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Ready for some wild legal loopholes that make you go, "Wait, what?" We dove into a crazy online thread where lawyers spilled some seriously funny and bizarre stuff the law actually lets slide. From bears crashing college dorms to buying air miles with pudding, this is not your usual boring law talk. Let’s jump right in!

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#1

Wait, They Actually Ranked These Hilarious Legal Loopholes?!

anon , Caspar Rae Report

Ever see those parking tickets that say the lot isn’t responsible for damage to your car? They’re bluffing. When you park there, they basically take your car under their care. So, if your ride gets messed up, they’re on the hook - even if they try to freak you out otherwise.

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Legal experts say a loophole is like a sneaky trick the law didn’t plan for. It’s when the written rules clash with the messy real world, and suddenly someone spots a tiny gap and slips right through.

People have been playing these legal games forever, not just to dodge taxes or parking fees, but also for some downright legendary reasons.

Take David Phillips. In ’99, this guy realized Healthy Choice pudding came with airline miles. So, by buying pudding by the pallet, he scored over a million miles for about $3,000. The company never dreamed someone would do that! Free flights for decades, just by eating pudding.

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    #2

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    gleenglass , Kindel Media Report

    In Oklahoma, if you were adopted, you can inherit from BOTH your adoptive AND biological parents. Hello, double jackpot!

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    #3

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    anon , pixaflow Report

    Lawyer confession time: If you have enough cash and come from the right background, there’s probably a way to wiggle out of just about any charge. Just sayin’. Money talks and the law listens.

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    Here’s a fun one: Lord Byron, a famous British poet, got annoyed that his college said no to bringing his dog into the dorm. Boris went full rebel and bought a live bear instead because the rules didn’t say anything about bears!

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    #4

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    itsnowornever , The Good Funeral Guide Report

    Juries don’t just say guilty or not. Sometimes, even if it’s clear you broke the law, they can decide the law itself is nonsense and let you off. This super-secret power of juries is called nullification, and most people don’t even know it exists.

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    #5

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    KingPharaoh , Ron Lach Report

    In Canada, you can swoop up movies, games, music, and apps without paying - just don’t try to make a buck off it. If your internet provider sends a threatening letter, just toss it. They can’t actually nail you in court for that.

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    #6

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    putsch80 , Strange Happenings Report

    Live in an oil-rich state? Odds are, the oil under your land isn’t actually yours. The person who owns the rights can just roll in, set up drilling, lay pipes, maybe build a pond for water, and do whatever it takes. No trespassing laws stop them? Nope. Tough luck.

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    Not only did Byron have a bear roommate, he even walked it around the campus on a leash. Legend has it he tried (and failed) to get the bear enrolled as a student because, well, who wants a bear taking exams next to them?

    His mischievous move is now famous, giving even his poetry a run for its money.

    #7

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    Aperture_Kubi , David McElwee Report

    Got a boss who brews beer? In Texas, if you make the brew yourself, you’re allowed to drink it even if you’re underage. Bonus: You can buy the brewing gear as a minor too.

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    #8

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    ClusterMakeLove , freepik Report

    No-fault divorces? Not so fast! In Canada, adultery still fast-tracks divorces. So some couples just staged affairs to get the paperwork done faster. They’d even file official statements confessing to their "tennis pro rendezvous." Drama, but efficient!

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    #9

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    iamplasma , August de Richelieu Report

    Lawyer here dropping an Aussie bombshell: If your company tanks and you destroy its books after it officially files for bankruptcy, you might escape big time liability. The law expects companies to keep records, but if you wipe them AFTER bankruptcy, it doesn’t count as "company" destroying them. You might get a slap on the wrist, but that’s about it. Sneaky, right?

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    Back in the 1800s, New York's 'Raines Law' tried to stop Sunday drinking by forcing bars to sell food with every drink. But the sneaky bar owners found a loophole - they handed out one sandwich all day long, passing it around like the world's hungriest relay race!

    #10

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    Joltik , Pixabay Report

    If you work retail, your boss might legally NOT have to give you a public bathroom - unless the store is huge. But if you’re pregnant, businesses can’t say no to bathroom requests. Take that, restroom rules!

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    #11

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    glider524 , Jerry Kavan Report

    In Ohio, you can get a DUI for riding a drunk bicycle, but not on a unicycle or tricycle. The law's clear - even if it sounds like a bizarre carnival rule!

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    #12

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    rarehugs , Pixabay Report

    If a cashier asks your ID for a Visa or Mastercard payment and you don’t fancy it, you can simply say no - if your card is signed on the back. Stores must follow their contract with the card companies and can’t force an ID check or a minimum amount for card use. Take THAT, store policies!

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    Basically, customers never really got to eat the sandwich, but as long as it kept getting handed off, bars were off the hook. Genius? Absolutely.

    #13

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    itsamiracle , Sandsun Report

    Working in a lab where dumping raw chemicals is a no-go? Not in this case! As long as you dilute stuff like DMSO with water below a certain concentration, the law lets you wash it down the drain. Same amount, just more watered down - and totally legal.

