make his true feelings about his new stepdad known.
Winnie, Tigger, and Eeyore
You may think these guys look like dweebs, but the truth is, they’re so cool they were the first family to own onesies. People love to post profound, uplifting Winnie the Pooh quotes, but did you know A.A. Milne’s famous characters represent neurotypical diagnoses?
Winnie has weight issues due to his love of sugar, Tigger has ADHD, and Eeyore suffers from depression. While we’re on the subject, what do Winnie the Pooh and Jabba the Hutt have in common? They both have the same middle name!
Merry Kissmass
Everyone loves a Christmas horror story, but not America’s Most Embarrassing Parents kissing at Christmas! Their horrified children look like they’re about to bring up their Christmas dinner, and must be wishing they were adopted or they could have their minds erased with a brain eraser.
In truth, the photo isn’t as bad as it looks. Everyone is sticking out their tongues, and Mom and Dad simply touched tongues. If you have embarrassing parents, don’t worry, one day you’ll be just like them!
I Believe I Can Fly
Photographer Liz Hansen took this wonderful, if slightly scary, snap of two swingers swinging their two babies on the beach. Mom and Dad are obviously not rocket scientists, because anyone with even the simplest grasp of physics knows that to swing a baby requires two tethers.
Yeah, it’s kinda hilarious, but we’re just glad they’re on the beach. Because if that sand were a sidewalk, the next series of photos would’ve come from the E.R.
Timberrrr!
Why is this baby taking a nosedive at the end of a long line of brothers, sisters, and cousins? Did he jump, or was he pushed? With her outstretched arms, his sister standing beside him looks guilty.
But the little girl’s lawyer later argued in court that her arms were outstretched as she tried to save him. Yeah, yeah, that’s a likely story! Millions of peeps have seen this photo as Ellen Degeneres featured it on her popular daytime show.
Gemme Outta Here!
Some funny family photos can reveal more than one story. To paraphrase Sesame Street, “Seven of these kids are doing the right thing, seven of these kids are kinda the same, but if one of these kids was having a tantrum, now it’s time to play our game, it’s time to play our game…”
But there’s also the added mystery of how mom managed to squeeze out eight children in the space of about 10 years. Did the stork get lost or something?
Say Hello to Chuck
We think this baby’s name is Charles, and his nickname must be Chuck because he’s just chucked up over his loving dad’s head! His heroic mom tried to save the day but was too slow, the deed was done.
Back in the old days, this photo would only have been rolled out when Chuck brings his high school girlfriend home to dinner. But in this age of social media, millions of people around the world have seen it. Sorry, Chuck!
Bottoms Up!
Remember the old joke about the airline pilot and his guide dog? Well, this looks to be a similar situation. Either that doctor needs his eyes tested, or the poor baby was a breach birth––where they come out of their mummy’s tummy upside down.
Or this baby is actually Eleven from Stranger Things, and she’s just escaped from The Upside Down. Whichever of these three options is the real explanation, it all makes for a topsy-turvy introduction to the world.
Third of a Second
This young family was standing in the doorway, waiting for someone to press the camera shutter, when their little girl––who’d been tugging on her mom’s hand––suddenly let go. The camera shutter opened and closed at the exact right time to see her a third of a second away from landing on the ground with a thud.
No doubt, there were tears and some wailing. But on the upside, she produced this perfectly timed photo which belongs in a museum.
The Aunt
Well, that’s one way to ruin a wedding! The bride’s special day she’s been looking forward to since she was five. The day the happy couple spent a year planning. Then, Great Aunt Violet arrives from Arizona and insists she performs her new-age acoustic interpretation of The Police’s “Every Breath You Take”, which she first rocked on a trip to the commune.
The looks on the faces of the bride, groom, and presumably the matron of honor and best man, are priceless.
Who’s the Dummy, Now?
You’d be forgiven for thinking this was the poster for a horror movie in which two ventriloquist dummies wreak havoc on a small Michigan town. The poor girl excitedly explained, “That’s me in the middle. This was a promotional photo for my parents’ touring ventriloquism act in the late ’90s. The vests were made just for the occasion.”
Can you imagine growing up an only child but having to compete with these two dummies for your parents’ love and attention?
The Addams Family Portrait
Family portraits are a nightmare for every family, but these guys take it to another level. The three youngest kids look quite normal, but just like their mom and elder brother and sister, they, too, will be tempted to join the dark side and become goths.
They’re destined to dress in black, keep lizards as pets, quote Edgar Alan Poe, mopily dance around their bedrooms while listening to The Cure, and never venture out into the sun.
Welcome to the 1980s
Author L. P. Hartley said, “The past is a foreign country; they do things differently there.” And if the 1980s were a foreign country, nobody would rush to visit again. A plague of bad mustaches and mullets infected men. Women broke out in a rash of highlights, backcombing, and perms.
But a more pervasive infection was about to be unleashed. Men, women, and children were infected by an even more serious disease. Stonewash denim swept the nation, affecting the minds and lives of everyone it touched.
The Swinging ’60s
This blast from the past proves that every generation has shameful family photos. Like a dark family secret, awkwardness pervades the dayglow New Kids on the Block T-shirts of the ’90s, the stonewash denim of the ’80s, the sideburns and bell-bottom flares of the ’70s, and continues all the way back to the Swinging ’60s.
Sporting matching turquoise pants, vests, and dandy cravats, this family were the coolest kids on their block. Although, one family member didn’t look too happy about it.
The Future Is Bright
Is the boy on the right a young Bill Gates? No, probably not. Gates would’ve been in his 30s when this funny family photo was snapped in the late-1980s or early ’90s. But while this nerdy fam looked like complete dorks and liked geeky things like computers, they had the last laugh because they were right and we were wrong.
Nowadays, everyone has followed this family’s lead because technology runs our lives. These guys were just ahead of the curve!
Merry Christmas, Everyone!
As snow falls outside and chestnuts roast on the open fire, Christmas is the season of love and understanding. It’s a time for peace on earth and goodwill to all men, women, and children… unless you come from a dysfunctional family. Then, Christmas and Thanksgiving are a time for arguments, shouting, and stern looks.
This photo is a great example because the longer you look at it, the more details reveal themselves. The tension and animosity had clearly been building for days and reached boiling point when the girl in purple said something wrong.
You Okay, Pumpkin?
Christmas, Thanksgiving, and birthdays provide the most awkward family photos, but Halloween isn’t far behind. The pumpkin became an integral part of celebrations, but instead of carving a spooky jack o’lantern, this family scooped out the squash’s fleshy yellow insides to make a mini crib for their baby.
The poor babe got into the spirit of things by being terrified. And no, that’s not a breathing apparatus – his irresponsible parents wrapped fairy lights around his face.
