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People Share The Most Expensive Mistakes They Have Ever Made


Nobody’s perfect and we’re all subject to making a mistake every now and then, but sometimes the minor blunders can end up having hefty financial consequences. From simple slip-ups to more deliberate flubs, mistakes can come with quite a price tag.

One Redditor asked the community what was the most expensive mistake they’ve ever made and the responses are wildly rueful.

Here are 24 stories of simple mistakes people have made that ended up costing them big bucks.

1. The Perfect Car: “Not me, but my best friend made quite a doozy. He was in a rush to buy a car and had saved a good $20,000 for one. He did a bunch of private inspections around our area, but never found one he really wanted. He finally found the perfect car that hit everything on his checklist: great mileage, full-service history, and in excellent condition. The only problem was that the buyer was on the other side of the country. Still, my friend was convinced this was the car for him and made the money transfer. The ad quickly disappeared and so did the car owner. It’s been 5 years and my friend has never caught the guy or got back his $20,000.” (Reddit user: Deako87)

2. Birthday Ball: “I was at my girlfriend’s parents’ holiday home for her birthday and was kicking around a ball with her nephews. My girlfriend came outside the exact moment I kicked the ball a bit too hard and it ended up knocking her to the ground. Not only did I destroy her $300 glasses, I also managed to smash the $2,000 watch her dad had just gifted her. He was not happy. Luckily, that story is from four years ago and we’re getting married in four weeks!” (Reddit user: thetoiletman1104)

3. Fired: “I made the worst mistake of accidentally leaving a stack of paper coffee cups next to the stove at the restaurant I was working at. Absolutely nothing in the restaurant was recoverable. The damage for equipment alone was a good several hundred dollars. Needless to say, I was fired and then put under investigation for quite awhile after.” (Reddit user: [deleted])

4. A glimpse of Luck: “I was drinking fairly heavily at a casino and managed to turn $50 into $700 on a slot machine. I had to pee, wasn’t thinking, and made my way to the bathroom. It was only after that I realized I had forgotten to cash out before leaving the machine. Tried to retrace my steps but casinos always have confusing floor plans. Decided to call it a night and just went back to my hotel room.” (Reddit user: secksydog)

5. Wrong Number: “Worked for a print advertising company a few years ago and was working on an advertisement that cost the client hundreds of thousands of dollars to have published for the year. I accidentally made a typo and inserted the wrong contact number for the business. The client ended up suing the company and ended up receiving millions. Oops.” (Reddit user: dcel8)

6. Free Housing: “I went to a school that did an annual draw for free housing. It was a big production and prizes were given out throughout the night with the big one being around $5,000 towards housing. I stayed for most of the night but then decided to go home and study. Guess who was called first? You have to be present to win. Shouldn’t have studied.” (Reddit user: Sharkbait_ooohaha)

7. Fencing: “I paid several hundred dollars to install a fence in my backyard. Two months after the job was complete and paid for, my neighbor complained that the fence was about 2 inches on his property and had to be removed. The fencing contractor said it had been done strictly according to a survey he procured. The neighbor ended up being right and by the time that was determined, the fencing contractor had gone out of business.” (Reddit user: Back2Bach)

8. Timing: “In my freshman year of college, I had a big exam that I thought was at 11:30 AM. Turns out, it was actually at 9:30 AM. The exam was worth 40% of my grade, which means I failed, lost my scholarship, and had to pay to retake the class again.” (Reddit user: fridayfridayjones)

9. Wrong Briefcase: “I accidentally grabbed the wrong briefcase from my office while I was rushing to catch a flight after work. Turns out, the briefcase I was in possession of had a loaded Walther P99 in it. Ended up getting a $5,000 fine from the TSA. Really stupid of me to say the least.” (Reddit user: cpsbooks)

10. Gastastrophe: “When I was a teenager, I had a part-time job at a Yamaha dealership that sold dirt bikes, ATVs, and motorcycles. I was told one day to deliver a Raptor to some address. Loaded up the ATV on the trailer and started driving the truck down the road. Noticed the truck was low on gas so I filled it up on my way. I made it about 1.5 miles before I realized the truck was running funny. Found out I put gasoline in a diesel truck. Was fired about 4 days later.” (Reddit user: Al_Vino_Vino)

10Diesel Truck Resource

11. Distraction: “I was driving down the street with some friends when a woman blew a kiss at me from a bus passing by. I leaned over to my buddy and said, ‘Hey! Did you see that? That girl just blew a’ CRASH. Ended up running into the little VW Fox in front of me, which resulted in him ramming the Audi in front of him.” (Reddit user: bassistmuzikman)

