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20 Most Embarrassing Prom Photos Ever Taken

High Life
20 Most Embarrassing Prom Photos Ever Taken

Prom is such a huge American tradition. There is nothing more Americana than the high school senior-year prom. Its roots are staked in an old and rich sub-culture tradition. American films, television shows, and all other forms of media entertainment have highlighted this whirlwind event. It’s the familiar comfort blanket that warms the heart and the memories of a more youthful time period in someone’s life. Prom is such a huge deal in America that it even started to spread its influence to other countries, where these countries now hold their own version of a ‘prom’. Prom is something you either love or absolutely hate with a passion. For the most part, many American teenagers participate in this event by going through the awkward phase of “prom-posing” to their dates, going shopping for the right dress or suit, and buying the right corsage. It’s all very exciting and kind of a right of passage for students. It’s an event people look forward to because it’s the last year students will ever be with their peers. Again, this could either be the best night, or the worst night of a teenager’s life. When the hustle and bustle of getting to prom is set, and the limos arrive with their dates, families and friends gather to anticipate the opportunity to take many photographs. Yet, prom photos can also be notorious for showing the most embarrassing moments of a teenager’s last-year experience. Below are 20 prom pics that have to be the most embarrassing pictures ever taken.

20. Put Your Hair Up & Spin It Like A Helicopter

When you look at this prom picture, the first thing you’ll notice is the hair. I mean, there are other horrendous things about the photo to look at, like from the all too casual denim suit of the prom’s date, to the awfully tacky lace-dress. Let’s not forget those weird spacey sunglasses. But the hair has to be the cornucopia of all prom hairstyles. At first, you think it’s a bird. No, it’s a plane. Nope, the hair is shaped and molded into a helicopter. You can’t tell if the hair-blades can actually spin or not, but maybe it’s better if they don’t. Just imagine if there was a tiny little motor tucked inside the hair piece, and the denim-clad prom date just maneuvered it with an electronic controller all night. How would it detach? How would it land? This prom photo definitely captures something unique and architecturally inspiring.

19. Daddy Said Don’t Touch Her

So, either this prom date got a good lecture from his prom date’s father, or he’s extremely germaphobic. This has got to be one of the most awkward prom photos taken. Does he know it’s not a crime to gently put your hands on the shoulders of your date? Whatever her father told him must’ve been something harsh and fierce. The hands aren’t even positioned naturally, which makes the whole pose weird. His hands are stiff as a board, and it’s just the silliest thing ever. You have to wonder how the prom date (who appears to be Blake Lively) must’ve felt seeing the end result of this photograph. Did they take another? Did they pose in another position? Perhaps there was no hope in doing either, because this prom date was stern in absolutely not touching her. Poor girl (uhh, Blake). Maybe he is germaphobic? How would they dance? They’d at least have to slow dance to one song, right?

18. Arm-Length Girl Power

Okay, who ever thought of this awkward prom photo stance needs to be fired. Aesthetically, it makes absolutely no sense. Are they friends? Are they sisters? You wouldn’t be able to tell based on their pose and expression. It seems more like two girls who sort of like each other but really don’t, and are just barely tolerating each other until they get to prom. Once they get there, they’ll probably go off in their separate ways with their dates and dance the night away. If they’re supposed to be close, it sure doesn’t look like it. Way to go, photographer. Two thumbs way up in helping to contribute this photograph to this list of embarrassing prom photos. Now, every time these girls surf the net for prom-themed images, they’ll know they didn’t make the list for best and most awesome prom photos. Instead, these girls will be on this list for being one of the most awkward ones.

17. Don’t Wear Green

Imagine a couple walking into their prom and they right away notice a green backdrop. When the couple goes up for their prom photo, they’re excited to have any backdrop that their little prom heart desires. Excited that they have different choices to choose from, the couple opts for the chic Caribbean theme backdrop. As the photographer counts down, the photo is quickly taken with the click of the shutter and that’s that. Well, at least the young couple thinks so. However, the couple failed to realize that their prom attire matched the green backdrop. What is soon to follow is not only this hilarious embarrassing photo, but knighting them to the halls of internet infamy. Listen, it’s better to just go with the traditional baby blue or steel-grey prom backdrop that your mother probably used back in her high school heyday. Things that claim to be better are not always so.

