45 People Reveal Their Costliest Mistakes To Date

Most of us make some questionable decisions with our finances at one point or another. Whether you impulsively purchased a blender that ended up sitting in the closet collecting dust or accidentally payed a scammer for “concert tickets,” you certainly weren’t the first person to make that mistake.

But unfortunately, sometimes the unwise decisions we make with our money end up having long-term effects. Redditors have been confessing some of the most expensive mistakes they’ve ever made, so we’ve gathered their most painful regrets below. Feel free to use this list as a reminder of what not to do with your money, pandas, and be sure to upvote the warning tales you think everyone should read!

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Losing my USB that had 50 Bitcoin on it. It was a prize for getting 2nd in a guitar hero contest hosted by the university I was attending.

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Freshman year of college, I thought my final exam was at 11:30. It was at 9:30. The exam was 40% of my grade, so I failed. I lost my scholarship and had to pay to retake the class.


Not enrolling in my company’s retirement plan that offered 5% contribution match. Lost five years of free money.


Not taking diabetes seriously cost me the vision in my right eye.

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Taking out a $5,000 loan to help my Mom with her very very past due bills.
Long story short, she ends up missing bills again and not learning her lesson.

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Went to an Ivy League school for nursing school. Now I have $90k of debt, literally no one cares where you went to school, my peers who went to community college or state schools are doing the exact same job and buying houses.

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Marriage to a narcissist. They always think they are right. I had a house and stock portfolio. We get asked to join in on a property investment. I was in love/gullible.
He was self-employed. I quit my job to be a SAHM which I don’t regret but there went that career and retirement plan. Then came the market crash and the business he ran suffered a huge hit. If I had $50 I would try to make it last a week to feed the kids and us. If he had $50 he’d buy steak. Once he made a pile of money but instead of paying down debt, he bought his kid a BMW. His ventures were always huge things; couldn’t handle being an employee… feast or famine but he controlled all the money. Divorce was long and drawn out and cost a lot. I had to drive the new expensive car that we could never afford until the divorce was final. In the meantime, the water pump failed and I had no choice but to fix it. Stupidest car choice ever. I feel like I got reset back into my 20’s financially, buying my first new to me car a year ago. Can’t afford a house because of the current market. Will never hand over financial decisions to anyone else ever again.


I lent an ex $5,000. Never saw him or the money again!

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My most recent was going to the doctor.

Went for a PAP smear. Asked 4 questions relating to my birth control and the vagina since I was seeing a gyno that day.

Received a $413 bill because the 4 questions I asked were “deemed outside the scope for the appointment”. Over $100 per f*****g question.

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Not caring for my teeth when young.

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Selling my last house – I invested more into it than I got out of it profit-wise when I sold it.

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I thought the US stock market would continue to plummet during the pandemic. But I was dead wrong and I lost a tremendous amount of money.

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Agreeing to not having the septic tank inspected before closing on our home. It was pumped recently so it must be fine, right? Turns out it was actually in bad shape and needed to be fully replaced. Over $20,000.


My father died in 2007 and left me and my sister $115k each. I used it to buy a new house.

I was 25 at the time. Didn’t know s**t about the process to buy a home. So needless to say I bought something I couldn’t afford. Then the market crashed in 2008. I lost the house and my inheritance.

I was more upset about blowing my fathers savings than losing the house. Lesson learned.

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Forgot to turn in FASFA on time and lost out on $5,000 worth of grants.. had to end up taking loans out. Tough lesson but it taught me to pay attention to deadlines.

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Solar System. $20,000.
Haven’t saved a cent.

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Started smoking at 14. On and of for decades, off for over a year now, but I must have spent enough to put a down payment on a house between the cigs and associated health issues. Don’t start kids, not even one!


Got in a fight while on an exchange program, ended up awaiting trial in jail for a year before being released. All loans and scholarships were cancelled.

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I answered honestly during a medical evaluation when I could have easily just checked no next to everything on the form and now I’m at risk of not being able to get the career I desire because of it. Even if I somehow do manage to avoid being completely denied, it still will have cost me thousands of dollars in psychological testing.


Left my laptop on the front counter of my work while going into another room. We are in a major homeless area. Came back 15 minutes later and mine and the receptionists laptops were stolen.

Fairly decent laptop more than the actual equipment, lost 10 years of work- scripts and plays, databases, artwork, and hundreds upon hundreds of lesson plans.

I now back up to the cloud all the time.


Unemployed in NYC for 3 months paying $4,000/month in rent.