12. Skinny Dip: “I was traveling across the States with some friends and about 6 days into our trip, we decided to take a break in Miami. We got drunk in Wet Willies and met some girls who thought it would be a good idea to go skinny dipping at 3 AM. When we returned from our dip, someone had stolen everything. Our clothes, wallet, phone, and passport were all gone.” (Reddit user: CrazyRetread)

13. Busted Pirate: “I am one of the very, very rare people who actually ended up facing consequences for illegally pirating software. Apparently, a company traced a pirated software license back to my IP. I ended up settling with them out of court for $26,000 as well as an additional $8,000 in lawyer fees.” (Reddit user: timothycavinaw)

14. Ladder Damage: “I worked at an automated car wash a few years ago and I was cleaning the tunnel where the cars come through. I was up on a ladder to reach the high parts of the walls because it was a particularly slow day. Later, I was directing a car through when I realized too late that I had left the ladder in the tunnel. One of the spinning wraps got a hold of the ladder and slammed it into the side of the car being washed. To this day, it’s the largest single damage claim the company has had to pay.” (Reddit user: Grizzy_Greene)

15. Meat Freezer: “Back when I was around 10 years old, I wasn’t really thinking and unplugged my dad’s meat freezer to plug in my N64. I didn’t think it was a big deal and nobody else seemed to notice. Turns out, it was a big deal. Thousands of dollars of meat all ended up spoiled.” (Reddit user: IDFSHILL)

16. Coatimundi: “The most expensive mistake I ever made is one that my dad will never let me forget. I was on vacation with my parents in Mexico and attempted to pet a coatimundi, who ended up biting me, naturally. I had to get rabies shots, which were not covered by our insurance, and ended up costing my dad around $600.” (Reddit user: juiceboxhero1)

17. Flood: “I got way too drunk one evening while my roommates were out of town and had quite the puke fest when I get home. For whatever reason, I ended up puking in the sink rather than the toilet. I turned on the sink to wash down the vomit but forgot to turn it off and passed out. I woke up 8 hours later to find the sink clogged and my apartment flooded. I live on the fourth floor and the damage reached all the way to the first floor.” (Reddit user: Sorry_Sorry_Everyone)

18. Baked Skates: “When I first started playing hockey, I bought a pair of skates and decided to bake them to soften the material. What I didn’t know is that you were only supposed to bake them for a good fifteen minutes, not an hour. My new pair of expensive skates were absolutely mutilated and melted.” (Reddit user: acleverusername42)

19. Expensive Chair: “My first job was working at a local country club. In my first week there, I accidentally broke the leg off a chair. I figured chair legs break all the time so I didn’t really consider it a big deal. Apparently, it was a big deal. This chair was over $2,000 and I lost my job that day.” (Reddit user: richmondrob)

20. Dream Apartment: “I was living in this incredible apartment downtown that was a steal for the price. Met a girl who I thought was the one and asked her to move in with me. That was an expensive mistake. She still lives there, I do not. Miss that place.” (Reddit user: Cat0zzy)

21. Canoe: “I was on a canoe trip and we were heading down a river with a number of large rapids. I, like an idiot, forgot to make sure my backpack was closed so that if we flip, it wouldn’t float away. We flipped and my bag goes floating down the river with the $500 worth of contents inside everywhere.” (Reddit user: NatD20)

21Wilds Of Ontario

22. Hefty Speeding Ticket: “I got a ticket for doing 90 in a 55. This wasn’t just any ticket. Ended up with huge fines, lost my license, had my insurance premiums increased, and to top it all off, I was working as a bus driver so I lost that job as well. Had to pay for quite a few Ubers for the following 6 months.” (Reddit user: Cjyogi)

23. Fireworks: “Being young and dumb, I was acting foolishly when lighting off fireworks. Ended up blowing up my hand and the surgery to fix the 5 bones cost a cool $27,000. That cost isn’t even including the two casts, pain meds, physical therapy, and two braces I needed to get.” (Reddit user: Gusgus73014)

24. Expensive Fall: “When I was a teenager, I got way too drunk and ended up face planting onto a glass coffee table. Not sure if that qualifies as a mistake as much as it does an accident, but it definitely cost me. Had to pay $5,000 in dental work just to have a normal smile again.” (Reddit user: [deleted])


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