Awkward Embarrassing Family Photos That Should've Stayed Hidden
By Sarah Norman | September 5, 2023
We really like this couple
You know what? We really like this couple. They're happy, and they're dressed up in their smartest outfits, it just looks like there's something a little... off? It's almost as if two different mice ran across the room at different angles, drawing the attention of this couple right as they were taking the photo. It's a shame that digital photo technology didn't exist at the time because we're sure this couple would have loved to take a second stab at this snapshot.
Leave the top hat at home
Let's not mess around here, the eye is immediately drawn to the top hat and wine colored ruffled shirt that the guy in the back is wearing. His entire soap opera bad guy vibe supersedes the guy who's been caught off guard on the side. At least the gals look gussied up and ready to have a good time. If only they didn't have to hang out with ol' top hat guy back there.
What Were They Thinking
Folks, let's get into this supremely strange wedding photo. You can see what's weird about it, we can see what's weird about it, but why does it exist? What was the thought process behind saying, "You know what would be cool? A photo of my wife bursting out of my chest like the Xenomorph from Alien. Let's make that happen so we can hang it on the wall and use it in Christmas cards ASAP."
That may not have been the exact thought process but we can't imagine why a couple would have this printed up unless they just decided to have a goof.
Get in there
Oof. This kid definitely has some sass but his placement is all wrong. Kudos to his big brother for working his way through the embarrassment to try and make the most out of this family photo. This awkward, happy family is giving us waves of nostalgia for going on a trip with our family and looking totally goofy in all the photos.
The "happiest" place on Earth
Just because Disneyland is full of fun and adventure for the whole family that doesn't mean that you have to enjoy it. We're hoping that this is an end of day photo and that the snapshot that they had to have taken at the start of their time in the happiest place on Earth has at least a couple of smiles.
For the perfect prom photo make sure you leave the blinds open
There's nothing awkward about these teenage lovebirds (the patterned jacket is a little bit much), what we're focused on is the "artistic" photo taken by someone's mother. The kids should be the focal point of the photo, but for some reason whoever's behind the camera decided that the best thing to do would be to highlight the venetian blinds on the right. At least they look happy (the kids not the blinds).
You thought your family portraits were awkward?
And you thought your family portraits were awkward? These three are in a close race for the MOST awkward person in the photo. To be fair to mom, it's not easy to corral a wild animal, and that cat looks like it wants to take the head off the photographer. If we have one note for these folks when he find a time machine it would be to switch up the colors. Change the wall paper or get a couch that doesn't blend in like camouflage. Switching things up would make this at least 10 percent less awkward.
The hair… oh the hair, ladies! No worries though, Dude looks like a proud peacock… even without any hair!
Dress to impress
When families dress in matching outfits for a trip it can be cute, but it's mostly just kind of creepy. We know that this family is making sure that no one gets lost. It's not a bad idea at all, we just wished they'd gone with something a little cooler like matching cowboy hats or maybe monocles. This very '80s look is definitely dated, but don't be surprised if you start seeing hipsters rocking something similar some day soon.
The couple who flannels together stays together
Is this not the most '70s prom photo you've ever seen? Starting from the bottom - the shag carpet squares and paper mushrooms are straight out of art class (and we're not talking about a super successful art class either). The mushroom are so mind boggling that they almost overshadow the dual plaid outfits that these two are wearing.
These two deserve props for wearing matching flannel suits to prom, but they must have been so sweaty. Hopefully there was AC in the gym that night.
Are you sure this is the shot you want to go with?
This is just painful. Neither of these kids look particularly excited about going to prom, but maybe that's just because their pre-dance picture looks like a last known photograph. We're crossing out fingers that the kids were allotted a second photo to remember the most fun night of their high school careers.
A Chicken and an Accordian
The only thing more awkward than the accordion in this family photo is possibly the family chicken! We have to imagine that if you're bringing a chicken to a portrait studio that it's well behaved. If not, the cleaning fee for this photo alone must ave been astronomical.