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    #14

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    JediMasterEvan5 , Katelyn MacMillan Report

    Illinois says you can marry your first cousin - if one of you is over 55 AND sterile with a doctor’s note. Talk about specific dating rules!

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    #15

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    LegalDad , Atlantic Ambience Report

    Heads-up: In many states, it’s not just about hitting the legal alcohol limit (.08), but if even a little drink messes with your driving, you can still get slapped with a DUI. So next time someone brags about being "under the limit" after three beers, remind them the law doesn’t always agree.

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    #16

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    jumbobrain , Juan Fernandez Report

    Fill up at a UK gas station but can’t pay? They’ll give you an IOU form, and legally, you don’t have to come back to pay it. They can send you a few reminder letters, but taking you to court costs more than your debt, so they usually just give up. Score!

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    #17

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    anon , Seyed Amir Mohammad Tabatabaee Report

    In Germany, if you take something with the honest plan to bring it back intact, it’s not technically stealing. Except bicycles. They get the red card every time.

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    #27

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    ohiohiohio , Ruthson Zimmerman Report

    A clever move by some police departments: they pay private companies to manage their GPS records, so citizens can’t request them through public records laws. Wanna check where their cars have been? Nope, not happening.

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    #28

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    anon , CTV News Report

    Here’s pro advice: Always refuse the breathalyzer after a DUI stop. It might get your license suspended temporarily, but the test results can be a nightmare to fight in court. Also, if you want to seriously get away with a crime, keep shut and don’t text or talk on your phone near the scene. The less evidence, the better!

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    #29

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    veyster , Wesley Tingey Report

    In Louisiana, kids can’t sue their parents unless they’re emancipated first. But parents? They can totally sue their kids. We’re guessing insurance reasons, but it’s still a pretty wild rule.

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    #30

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    sleepyzootoo , Curated Lifestyle Report

    Here’s a brain teaser: committing a crime a few feet apart can change everything. If it happens on federal land like a national park or a highway, you might get smacked with harsher charges than if it happened just next door on state land. Geography is the new legal poker!

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    #31

    brolix Report

    Check this out: people sometimes write ridiculous stuff on checks just to mess with bank tellers. And you know what? Sometimes it works! One guy endorsed a check saying if the company sent him mail ads, he’d get paid $500 each time. They cashed it, and he won the court case when it came up. Talk about cheeky!

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    #32

    athennna Report

    If someone swipes something from you, guess what? You’re legally allowed to break in and grab it back - just don’t hurt anyone. It’s like a personal ‘finders keepers’ permission slip from the law!

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    #33

    Twistatron Report

    This is so weird it has to be true: UK taxis (called hackney carriages) legally have to carry a bale of hay in the back or be able to carry one, to feed at least one horse. Because obviously, horses need rides too?

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    #34

    StainlessSteelRat Report

    Get a parking fine from a private company at the mall? Don’t panic. Those are just invoices, not real fines. They can’t really take you to court over them, and can’t charge more than what a parking spot costs. Win-win.

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    #35

    dweckl Report

    Contracts might seem set in stone, but their interpretation can change with new laws. That late fee you agreed to pay by the minute? It might be enforceable today... but not tomorrow. The law likes to keep people on their toes.

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    #36

    anon Report

    When you lend money and get a lien on someone’s goods, bankruptcy laws sometimes let you swoop in and claim more than you’d expect - even sharing assets with other creditors. It’s like corporate finance magic, but backed by the Supreme Court.

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    #37

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    Nope- , Bastian Pudill Report

    In a spooky area of Idaho, committing a crime might happen where there are literally no people to make up a jury. The 6th amendment says your jury has to be locals, but locals don’t live there. Legal loophole or just a weird oversight? You decide!

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    #38

    TexanInExile Report

    Lawyer says: You can only be charged with mayhem if your victim actually loses a body part. So, a scratch? Not quite dramatic enough.

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    #39

    Kindaclever Report

    If you just watch someone drown, the law doesn’t blame you. But start trying to save them and then quit? That’s when you might get into trouble. Moral of the story: Be all in or be out!

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    #40

    InVultusSolis Report

    Store security isn’t a cop. If you steal and they tell you to stop, you can just keep walking. If they touch you without a real reason, that might be a case of battery or false imprisonment. Don’t say we didn’t warn you!

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    #41

    meerkat_cousin Report

    If you’re slapped with a lawsuit and ordered to pay, Michigan’s got a quirky list of what you can’t lose, like family photos, a pew at church, certain farm animals, and enough fuel and food for half a year. Neat, huh?

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    #42

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    UncleDrunkle , Hyundai Motor Group Report

    Own a business? Buying a large SUV scores you a $25,000 tax CREDIT - not deduction - every year! Buy, sell, repeat, and you might actually earn money for owning a car. Check out Section 179 if you don’t believe us.

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    #43

    Wait, They Actually Ranked These Hilarious Legal Loopholes?!

    anon , cottonbro studio Report

    Here’s one to file under "Who knew?": You can’t arrest a married couple for the exact same crime. The law won’t let you put both behind bars for that.

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