High school is an awkward time for everyone. There doesn’t seem to be as many cliques as there used to be, but there is still absolutely a social pecking order. The cool kids may not be shoving nerds into lockers, but they probably aren’t eating lunch with them either. That being said, even the coolest guy in the school can look back at old pictures and say, “What was I thinking?”
Prom is the culmination of the awkward. A bunch of 17-year-olds dress up in tuxedos and expensive dresses to dance for three hours, drink illegally, and make bad decisions at the after-prom party that have the potential of sticking with you for a lifetime. Everyone loves to take photos of the event, especially now. But those photos often serve as painful memories rather than fond ones.
These pictures represent the innocence and cringe power of youth. Apart from a select few, most people don’t love the way they went through high school. There are multiple things that we wish we could all take back. People say that things get better, and they do for the most part. But anyone who tells you that you’re going to forget your most embarrassing high school moments is a liar. Those stick in your mind forever.
15. At Capacity
This has got to be the worst-case scenario for most of the people on this dock. Tuxes are usually rented but dresses are usually bought. Meaning, most of these girls ruined their prom dresses. They’re going to be soaked for the entirety of the prom now. The shoe situations are going to be a mess.
First of all, this is just some terrible craftsmanship. Couldn’t they have just built a few extra support beams? Someone’s uncle is going to get an earful after this debacle.
Those few people on the side are the best part of this picture. At least eight people walked away dry and laughing, which includes at least one kid whose date went into the drink. Hopefully, they’re only going to prom as friends because that’s not someone you want to be attached to all night.
14. Carrot Boys
As a former high school student, I feel qualified to announce that high school students don’t know anything about anything. Apart from the fact that most of us were at least 25 pounds lighter in those days, most of the pictures from high school just embarrass us.
These two gents will be particularly embarrassed when they look back on their prom photo in 10 years and see themselves looking like they were grown in a Jersey Shore garden. I’m sure they were going for that look, but they spent a little too long in the spray tan booth.
13. Planning Ahead
It’s always important to be prepared for anything life throws your way. All successful prom dates end the same way, and these couples know the importance of planning ahead.
The word “savage” gets thrown around a lot on the internet these days, and taking a prom photo in front of a Planned Parenthood is absolutely savage. This is the most intentionally funny pictures on this list by far. Sure, there are some unintentional laughs in here, but none can compare to this. These two took the #1 s*x-having night in history and turned it right on its head. Great work!
Is this a photo you’re going to want to show your kids? Probably not unless you want to show them what happened to their would-be little brother. Still, these two just did it “for the lolz” and succeeded. Great prom pic 10/10.
12. Big Game Dancers
These are two people who you probably don’t want to share a limo with. These don’t look like the kind of people who would go on a murdering spree, but if they see a buck, then they’re most likely jumping out of the sunroof to take a shot. Furthermore, these two lovebirds better hope there’s no gun-play at any of the after-prom parties or else the police are going to be looking directly at this couple.
My first instinct was to declare that this photo was obviously taken in the south. After some deliberation, I decided that it was probably taken somewhere that guns aren’t as popular. If you pose with a rifle in Texas, no one is going to care. If you post this in Massachusetts, you’ll get the desired reaction.
11. The Villain
Has there ever been a more sinister-looking kid in a prom photo? You can’t tell what happened to make this young man so angry, but it must have been something pretty terrible. This is the face you make when you find out that your classmates are about to “Carrie” you.
Everything about this picture has “future supervillain” written all over it. The flower, the ill-fitting suit, the scowl—all of this is just a preface to his eventual quest for world domination. The girls who are the subject of the photo are cast aside, as the eyes go directly to the kid plotting his revenge in the background. This is the exact origin story of a number of supervillains.
The aspect of this picture that shouldn’t go unmentioned, though, is that blue dress. That’s a little racy for a high school prom, no? She’s basically wearing a fancy skirt connected to a fancy bra with a thin layer of mesh.
10. Looking Sharp
The people who make their own prom outfits are a special breed. They may not be the same individuals, but they certainly fall into the same category.
Duct tape seems to be the most popular ingredient in DIY shiny outfits, so it’s fair to assume that at least some of these outfits were made with the substance. That tux has duct tape written all over it. The dress could be multiple things—a table cloth, a tarp, an oversized checker board. The sky’s the limit.
It’s not completely lame to make your own prom outfit (it kind of is). You can make them look good, and if you have a funny idea, then you’ll be the talk of the school. These outfits, though, just look bad. They definitely started with the dress and factored the tux in after, which makes for a bad look for the guy in particular.
9. Big Pimpin’
It’s not every day that you see a “Pimps ‘N Hos” themed prom, but this high school does it big.
To be fair, this is a very funny idea. There are a few reasons how this date situation took place. The first is what the guy wants you to think—that he is such a baller that two girls were both dying to be his date. That’s possible, but it seems much more likely that these girls are best friends, and this nobody in this picture had a date. The guy was probably friend-zoned into oblivion, so his only response was to take two girls and make some people laugh.