Normal airport behavior
The only awkward thing about this photo is that someone thought it would be a good way to capture the end of a long trip. Who hasn't wanted to lay down in an airport and press your face against the cool tile while you wait to board? Is the floor gross? Absolutely. But it's just as good as sitting and staring at all the other passengers for a couple of hours.
Just happy to be here
These two look like they're having a perfectly fine, albeit awkward, time. As much fun as it was to go to prom there's something mortifying about having to get dressed up in a suit like an adult and have fun. Wouldn't it just be more fun to meet up in a basement and dance to music on the turntable? Honestly, prom is a once in a lifetime experience that has an unfortunate dress code that lends it self to being totally awkward.
Talk about awkward… Two of these family members are wearing heavy, outside coats and... that is an opossum… in the family photo! Nothing beats the thousand yard stare of the kid in the red who's clearly terrified of being mauled by that opossum. This must have felt insane at the time, but hopefully everyone had a nice laugh when it was all said and done.
What in the world were we thinking? The '70s was a time of pushing traditionally normal limits. Everything from fashion, political, moral, musical and socially accepted standards were being challenged. At the time, it was all the rage to go out and jump on the bandwagon for the latest craze. Looking back now, however… well, let’s just say that more that a few of us have some regrets. Even more unfortunate is the fact that a lot of it was captured on film for all of eternity.
'Jungle Love' indeed
What was going on with prom themes in the Groovy era? Even without being in an overly PC era "Jungle Love" seems a little over the top for a dance with a bunch of high school students. Whatever happened to a theme like "A Night Under The Sea?" or "Racecar Madness?" Maybe that second one isn't so hot, but it's way less problematic than "Jungle Love."
This isn't your standard family photo and that's what makes it so darn awkward. There's so much to take in with this photo; the giant bottle of white wine, the tiny satin short, the grandma slamming that glass of vino, it's a perfect encapsulation of life at the end of the '70s. It's likely that if the photographer had picked a moment one second in the future in one second in the past that they would have snapped a more friendly and less awkward photo, but that's what makes this photo so good.
It takes something special to make a superbly weird family photo, but this family managed to do it. From the name tag on the mother to the *checks notes* chimpanzee dressed like Santa Claus. Unlike many of the photos included here we totally get why this snapshot exists. Why wouldn't you pose next to a monkey in a Santa suit? That makes total sense to us, we just really wanted you to see this totally wild snapshot. Hopefully this family (and everyone covered here) is doing well and living a much less awkward life than they are in these photos.
Many people consider their pets a part of the family but there are just no words for this family photo! Actually, here are a few more words: We absolutely love how much this guy loves his cats, and it puts a smile on our face to know that he risked life and limb to get them to behave so he could have this snapshot on his refrigerator for the rest of his life. Just because a family photo is awkward doesn't mean it can't be sweet.
To be completely honest this is less an awkward family photo and more of an awkward family ad, but we just had to share it with you because it's completely unhinged. Obviously there's the weirdly unclothed couple relaxing beneath a blanket made of shag carpeting with a cat, that's enough to make sure it's posted here, but then there's the very '70s feast that's laid out in front of them.
What would you want to dig into first while you lounge in the buff with your love, corn on the cob, a giant croissant, what looks to be potato salad, or some gingerbread men? There's no wrong answers here folks.
Fitted
There's something very Devo about this family photo. Not only are they clearly ready for some kind of seaside/space adventure, but they all look like they really enjoy whatever it is they're doing. Once again our eyes are drawn to the dad who's clearly having the best time of his life while wearing full scuba gear and moccasins.
This is a stone cold awkward family photo classic. There's so much to love about this photo, but our favorite detail is how lovely the mother looks cradling her baby. Her hair is on point, she's got a great smile, and she's ready to show off her lovely family, unfortunately her husband didn't really get the memo. He looks like the photographer just told him that his childhood dog wasn't sent to a farm. It's brutal.
