Reddit | pajameralls

14+ Times People Cheated The System In Hilariously Unexpected Ways

Sydney Brooman 17 Jul 2019

How does that one saying go? Rules were made to be broken? Okay, maybe all of us can't socially afford to go around breaking actual laws, but if we're clever enough, there are still ways of getting around those rules to achieve what we want.

The average Joe can always find a loophole, but it takes a true hero to create a loophole through which to cheat the system.

1. Letters Home

Reddit | I_Killed_My_Friends

This kid was 'forced' to write his parents letters from summer camp each week to talk about all the fun he was having.

He did write the letter, but definitely not like it was intended to be written.

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2. Well-Trained

Reddit | shockhead

"I told my husband that the dog couldn't sleep in our bed," one woman shares, "so he brought the bed to our dog."

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3. He Wears Short Skirts


These boys decided to protest a school rule regarding not being allowed to wear shorts by wearing skirts instead. Pretty clever if you ask me!

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4. Carry On

Reddit | dev_maxpayne

How do you travel with a big pup when there are public transit rules stating that your dog must be small enough to fit in a carrier? Make the carrier fit your dog.

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5. Pine-O-Lan-Tern

Reddit | alexschwarz_1

This young man wasn't allowed to bring pumpkins into his dorm room during Halloween, but there was nothing in the fine print about carving other fruit.

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6. Rolling Down The River

Reddit | TX_Ag_2010

"I asked her to come home with rolls," this man writes, "I mean, she technically did, but this is totally not what I meant."

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7. One Man Show

Reddit | rootired

To be fair, unicycles aren't listed on that sign, so in my opinion, they're free game!

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8. Read Between The Lines

Reddit | tsaylor

There's this popular meme about cats shoving themselves into cardboard boxes that goes "if it fits, it sits" and I feel as though that's very applicable here.

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9. Pokey


"We aren't allowed to open the thermostat to change the temperature in the office," this woman shares, "but we've found other ways..."

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10. Cupception

Reddit | egglessomlette

"It's company policy that all drinks at our desks have to be in cups with straws," this man writes, "I've broken no rules here."

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11. Hand Me Down

Reddit | corpratepirate

When you have a school dress code that says you have to wear a belt at all times, and you've forgotten your belt at home, the logical thing to do of course would be to make your own.

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12. Tippy Toes

Reddit | rerational

"Told my son he wasn't allowed to go outside," this dad shares. "This kid's gonna be a lawyer some day."

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13. Flower Girl

Reddit | overkil6

This girl's mother told her that she couldn't walk on people's lawns in order to pick flowers, and it turns out she doesn't need to.

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14. Breathing Room

Reddit | mklieber

The best loopholes are the ones that are obviously not okay, but that you just can't argue with.

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15. Ticket To Ride

Reddit | tjasaday

"Whenever I park my car illegally, I give myself a fake ticket before I leave," this man writes. "Works like a charm every time."

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16. Seedy Behavior

Reddit | kittkat03

"My husband told me I couldn't buy any more plants," this woman shares. "Look who's the big boss now."

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17. Free Samples

Reddit | berniethecatch

Beat the heat and beat the capitalist powers at the same time.

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18. Staying Pawsitive

Reddit | Pieman36912

The ottoman is not the couch, so this clever customer is not strictly breaking the rules about not being allowed on the couch..

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19. 'A' For Creativity

Twitter | @sindypnoel

Getting a 'B' from the health inspector is like getting lemons from life - just use it to make brunch!

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20. Credit Where It's Due

Reddit | MCmevin

This guy used a receipt to fake his way into a release party. I'd like to see someone pull that off after a trip to CVS though.

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21. Teamwork Makes The Dream Work

Reddit | darinda777

Some places don't allow drinks poolside, but where there's a thirst and a friend, and about a hundred straws, there's a way.

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22. Not Wrong!

Reddit | Blahson

I mean, if they're going to give you the answer, you've got to take it, right?

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23. Virtual Reality

Imgur | reviewstl

"Not exactly what I had in mind when I told my son it was too nice out to play games inside."

Wish I had thought of that when I was a kid!

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24. Lurking Below The Surface


"I work in an office where professional attire is required," this person wrote. "Little do they know..."

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25. Both Sides Now

Reddit | sansix

"My teacher said that we could only write our cheat sheets on one side of the paper," this kid shares, "I aced that test."

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26. Chip Off Your Shoulder

Reddit | pajameralls

"My mom wouldn't let me paint my room," this girl writes, "So I had to get creative with those free paint chips they give you at the hardware store."

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27. Excelsior!

Reddit | EarlyHemisphere

"A class of students were required to pick a Marvel character to embody within a resume and cover letter. This is what one student handed in."

Pure genius.

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28. Challenge Accepted

Imgur | Clarence1212

Just going to go out on a limb here and say that this car probably doesn't have a hybrid engine under the hood.

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29. Double Trouble

Reddit | sporkachoon

"Told my kid he could only have one bag of gummies," this dad shares, "He walks up and hands me this. Honestly, I'm not too worried about the future of this country."

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30. Isn't It Romantic?

Reddit | shewayout

"My friend goes to a school that doesn't allow the opposite sex in their respective dorms, so this is movie night..."

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