Legal Loopholes That Feel Still Illegal When You Use Them

A modern loophole is defined as "an ambiguity or inadequacy in the law or a set of rules." Historically it meant a "small opening through which small arms may be fired" or a "similar opening to admit light and air or to permit observation."

So how did we get from point A to point B?

In 1591, the first figurative use of loophole—the modern definition—was recorded in print as an "opening that allows one to avoid a rule, law, or obligation." Figurative loopholes are usually not well known, so perhaps that's why the term for a narrow opening was chosen for this alternate meaning.

But who knows for sure? English evolved with a lot of outside influences then evolved further with cultural changes.

The use of the term loophole has fallen off in the digital age to be replaced by "hack" or "life hack."

Reddit user CryptographerFinal56 asked:

"What's a perfectly legal loophole that feels completely illegal when you use it?"

Freebies

"Yesterday I went to the pharmacy at a place known for its mile-long receipts filled with coupons."

"One coupon was for $2 off any item, so I got a $2 bottle of water and they just let me take it for free."

"Felt amazing."

~ themonicastone

Price Matching

"There’s a Tractor Supply (the store) online hack, where you can search any store in the US on the website, find your item cheaper than your local store."

"Add it to cart and then right before you pay, change the pickup location to your local store. The price stays the same as the cheaper store."

"I saved a ton of money on stall mats for my home gym this way."

~ 7empestSpiralout

Doesn't Seem Right

"Taking a left (instead of right) on red from a one way street to a one way street."

"Legal in Boston."

~ Gammondorf

Merch Protection

"I saw a concert at a venue that didn't let you leave and re-enter once you were inside. I was telling the merch guy I wanted to buy a poster, but not have to hold it all night.

"He said, 'Just say you have asthma and you need your inhaler, if it's a medical issue they're not allowed to ask you any questions'."

"I was hesitant because I really didn't want to not get let back in, and he was like, 'C'mon, come with me'."

"He goes to the door, tells security, 'Hey, this kid has asthma, he needs to go get his inhaler'."

"I took off running, not even thinking about the connection, brought the poster back to my car, walked back to the side entrance, they stopped me and I was like, 'I was just in there!' and they were like, 'Eh, let him go'."

"I actually still feel a little guilty about it, but it definitely worked! Gave the merch guy a fist bump."

~ wossquee

Technically True

"Student discount on Apple.com for my, uh, student in kindergarten."

"The Mac MegaPro M6 Extreme with 800TB of RAM, 9 Nvidia ZTX video cards, and 600 PB of storage is for my little Kendall, kid's a genius."

~ PabloMesbah-Yamamoto

"Yes, I need this brand new M2 Mac Mini for my homeschooled child."

"Oh what’s that? You don’t need any paperwork proving the homeschooling or even the child’s existence? Coolsies."

~ connorgrs

Not Theft, But...

"Gettin' a free sandwich every time I do the 2-minute fast food receipt review, even on my free sandwich. I know what they pay for ingredients and my finished meal costs less."

"Am I 'working' for my $3 discount? Is my review really worth that? Or are the masses subsidizing my meal and the system would collapse if everyone were as stingy as me?"

"Who knows. Who cares? I feel like I've killed a Tamagotchi. That's not animal cruelty, this ain't theft, it just don't feel like it's supposed to be this way."

~ Jsenss

Cake For Breakfast

"I can buy birthday cake even when it's not my birthday."

~ Appropriate-Trier

"My family has been buying cakes from a specific place for ages, usually for birthdays."

"One day after I got my driver's license I realized I could simply go there and buy a cake. Got quite a few 'surprise' cakes."

~ noTHOTS_noOPPS

Obeying Traffic Laws

"UK here. Driving in the bus lane when it's not bus lane time."

"The road near me gives a whole lane over to buses from 16:00-18-00."

"I drive home from work at about 15:45 in the 'bus lane', past miles of queuing traffic."

~ thecauseoftheproblem

Why We Don't Tax The Rich

"Incorporating your business in the Cayman Islands to avoid taxes."

