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47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
CuriositiesSEP 9, 2025

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity

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There are rules to follow in every part of life. You better abide by the rules of the road when driving, and if you want to keep your job, you must follow your workplace’s guidelines. Even when you’re enjoying dinner, don’t forget to keep those elbows off the table!
But occasionally, people spot little ways to work around the rules to benefit themselves. Redditors have been sharing the most brilliant loopholes they’ve ever discovered that they happily exploited, so we’ve gathered their most amusing stories below. From clever ways to get free food to tricks that allowed people to save hundreds of dollars, enjoy reading through these tales. And be sure to upvote the loopholes that you would have gladly taken advantage of as well!

#1

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
I used to work at papa johns to pay my way through college. There was a contest we had where if you got someone to "upsize" their pizza from like a medium to a large for an extra $2, you got points towards movie tickets. A large was simply $2 extra normally anyways. Anyone that ordered a large, I simply put in a medium and "upsized" it. I won every f*****g week. My coworkers didn't notice this obvious loophole and it didn't cost the customer extra so I didn't have a problem with this morally gray area. Free movie tickets every week was a huge in college.
68points

#2

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
I didn't find this loophole but my friend did: A few years back, an online store had this promotion where whoever spent the most money over a month would get free round trip airplane tickets to anywhere in the world. My friend (who's a f*****g genius) found that one thing you could buy on the site was a gift certificate. So he bought a $25 gift certificate and kept spending it on another $25 gift certificate. So he ended up spending $25 on round trip tickets to Australia.
53points

#3

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
Back in the 1960s, the school district in my hometown was broken up and absorbed into the surrounding districts.
Fast forward to 2003. I'm applying to colleges. I discovered that there is a scholarship fund for people living in that old district's area. The district is gone, but the scholarship still exists!
I applied, and got the scholarship. I don't think there were any other applicants.
53points

#4

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
When I was in high school I applied for a summer job with the county. As part of the "unbiased" application process, each applicant was asked to take an intelligence test.

The test consisted of about 80 questions. Each question was four or five line drawings, and you had to put an X in the box next to the one that didn't belong. Pretty easy.

I happened to notice, though, that the test paper was two part, which is two sheets of paper that are attached together back-to-back with a sheet of carbon paper in between. I could peel the sheets apart and look inside: the second sheet just had a bunch of boxes printed on it, and I could see from the first few questions that I'd answered that the Xs I'd marked ended up in the printed boxes on the second sheet thanks to the carbon paper.

So, I did all of the questions with obvious answers, and if I was unsure, I just peeled the paper apart, noted where the box was printed on the second sheet, and made sure I got it right.

Of course, I got 100%. I figure that if you can cheat on an intelligence test, you're pretty smart.
52points

#5

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
Not very impressive but at my highschool we had to wear a buttondown and a tie to class every day. One of the kids realized that they never specified what kind of buttondown it had to be so he wore a hawaiian shirt to class with a tie. Technically it met the dress code so it stuck.

Pretty soon most of the school started wearing hawaiian shirts with ties to class. We looked like a bunch of ridiculous Jimmy-Buffet-goes-Mormon types but it was worth it to spite the system. They changed the rule to ban hawaiian shirts a week later.
52points

#6

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
My brother once yelled "last one to jump in the pool is gay," and then jumped into the pool. However, I figured out that if I did not jump in then technically he would be the last one in the pool, and he is still gay to this day.
51points

#7

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
My college campus had a cafe with Deli and salad bar, the deli sandwiches were way over priced, like 8$ for a standard turkey sandwich. But the salad bar was very reasonable. (Subsidized to promote healthy eating)

So I found that the Salad bar had all the same ingredients as the sandwiches, the meat was just shredded. The Deli would sale slices of bread for $0.25 each, so I would just buy the bread, load up and weigh my “salad” and grab some free mayo and mustard packets, then build my own sandwiches for under 2$. Used that trick for my last two years.
50points

#8

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
Walmart ran a promotion years ago on their groceries. Find a lower advertised price, they'll give you double the difference back. So, I'd go through the Sunday ads looking for items that end up free. For instance , items where Walmart would charge $2.99, but Albertsons had them on sale for $1.49. The difference is a buck fifty, so doubled I'd get $3 back on each one i bought. I would get tons of free items! Granola bars, yogurts, cereals, cake mixes, fancy breads, lots of things. tons of different foods. Lots went to the food bank, but I ate like a king for a year and a half.
45points

#9

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
My dad figured out a good one back in the 80's. Just like they do now, back then cable companies would give you a free weekend trial of a premium channel (HBO, Cinemax, etc) in an effort to get more people to sign up for those channels and pay more. However, our cable company's method of giving you access to the special channel was to send a signal to your cable box which unlocked the channel. To turn off the channel at the end of the free trial, another signal was sent. My dad figured out that the signal to lock it was only sent for a short period of time, so before the end of the free weekend, he would unplug the cable box and then plug it back up the next day. Since the box never got the signal, we would have a free premium channel for a while. Usually after a month or two it would get shut off so we'd have to wait for the next free trial weekend.
42points

#10

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
I was working maintenance at McDonald's when they did a Best Buy bucks promotion. Large sodas and large fries had a scratch off that was worth at least $1 at Best Buy.

I would go through the trash daily, pulling out all the discarded scratch offs.

