Growing up is hard, especially when trying to find your own identity as a teen. Whether you opted for a unique haircut or had a signature style all your own, at some point you probably tried to stick out from the crowd.
A lot of times these attempts at individuality are captured forever in a picture taken by a friend, family member, or a professional photographer. This can lead to some shameful memories as you seek to leave that part of your life behind, but for whatever reason, the photo still exists, either kept by your mom or found online.
These brave individuals have decided to share their most embarrassing moments, forever immortalized in a picture. Here are some people who have had an awkward stage in their life as shown in these hilarious photos.
High school kids have the strangest obsessions, as evidenced by the sais this kid is holding. More often than not, these passions result in somewhat awkward pictures. Pictures that they eventually come to regret, except this guy who says he has none for this awkward picture.
Is this guy a wannabe Pokemon trainer, a magician, or something else entirely. He seems a little too old for Pokemon, but who am I to judge. If dressing up in a cape and carrying around a Pokeball makes him happy, then more power to him.
While you might think it cool to build and wear a set of KNEX body armor is cool, trust me, it’s not. And if you do happen to build this set of geeky armor, make sure not to take a picture of yourself wearing it.
When this teen was told to dress up to receive an award I think he was thinking of the wrong kind of dress up. I bet from that day forward his friends always called him Cowboy.
If this is supposed to be a before and after photo, I can honestly say I can’t tell the difference. This guy must be a vampire because he looks exactly the same to me in both pictures. The guy in the photo says the first photo was awkward, which makes the second photo what? Even more awkward?
This is what happens when you are a Goth but still want to have a family. This family portrait features a cute little baby sandwiched in between his Goth mom and dad. And while those are his real parents, it does look they stole someone else’s kid for the photo.
This girl’s cat vest is to die for, and according to her was homemade. Also, according to her, you can get one for yourself by PMing her on Reddit. If you do contact her for a vest, make sure to ask her why she is so angry in this photo.
For his graduation picture this senior decided to wear his Sonic uniform. Now, I call that dedication. At least he had his life’s ambition in mind when he had his photo taken. Though, I would hope he would aspire to more than being a cook at his local Sonic.
What happens when you are young and naive? You end up with literally no bangs. This poster says she was the age of 10 when she realized that no bangs meant you grown them out, not cut them off as she had been led to believe. I can’t tell if her parents had this done or she did this to herself.
This redditor claimed the editors of his college yearbook from a conservative Christian college photoshopped his punk rock spikes into a fluffy afro. i guess that is possible, but he could just be embarrassed by his hair style.
This is what you get when you want to be unique, but still want to appear somewhat normal. Is this like a reverse mullet? Party in the front and all business in the back? And what is up with that smiley face taped to the front of their shirt?
Nothing says adult like a cig hanging out of the corner of your mouth, never mind the teddy bear t-shirt. If she keeps smoking like that I can guarantee that it will make her look older, as cigarette smoke is said to age the skin, among other bad side effects.
Poor kid. I hope he eventually grew into his overly large head. I can just imagine the teasing he had to suffer from when he was little. It doesn’t help that this redditor’s family got in on the joke by calling him Fivehead when he was a kid.
Why would you do your hair like this? It looks like she stuck a fork in a light socket. Either that or she has a peacock attached to the back of her head. The fact that she said she spent an hour doing this to her hair everyday is beyond explanation to me.
What happens when you mix NSYNC and fanaticism? You get a high school student with frosted tips and see-through colored shades. You also get a priceless photo for ridicule by friends, family, and the Internet for the rest of your life.
Is it me, or does this kid look like a young Guy Fieri? He’s even wearing the signature shirt with flames. I am curious as to whether the kid can cook like the famous chef. Maybe his specialty is peanut butter and jelly sandwiches.
17) Video Games are My Passion
Here is a young man passionate about his video games, especially the Legend of Zelda. Being a Zelda fan myself, I can see why he wanted his senior picture taken alongside his favorite pastime. In my opinion, you can never have too many video games in your life, at least until you get married.
What business does 7 year old have taking glamour shots? They should be busy worrying about playing and having a good time as a kid, not glamming it up for the camera. I do appreciate the shiny star earrings though.
Now, this is dedication. Here is a young Star Trek lover who went all out for their favorite genre and show. Forget the fact that this is a girl, that anyone would shave their head to appear like favorite Captain Jean-Luc Picard is beyond me.
