Family photos aim to preserve beautiful moments, but often capture awkward ones. As the saying goes, all happy families are alike, but each awkward family is uniquely so. Despite our share of bizarre family photos, none are as strange and funny as the ones you’re about to see.
Creepy Bunny
This Easter picture, meant to be innocent, ended up resembling something out of nightmares. The eerie, black-eyed bunny emerging in the background, enveloped in smoke, the crying girl, and the oblivious boy create an unsettling scene. Let’s hope their Easter dinner was far more pleasant than this unexpected and creepy photoshoot.
He’s Got the Blues
The now-adult man sharing this fantastic photo reminisces, “My dad used to capture some of the best moments from my childhood.” Fast forward to the present, and he could easily blend into the lineup of an alternative emo band.
What Went Wrong
What began as an innocent birthday party took a swift turn, resembling a miniature version of Lord of the Flies. The boy on the right, laughing hysterically, adds an extra layer of concern to the scene
Memory Lane
Challenge the notion that birds lack emotions with this heartwarming photo of a parrot nostalgically reflecting on good times, positioned beside a picture of itself and its owner. A loyal companion like this, adorned with remarkable crest feathers, is certainly something we’d all wish for.
The Wedding Crashers
In ancient England, unmarried women sought good luck by attempting to tear pieces from the bride’s dress. Nowadays, the tradition has evolved to catching the bride’s bouquet, but we can imagine this determined group would go to great lengths on the dress too, given the chance.
Baby Farley, that you?
Schuyler Sharp shared a humorous baby picture on Reddit, and predictably, it went viral. In the photo captioned, “The only baby photo I have…wonder why?” Sharp’s big-headed, double-chinned baby self became the subject of Reddit roasts. Despite the playful comments, Sharp embraced the attention, stating, “It’s just a silly picture. I knew people on Reddit would destroy it,” when discussing his unexpected internet celebrity status with the Fremont Tribune.
Run for It
We’re all familiar with that classic family meeting scenario—the group gathers, someone courageously sets the camera timer, and sprints back to join the photo. However, in this particular shot, the woman didn’t quite make it back in time. Instead, we’re treated to a delightful image of her mid-run, arms swinging and all, creating an unintentionally glorious moment.
Face Off
This endearing family photo is flawless in its imperfections: each family member looking in a different direction, the little boy expressing discontent, and the other child attempting to hide. Both parents appear weary, and from this brief glimpse into their lives, it seems we may comprehend the reasons behind their fatigue.
Where Were the Authorities
The so-called “good old times” may have had their charm, but they certainly weren’t synonymous with safety. This photo of a mother and daughter riding a chairlift without a safety bar, with the mother using her arm as a makeshift guard, is enough to make anyone’s hair stand on end
Who’s the Boss?
This stylish duo once again affirms the saying that many dogs bear a resemblance to their owners and even adopt some of their personality traits. The guy’s caption adds an extra layer of charm to this heartwarming picture: “My dog showing my girlfriend that I’m his…”. The question arises: Who will end up in the doghouse tonight?
Full House
Firstly, kudos to all thirteen family members for squeezing into what appears to be a compact studio. Secondly, the range of expressions is downright comical; some exude excessive excitement, while others, notably the family patriarch, seem like they can’t wait to make their exit.
Nose Job
This family photo could have been truly charming if not for the boy’s bruised nose, although he does seem oddly proud of it. A valuable lesson learned: avoid roller skating the day before a photo shoot. Perhaps the COVID quarantine has an unexpected silver lining after all.
Caught on Camera
Sing it with us: “It’s the Circle of Lifeeeeee… And it moves us all.” During a family trip to the zoo, this unsuspecting girl’s parents captured a seemingly innocent photo of her, only to later discover an unexpected sex education activity unfolding in the background.
Food Coma
This kid does what many of us secretly desire at the end of a satisfying meal: skip the small talk and dive straight into a food-induced nap. Let’s be honest, there are likely worse choices for a makeshift pillow than mashed potatoes.
Knife Party
In our awkward family album, a featured hairstyle, an assault rifle (complete with a knife!), and a parrot somehow come together to create a seemingly normal ensemble. Interestingly, it’s worth noting that pet parrots can be trained to attack on command, suggesting that this couple might be even more hardcore than they appear at first glance.
Slam Dunk
Pregnancy photos can sometimes be cringe-worthy, but this one certainly sets a high bar. Despite the awkwardness, who knows, the unborn child might just grow up to be the next Jordan—given the father’s apparent enthusiasm to make it happen.
