'I Smoked My First Cigarette': The Most Expensive Mistakes People Have Made.

Saving up money is already difficult enough. Now imagine having to deal with unnecessary expensive mistakes on top of that. But mistakes are mistakes and you learn from them. Hopefully ... 

In this article, people share the most expensive mistake they ever made and completely regret it.

[Source can be found at the end of the article]

I paid several thousand dollars to have the backyard fenced in.

Two months after the job was complete and paid for, a neighbor complained that the fencing was about 2 inches onto his property and that it had to be removed, even though the fencing contractor said it had been done strictly according to a survey he had procured.

Turned out the neighbor was correct. By the time it was determined, the fencing contractor had gone out of business.


Had a part-time job as a teenager at a Yamaha dealership that sold dirt bikes, ATV's, and motorcycles. I was told one day to deliver a Raptor to some address. Well, I loaded the ATV up on the trailer and took off in the truck down the road. I noticed that the truck was low on gas so I pulled over and filled her up. I made it about 1.5 miles down the road and the truck started running funnily and eventually cut off... I had put regular gasoline in a diesel truck. I was fired about 4 days later.


I was going through a bad time and thought buying a new sports car would solve my internal issues. It didn't and I was stuck with debt. It was sweet to drive and I loved the looks it got, but it did little to resolve my actual problems. I paid it off and sold it 3 years later for a net $30K loss.


A guy I knew during college decided he was fed up with all of the work we had to do at school and quit. When we were already done with 3/4 of our time at school, he also quit the coffee shop job we happened to have together randomly.

I graduated less than a year later and fortunately found a job right out of school. He nearly lost his apartment, got another job at a different coffee shop, and still had to deal with all the college loans he'd already taken out.


I was driving down the street and a woman blew a kiss at me from a bus passing by. I leaned over to my friends to say, "Hey guys! Did you just see that? She blew me a.." CRASH ... ran into the little VW Fox in front of me and then he rammed the Audi in front of him. That sucked. I totally destroyed the VW.


Getting involved with an alcoholic, thinking I could change them. Spent about $20k in rehab fees for her. She was drinking within three hours of checking out. I honestly had no idea that she even drank until we lived together. 


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Married my college girlfriend. Turns out the things you look for in a woman at 19 get old at 35.

She was a stay-at-home mom who didn't want to mother. So I bit the bullet and left with my daughter.

It cost me well over $700,000 and counting, but I have my kid and she's worth every penny.


I was travelling across the States with my friends and 6 days in we got to Miami. We got drunk in Wet Willies and met a couple girls and we decided, at 3am, it was a good idea to go skinny dipping. We all got naked and ran into the sea, leaving EVERYTHING on the beach. We got out of the sea after messing around for a while and someone had stolen all our stuff. They took everything.

I lost my wallet (with $300 in it), my iPhone, my passport and not to mention ALL of my clothes.

We all had to run back to our hostel naked which was a good mile away.

Still got laid. But I'm an idiot.


$100k on two degrees.

First was $60k, and was basically useless due to a combo of the job market when I graduated (5 people per 1 job) and not working while taking classes.

Second was $30k more and $10k in interest since the old ones were deferred too long. Then I found out (as I'm about to graduate) that the state can cover my tuition as part of rehab/job training due to disability.

I finally got a "real" career-oriented job in my field... and 9 months in, my vision deteriorated to the point I'm on long-term disability and no job.


I pretended to hurt my back when I was a kid in order to get out of going to school. So, mom takes me to the doctor, I get an x-ray taken, and as it turns out there was actually something wrong with my spine. Didn't hurt at all, but they put me in a torso brace for 6 months anyway.

Remember, if you're going to fake sick, just stick the thermometer under hot water instead.


Missed a 8 road-tax payment on a motorbike that was stolen. I also moved addresses so never got a single letter. It tallied up to nearly 8,000 after 7 years of my not paying it, 25 per letter + 15 admin fee + a monthly, then weekly and finally it went to a daily penalty.

It was almost the most expensive mistake. I got away with paying only the 48 for first letter + admin fee + the outstanding balance of 8.


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I dropped out of college for a year because I was just lost. No direction, not sure what to do with life. I was at the most expensive school in the country.

Oh and my parents were paying for most of it.

Had to pay for 2 years of college on my own, etc. $60k of loan debt. Paid a lot out of pocket, too.

Don't just go to college. Figure out what you want to do.


Do you remember the Find The Impostor M&M ad campaign they had going on in the late 90s? Where if you found the gray M&M you won $1,000,000. Well Im about 9 years old, sitting in the back of my parents car just popping M&Ms in my mouth, when it happened to catch my eye, but it was too late. It was already on its way in my mouth and crunching down. I pick out a small sliver of it, and sure enough it was gray. My parents never believed me, they said I just sucked the color off. But I know I ate a million dollar M&M.