I got a free computer that year for Christmas. I also had the poor cashier at Best Buy in tears. She had to manually scan each scratch off and verify the dollar amount.
41points

#11

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
Local radio station had a contest where you call in when they play same artist back to back to win a prize. Turns out they had a "now playing" and "up next" feature on their web site. My girlfriend at the time would start calling in before the second song even came on. Won tons of prizes ranging from concert tickets to a laptop.
39points

#12

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
There was a drink machine in college that was $.75 for a juice. If you put a dollar in it gave you 5 quarters in change. I got a juice everyday for months before they finally fixed it.
38points

#13

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
When I was a freshman in Highschool my geology teacher told us we had to make a presentation about igneous, sedimentary, and metamorphic types of rock. He explicitly said he didn't care how we did our presentation, but it needed a visual. I asked him to specify how much he doesn't care about the content of the presentation and what is allowed to be up for interpretation. He clarified that you could do a song and dance for your presentation if it was relevant to igneous, sedimentary, and metamorphic.

I did an interpretive dance.

Relatively no effort, a sprinkle of shame, and a reluctant A-.
37points

#14

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
When I was a kid my town had a "slow bike race" tournament. So the objective was to cross the finish line in last place, the key is to keep your balance. Well the rules stated that each time your foot hit the ground you would have 5 seconds subtracted from your time. But it didn't say anything about keeping your foot planted on the ground. So once the race started I just stood there and waited until everyone else finished, waited a good 5 seconds after that, then just rode across the finish line.

Ultimately they didn't let me win which I think is horse s**t because they wrote s****y rules and a 12 year old found a loophole.
35points

#15

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
My high school had a stupid rule that banned you from attending prom if you went to a saturday detention that semester. I got in trouble and was assigned to Sat. D-Hall, but my girlfriend really wanted to go to prom. I just kept skipping it and they kept adding more until they rolled it into a day of actual suspension. They had no rule barring you from prom for an out-of-school suspension so I got a day off and took my girl to prom.
34points

#16

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
We rented an apartment in a Spanish resort via a travel agent. We had to pay a deposit for the key but that would be refunded when we returned the key.

At departure there were lots of people that had thrown away the paper they gave you when you paid the deposit. So no money back but they did take back the key. That was just a scam they had going.

I knew we still had the paper but it was in out suitcase and I didn’t want to go searching for it. So when I presented the key the asked for the paper and “no paper, no money”. So I calmly said: “Then I keep the key”.

The man’s brain went full-stop. He looked at his partner, they talked to the travel agent present. Huge panic. So I explained again: no money, no key. It was as special security lock so it would cost them a lot more to make a duplicate.

The agent, who was in on the scam, asked what I was going to do with the key. “Nothing”, I said. “You keep the deposit, I keep the key. No problem for me.”

I got my money back and they got the key. I told everyone who was behind me in the queue what to do.

I’m in IT, looking at procedures for loopholes is my job
33points

#17

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
Math lesson

Teacher: For this project you will work in groups of less than seven.
Me: Sir, one is less than seven.
...
Teacher: Ok, fine. Do it all yourself then.

I got 70% on this assignment, highest mark I ever got in group work.
32points

#18

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
My university was trying to encourage people to walk so if we download a specific health tracker that's connected to our account, it would convert steps into points. The points would get you stuff like free coffee, mugs, discounts for stuff and the most expensive prize: a university hoodie which costs about £30.

Now, the health tracking app is pretty basic, it won't let you log your steps manually however it does let you connect with other health apps. I found a health app that would let me add in the steps and I logged in an equivalent of 50 km a day and in a few days of logging manually, I would get myself a hoodie or two and I didn't get caught.

However, I told my friend about it, and he really perfected the method of getting more steps a day, because apparently there was a hidden physical limit to how far a person can walk in a day, but he managed to trick it by setting his height to be 1 cm and because the shorter you are, the more steps you need to take to cover the same distance.

In the end he claimed about 10+ hoodies and he would just get them for anyone who asks. The uni found it suspicious, so he received an email telling that the activity had to stop unless he could provide evidence that he walked that much.

Another friend had a different method. You get points just by being friends with them on the university health website. He also found that he could access a list of everyone who had an account in that website. So he made a python script that would automatically send a request to everyone, earning him points.
30points

#19

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
Our local Tesco accidentally had 2 offers for Terry's Chocolate Orange at once, so if you bought 4 (or a multiple of 4) they GAVE you 50p.

Tried not to a***e it since if they noticed they change it, but bought 4 chocolate oranges with other stuff through the self checkout every day for almost 2 weeks before they corrected it.

I planned to save them for Christmas presents but Christmas was 4 months away, and you know how delicious Terry's Chocolate Oranges are.

EDIT: To all non-Brits out there since apparently they're not sold elsewhere: they're f*****g delicious. If you ever come to England do yourself a favour and buy one, or find a "foreign confectionery" shop and hope they sell them there.
30points

#20

47 Loopholes So Good, People Just Couldn’t Miss The Opportunity
In third grade, our teacher had to leave the room for some kind of emergency, and left one of the students in charge (the "teacher's pet", of course). The teacher said that we were not allowed to talk, and if we did, we would have to write 100 times "I will not talk in class when instructed not to", or something like that. Well, my friend and I were bored, so we started writing out the "punishment", and when we were finished, proceeded to talk to each other until the teacher returned. The student left in charge wasn't sure what to do. It was hilarious.
30points
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