~ friendly-sam

"Just remember, tax avoidance is legal, tax evasion is illegal."

~ waterloograd

Backdoor Roth IRAs

"Backdoor Roth IRAs are strange to me."

~ Esk__

"I work in the industry. This is one that trips up advisors as well as customers."

"They think it’s written in the IRS code, but it isn’t. It’s just an after-tax IRA contribution and immediate conversion to Roth."

"Don’t forget to do the conversion though!"

"If you end up leaving it in the Traditional IRA, and later fund the traditional IRA with tax-deductible contributions, the after tax portion becomes nearly impossible to get out tax-efficiently."

~ tiplewis

Sticking It To The Man

"Paying with debit on purchases around 25 cents or so just so places like Walmart will lose money on the transaction."

~ datNorseman

Is It Or Isn't It?

"The extremely murky legal waters of downloading ROMs because you 'have the discs'."

~ Prestigious-Part-697

"Pirating mid 2000s games speaks to the millennial IT soul."

~ mechajlaw

The Size Of The Refund

"DoorDash (& other delivery) would mess up my order but if an entire item wasn't missing, they'd do a tiny partial refund even though I didn't receive the food I ordered. Forcing me to pay for food I didn't order."

"Example: I could order a cheeseburger with onion rings, bacon, BBQ sauce and just receive a plain cheeseburger, and they'd say since it was just missing a few toppings I'd only get a couple bucks back. Basically forcing me to pay full price for an item I didn't even ask for."

"Another example: ordering a pizza with pepperoni and jalapenos, having it arrive with only jalapenos. I'd get a $2.50 refund for a missing topping and be stuck with a pizza I didn't order."

"Loophole: in the examples above, rather than say my bacon cheeseburger was missing toppings, I'd just say the entire item was missing. I'd tell them I received a burger, but not the burger I ordered, which isn't lying."

"My bacon cheeseburger was completely missing, and I got someone else's burger instead. Same with the pizza—it wasn't just missing a topping, I ordered one pizza and got something completely different."

"It's a different way to frame it, but it isn't dishonest, and it's important because if you got the wrong item, it's a full refund. If an item was prepared incorrectly, you get hardly anything except food you didn't ask for."

~ dsmcdona

Dog Eat Dog

"There is a gas station chain in Pennsylvania that had 2 for $1 hot dogs for a long time. At one point, they put ordering screens at the gas pumps and you got $1 off if you ordered there."

"There was no rule about having to actually be getting gas, so you could pull up there, order your 2 for $1 hot dogs, get $1 off for ordering at the pump, go in, and get your 2 free hot dogs."

"Eventually they changed to make it a free fountain drink if you ordered something else outside which is still nice, but not as one sided."

~ dkviper11

Lumber Exchange

"I install windows and trim them out. My work throws out scrap boards that are too short to fit on our very limited lumber rack."

"I pull them from the dumpster and bring them home because free wood is free wood. When we are working in my area, I trim the window from what I have in my garage."

"My company reimburses me in linear feet. This is how I get free full length boards."

"To clarify:"

"-We don’t have the space to store a lot of boards, so if we have a say 4’ cutoff it generally goes in the dumpster unless someone wants it. Someone always takes those for a shelf or something or for a job the next day that we know we can use it for."

"-I want it, because I have use for 4’ boards."

"-it’s encouraged for us to take home cut offs, but not full 16’ or 8’ boards. We save those."

"-it’s unfortunate we can’t store those cuttoffs because they are often all we need. I bring those back to the worksite from home when we need them."

-my boss says that once it hits the dumpster it’s mine. If I supply 4 4’ boards from my own house, I’m 'owed' 16 linear feat. I take home a full 16 footer because I’m swimming in scraps, but sometimes need full boards."

"-my boss is aware this is dysfunctional as f*ck. We are working on improving our lumber storage."

~ youvegotnail

Is there a loophole or life hack you use that feels wrong?