If we had a time machine we would jump back to a Christmas party at this family's house just to see if this awkward photo was hanging up on the mantle.
Grandma was clearly ready to take this photo, everyone else not so much. We put the onus for this awkward photo directly on the photographer, he could have easily gotten everyone to make a nice face for their photo so they didn't look like someone just pulled a live skunk out of a bag in front of them.
Although this is an awkward photo, it probably captured the true essence of this family dynamic! I must say that I am sure they are not alone; just unlucky enough to be caught on camera.
So that's what they mean by 'plenty of fish in the sea'
Some photos are so perfect that there's really nothing to say. We love this photo so much that it should be in the Louvre. We're not sure what section so we'll just petition France to add a new wing.
Calm down, dad
Honesty has always been the best policy. This little girl was definitely being honest about how she felt about being in this family photo and Dad is a close 2nd… SORRY, Mom... awkward!
Years ago, we didn’t have the luxury of the digital photo to decide if we wanted a retake. We proudly posed and waited for the film to be developed only to find out that, well… we may have missed the mark. The only problem is that while we want to forget, we can’t! Even if the photo gets stored away for safe keeping, it usually rears its ugly head at some point.
It could be safely said that every family has that “one” relative; we all know what that means. No family is perfect, and those imperfections are all the more obvious when they are captured by the camera. That’s right… the camera doesn’t lie! Below you will see some of the craziest and awkward family photos from the groovy era.
A picture is said to be worth a thousand words. Well, in the case of some of the pictures shown below, all the words in the world couldn’t begin to explain or make sense of what you see. It’s almost a toss-up between the bad hair and clothing choices to the subject matter and what people thought would be nice to commemorate.
This is a family photo from the groovy era that is a classic example of a good thought gone bad. Even though this photo is clearly posed, it still must have been a nightmare to put together, and for what? Hopefully everyone included here had a good time taking the photo and, you know, had a good laugh after everything was said and done.
It’s a little difficult to pick out where the hair stops (Mom & Dad) and the background begins. I think the Groovy era let this family down. As odd as the matching hair color is we have to give a HUGE shout out to the two kids in matching leather jackets. They may look like they just left auditions for a stage musical of The Road Warrior, but it's honestly super cool that their parents let them go full WWF for their family portrait.
If this isn’t just the happiest family photo, I don’t know what is. The funny thing is that this photo may even have made it to their friends and family on a holiday card! Unfortunately, if that was the case, it will potentially be around for many years to come. The pattern on the couch is seriously going to haunt us.
These pictures don’t even scratch the surface of the awkward family photos floating around out there. Don’t be too quick to judge, though, because I’m sure you have some of your own!
End of the line
A random field in South Dakota? Check. A wacky looking Welcome to South Dakota sign? Also check? Everyone clearly fresh out of sitting in a car for five hours and lined up in a row according to height? Triple check! Now this family knows how to take an awkward vacation photo.
How's the weather up there
No one can help what they look like, but that doesn't mean that their photos are any less awkward. Being a teenager isn't fun. Our bodies change, we grow in strange ways, and some young people get growth spurts that see them go from 4'11" to 6'1" overnight. That kind of thing can be a boon for the basketball team, but it makes prom photos an absolute nightmare.
As far as awkward family photos go it's actually pretty normal, or at least it's normal until you take a look at that kid's hair in the back. It wouldn't be so awkward for this youth to have a fun little hair flip if he weren't completely matching his mother. He's really caught in the amber that is the family photo from the 1970s, we hope that he figured out his look later in life. You know, like his little brother who looks like an absolute stud in that truly insane polyester shirt.
Here are Groovy History we love our awkward photos, and there's nothing more awkward than going on a long summer trip with your family. You're stuck in a car for hours at a time, you're eating fast food, and dad is getting angrier by the second at everything from the traffic to your little brother to the fact that no one will pose for a picture with the world's largest thimble.