This kid’s suit is something else. The bedazzled collar and cuffs match spectacularly with the “PIMP” mug he made in art class. The split colors were probably made by someone’s mom/aunt so it likely made for a cheap alternative to renting a tux.
8. Caught Staring
This is just an unfortunate time to snap a photo. When young men and women get together, eyes are going to wander. That’s just how things go. Unfortunately, catching a glimpse is a skill you need to develop. You have to be 100% sure that there will be no photography, and even then, the glimpse can only be for five seconds or less.
Any guy has to feel a little bad for this young man. It’s an unfortunate truth. But whenever a woman’s boobs are partially visible, we have to tell ourselves, “Don’t look down. Don’t look down. Don’t look down.” This guy looked down and paid the price. Now, he’s immortalized on the internet as a prom photo fail.
7. Cat People
This might be the creepiest prom photo on the list. First of all, it’s hard to determine what the general take on cats are here. They seem to like cats, but the giant tiger pelt says otherwise. On second glimpse, they may have sinister intentions with that cat. Get out of there, Sprinkles!!
These two look nothing alike. But at the same time, they’re very much giving a siblings/ cousins vibe in this picture. If they’re not related, then they may be soulmates because the level of disdain these two seem to have for the world is unmatched.
Much like the relative debate, it’s hard to tell if this kid is sporting an extremely pale mustache. If he isn’t, then he should be because it would tie his entire look together. If you want someone to buy beer for the after party, here’s your man.
6. My Date Goes To Another School
It’s a classic high school trope to have a fake girlfriend that goes to another school. This seems to be a thing that hardly ever happens in real life but is all over the internet. Well, this young man took it a step further by bringing a cardboard cutout of his dream girl to the prom.
If you can’t get the girl you want, then you might as well paste her picture on some cardboard and pretend. It’s not going to be the most stimulating conversation he’s ever had, but that’s the sacrifice you make by bringing a fake date.
5. Blending In
Wow, I wonder how these two got their heads to float like that. Oh wait! I get it now! They’re wearing camouflage outfits!
If you think that joke is played out, imagine how these two felt after hearing it for four hours of prom. This poor girl had to suffer through hours of people bumping into her and saying, “Oh, sorry, I didn’t see you there.”
I say that the girl had to suffer through these jokes because the guy 1,000,000% came up with this idea. There are some camo prom combinations on the internet that are mutual, but this is the face of a guy who said, “I’m not going unless we wear camouflage.” On top of that, he’s the token high schooler that’s looked 28 since freshman year.
4. True Love
There’s no love like the love between a young man and his gaming console. At the end of the day, the Xbox is always going to be there. It has Netflix, games, music—everything you could possibly want. Who needs a girlfriend when you can just play video games? That’s been my attitude for years. Sure, it comes along with some crippling loneliness, but you know what a great cure for loneliness is? Xbox.
There’s a chance that this guy brought a date and an Xbox, but the best-case scenario would be that he didn’t even ask anybody. This stud knew exactly what he was doing by bringing an inanimate object to prom. He doesn’t have to deal with any of the drama, he can dance with anybody he wants, and there’s no pressure for after-prom activities. All he has to do is find a TV and a plug, and play the night away.
There are some bizarre photos on this list, but these two have to be some of the strangest. Wearing a wacky tux is one thing, but posing for a photo where the guy is riding the girl like a horse is another level of obscurity.
It’s hard to tell whether this was a photo taken at prom or if it was a prearranged photo taken at Sears. Either way, it’s hard to imagine an adult approving of this. It’s not explicit, but it has some s*xual undertones that are hard to shake.
It’s hard to imagine the girl being okay with this photo either. She got all dressed up for her big day, complete with a tiara, but then made it to prom only to be straddled and have her hair pulled by a 17-year-old with a soul patch. Great memories!
2. Barney Fans
It’s pretty weird to be a fan of Barney past the age of 7, but to each their own. This young man was just so passionate about the big purple dinosaur that he wanted to wear a costume to prom.
This has to be some kind of a joke or ploy. He may have lost a bet and had to wear this costume to prom; that or a dare is most likely the explanation. The other possible reason why this guy wore a Barney costume is that he was trying to sneak in. He could be a boyfriend from another school or even a worried dad. He couldn’t get in if he came in a regular tuxedo. But disguised as Barney, he can go anywhere.
1. Prince Charming
Every girl wants to be made to feel like a princess on prom night, but not many girls come closer to the real thing than this one. This guy is a certified role-playing master. By the time this picture was taken, this girl has living her fantasy.
You can tell by the look on that dude’s face that he’s the catch of the friend group. He had his pick of nerdy-girl prom dates, and this young lady was fortunate enough to get the call. His dead-eyed confidence tells the whole story.
The outfits have to be mentioned, though, as you can’t take a prom photo with a winged dress and get away with it. The most savage outfit at the whole prom may be worn by this guy. Those are jeans poking out of the bottom!
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