Nobody really loves posing for group pictures, but a lot of these prom pictures are just disastrous. From cringeworthy dresses to poorly timed photobombs, if you can think of a way to mess up a shot, it's in here...
Guys Night
Whether they went to prom together by choice or not, you can't admit that they don't look super cool. Right? It was the 80s, they get a pass for their poor haircuts and ill-fitting suits. Other than that, they're the hottest bachelors at the dance.
Back When She Was "Fifteen"
Yep, that's who you think it is. When Taylor Swift lived in Pennsylvania, she attended her high school's prom with a group of friends, and she looked stunning! The whole group could have gone easy on the spray tans, but that's the early 2000's for you.
Is That Topanga and N'Sync?
I hope I got my 90's references right. When worlds collide! I wonder what the crowd reaction was when the "Boy Meets World" star walked into her high school gym with Lance Bass on her arm.
Young Jessica Alba
Not totally sure what's going on with the dress, but Alba still looks great at her prom back in the early 90s. I wonder if her date still talks about the fact that he got to date a celebrity before she was famous? I sure would. I'd hang that photo on my fridge.
Prom King Ferrell
Funny guy and SNL king wore a different crown before he was a cast member on the sketch show. Looks like he and his date won prom Prince and Princess. Clearly he's always been the jokester he is today.
You Snooze, You Lose
He clearly didn't get the memo that these girls weren't taking dates this year. He brought flowers and everything. Judging from his tie, it looks like he was hoping to take the girl in the white dress, but she had other ideas.
Who Says You Need Dates?
These girls don't need a boy to take them to prom. They have other plans. How adorable would it have been if they'd managed to get little coordinating ties on these guys? If they could have done that then, by all means, take your chicken to prom, he looks handsome!
Squad ROYGBIV'd Up
If you can manage to see past how incredibly cringey this is, then you can admire the amount of planning that went into this ensemble. Something tells me that they rolled up to the dance without dates, though...
Yes, That's Danny DeVito
When you can't find a date to the prom, you stage photos with your favorite celebrity. And if your favorite celebrity happens to be Danny DeVito, then even better. I wonder if the real actor ever saw these photos circulate the Internet. I'm not sure if I'd actually want the real guy to show up at my door, though.
Going Down
I don't know why they thought standing on a clearly flimsy bridge was a good idea. It's not even that photogenic, and now their photos and outfits are ruined. It doesn't look like anyone made it out of this mess unscathed. They won't repeat this next year!
Accident Waiting To Happen
You'd think they'd know better than to cram fifty people onto a small deck? There's no way it'll hold that much weight, and look! It doesn't! Hopefully, nobody got hurt, but they're probably regretting their decision to skip school.
Someone Didn't Get The Memo
Is this somebody's dad? Somebody's date? Can he get out of the photo now? The poor guy on the end is clearly uncomfortable. Where did this 1920's Strong Man come from?
Prettiest Date On The Farm
A recurring theme here is girls ditching the "human" date and posing for their photos with cardboard cutouts, chickens, or even another farm animal. I don't understand their reasoning, but both look great here, so I hope they had an awesome time at prom.
Guns Out
The exact conversation the dad had with the date went something like this. Needless to say, I don't think he'll be trying anything tonight. If I were the daughter I'd be a little nervous, too.
A Family Affair
This couple wanted their moms to hop in the photos, and how cute! It's definitely very awkward for everyone involved, and I'm not sure why they chose this particular pose, but it's a day to remember nonetheless. They'll likely look back on this and laugh.
Fear Factor
What is it about dads needing to intimidate their daughter's date with a gun? Has there ever been an instance where this ended badly? Do they want their daughters to resent them forever? Because this is a sure-fire way.
No Drama Here
At least everyone here has a human date this time. Who does this llama belong to? Where's his tie? He's not ready for photos. We also can't overlook the knee-high red leather boots on that girl.
"I Didn't Know You Were Taking Pictures!"
Why are all dads this weird? Why can't they just take a normal picture? This girl is going to look back on this photo and cringe. It had the potential to be great and he had to go ruin it. Hopefully, he did this before her date showed up.
"Wait, I Made It!"
I hope that's just a friend who was late to the party and not some creep out to ruin prom photos everywhere. It looks like he's wearing the same coordinating colors as the other guys, so it's always possible he just didn't make it on time. Either way, hilarious.
