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Hilarious Stories: Stupid Things You Did as a Kid to Try to Look Cool

Stupid Things You Did as a Kid to Look Cool

Everyone has that one memory from childhood that makes them squirm on the inside to remember it, don’t they? Being a kid can be hard sometimes – particularly when being ‘cool’ doesn’t come naturally. In fact, sometimes the harder you try to be cool – the more your ‘awkward’ shines through instead, as these Reddit users’ hilarious stories attests to.


In the 2nd grade, I thought it would be cool to record a song on a cassette tape and basically make a shout out to everyone in my class. It went something like “Hey Alex! How ya doing Sam?! I like your shoes Colleen! etc..” I made the teacher play it in class. Less than half way in I realized I had made a huge mistake…Longest 4 minutes of my childhood.


I molded a paper clip to look like a retainer and wore it to school. All the cool kids had dental work in fourth grade.


Fell going up the stairs at school and tried to play it off like I was relaxing or taking a break. In the middle of a flight of stairs.


Oh god. My friend and I would go to the mall with backwards clothes, however we didn’t have the loose-fitting “urban” style of attire. The whole thing looks considerably weirder with tight jeans and t-shirts.


When I was about six or seven years old, we had a school assembly on name-calling. The teacher giving it introduced the by asking which students had nicknames, and what they were, etc. before moving on to talk about the different between nicknames and bullying.

I always wanted some cool nickname. I remember one of the kids going to the front of the hall saying his name was Red Ranger or some shit because his name was Jason (like the red Power Ranger) and I was incredibly jealous.

In my idiot-small-child brain, I thought If I make up a nickname now and tell the teacher in front of everyone what it is, everyone will start calling me by that name, and I’ll have an awesome nickname!.

I guess I didn’t have much time to think, and that combined with being a small child/moron meant that the best I could come up with was Mega Sting. So I went up and said in front of the teachers in the room and the whole school that my nickname was Mega Sting.

I told my family when I went home that I had a nickname and that is was Mega Sting and as any good family would do, they’ve never let me live it down since. I’m twenty-four now.


I used to carry a skateboard around. I had no idea how to ride it without falling on my ass, so I just never rode it. I carried that shit everywhere.


3) Third grade, liked a guy named Ben who had spiky hair. Told all of my friends that he had given me one of his “spikes” from his hair as a symbol of our love. Kept some pieces of my cat’s fur in a plastic bag labeled “Ben’s Spikes” in my locker. And yes, other girls WERE jealous. But eventually I think he found out and it was super embarrassing for me.

6) My mom and grandma were both really big-breasted, but as luck would have it, eighth grade rolled around and I was still not developing much in that department. I looked up online “What to do if you’re flat chested” and the Internet suggested that I could stuff my bra. Taking this literally, I found a bunch of stuffing (the kind that goes in stuffed animals) in my mom’s sewing stuff and filled in my bra. I thought it was brilliant because it did look fairly real. Disaster struck when I used this method with my bikini top. I jumped into a pool at a pool party and my “boobs” became waterlogged and completely deflated. One of my more outgoing friends pointed it out in front of everyone: HER BOOBS JUST DEFLATED!!! I still wore the stuffing to a few more pool parties. I think my logic was that it would be more obvious if I suddenly stopped doing it. :-\


When I was in 2nd grade, I tried to impress this one girl I really liked by giving her the swing I was on. Of course, that wasn’t good enough, I had to jump off the swing too. So I jumped off and landed on two feet, but my momentum carried me forward and I went straight into a nearby tree, breaking my right arm. Later, when I got a cast, I thought I could still impress this girl by being “badass” and getting a pink cast. I was made fun of by all my guy friends for months.

It paid off though. She’s now my wife.


I cut my eyelashes off when I was ten because the boy I liked was dating a girl with almost non-existent eyelashes and mine were really full and long and I thought he might like me more if I looked like this girl.


I got my hair iced blonde because many of the popular boys were doing it, and tried to gel my hair like they did.

Having no experience “gelling”, I showed up to school with awkwardly over-gelled hair and a giant glob of gel somewhere in the middle of my hair. Which was subsequently pointed out in the eloquence expected of 7th grade boys.


In the first grade I acted like I had a walkie talkie-like device built into my belt and I would whisper things to my belt acting like it was being sent to the FBI or some shit….I was known as the kid who talks to his belt.


I was trying to impress a girl while I was in grade school, year 6.

My idea of cool-people attire was baggy clothes and backpacks that hung down to your knees. I deliberately walked home the same way as this girl, and as soon as school got out I’d put on a really baggy t-shirt, so many sizes too large, and let my backpack straps out so they were hitting my knees.