16. Roll Them Pants Up

This picture could have been so adorable. Compared to the football-themed prom pic, I feel like this is a cute way to involve the love of a sport into a specific event. The pretty girl dressed in a hot pink tutu-inspired prom dress balancing herself (impressively) on one leg on top of a soccer ball should be given credit to the creativity of the photo. But then, you pan over to the boy, and everything seems fine until you see his pants rolled up. To show off soccer socks? To say to the world that you’re the David Beckham wannabe? First of all, just by the plain fact that the prom date is balancing on an actual soccer ball, screams enough flags that soccer is involved. It also helps that the image is taken on a field. Do the socks really matter? Why plain black? He didn’t even attempt to match her dress. He made it awkward.

15. ‘Jacks’ Jumping Over Their ‘Jills’

What a lovely group of kids getting ready for prom. They’re all dressed up, and look like they’re ready for a night out on a town. But, before they go and have a great time, they have to take one last picture to make it count, right? Well, this brilliant photographer had a bold idea to have the male prom dates leap over their female prom dates like Leap-Frog. The three guys in the middle look like they’re barely going to make it. Two of them aren’t even looking up at the camera. Look at the two guys on the far right and left end. I don’t think they made it over their dates’ heads. One guy’s foot looks like it’s too late, and the inevitable probably happened. I wonder if they made it to prom, or if they had to switch it up and go to the ER.

14. It’s Better On A Phone

Whatever happened to the good ol’ fashion way of taking a photograph? Gone are the days of simplicity, and now are the days of intricate and over-the-top photographic ideas. This couple decided that embracing each other in the typical fashion was “old fashion,” so they opted for a more millennial approach by using their iPhones. The concept would have been cute, and would have worked, if only the execution was better. Not only is the couple making a choice to use phone images of themselves looking stiff and boring, like they’re taking passport photos, but they both refuse to show a more intimate emotion and expression as they stand (literally) next to each other. Wouldn’t it be grand if they decided to do different fun poses in the camera, and then having the photographer zoom out to encompass the two individuals in a warmer embrace? No? Well, at least they practiced for their driver’s license photos.

13. Barney And Friends

Who knows when exactly this was taken, but this has to be the most embarrassing and weirdest prom photo ever. Everything seems normal. The girls are primped and wearing their frocks, but then you start to pan your eyes towards the backdrop and you have one creepy prom date stare and a random dinosaur. It’s not just any dinosaur, it’s f*****g Barney. For those who have been living under a rock, Barney was a very popular children’s educational TV show, which aired on public television networks. We’ve seen some bad work by some photographers, but this is just priceless. Whoever took the photo and thought of the idea was tripping hard on something. There is no reason for a Barney mascot to appear anywhere (least of all) at a high school prom photo. Let’s not even get started on the death stare this guy is making while standing next to said mascot.

12. Annie Get Your Gun

Isn’t it great to see a shotgun wedding every now and then? Oh, wait. This is a prom photo. That’s embarrassing. Dad just couldn’t help himself from joining the festivities the only way he knows how—loaded and armed. He’s proud of his little baby girl dressed all nice in glittery blue, like a little mermaid. He reckons that he doesn’t have to talk much sense into her prom date because he’s made it absolutely clear that he likes to hunt, especially the most dangerous kind of animal—male prom dates. By the look on the prom date’s face, his expression says it all. Dressed in his dapper, matching blue suit, with both hands way up, he’s letting everyone know he’s taking a page out of the ‘don’t touch the prom date’ rule book, and not risking any chances. Most wouldn’t either. Although, this was probably taken out of fun. This is just way too embarrassing.