I was on a canoe trip down a river with a number of large rapids and I forget to make sure my backpack was closed and stuffed in the boat so if we flipped it wouldn't float away. The other person in my boat said we shouldn't run it with gear but I said we'd be fine and he relented. We flip and my bag goes floating down the river with about $200 worth of gear in it, the worst part is my wallet was in that bag with most of my IDs. 


I accidentally left an asiatic Lily plant out in my apartment when I went to work. When I came home, I noticed my cat had chewed a bunch of leaves off of it, and possibly swallowed some. I immediately looked it up online and saw that lilies are extremely toxic to cats. They can cause kidney failure from ingesting only a small amount. I had to rush him to a 24 hour emergency vet, where he had to be treated with high volumes of fluid via IV for 48 hrs. My big floof made it out alive and I couldn't have been happier he was ok, but the whole ordeal cost me close to $3,000.


This was at my first real job out of college doing data processing for a print and mail shop. About 6 months after hire, I copied and pasted address data, but I was off by one row. We discovered the mistake after 10,000 booklets had been addressed and the whole lot had to be re-printed. A $20,000+ mistake.

I drafted a proposal for a new Q/A process before I was called into the owner's office. When he was done yelling and cussing at me I accepted responsibility for the simple error and explained how we could avoid the same and similar issues from occurring again.

The damage was about $20k. 

He didn't fire me and I learned one of the most important lessons in my career: how to handle failure.


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I borrowed so much for tuition, went to the wrong school, and there were so many clues that I was at the wrong school the first semester, but I chose to ignore those clues. I stayed for years. I changed my major too late into my program...I just made a LOT of bad choices. Now I have a lot of debt that will prevent me from probably ever owning a house.

So learn from me! Pay attention to the signs around you! If you don't feel like the school is right for you, don't stay! And don't borrow your way through school! Scholarships are available! Listen to your gut. I wish I had.

Oh, I also threw away a million-dollar game piece because I thought it was too obvious to be a winner. It was in the early 90s and would have totally paid for college! I was so pissed at myself. Now I keep all of those stupid game pieces until well after the games are over.


My best mate made a doozy. He was in a bit of a rush to buy himself a car. He had a nice little nest egg of $20,000 put aside just for this purchase. He did a bunch of private inspections around our area, but he just couldn't find one he wanted.

He finally stumbled across the perfect car for him, great mileage (all country driving), full service history and in excellent condition. The only problem? The buyer was on the other side of the country. For whatever reason, my mate decided to contact the dude and organize the purchase. After the money transferred, the ad disappeared and so did the car owner.

I just have no idea what was going through my mate's head. It has been 5 years and they never caught the fraudster and my friend never got his $20k back.


Taking the wrong backpack out of the trunk of a car that I hitched a ride with. I wound up with a bunch of girl's clothes I couldn't wear and without all the traveller's checks in my pack. Made for a difficult summer.

And a quick explanation about the traveler checks for those who think it should have been easy to get my money back:

This was late 60s, no credit or debit cards for teenagers, no mobile phones etc. A lot of people scammed with travellers checks and almost certainly the person who got my pack managed to use all or some of my checks. Banks were in no hurry to reimburse.

In addition, I was dumb as a rock and had my ID and the paper with the numbers of the checks in my pack as well. Thus no chance I could get the money back while on the road.


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Working as a teller at a bank, I made a mistake on a change order for a business customer. She had called in advance so I had everything prepared and it was sitting in my bottom drawer. When she arrived and gave me the money I counted it, put it in my top drawer then put her change into her bank bag. 

Somehow an extra clip of 10s ($250) got into the bag as well. I knew that's where it went because it was only my second cash transaction of the day.

The bank called the lady, who was the manager (I guess) at this diner nearby. She denied having been overpaid. This happened on a Thursday, the following Monday I was fired. 

I was unemployed nearly three months after that, depleting all my savings, racking up credit cards, and taking a crappy installment loan with exorbitant rates. 

I've only just recently found a job. Fast food, paying $7.50 an hour. I haven't been able to pay this month's rent or any bills. One of my bank accounts is overdrawn by nearly 400 dollars. I feel like I'm never going to get out of this hole. All because I made a mistake and the lady couldn't be an honest person and bring back the money.


Trying to get into Lolita fashion "because I wanted people to think I was a princess."

I was too big for it at the time so nothing fit. But I still bought expensive stuff from Angelic Pretty anyway and squeezed my butt into it. This resulted in me CUTTING UP A PAIR OF $60 TIGHTS from a now-discontinued set to wear them as "knee high socks" because they wouldn't fit as tights. Guess what? They didn't fit as knee high socks either. 

My friends stopped me from making mass frivolous purchases of the more expensive stuff, but if it weren't for them I absolutely would have been a stupid little idiot and bought 3 $400 JSKs that an unemployed college student could not in any way afford. And that I wouldn't have fit into in the first place.