I remember trying to do a swagger walk while walking in front of her. I ended up having so much swagger the bag straps broke, and I dragged my backpack along the ground, spilling out all my books and my lunchbox everywhere. I was so embarrassed I ran all the way home leaving a trail of residue and all my hopes and dreams.


I never had bubble gum before. Some kid gave me some, and when I was sick of it, I put it behind my ear like the girl in Willy Wonka. I had to get gum cut out of my hair that day.


When I went on a family holiday, I was crushing really hard on this girl who was like 9, I was 6 at the time, that was in the whole “kids activity group” at the hotel. All week, she’d been really involved, so I thought that I should try and get involved as well, to try and win her over. So, I take part in a dress up competition wherein all the kids that took part would be paraded in front of all the hotel guests in a little competition. Naturally, I pick the batman costume. When the time comes for me to strut my stuff, the host-guy-person says to me “What’s your name there little guy?” to which I immediately reply “I’m Batman”.

Somehow, the DJ had read my mind and, without hesitation, started playing the original batman theme song. I take it upon myself to start showing off, running around the stage, punching and kicking the shit out of the air, looking like an absolute mini-bat-boss, when the worst happens.

I trip over my shoelace, (which I tied myself earlier in front of the girl to show how mad my skills were) but couldn’t brace myself for the fall, as I was gripping my cape really tightly. That shit doesn’t help you glide in real life. I fall on my face, pop my nose, look up, and this girl is right there in the middle of the audience just staring at me as the whole room goes quiet. So there’s me, blood pouring out my nose, the whole audience absolutely silent, trying to be ice cold, and I just burst into tears.

I won the competition but ultimately lost the girl. Worth it.


When I was in first grade, I’d just moved to a new school. I didn’t know anyone and being an 8 year, I wanted to be cool. During the first day of gym class, the teacher asked for everyone’s name, and if they had any nicknames they went by. What he meant was, “If you’re Matthew, and you want to be called Matt, say something.” What I heard was, “If your name is John, and you want to be called ‘Donatello’ after your favorite Ninja Turtle, say something now.” I didn’t live that down for a while…


Wore earphones with the jack in my pocket not connected to anything for the walk to elementary school.


For some reason, I thought orthodontic braces looked very cool so I tried making some out of aluminium foil… Aiy yai yai that tastes very strange when you bite down on it…


Remember those pants that zipped off and became shorts? Get this, one leg zipped…one leg unzipped. Oh yeah, it was a shorts/pants combo.


I thought I could impress people by reaching up into one of those rip-off toy machines with the claw and snatching out one of the toys from below…I ended up getting my arm stuck and crying in front of a whole grocery store.


I’m in fourth grade, I had just finished watching Die Hard 1 & 2 and I wanted to be John McClane. Of course the first logical step to becoming McClane is to look like him. Back then I had no idea what a receding hairline was, so I attempted to recreate Bruce Willis’ ‘hairstyle’ myself with hair clippers and the bathroom mirror. Judging by the looks I got when I left the house, I must have looked like a pre pubescent crackhead. Anyway thank you for posting this question, because I totally forgot about the day I learned what male pattern baldness is. Yippee ki yay Motherf**ker!


In third grade, my teacher asked the class if anyone had any allergies. I thought I would instantly look cool if I had an allergy, so I had to come up with something unique:

I told my teacher I was allergic to salt.

Every time there was a class treat, I wouldn’t get to have it because it had small amounts of sodium in it. The kids in my class felt bad for me so they would bring me sodium free treats (pop-rocks usually).

It became really awful because all of the kids in my class were aware of what had salt in it, and whenever I was eating something in the cafeteria, like a piece of pizza, they would question me, and I would act like I didn’t know it had sodium in it, then be forced to throw it away. It literally got to the point where I would hide from everyone during lunch so I could eat.

This lasted for third grade and fourth grade, until my fifth grade teacher realized that sodium is necessary for life, and called my parents.


What did you do as a child to look cool, that is totally hilarious/utterly embarrassing in hindsight?



Jolene enjoys writing, sharing and connecting with other like-minded women online – it also gives her the perfect excuse to ignore Mount-Washmore until it threatens to bury her family in an avalanche of Skylander T-shirts and Frozen Pyjama pants. (No one ever knows where the matching top is!) Likes: Reading, cooking, sketching, dancing (preferably with a Sav Blanc in one hand), social media, and sitting down on a toilet seat that one of her children hasn’t dripped, splashed or sprayed on. Dislikes: Writing pretentious crap about herself in online bio’s and refereeing arguments amongst her offspring.

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