11. Hey, It’s Hay

Nothing says your school and prom are located in the middle of the deep country like taking a large group prom photo on giant barrels of hay. You do have to commend the girls on how they got up on the barrels with their high heels and poofy dresses on. If you tilt your head and squint your eyes, maybe this could be a really fun and cute prom photo. However, it’s outdated and the couples just look plain awkward in their poses. Three of them aren’t even looking in the same direction. Then, let’s point out the obvious tackiness, which is that dreaded “prom” sign. There’s a distinct difference between prom attire and other formal event attire. We get they’re going to prom because not only do they look too young to get hitched, but the corsage and the tacky bright chiffon fabric gowns pretty much give the secret away. It’s definitely not a Quinceañera.

10. Just Wrong

Out of all the prom photos in the world, this literally has to be the most WTF moment. This is just plain wrong. So wrong, on so many levels. First of all, let’s talk about how this is not only degrading for girls to see, but also highly inappropriate. What school in their right mind would agree and allow this photo to be taken? Perhaps it was taken off school grounds? Where are the parents? What did they think? So many questions yet so little time to actually get them answered because people have to be too busy busting their gut looking at this intensely embarrassing prom photo. Everything from the backdrop to the rug to the expression is embarrassingly painful. Is pulling her hair that necessary? She’s not a pony, she’s your prom date.

9. Stand On One Leg Contest

Here’s another example of someone taking a picture of these girls who should not be working as a professional photographer. These girls look cute in their little black dresses with their hair done all nicely, and some buffoon directed them to embrace each other but with their backs turned. That could have been the end of it, but nope. The photographer wanted to add a little something extra, so he/she asked the girls to lift one leg up like they were show horses. What was the point of this? Showing the bottom of their soles really isn’t that impressive. Now reverse the pose and make the girls facing forward to the camera. This still wouldn’t work, and is one of the most awkward and random poses ever. The girls probably even feel like this is stupid, and already know the picture isn’t going to come out looking right or at least normal.

8. Prom Pimp

This prom picture is just epic. You got to hand it to the fellow for being creative and pleasing both his prom dates. That takes some nerve to bring two dates to prom, while holding a massive ‘pimp’ chalice. Let’s take a moment to deconstruct their outfits. The colors are clownish and the satin material doesn’t help to elevate the look. There are Halloween costumes made out of better material. The side cut-outs are tacky and the dresses look more like nightclub attire rather than age-appropriate prom outfits. But, the pièce de résistance has to go to this big man in the middle of the two girls. Not only did he come prepared with his own sipping cup, but a cane as well. His whole suit is split right down the middle seam. He’s the spitting image of Two-Face if the Batman character decided to go dressed up as a pimp to prom.

7. Cats & Prom

Here’s a prom couple who are definitely meant for each other. If it wasn’t for the cats, this actually would have been an okay prom photo. Yet again, people are always trying to find something extra to make their prom photographs more special than they have to be. Now, there are animal lovers; and then, there are crazed animal lovers who want to live, breathe, and walk everyday with their pets. Let’s not get it twisted. Pets are great. They’re awesome companions, and most of the population has at least one pet or has had a pet in his/her life. Besides that note, there’s a time and a place for animals. Maybe to some, this line is blurred or doesn’t exist. Clearly, this prom couple doesn’t care. If they’re going to dress up for their prom, so will their cats. The black cat doesn’t seem interested, as it’s pushing itself away.

6. The Princess & Her Cow

Speaking of bringing pets into the mix of prom traditions, let’s look into this silly and awkward prom photo. This innocent and sweet girl looks fresh as a spring daisy with her wavy brunette locks pinned delicately back, while giving the best darn prom smile she can. However, it’s really hard to ignore her potential prom date in this photo. You may have thought bringing cats was an overkill. Well, what about barnyard animals? I’ve heard and seen pets being a part of a lot of traditions, but this has to top the cake in the most embarrassing prom photo ever. There’s no explanation or reason as to why this girl is posing with her cow. Is it even her cow? There’s also no clarification about her actual prom date, unless the cow is literally it. This girl’s high school must be absolutely massive to allow dairy cows into the facility.

