Pop Culture

20 embarrassing but very relatable stories of people doing 'stupid' things to look cool

We've all been there.

genz z trends, ask reddit

Cool becomes cringe so very easily.

There's a glorious point in adult life when you suddenly realize that other people's opinion of you doesn't hold the same sway. You've cultivated enough of an authentic tribe and self-assurance that you are truly liberated from caring about how you come across—hopefully without the overcorrection of losing any and all social awareness.

But until that time comes, our adolescent selves will do things that are, as the kids say, totally cringe in order to blend in with a friend group, impress a childhood crush, emulate a beloved celebrity or feel just a little more grown-up. Sometimes these seemingly "cool" behaviors become the detriment of our own health and well-being in the long run, when they lead to addiction with drugs, alcohol and cigarettes. Other times, if we're lucky, we just wind up with a very embarrassing story to keep ourselves humble.

Which brings us to Reddit user u/Beneficial_Form8563, who asked "What is the stupidest thing you have ever done to try to be cool?"

As you can imagine, the answers were wild. No matter what outrageous thing each person did, they all left with the same bit of wisdom: Turns out this wasn't cool after all, I'm much better off just being myself. That's pretty much the theme of every young adult's life, isn't it?

Scroll below for 20 of the absolute best from the comments. And by best, we mean absolutely embarrassing. Enjoy.

1. "When I was 8 my sister had her friends over, all teenagers, and trying to be cool I jumped on the trampoline in front of them and told them I’d do a backflip. I’d never done a backflip so I landed on my neck, bounced off the trampoline and broke my wrist."

– u/Artemis64z

2. "Wore my pants backwards during the 90s when Kriss Kross was popular, so glad we didn't have social media back then."

– u/-Rocjames77

3. "Got pulled over for playing my car stereo too loud. Took the ticket, turned it back up. Took another ticket, turned it back up. Took a third ticket, turned it back up. Spent the night in jail."

– u/Small_Kick_5912

4. "Tried shotgunning a beer in front of my crush. I sneezed midway through and the beer came out my nose. Hurt really bad."

– u/Red_Christmas_Lights

4. "In 1st grade, I was very jealous of people with glasses. I wore an old pair of my mom's sunglasses and said they were prescription…My teacher saw right through it, of course.I kept taking them off to read the chalkboard and she told me to put them back on…

She called my mom and explained the situation. Mom picked me up from school and all I remember is denying it, and then my mom expressed her disappointment that I'd lie to her and to a teacher. So I told kids I switched to contacts (which were barely a thing then, especially for kids)."


– u/ahhh_ennui

5. "Rubbed poison ivy all over my face. It was the last day of school in 7th grade and since I’d never gotten poison ivy before I was convinced that meant it didn’t affect me. So I started bragging really loudly to everyone around me that poison ivy doesn’t affect me and nobody believed me so I grabbed a bunch and rubbed it all over my face.…

Spoiler alert: it definitely does affect me. That was a rough start to summer vacation."

– u/thumbingitup

6. "Jumped off the top of the jungle gym to show off to my crush from school…. I was 10 and it was at least an 8 foot fall. Landed on my feet, then my knees, then my hands….so cool, so amazing, wouldn’t do it again."

– u/GadisRKO

7. "This is so cringe but I pretended to play street hockey when I was in 5th grade because I thought it would make me seem tough. I was about an 80 pound nerdy girl and truth is I just really liked reading cat related magazines and collecting Polly Pockets. I would do things like wear a fake sling for my arm and claim I sprained it playing street hockey 😩"

– u/RhodeIslandRedChick

8. "Did the worm in front of a crush in elementary school one time. No music or anything…That one is a mainstay in my nighttime embarrassing memory replay."

– u/SithSkate03

9. "Had my mullet cut off but left a rat tail, then had it braided."


– u/TrailerParkPrepper

10. "Buying designer clothes and shoes."

– u/BrilliantMaybe4086

11. "Told someone I had a pet turkey. I have no idea why, I was like six and thought it would be cool. How did I get out of the lie? Well, conveniently Thanksgiving was right around the corner."

– u/Whickerchair

12. "In second grade I forced my mom to sign "Nolan Ryan" on my ball and took it to school to tell everyone I caught it at a game. It didn't take long for it to be pointed out that what I had brought was in fact a softball, not a baseball."

– u/wandering_nobody

13. "When I was in third grade, I told my friends that I met Power Rangers. In a train. In India. South India. During vacation. Cool Max 😎 "

– u/Historical_Love7860

14. "Not as bad as most, but I remember walking 15 - 20 feet behind my parents when we’d go to the mall. Nobody ever caught on that I was with them, right? My wife and I laugh about our kids doing the same thing."