But Make It Fashion
This couple took the concept of "vogue" to a whole new level. They're not matching, first of all. And second of all, what kind of prom allowed this to be taken? I can't tell if they think they're funny or if they're being serious.
Ready To Go
He looks like he just woke up and is ready for prom. Forget about hair and makeup, you're running late! Hopefully, his date is a little more photogenic.
Down In Front
I can appreciate the matching outfits, sure. But what I can't get past is the little guy in the back, a noticeable foot or more shorter than the rest of the guys. Oh, man. Someone at least get him a step stool or something.
Two Date Is Better Than One
The 90s were weird. Or the 80s. Or both. This was likely a super acceptable move and nobody would have questioned it. I wonder what their relationship dynamic is like.
Mini Me?
Is this a stab at Dr. Evil and Mini-Me? Is that...okay? And what's going on with her dress? Why doesn't anyone know how to just pose for a normal prom picture anymore?
Prom Dream
I don't know how he did it, but this guy is pretty pleased with himself. He somehow snagged five dates. Some guys can't even get one! And they all look like they want to be there! Good for him honestly.
It's Not a Phase
If they both told me "it's not a phase," I'd believe them. I wouldn't even question whatever it is they're talking about. The extreme undercut haircut and the matching padlock necklaces speak volumes.
Nothing But Class
These two look chic in their black and white ensembles. The subtle mullet haircut paired with the tophat is just the chef's kiss on top of the whole look. I hope they won Prom King and Queen because they came dressed to impress.
A Suit Made of...?
I have so many questions. First (and most important), what is he wearing? What is that suit made of? Why did he agree to it if it was her idea? There's nothing wrong with a classic black tux, but I guess when you want to make a statement, you really make a statement.
Your Parents At Prom
This looks like the same photo that every mom has in their scrapbook of her high school prom. The understated outfits, the muted colors, the awkward date, it's all there. For whatever reason, we all wanted to have exactly the same experience when we were younger because of course, we all thought our parents were "cool."
Girls Just Wanna Have Fun
The best part of this picture is the girl in the front, leading the crew. Every single facial expression is unsettling, the dresses are awkward, and the scenario, in general, is lame. I'm sure they all thought this was a good idea at the time, but it's really pretty tragic.
Prom Parade
Okay, this is kind of cool. A prom parade to pregame the dance looks awesome. They're clearly having a great time! And their dresses are adorable, too.
I Don't Know Where To Look
This photo is like a car crash. I want to look away so badly, but the hair, the teeth, the glazed eyes on that girl...This might be the winner of the worst prom photo I've ever seen. Why did he think that hair was a good idea? She definitely doesn't love it.
Eyes Up Here
Whoever took this picture captured it right at the most unfortunate moment. He hasn't been caught yet, but he definitely shouldn't blatantly stare at his date like that. He's going to see this photo and be so embarrassed. And she's probably going to be super mad at him.
Bad Timing
Or maybe perfect timing? Everyone in this picture is affected. Not a single person seems to have been prepared to begin with, but the tie in the face really just makes it. I'm glad whoever took the picture captured this perfect moment.
Absolutely No Context Necessary
Prom 2003 looks absolutely insane. Is Barney... a date? Is he just there? I'd love to know some context, but I also think it's so much better that there isn't any. Also, somebody should have told the guy that his pastel purple tux doesn't match any of their dresses.
Too Cool For School
There's so much going on here. The sunglasses. The top hats. The white gloves. The fact that there's so much lace on everyone's outfit. The best part is, everyone looks thrilled to be there. They're all really happy with the look.
Proms Can Have Themes Too
Unless this prom was Halloween themed, I want to assume this couple didn't just show up like this on their own. There's no way they'd be allowed in. The full-face makeup is a lot, and the tight red gloves are certainly a statement.
Even The First Lady Went to Prom
Check out Michelle Obama's classy prom picture! That gold dress and jacket are so chic, I'd expect nothing less from her. She didn't meet the future president until a few years later, but she and her date look great together here. I'm sure they won Prom King and Queen.
Pre-Prom Glamour Shots
If I had the time and the energy, I would have gone all-out like this for my prom too. The dress is fabulous, the backdrop is straight out of that "Beauty School Dropout" scene in Grease, and the perfectly coordinated outfits are above and beyond.