Granted, it is hard to smile when you are just starting out in society, in the first grade, according to this redditor. You never know when a smile is too little or too late. Which makes it even more awkward since first impressions are important. He is forever known as the kid who smiles too much.
What exactly is urban hip-hop anyway? Doesn’t hip-hop come from an urban setting anyway? It’s hard for me to determine exactly how you can make it any more urban than it already is. I guess it means you wear parachute pants and a matching Kufi hat.
I’m not quite sure what is going on in this picture? It looks like they dressed themselves for school. I don’t know if I could wear my pants up to my waste like that. It looks very uncomfortable to say the very least.
23) Hobbits of the Shire, Unite!
This redditor looks to be a lover of The Lord of the Rings, especially the hobbits of the Shire. It seems her mom tried to tell her she would regret the photo later on, but she seems to be proud of her hobbit heritage.
24) The Best Ninja in the Land
This young student is showing his love for Naruto, a popular Japanese anime, where the lead character is seeking to be the best ninja in the land. He even wears his Naruto headband wherever he goes, even to school.
Here is another lover of geeky things. this time it is the kid favorite Pokemon, and Charmander in particular. Charmander is one of the most beloved characters on the show, right alongside Pikachu, Bulbasaur, and Squirtle. Later on he becomes the awesome Charizard.
Girls in the 80’s did not have the monopoly on poofy hair. Boys also got in on the action, especially those who listened to all of the popular hair bands back in the day, such as Motley Crue, poison, and a whole slew of others.
27) Parachuting Into Homecoming
Here is a blast from the past, parachute pants. If you wore parachute pants back in the day, then you know how cumbersome they could be, especially on a windy day. Hopefully, this wearer didn’t encounter any high winds on the way home from the Homecoming dance.
Most of us went through a rebellious phase when we were younger, but not all of us went through the I want to be way different and so will act like I worship Satan phase. This redditor even wore the upside down cross earring to put a nice touch on the look.
29) I’m Just Super Saiyin’
This Dragon Ball Z fan likes to show his devotion through the clothing he wears. Here he is rocking Vegeta on the front of his shirt and sporting the totally out of this world makeup. True fans of the show will know what I am talking about.
So, what do you do when you really like the actors from the popular teen movie Twilight, but can’t get them to come to your birthday party. Why, use cardboard cutouts instead. Hey, it looks just like them and no one will know the difference. We’ll be so cool!
31) Hey, the 80’s Called, It Wants Its Wardrobe Back
The only people I know who wear full Adidas gear are rappers from the 80’s and 90’s, as well as those who want to be like them it seems. This teen seems to have the arm fold and the lean down pat though. So, at least she looks the part.
According to this redditor, he liked to wear three-piece suits when he was a kid. What was he, a reincarnated lawyer? At least he stayed a kid at heart and carried his toys in a briefcase.
This redditor was trying to be edgy when she was a teen by posting mock photos of her cutting herself on her MySpace. It’s only in retrospect that she realized how silly it looked. Seriously though, cutting is a serious issue that demands some serious attention from any adult who knows someone that does this to themselves.
When you love your country and want to show it to all around. Wearing an American flag shirt is not just restricted to country singers named Garth, but can be worn by anyone who wants to show their fellow countrymen, and others, just how they feel about this great land of ours.
Whoop, whoop fam! It would seem Insane Clown Posse, or ICP, was a thing back in the day. As a matter of fact, it is still a thing today too. This redditor says he wore this ICP makeup to his prom, in addition to taking a mop as a date. That must be a thing too.
36) Bowl Cuts and Video Games
Here is a stereotypical image of a kid back in the 90’s. A bowl cut, sitting on an inflatable chair, and playing a Gameboy. The kid in this picture even has an inflatable foot stool to go with his inflatable chair, the ultimate in 90’s comfort.
Many kids have certain quirks and obsessions that tends to set them apart. Take this kid for instance. For some reason, he thinks it’s cool to wear two watches. I honestly don’t ever remember that being a thing, unless you were a shady watch salesman that is.
Ignoring all of the obvious spelling errors on this resume, I could see giving this kid a shot if I was offering a job. The deal breaker for me is the photo. He should at least wore a dress shirt, pants, and tie. Instead, he chose to dress in slacker casual. Bad move!
This person has no fashion sense at all. And while it is nice to be color coordinated, neon green is not the best of colors to pull off a coordinated look. Is this Neon Joe Werewolf Hunter’s or the Grinch’s distant relative?