In addition to that, it turned out I hated the outfits in the first place and just wanted them "to be a princess." I'm for the most part a boyish dresser, with touches of femininity here and there. I'm happiest in gamer tees. I'm always outside. I'm running and playing 80 percent of the time. Where the heck am I gonna wear expensive Lolita clothing?


I'm a college student, and as a result money is tight. Well last Thursday, my fraternity friend came over to my townhouse. When he got here (10:30), all the visitor spots were taken. He was only gonna be over for 45 minutes to an hour, and it was late at night so I said ,"Just do it. Nothing will happen, and if it does, I'll pay the fine." So reluctantly he agrees and parks and we go inside. About an hour later, he's leaving and we go outside to find his car is gone. 

So we drive my car to the impound lot around 11:30 and go inside. I ask the lady working the counter when the car got towed, and she said at 10:55. The car was parked for 25 minutes before getting towed. I tried to persuade her into letting us take the car, but bless her heart she had to do her job. Five minutes later, my friend had his car back, and I was out $160 (not a lot for some, but I'm broke as is).

Moral of the story: dont mess with towing companies. 


Leaving my keys in the ignition while I waited for someone to pick me up while drunk. $40 bail, $200 to get my car out of impounding $4000 lawyer, $320 for a negligent driving fine, losing my license for 60 days, trying to ride a bike for transport when I fell off and broke my arm: $50 hospital visit, $2000 loss of wages (couldn't work), $100 license reinstatement fee out of state, $15 for a driving record, $75 for a psych evaluation, $500 reinstatement fee for my home state, and $300 paying for rides.

A combination $7490 mistake.


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I used to have a new car bug. I didn't really care what I owed, as long as I could make the payment. I had rolled about 4 vehicles worth of negative equity into this latest truck. The lender capped what they would loan at 125% of sticker. We were sitting at 127%, so the dealer actually started adding accessories at dealer cost (but full retail value on the loan) in order to drop the vehicle back down to 124.5% of sticker. So I signed on the line for $47k, 0.9% for 66 months.

Fast forward 12 months and my wife loses her job and I had to change jobs and take a pay cut. We lost 40% of our income. I called up the lender and told them I wanted to do a voluntary repo. They thanked me for not trying to play hide and seek with it, and took the keys.

Vehicle goes to auction, sells for $18k wholesale. I'm on the hook for about $20k difference (I had made one year of payments on time).

I get a 12 month agreement from them on a payment plan for around $400 a month. At the end of 12 months, they'd take a cash payment for 50% of the balance. I liquidated and managed to make that payment on time. All up, I burned $25k on that truck (and the negative equity from the others), and completely changed my habits.

Now, I only buy cash cars. I've been on my current one for 8 years now, and it cost me $8k cash.


About 15 years ago I met a girl, we'll call her Betty. We met online and got along well. Things moved along well, then she lost her apartment. I had room so asked her to move in. Mistake 1.

We're living together, I think we're both feeling "meh" about the relationship but weren't ready to break up. I should add she didn't want to break up because I was paying the bills and she had no place to go, and no money due to her truly impressive ability to lose jobs.

So we're going along and all of a sudden she gets sick. We're talking major surgery sick. She had no health insurance but I did through work. So what did I do, being the stand up guy that I am? I married her to get her on my health insurance so she could get better. Mistake 2.

She had multiple surgeries and procedures, and of course couldn't work. I was lucky enough to have been given stock for birthday/ Christmas gifts by my father and they'd gone way up. I was sick of apartment living and wanted out of the city and back to the suburbs.

I cashed in all the stock and bought a small house for us to live in. She was getting better physically and began working in an office. We still weren't getting along but we weren't not getting along either. 

She needed a car to get to and from work as hers was a piece of crap. Her credit was a mess so I co-signed a car loan thinking that she could afford it if things at the very least stayed where they were for her financially. Mistake 3.

Some time goes by and I begin to suspect there's some funny business going on with her and her boss. Lots of texts, talking too much about him, late meetings etc. The usual signs of a cheater, I suppose.

I call her on it and she says she wants a divorce. I didn't have any proof of said cheating at the time so she filed due to irreconcilable differences.

Needless to say, I got my butt kicked in the divorce. To make matters worse, she was chronically late on the car payments which killed my credit. I managed to keep the house, thankfully. It did cost me though.

A few months after the divorce, I find out that she and her boss were living together and he'd left his family.

The boiled down to the most expensive mistake I've made was getting married for the wrong reasons. I hope I did get lots of cosmic karma for being a stand up guy and getting her through her illness.



We are told that, if you're not confident, you should just "fake it til you make it."

This is great--in theory. In practice, sometimes "faking it" can have extremely real and terrible consequences, which these people found out the hardest of hard ways.

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