5. Obviously, They’re Not Cheerleaders

Well, if you can’t find any prom dates, go with your best pals. If you’re in a club or some sort of team, might as well go with them, right? What’s better than being around people who you’ve known for a while and spending one of the last school celebrations together, besides graduation. This photo exemplifies that, but in a cornier way. Clearly, these girls aren’t cheerleaders and absolutely don’t know much about the sport. Sarcasm aside, the girls look pretty and ready for a fun night, but did they really have to recreate some sort of Bring-It-On-themed prom photo? If these girls have prom dates, I wonder what they did. Oh I know, the prom dates were probably told to jump over the girls’ heads to match the athleticism. Again, whatever happened to just enjoying the moment, taking a nice picture, and then moving on with the prom experience? Oh, well. Hip-hip-hoorah.

4. X-Rated Prom

These girls are surprisingly going to the prom, and not to their local seedy go-go lounge. It’s not a new phenomenon for teenagers to act all grownup and wear more grownup clothing, but this just takes it too far. Prom is not the place to test out new avant-garde fashion recreations that you were inspired by, either from a magazine or an outfit seen on a celebrity, unless it’s done well and tailored appropriately. The girls have amazing bodies, but they’re exploiting and showing way too much skin for their age. They’re sending a wrong message and proms are not always the safest places. Stories have surfaced of teens being drugged, assaulted, and even reported missing because of a lack of common sense. The homemade pasties and the random slits and cut-outs clearly show a lack of common sense…and class.

3. Football Comes First

This Romeo seems to have one thing, and one thing only, on his mind—football. The girl probably spent a fortune on her dress, let alone spending time and energy on her hair and makeup, yet this knucklehead wants to hide their affection with a giant football. I’m sure, in his mind, it seemed to work better and even probably came off as (dare I say) romantic. However, it failed. Why wouldn’t you want to show off your date’s affection? Their friends probably already know and have probably seen all the PDA they need to see during their last year. I doubt he’s fooling anyone with being shy and coy about his feelings towards the pretty lady in pink. This pose looks pretty intentional. You tend to wonder if this is what she had in mind for a romantic prom photo, or if she was just as shocked that her face was replaced by a massive pig skin.

2. Once Upon A Time In The ’80s

Before the list comes to an end, there needs to be a proper shoutout to all the horrible ’80s prom photos. Every decade had its bad and worst moments when it came to prom, but the ’80s were not only notorious for bad prom photos, but was also an overall unforgiving time for hair and fashion. This unfortunate prom photo is no exception. Everything from the overly hair-sprayed and frizzy blow-dried locks to the bland and mismatched taste in ’80s fashion just screams embarrassment. This couple was photographed in 1988, against a calming seascape backdrop. Good thing the backdrop wasn’t one solid color, and good thing their outfits didn’t blend into the backdrop. But perhaps, they should’ve been. The girl tried at least. She’s at least wearing a dress and some hosiery paired with some heels, but this Ferris Bueller wannabe looked like he just put on his favorite pair of comfy sweats and called it a day.

1. Prom For One, And One For All

The number one spot for the most embarrassing prom photo has to go to this brave soul. Dressed in his fitted tux with a little matching yellow corsage, he looks like someone really down on his luck. Did his date bail? Was he lured in by his bullies as a prom prank? Did his group of friends dare him to take a lone photograph? He’s probably one of the many students who’s glad that high school is finally over. His facial expression says it all. He’s completely over prom. Going to prom alone is not easy. Some don’t even take the risk, and instead choose to stay home and reject the whole tradition. This guy pushed through and defied everyone’s expectation. He came, he saw, and he conquered the prom photo hands clasped. He’s probably making millions by now in Silicon Valley, and couldn’t care less about this photo or the prom.

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