Wedding Surprise
It seems humans aren’t the only species that enjoy a bit of romance. This joyful newlywed couple had their best friend naturally join the wedding photoshoot, but upon reviewing the pictures after the big day, they likely realized that their furry friend was a bit more excited than they had initially thought.
Toga Party
It’s uncertain whether the women (mothers? sisters? mother and daughter?) and their son are donning identical dresses or if they’re collectively veiled under the same sheet. The idea is unclear, but the outcome is delightfully awkward.
Naughty or Nice
Everyone appreciates a good mall Santa, but it seems this particular Santa might like everyone a bit too much. Despite posing with a family, including a husband and a baby, he struggles to keep his eyes to himself. Looks like this Santa won’t be receiving a gift this year.
Outdoor Adventures
“First look at the 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—perhaps not the most harmonious combination in hindsight.
Party Down
In a group photo as extensive as this one, it’s no shock that not everyone remains cheerful throughout. The toddler in the front is in the midst of a tantrum, and the contrast between his anger and the rest of the group’s smiles makes this photo truly priceless.
Little Miss Sass
In a sea of generic yearbook smiles, be this girl. We adore her rock-n-roll attitude, and if this is her vibe in pre-K, we can’t wait to see what the future holds for her—she’s destined for a bright future.
Inappropriate Much?
Many touristy areas offer ‘old-time photoshoot’ studios, and tourists, being tourists, often seize the opportunity. However, this mother-daughter duo likely regretted their spontaneity once they were back home and took a fresh look at this, shall we call it questionable, picture.
Just Rolling
This girl’s epic eye roll could easily replace the eye-rolling emoji. The stark contrast between her sassy attitude and her parents’ wholesome look, accentuated by her black attire against their light colors, only adds to the perfection of this picture.
Squats & Shots
While everyone loves a good sorority squat, perhaps a bit more judgment should be exercised before going for one. We have a feeling this family might not have been too thrilled about the outcome of their photoshoot—although, to be fair, they did appear quite pleased in the moment.
Forever Engraved
In what was likely intended to be a romantic wedding photo, portraying the idea that the new husband is ‘engraved’ in his bride’s mind, we can’t help but think “Can’t Get You Out Of My Head” could be this couple’s perfect wedding song.
All Over the Place
Who knew that a single photograph could encompass so many angles and expressions? We’re delighted to have been enlightened. More than just a photo, it resembles a movie poster, capturing various scenes and highlights from what could be a feel-good, albeit occasionally emotional, family drama.
Dream or Nightmare
This ’80s photography style may have faded into obscurity, but it left behind some photographic gems. In this picture, the girl is likely intended to appear joyfully gazing into the future, yet her reflected expression looks so shocked and disgusted that the contradiction is downright hilarious.
The Unrequested Promotion
His sign proudly declares “promoted to big brother,” but his somber expression gives him away. The mom who shared this endearing picture wrote, “‘I didn’t ask for this,’ said our very stubborn 2.5-year-old. He had the same expression in every photo from the session.”
D.R.A.M.A.
We absolutely adore this family’s dramatic style, and we’d love to join their tribe. From the youngest daughter’s perfect style to the brother’s over-the-eye hairdo and the matriarch’s strong posture, it’s a shame family reality shows weren’t a thing in the ‘8
Snowed In
A blazer, a baseball cap, and an elegant handbag on a ski slope? “I am the Pink Panther and the Michelin man’s hybrid in the middle,” wrote the woman who shared this ’90s photo of herself and her parents. “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.”
Ride of Horror
Grandma, who came to visit the grandkids in California, unexpectedly found herself on the brink of a heart attack during Splash Mountain. Fortunately, she wasn’t alone on the ride—Grandpa was there to lend his support. Now, that’s what we call true love.
Crying Fest
No one seems to be in a cheerful mood in this photo, not even Elmo. Upon closer inspection, the girl on the left appears rather pleased, leading us to suspect that the cryfest might have kicked off with her snatching the pacifier from the now evidently upset baby. The brother, it seems, shares in her pain.
Thumbs Up
Before the advent of the selfie stick, obtaining a decent photo while traveling often meant relying on a friendly stranger to take your picture. This photo is particularly amusing because it captures the precise moment when this couple attempted to signal their volunteer photographer about the finger blocking the camera.
The Furby Made Me Do It
The sinister expression, the oddly-cut bangs, and the placement of the Furby all combine to make this photo incredibly amusing and just a tad creepy. We’re confident that this little girl is now all nice and grown-up, and we’re delighted to inform her that if she still has her doll, Furbies are actually being sold for a few thousand bucks these days.