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Tried messing with stocks out of boredom during Covid. Ended up getting into options and getting myself in a hole.

Instead of accepting my losses, I continued to make more risky investments, if you can even call them that. Ended up losing about $20k or so over the course of 8 months. I was engaged when I started getting into this and got married about halfway through and did all of this without my now wife’s knowledge.

We decided to start looking into buying a house and I had to come clean prior to applying for loans, so that I didn’t cause some long-lasting damage to us financially. It was a rough conversation and we ended up moving in with my in-laws as we try to recoup my losses and buy a house down the road.

Was definitely a tough stretch of life. Contemplated suicide and thought my marriage would be over before it even started. Thankfully, my wife had enough forgiveness to let me make things right. We both have good jobs and it wasn’t really a life-altering mistake when all things are considered. In therapy now to deal with the mental and marital issues that arise throughout the process.

I strongly advise anyone in a similar situation to cut your losses and have the difficult conversations sooner rather than later.


I made a one letter typo on one page of 18 export documents to Saudi Arabia. Container sat in port for two weeks before they told us they couldn’t clear because of the typo, and then I had to mail the amended documents to them because they don’t accept digital ones. Whole thing cost $8000.

It was my second week at the job and I never made a typo again.


When I was like 10yo I tried to call a TV game (clearly a scam) a Bunch of times. My mom’s phone bill came at around 200 bucks which was a lot for her at the time but she forgave me u_u worst thing is I was with my grandma and she kept encouraging me to call so we could win hahaha so adult supervision wasn’t enough I guess.


Buying into shallow beauty habits. I cringe at the thought of how much money I spent on hair, nails, club outfits, accessories, etc. All cause I was a vulnerable teen convinced by my society that I wasn’t beautiful enough and I needed to pay to get right. I can’t imagine being rich and feeling that way with the ability to go further and get surgeries….sheesh….that’s like an endless bill all cause society is in the business of making people feel like they’re inherently flawed…


My Amazon shopping addiction.

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Rushed into buying a car. Bought a salvaged vehicle that looked like it was in great shape. It drove fine, and it was exactly what I needed at the time. About a month in some frame damage was discovered that made it hard to steer, and there were NO F*****G AIRBAGS! I tried to turn around and sell it once I found out, but I couldn’t in good conscience sell an unsafe vehicle to anyone. So I pay $7K to install new airbags and have a few other things done. Once the car was safe, I felt like I could stick with it a little longer…then the transmission started leaking. I had grown attached to the car by this time, so I figured I’d at least get an estimate on fixing the leak, even if it meant dropping the transmission. Mechanic gave me a call moments after I dropped it off to tell me he was worried that if he dropped the transmission he wouldn’t be able to put my car back together, because the repairs on the car were so bad the transmission was essentially holding the whole front end together!! Sold it for scrap and basically lost $15K total on that terrible purchase.


Toss up between my last marriage and the time I ran my boss’s $3.5 million yacht aground on a submerged sandbar on the Intracoastal Waterway south of Charleston, SC.

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Bachelor’s in Anthropology, Minor in Music.

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Going through nursing school just to drop out when I decided I no longer want that career.

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I was on my honeymoon in Italy and had reserved and pre-paid for a rental car up front. When we arrived at the rental booth, everything was in order. The car was ready; all I needed to do was insert my credit card and enter the pin. That’s when I realized I didn’t know the pin code for my credit card. We were able to rent a car in the end with another agency, but by not remembering four measly numbers, we lost almost 900 euros.


Back in June I went to Africa for charity work and got sick drinking from a private well. I’ve been in hospitals for four months now and because most of that time my health insurance didn’t cover me outside of the country I owe the government $170,000 for covering my hospital stays in the Congo and Kenya.

I can’t leave the United states until I pay it off, but I’m already disabled from a car wreck a decade ago. I don’t know what I’m going to do.


Bought a house 50/50 with my brother in law. I was in university full time and working part time. So not a lot of extra time to keep track of the house stuff. First year ends, find out the join house account is over drawn by $3000, because they hadn’t been putting their share in the account. I pay that off, then the end of my second year… 3 leans against the title in his name…. over $45,000. Try to sell house for 2 years… no one will touch it, I have now taken out all loans I can to keep the house… bankruptcy, foreclose, lose over $250,000 dollars on what it was valued over what we had paid for it, not including the $15,000 down payment, and the $20,000 of reno’s I paid for.

Life lesson learned: never go into anything financial with family.