A Shame You Can't See Her Dress
I'm just going to point it out now so nobody misses it: there's a kid hiding in the tree in the top right corner. He makes the picture. I'm not concerned about the horribly tacky camouflage dress or the shirtless dad with (another) gun. That kid wins prom.
Strike a Pose
This is likely the part where the photographer said, "Okay, now let's do a fun one," and this is what they came up with. A lot of questions about this... The rug is unsettling for sure. It's also really tacky to wear white to prom. This is just not working.
Somone Get Her a Brush
Before you Google—yes, that's Jimmy Fallon. If only his date had brushed her hair before they left. Why was this a trend in the 80s? Why was messy, tangled hair such a look? Jimmy also looks like a vampire next to her. Poor guy.
Two Sizes Too Small
Something tells me the tight-fitting dress was purposeful. Her date definitely doesn't seem to mind, but is she able to breathe? That looks super uncomfortable...and tacky.
Major Flex
They're literally sitting on a pile of diamonds. I think prom is probably beneath them at this point, they should be at a gala or something. Look at her face, she knows she's worth it.
You Come Here Often?
I like the fact that the guy got creative with their pictures and used props. The tree was just there so of course he's gotta do something with it. She seems confused but is going with it. I'm sure he told it some cheesy pickup line, too. The tree, not the girl.
What Kind of Prom Is This?
I hope there were no dads present at this photoshoot because they wouldn't make it out the door otherwise. How was this a good look for prom? What were they actually thinking? I'm not on board with this one.
Awkwardly Far Apart
The pose for this one is just so awkwardly staged. They're so far away from each other, you can't tell who is going with who, and one poor guy doesn't even have a date. Can we also address the top hat and cane guy? Why is there always one?
The Prettiest Prom Date Ever
I have never seen a prettier girl in my whole life. Look at how she's looking at him. He knows he won. I hope they actually went to prom together. I don't think the crowd could handle this much cute.
Party Time
You know any guy who shows up to prom in a white suit means business. They clearly brought the party with them. Look at those boring losers in black tuxes, how uncreative.
Taking "Matching" To a Whole New Level
I don't know who's working the plaid suit better, him or her? They even have similar hairstyles. I'm fully impressed by the commitment to this look. It even looks like they won some kind of award.
Skip the Spray Tan Next Time
I know it's pretty popular for girls to get spray tans before the prom, but this is just on another level of bad. Her makeup is all wrong. She definitely didn't take into account the camera flash.
I Can Be Your Hero
I hope their slow dance was to that Enrique Iglesias song. I can't tell if this is lowkey kind of cool, or if this is the dorkiest thing I've ever seen. The work that they put into coordinating the dresses to the heros is spot-on, though.
Painfully 2000's
Snapbacks and short dresses and blunt bangs. This photo screams 2010. Let's just hope this bridge doesn't collapse too.
Your Parent's Prom Part 2
The '70s were also weird. Her dress isn't awful, but it definitely wouldn't work today, even on the most thrift store-savvy girl. He looks like he was in the middle of saying something right as the camera flashed, and you only got one shot back then.
"Smile?"
Either they didn't want to go to prom together at all or they weren't ready for the picture. Her dress looks like it's made of tissue paper her hair is, unfortunately, a mess. Not a lot going right for these two.
Take Your Brother To Prom?
These two look super close to being siblings. They could be, I guess that wouldn't be horribly weird. One looks way more excited about going to the dance than the other, though.
I Can Show You The World
This galaxy-themed prom was a swing and a miss from me. I'm not feeling her hairstyle, the backdrop is cheesey, and the leopard clashes with the glittery blue top in the dress. I wish the early 2000s hadn't been so tragic, but if I had to live through it, so did you.
"Do We Have To Go?"
She at least looks a little bit interested in going out with him. He just fully doesn't want to be there. Poor girl. This was supposed to be fun!
Awkward Celebrity Prom Pics
How did someone end up with One Direction-era Harry Styles as their prom date? And whoever went with Rihanna better still be gloating about that today. I sure would be. She still looks great even then.
Is That Bruno Mars?!
You bet it is. And he's still short. I'm sure he was a fun time at prom, though. He's got some great dance moves!