Just your friendly neighborhood Spider-man trying to pay some bills. At least he is entertaining people while dressed as his favorite superhero. That does look like some Benjamin’s he is holding there. I wonder where I can find a Spidey suit.
This teen has seen too many gangster movies. I wonder if he knows that gangster fashion dies back in the 1920s. At least he has the whole outfit going on, including a suit, vest, tie, and hat. That swing though!
This is what happens when you are oblivious to how awkward your parent’s love can make you look. Kudos to the parents for giving their son such a shirt. I just hope his classmates are understanding and don’t give him a hard time. It is from things such as this that scarred childhoods are made.
The love some teens have for a favorite childhood character is so strong in some cases that it overrides common sense. While cute, this teen should probably not have brought these props to her to get her senior pictures. Now, she will forever be known as the Marvin the Martian girl.
While this look might have made sense and seemed cool at the time, in hindsight it was probably not the smartest of fashions, especially if you wore it to school. And forget the toy gun, that alone would have the teachers asking some serious questions, or at least it should.
Poor Santa, surrounded by Goth kids with no way out. It looks like he is trying to take it in stride though. Oh, what it must have been like back in those days when everybody wore makeup and so much black.
I have no idea why this kid is going for the Little Satan look. Is he trying to send a message that he is a little devil, or maybe he is trying to blaze his own style trail. Either way it is creepy looking, especially with that creepy smile he has on his face.
While this redditor seems to think this is the coolest senior picture ever, I would disagree. Unless he is riding a horse or a motorcycle to school, why would he even be wearing them in the first place?
If you are going to play soccer in your new hairdo, expect it to not make it through the entire game. This cute little girl seems to be having a bad hair day on the soccer field. I hope she at least can play, making it worth destroying her hair for.
Here is a classic look. Who remembers the kid that had to wear the weird headgear for their retainer? Or, maybe, you were one of these kids yourself. Hopefully, it was worth all of the ridicule from your classmates. Now, you have great teeth at least.
Here are two big-haired beauties. The one on the right is obviously a Goth queen. She does look majestic in her black clothing and black hair, and her makeup is on point to. I wonder if she si still a party of the Goth scene.
There is nothing wrong with being in dance club. I do, however, think that the person who came up with this particular costume should be shot. I mean, the colors alone are enough to make you throw up.
The original intent of this haircut was to be a representation of the rising sun, something this redditor thought would be a good idea. As you can see from the results, this whole haircut was just a disaster waiting to happen.
53) May the Odds Be Ever in Your Favor
I guess all middle school students should learn to shoot a bow, you know, in case they have to fight for their lives in a dystopian society-style hunger games. Either that or this girl is taking her D&D role-playing to a whole other level.
This high school student thought it was cool and edgy to wear a gas mask to school. The only time it would be cool to wear such a thing in my book is if there was actually some kind of gas leak or someone farted in class and it stunk really bad.
This teen was caught dressed as a Goth in a photo as a young man. While his sister thinks she is embarrassing him by showing off such photos, in actuality, this redditor has no regrets for his past choices and even embraces what he once was.
56) Suit? Check. Chain Mail Vest? Check. Sword? Checkmate.
While extremely nerdy, this high school senior has the best senior photo ever. You have to admit that wearing a chain mail vest and tie under his suit and using a real sword as a prop is pretty cool.
57) My Prom Date, the Mop
Here is a former student who took a mop to his prom instead of an actual date. That must be a ting now as I remember clearly that if you didn’t have a date for the prom, you usually went alone or didn’t go at all.
I remember skater boys from my time in high school. While initially considered slackers and uncool, they have come into their own over the years. All together now, “He was a skater boy. She said see you later boy. He wasn’t good enough for her.”
Here is a kid wearing wide bottom jeans and carrying a homemade sword. Honestly, you wouldn’t catch me dead wearing such a thing. I don’t see how you can even walk in those. Now, the sword on the other hand, that is something else entirely.
What in the world is going on with this guy’s hair? This redditor calls it an infinity chinstrap. I call it a bad haircut. At least he got wise and got rid of it once some girl told him it made him look like a sunflower.
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Throughout their life, people get caught up in a lot of things, some of which can put them in awkward situations. The best part is when it is caught in a photo for all the world to see, or to come back to haunt them once they are older, and hopefully, far wise.