My wedding. I wanted to get married by Elvis in Las Vegas just the two of us but my fiancé had visions of wearing white tie and tails. I was insecure and just went along with it and the entire evening was SO stressful and one of the worst nights of my life because I was so worried about what everyone thought and if they were having a good time. It’s been 23 years and I can’t bring myself to even look at pictures. We’re happily married now but the wedding was just a colossal waste of money.


I bought an old overpriced Ford Bronco. That thing hated me with passion. Each time I would try to drive it, it didn’t want too or worked for 10 minutes and then pretended to die. I think he had something against Women because all the Men who tried said it worked like a charm.

Sold it for half I paid for. I hope it’s rusting in a field somewhere.


Not doing more research into hiring a roofing contractor. Paid $13k for the shittiest job ever. Flashing messed up, rotten sheathing not replaced, nails blown clear through the singles, reusing shingles when they started running low, water running behind my siding, no flashing around my chimney, it was a s**t show. They didn’t even cleanup, they left the old roof and nails strewn across my backyard and lawn. I pushed and pushed and next thing I know, he’s disappeared and I have water running in my house. My insurance guy refused to help and I had to hire an honest roofer and redo the entire job for another $13k. The second guy cut me a break since he knew I was in a bad spot.

Last I heard, that guy was banned from doing work for a few insurance companies, but he changes his name and moves to another city of state often. He would take the money, hire random migrant crews but not give them enough for material (shingles, caulk, flashing) and demand the jobs all be done in 1 day.


Second marriage. She spent a LOT of money without my knowledge, including my retirement account.
I’m 64 and will be working until I die.


I saved money for years and became doctor in my country (a poor one). Freshly graduated I came to the US thinking I could apply for more medical training and becoming doctor there too, but it requires to very expensive exams and courses. I ended up investing ~$45k in coming to the US, obtaining a visa, paying rents, paying courses, paying very difficult exams, doing clinical rotations, obtaining letters of recommendations. After 2 years of challenges I finally became elegible to apply, but the thing is, applying for medical training requires expensive fees to pay (capitalism! yeah!). 6 years passed I was never accepted into medical residency. Foreigners with visa cannot legally work in the US to cover expenses, which sucks a lot, and we have disadvantages to apply due to shortage of positions. I returned home after covid started.


When I started working in an operating theatre, I knelt down under a surgical microscope, promptly forgot my surroundings and then got up quickly and ungracefully. My back hit one of the handles, causing $10,000 worth of damage to a $500,000 piece of equipment. I was three weeks into my new job.


I didn’t know how to use my direct investing feature on my bank. I was looking to invest a few thousand dollars in Apple stock back in 2015. The 24/7 guy who answered the broker line could’ve placed the trade for me but said I’d pay less fees if I did it myself online. I said no that’s fine, I don’t know how to use the website, please place the trade.

He said he’d have to charge a small commission. I said that’s fine! But he kept saying no no you’ll pay too much and encouraged me to figure out how to do it online.

I couldn’t figure it out.

Is worth like 500% of what I would’ve bought it for.


Six months ago I moved across the country for a job that wasn’t as advertised and now I’m moving again. I don’t know if I can call that a mistake though, unless trusting any employer to be honest about a job is a mistake.

As far as pure mistakes, probably knocking over a glass of water and ruining a brand new expensive laptop. It even damaged the hard drive controller and I lost basically all of my writing from my undergrad days.


Invested in a brewery. Turns out these guys made great beers but were completely useless at running a business. They’re still operating but are going downhill fast, and my investment is going down with them. There’s absolutely no way I’ll get any of my money back.


Buying a $130K Tesla. So not worth it. May sell it in today’s inflated used car market and just get a Prius.

Second biggest? Buying some magic mushroom stock on the first day it went public. I’m bagholding and about $15K in the red.

For everything else, I have a midas touch.


Paid for my first car with a $10k line of credit. Paid the line down to $5k and then moved out of my parents place. Because I paid down the $5k so quickly, the bank increased my limit to $20k and over the next 5 years I maxed that s**t out. It’s been closed for three years and I still have $15k to pay back.


My parents have horrible horrible credit score and got scammed at a car dealership to buy a rebuilt truck $8000 over kbb value at a 18% interest rate.

Me. Wanting to be a good son co-signed on a brand new 2019 Chevy Silverado. Got them a 0% interest rate and put $5000 of my own money down to so that for them. With the promise they would pay it back.

3 years later they were more than 45 days on more than 20 payments. I’m now ready to put down another $5000 to force them to refinance it so I can have a future.
Source: boredpanda.com

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