Road trips with your family can be brutal, but hopefully we can all find a little humor in these awkward photos of families doing their best to make it home by the time the leaves turn and fall sets in.
Cool dad, or really cool dad?
You can always count on dads for a couple of things: driving for an insane amount of time on a road trip, and doing anything they can to embarrass their kids. Just get a load of this dad in his Michael Jackson shirt and plaid shorts (and black socks, don't forget those). There's no way that he actually wants to look this uncool, but he knows that he has to do it for the sake of his children.
No pants, no problem
It's a shame that this kid is the shortest out of everyone in the photo because they could have hung out in the back and no one would be the wiser of their wardrobe malfunction. Hopefully they're just wearing short-shorts and didn't actually forget to pack any bottoms in their luggage. Aside from the no pants of it all, can you think of a more beautiful place to take a snapshot than in front of a trash can?
When you're over vacation
Everything about this photo makes us cringe. This family just wanted to have a nice snapshot in front of their very cool Volkswagen Beetle but it's clear that this girl is done with vacation in a major way. She's so over it that she left her mom hanging at the last moment before their self timer went off. That girl has definitely never stopped hearing the end of this one.
Photobomb, literally
You know when you stop to take a nice snapshot and someone runs in and throws up bunny ears or something goofy like that? How would you handle it if instead they blew up a massive section of the desert behind you? If you're anything like these kids you're pretty chill because you know that mom wants one good photo of you on vacation. This is one awkward moment no one forgot.
Is the TV going to prom?
Not only do these kids look great, but the Kodachrome photo looks fantastic too. Once again we're seeing a couple of kids whose pre-prom photos are hamstrung by a photographer who just has to show off their wonderful house. A note to any parent out there who are getting ready to snap a shot of their prom ready kids - focus on the young people, not your exciting new appliances.
It's not Africa but it'll do
Once again the dad is the real MVP of this photo, he's really trying to make it happen with all of the pointing and face work but his family just can't get into it. Well, the two girls on the right are giving it the old college try but how excited can you be in a room full of taxidermy animals? It's a wild life whenever you're on vacation with dad this goofy.
Don't turn around
Nature is one of the many wonderful places to visit on a family vacation, it's just that nature also comes jam packed with wild animals who'd really like to take a chomp out of you. This may be an incredibly awkward (and really well framed) snapshot, but when you think about it this is also a metaphor for life.
My family is my co-pilot
This family looks great and all but if we see them loading into the cockpit on our next flight we're getting a refund, going home and watching some TV.
Whatcha got in there?
It's fascinating to see a little bear family paying a visit to a little human family. Now, is the bear family trying to figure out if they can chow down on the little human family? Of course, but it's still really cute.
Have a nice trip?
There are really no words for how funny it is that this poor tourist went backwards over a safety railing at a gorgeous temple while posing for a photo. The monks at this place must still be talking about the day this guy took a swim in their koi pond. Even if they've taken a vow of silence they're definitely thinking about it.
Nothing like a trip to New Orleans
For two cool guys who wanted to visit a mausoleum they don't look all that excited about it.
What is it about looking into our pasts to see how goofy, and awkward we looked in our youth that we love so much? Maybe it's schadenfreude of seeing people in their insane outfits showing smiling without seeing how silly they look, or maybe we there's a small pleasure in knowing that as ridiculous as we looked at our own high school prom we grew out of it and we're living normal lives without powder blue top hats or dresses that match our parent's curtains.
A magical evening
Prom photographers should really have someone on staff to make sure the couple's they're taking snapshots of have matching facial expressions. There's nothing worse than seeing a young guy who's thrilled to be at the prom, and a date who would rather be anywhere else (or with anyone else).
Up in smoke
Everything about this photo is setting off our awkward alarm. Not only is the smoke machine working overtime, but this guy's wide lapeled flannel jacket and bowtie is almost like his second date. This really was an era of interesting fashion choices. When else would someone decide to go full on Bay City Rollers to the most magical night of their young lives?