– u/trashcanfairy

15. "2010. Cringe central. I started rapping at a party.💀💀💀"


– u/idontkillbees

16. "Write 'special edition' with a magic marker on a Lego box."

– u/Temporary_Ad_5947

17. "In elementary school, I was a pretty strong reader, but I heard some of the cool kids read out loud and have a lot more trouble and stumble over their words. In order to be cool I would imitate their reading style and stutter or act like I was sounding out words any time I had to read out loud."

– u/James17Marsh

18. "Back in middle school, I thought people who chewed gum look cool for some reason, so I started to imitate the motion all the time, even when I wasn’t actually chewing gum. Started a lifetime of teeth grinding and by the time I was 30…Had to reconstruct some teeth eventually and now I wear a mouth guard even when taking a 20 minute nap."


– u/thecynicroute

19. "Somehow I got it into my 14-year-old head that my ticket to the esteem of my peers was to mope around wearing all black, writing and living the most gawd awful angsty poetry… I guess I thought the other kids would consider me some brilliant, nascent philosopher and come for my counsel? Fortunately, I outgrew all that just in time to make a few actual friends in high school."

– u/zazzlekdazzle

20. "I tried chugging 3 beers at once out of a very large glass to impress a girl. It worked and she was impressed. Then she wanted to show her friends. Beer 4-6 didn’t go down as smooth and I projectile vomited all over her living room furniture. Never heard from her again."

– u/Snowman4168

All images provided by Prudential Emerging Visionaries

Collins after being selected by Prudential Emerging Visionaries


A changemaker is anyone who takes creative action to solve an ongoing problem—be it in one’s own community or throughout the world.

And when it comes to creating positive change, enthusiasm and a fresh perspective can hold just as much power as years of experience. That’s why, every year, Prudential Emerging Visionaries celebrates young people for their innovative solutions to financial and societal challenges in their communities.

This national program awards 25 young leaders (ages 14-18) up to $15,000 to devote to their passion projects. Additionally, winners receive a trip to Prudential’s headquarters in Newark, New Jersey, where they receive coaching, skills development, and networking opportunities with mentors to help take their innovative solutions to the next level.

For 18-year-old Sydnie Collins, one of the 2023 winners, this meant being able to take her podcast, “Perfect Timing,” to the next level.

Since 2020, the Maryland-based teen has provided a safe platform that promotes youth positivity by giving young people the space to celebrate their achievements and combat mental health stigmas. The idea came during the height of Covid-19, when Collins recalled social media “becoming a dark space flooded with news,” which greatly affected her own anxiety and depression.

Knowing that she couldn’t be the only one feeling this way, “Perfect Timing” seemed like a valuable way to give back to her community. Over the course of 109 episodes, Collins has interviewed a wide range of guests—from other young influencers to celebrities, from innovators to nonprofit leaders—all to remind Gen Z that “their dreams are tangible.”

That mission statement has since evolved beyond creating inspiring content and has expanded to hosting events and speaking publicly at summits and workshops. One of Collins’ favorite moments so far has been raising $7,000 to take 200 underserved girls to see “The Little Mermaid” on its opening weekend, to “let them know they are enough” and that there’s an “older sister” in their corner.

Of course, as with most new projects, funding for “Perfect Timing” has come entirely out of Collins’ pocket. Thankfully, the funding she earned from being selected as a Prudential Emerging Visionary is going toward upgraded recording equipment, the support of expert producers, and skill-building classes to help her become a better host and public speaker. She’ll even be able to lease an office space that allows for a live audience.

Plus, after meeting with the 24 other Prudential Emerging Visionaries and her Prudential employee coach, who is helping her develop specific action steps to connect with her target audience, Collins has more confidence in a “grander path” for her work.

“I learned that my network could extend to multiple spaces beyond my realm of podcasting and journalism when industry leaders are willing to share their expertise, time, and financial support,” she told Upworthy. “It only takes one person to change, and two people to expand that change.”

Prudential Emerging Visionaries is currently seeking applicants for 2024. Winners may receive up to $15,000 in awards and an all-expenses-paid trip to Prudential’s headquarters with a parent or guardian, as well as ongoing coaching and skills development to grow their projects.

If you or someone you know between the ages of 14 -18 not only displays a bold vision for the future but is taking action to bring that vision to life, click here to learn more. Applications are due by Nov. 2, 2023.

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