12 Laugh-Out-Loud Stories of “Trying Too Hard”

We’ve all been there, haven’t we? That cringe-worthy moment when you tried a bit too hard to be the coolest kid on the block, only to realize later that it might not have been your finest hour.

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#1 The Kriss Kross Confusion

Happy multicultural retro styled friends looking away
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“Wore my pants backwards during the 90s when kriss kross was popular, so glad we didn’t have social media back then.”

Ah, the 90s – It’s amusing to think that someone actually wore their pants backward to be part of the cool crowd. What’s even funnier is that they’re grateful that social media wasn’t around back then to immortalize the fashion faux pas. Sometimes, being cool is all about hindsight.

#2 Trampoline Tragedy

A kid / child jumping on a trampoline.
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“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.”

Trying to be the “cool kid” among older siblings and their friends can lead to daring stunts. In this case, an attempted backflip on a trampoline turned into a wrist-breaking endeavor. It’s a perfect example of how youthful exuberance can sometimes land you in the school of hard knocks.

#3 The Glowing Tan

Handsome young shirtless man sitting on sun lounger and applying sunscreen lotion on parking
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“Tanning booths. Had a lady friend that was into those. I only did it like 5 times. I was so dark, the grey hair on my chest were literally glowing.”

#4 The Mike’s Hard Mishap

Disheveled drunk or female high on drugs at a nightclub
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“Went to a party and chugged 6 Mike’s Hard Lemonades and then threw up for several hours. Nobody else at the party was even a little drunk.”

Parties and overindulgence often go hand in hand. Chugging sub-par liquor might seem like a good idea in the moment, but trying too hard to be the life of the party can have decidedly uncool outcomes.

#5 The Deafening Dilemma

transportation and vehicle concept - man using car audio stereo system
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“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.”

The battle between your car stereo and the local authorities is a classic tale of rebellion. It’s a testament to how stubbornness can sometimes override common sense in the pursuit of coolness.

#6 The Drink vs. Dignity Dilemma

Young male friends having fun together and drinking beer indoors
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“Spilled my drink to hide that I pissed my pants. Was too cool to say I needed a bathroom.”

Nature’s call can be an insistent one, and it often strikes at the most inopportune moments. One user’s attempt to discreetly hide an accident by spilling a drink instead is an ironic twist on trying to save face. It’s a lesson that pride can sometimes come at the cost of common sense.

#7 The Hoodie Heatwave

African american man with smartphone in a hoodie
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“In junior high I wore a hoodie all year because I thought it would make me look gangsta. This included those balmy 90+ degree Texas days.”

Ah, the awkward years of junior high when trying to be cool often meant making fashion choices that defy logic. Wearing a hoodie in scorching Texas heat is a humorous reminder of the great lengths we’ll go to fit in. It’s also proof that hindsight is indeed 20/20.

#8 The Turkey Tale

Photo of disgusted guy hold plate baked turkey wear specs suspenders shirt isolated yellow color background.
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“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.”

As kids, we often spin tales to impress our peers. This user’s story of claiming to have a pet turkey takes the cake. Conveniently, the story coincided with Thanksgiving, providing a seamless escape route from the lie. It’s a charming example of youthful imagination.

#9 The Spectacles Sham

Sunglasses are on the monitor. The sky is reflected in them. Tinted.
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“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. So I was, what, 6ish, wearing GIANT 1970s woman’s sunglasses and couldn’t see s***. My teacher saw right through it, of course (something I couldn’t do). She didn’t call me out, just humored me, to a point.”

#10 The Nolan Ryan Nonsense

Beautiful young cheerleader with ball on white background. Football.
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“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.”

#11 The Sneeze Saga

Beer in two glasses on wooden table, oktoberfest concept
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“Tried shot-gunning a beer in front of my crush. I sneezed midway through and the beer came out my nose. Hurt really bad.”

#12 The Broken Arm Act

Shouting angry asian kid on red background.
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“When I was in 3rd grade, I climbed a tree to get a friend’s kite down. I had a crush on her. When I was up pretty high, a branch broke, I fell and broke my arm. I went home acting like everything was cool and cried like a b**** as soon as I got home.”

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