If nothing else, this guy can hold his head up high with the knowledge that he has one of the greatest mullets of the 1970s.
This guy really doesn't want to go to prom
There's a thing that teenage boys do in prom photos in every era that's absolutely maddening - they pretend that they're not incredibly excited to go to prom with their best gal. This guy is a great example. He has his hands folded in front of him like he's been grounded and he looks like someone just told him that his pet gecko escaped from its terrarium. Could someone let this guy know that he's going to prom, not the morgue?
A magical night to forget
We love how much fun everyone is having here, we're even on board with the flowy peasant dresses and ruffled shirts, but what's happening with the "paper moon" that the school has provided? If it weren't for the stars in the background in the background we would have thought that the gals were sitting on a giant banana. Now that we think about it, maybe that's the school's mascot. The fighting bananas. Is that a thing?
There's nothing like going to prom with your dad
The '70s were a special decade. Not only was fashion and music changing, but teenage boys looked like a bunch of dads forced to go back to school. This guy in particular is giving dad at a wedding vibes. Do you think they carded him when he went through the door? Or did they just offer him a job as a gym teacher immediately?
Feet in the clouds
It's not easy to decorate an entire prom, especially in the Groovy era when you couldn't just order a bunch of stuff off of Amazon and bingo bango have a prom theme in the box. It's still a little sad that someone just threw a bunch of cotton on the ground to try and make it look like the kids were walking on clouds. It's a great concept but there's no way that people weren't tripping over the "clouds" all night long while getting their disco on.
Once again, please leave your hats at home
Top hats were definitely a symptom of the Groovy era, when every guy was trying to look like a sleazy character from a Cheech and Chong movie. While they're not so much a thing now, it still hurts to see them pop up in prom photos from the '70s when we know that so many young men wore while trying to look cool. These hats never work, and if someone tells you that you look cool in one of them then you'd better believe that they work for big Top Hat.
Captain fun
If there's one rule for young men in prom photos from the Groovy era it's that they cannot look like they're having a good time. It's illegal, they'll get kicked off the JV football team, and they'll be ostracized forever if they even pretend like they're excited to go on a date with a pretty girl. We're sure this guy was doing jumping jacks on the inside. Or at the very least he high fived himself when no one was watching.
All '70s All The Time
If we had to show someone what the 1970s looked like in one picture this is what we'd show them. The high collar lace dress, the space heater built into the wall, and wow oh wow that backdrop is something else. Let's not forget the oversized glasses or all that woodgrain. Each piece of this photo on its own is no big deal, but when you put it all together things get very awkward, very fast.
Promouflage
Hold up, do they really let disembodied heads attend prom? Are tickets half price? We have so many questions.
Chicago, there's nothing like it
Are there plenty of iconic buildings and pieces of artwork to pose with in Chicago to let people know that you visited the Windy City on vacation? Of course. But this couple aren't your average tourists. These two risk life and limb to get on the side of the road to pose under the exit for the 65. That's dedication to the Second City.
He's going to be hearing from Mickey's lawyers
Okay, very funny everyone. Who pranked this guy so hard that it ruined his prom photos? Did he choose to pose between the two random dots on the wall to make it look like he has Mickey ears? What are the dots supposed to represent? The more we look at this photo the more it feels like some kind of experiment that we're not understanding.
Who needs to win prom king when you can sit on the iron throne?
You know that you've got it made when you pose for your prom photos sitting on a wooden throne while your fair maiden of a prom date stands next to you. This seems completely off but they look like they're having a good time so who are we to judge? All we can hope for is that they took another photo where she got to take a load off for a bit. Remember, shoes in the Groovy era were meant to be seen, not worn.
End of the line
This great awkward family photo is the perfect encapsulation of going on a summer rip with your family. Everything is fun at the beginning, but before you know it you're sitting on the side of the road in the summer heat. Once again dad has come to the rescue, proving that he's the most integral part to a family photo whether it's awkward or not.