Sinking Feeling
We adore every aspect of this picture featuring a cute, chubby baby enjoying a ‘sink bath.’ While the baby looks incredibly snug inside, it does raise questions about how they were placed in there and the logistics of getting out.
Foul Story
Perhaps it’s time to retrieve the baby from the unmistakably marked ‘biological hazard’ bin? Fortunately, even though he appears to be a newborn, his instincts (or sense of smell) seem to be already strong enough to prompt him to shield himself from the perceived danger.
Ahoy Sailor!
Matching mother and daughter outfits? Cute. Extending it to include matching outfits for a doll? Now, that’s a less 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 the person sharing this photo. “Hard to say why we are all staring wistfully in different directions.”
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.
Double Trouble
For this unique photoshoot, each of the four sisters was paired with a (creepy) lookalike doll that resembled her precisely. Pay attention to the meticulous details in their haircuts and fashion. The reason behind this peculiar ensemble remains unclear, but the final result is undeniably striking.
Feeling Crabby?
This family elevated the birth announcement photo to a whole new level. The parents and older siblings are donned as red crabs, with the new baby girl symbolizing the pearl they seemingly just unearthed from the sea. They paid meticulous attention to details, as evident by the pile of wet seaweed strategically placed under the ‘oyster’
Santa’s Little Helper
Just a typical Christmas morning—opening presents under the tree and ‘borrowing’ everybody else’s best gifts. Honestly, we’ve yet to encounter a family that doesn’t have at least one disagreement during the holidays.
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 year… and well, this was the result.” Now, who says ‘white men can’t jump’?
One for the Ages
This photo is the epitome of awkward family photo perfection. Where to start— the matching perms, the two-inch-thick glasses, or the casual twinning that makes it seem like they accidentally dressed alike? If this iconic mother-daughter duo were part of our family, we’d proudly frame this photo and present it to every houseguest. It’s such an iconic shot! We also can’t help but wonder if they continued the tradition of taking identical photos in the following years until perms went out of style.
The basketcase
The story goes, ““My parents had brought me to a portrait studio, and apparently I didn’t want my picture taken. It was taken anyway, just with a surreal approach.”
It was a generation of what mom and dad says goes.
Not exactly a freak show
The wife shared, “In 1995, my husband and I eloped to Las Vegas to get married. Cirque du Soleil was just starting in Vegas at the time. Since we had a quick wedding and not many photos, we decided to get this epic wedding photo taken at our hotel. I do not regret a thing.”
Would have been better with a trapeze act or something.
Come and play
“I think this was around ’92 or ’93. My mom worked at a nursing home and these Sesame Street characters were there for the day (???). Can you tell me how to get, how to get to…never mind.” shared @robertson.squares.
What, no cookies? At least tell us there were cookies!
Moms are unbelievable
“Being a mom isn’t easy so while you try to get one kid to sleep you’re also playing with another.”
And husbands have the nerve to complain about a cold. Honestly.
Creatures of the night, rejoice
“There was a WWE show at Penn State back in 1995, and this cutout was part of the promotion. My husband worked there so we got to bring home The Undertaker to the delight of our two oldest kids and the confusion of our youngest.” says @kristaweidner
Wrestling fans all over are geeking out right now.
A beer and milk thing
“My father-in-law babysitting my daughter. I’m just thankful they BOTH fell asleep at the same time :)
But who drank the beer and who took the milk? Got you there.
The Count looking confused
“This is me as a child getting my picture taken at a local Toys ‘R Us. Not only am I getting my picture with Dracula but I am wearing Mork and Mindy suspenders and a Father Guido Sarducci shirt.” shared a certain Jason.
Well, Jason can brag about how he survived Dracula at such a young age. And that’s saying something.
50 of the most hilariously awkward family photos ever taken
Eduardo Gaskell
12.05.23
Family photos aim to preserve beautiful moments, but often capture awkward ones. As the saying goes, all happy families are alike, but each awkward family is uniquely so. Despite our share of bizarre family photos, none are as strange and funny as the ones you’re about to see.
Creepy Bunny
This Easter picture, meant to be innocent, ended up resembling something out of nightmares. The eerie, black-eyed bunny emerging in the background, enveloped in smoke, the crying girl, and the oblivious boy create an unsettling scene. Let’s hope their Easter dinner was far more pleasant than this unexpected and creepy photoshoot.