People Share The Most Expensive Mistake They've Ever Made


There is not a single person among us who hasn't screwed something up royally. It's just a part of life. Sometimes those mistakes are pretty costly. They may cost relationships, time, etc. - and sometimes they end up costing money.

A whole heaping buttload of money.

When this Reddit question popped up:

What's the most expensive mistake you've ever made?

we weren't really expecting the variety of answers we got. Sure we figured maybe some lost stock or a shattered antique vase or something, but we weren't ready for getting scammed by hippies, losing almost a million dollars worth of emeralds when they vanished from your pocket or accidentally causing a divorce over some cabinetry.

That's life, though... expect the unexpected. But maybe don't carry hundreds of thousands of dollars worth of gems in your pocket like they're no big deal?

Just sayin'.


Wasting my $11,000 inheritance on god knows what, I don't even remember. You spend a little here and a little there and next thing you know you're broke and homeless and could really do with a safety net but you were careless and it's now gone with nothing to show for it.

- Mad_Squid



I was in a hotel. Took some sleeping pills right before taking a shower. Turned the water on to let it warm up.
I wake up several hours later and the floor is soaked.

I was on the 7th floor. It was a standing shower. The maintenance guys who first showed up weren't even surprised. They said, "Yeah these showers suck, this happens more than you'd think."

When the building manager talked to me he acted like I had personally flooded his own home and slept with his wife. Estimate was around $30K in damage, that doesn't include all the room changes for everyone below me.

- torchoflittleton

Hippies In A Bus

A few years ago, I was working at a media production facility situated on a large industrial lot. The person who owned the lot was letting his friends, a hippie couple, park their bus / home near the back of the site, which was where my studio was. The people who associated with our facility were generally well-connected / trustworthy / successful people, so I didn't think much about it, and I became friends with the couple over the course of a year. I found out they couldn't leave the lot because their bus wasn't repairable.

One day, the boyfriend told me they found the perfect bus for sale, so I drove with him out to the lot where it was being sold and inspected it with him. The problem was he and his GF wouldn't be getting paid for a couple weeks, and they needed to confirm the purchase in a few days or the owner was going to sell it to someone else. You can probably see where this is going.

The boyfriend asked me if I could float them $1000 dollars until their next payday, to buy the bus and to get the old one towed away from the space next to my studio. I had just been paid decently for a project and had become good friends with the couple by this point, so I said yes. The boyfriend offered to give me a broken old motorcycle as collateral, which I appreciated but told him to just get me the money the following week.

When I returned to work the next day, their old bus had been towed but there was no new bus in its place. Just a decrepit motorcycle leaning against the fence. I tried to get a hold of the couple but my messages went unanswered, calls went to voicemail, and eventually their number was disconnected. I sent a message to their joint Facebook account and after a month or so they replied, saying that the motorcycle was the trade we agreed on for the $1000. There were some angry messages back and forth but it was pointless. They skipped town, cut contact with the owner of the property, and I never saw them again.

There's a Bruce Springsteen interview (I think it was with Marc Maron) where he tells a story about getting swindled in New York after a show. He said it forced him to reassess the energy he was putting out into the world, since it had made him such an easy target to be taken advantage of. Needless to say, I had to make the same reassessment about myself!

- superpyramid

White Pine

Not expensive for me, but for the state. I used to work for the division of forestry dispatching firefighters to wildfires. Two roads on opposite end of the county had extremely similar names. Took a call from a guy reporting a fire on White Pine Road. We were already on site for a fire on White Pine Lane. I said "White Pine? We have a crew on the scene already, sir!"

Came in the next morning and saw that there was a new fire on the map. White Pine Road. 700 acres. Whoops.

- heysuess

Health Insurance

I didn't get health insurance at work because it was too expensive and then I got 3 different cancers in 1 year. Oops.

This happened at 26 years old in the good ol' US of A. Cancer is all in remission now!

- ayelenwrites

A Fence


A fence.

Met this girl. Fell in love. Moved into her house. She wanted to fence the yard. I wanted her to be happy. We had a very nice fence installed. It was financed. We were saving up money every month to pay the fence off and it would have been 0% interest. Everything was working great. Then she cheated on me and gave me chlamydia. I saw her trying to put antibiotics into my food is how I found out.

Then I moved out. Then she took half of our savings account. Which was already fcked up because I put way more than half in there but if that's the price it takes to get her out of my life. Fine!

Then she says she isn't going to have enough to pay off the fence within the 0% interest period... because she took half the savings I also don't have enough. But it's in my name. So I was left holding the bag on a fence I did not own. I paid it off last year, but the whole thing ended up costing an insane amount of money.

F*ck her. F*ck chlamydia. And f*ck fences.

- outrageous_claims

Driving Tired

12 years ago I fell asleep at the wheel while working my job ~8:00 am after having been working already for 4 hours.

I was on a country road, went into the ditch and hit a culvert that flipped me 5 times as I went back across the road the other way.

Truck was totaled obviously, and I destroyed a row of hedges on someone's property. I'm not sure the total damage but the company's insurance covered it all. Definitely over $30g's though.

I came out with no injuries. No other vehicles or people involved (beyond the owner of the hedges, who came out and helped me call 911). Super lucky, and now I would never drive that tired ever again.

- btwork

Emerald City

I am a Gem Dealer and usually deal in fine colored stones. I lost 850k worth of emeralds in an exhibition while walking around with my friend. The emeralds were in my pocket in a plastic zipper and they were never seen.

- avidude99


I took out a $700 loan from the bank and lost it all in a Youtube MLM scheme in 2008 when I was an idiot in my early 20s.

Then I spent the next 10 years not paying off that loan and messing up my credit.

$700 may not seem like much to someone in a first world country, but I live in a 3rd world country and that is the equivalent of like $2,500-3,000 dollars in America at the time.

- Ahmneo


Shot my dads pistol at a rock wall, ricocheted Into my leg, $20,000 hospital bill.


$16k + Half

I screwed up a kitchen cabinet order when I was working at Home Depot. It was a $16,000 order and I checked the wrong box for the color/finish the wood was supposed to have.

The couple got a free kitchen from Home Depot, were out a usable kitchen for another 8 weeks while the order was being processed and long-story-short the got a divorce over all the stress.

So $16,000 + Half of everything one guy owned.

- official_fox_news


This happened when I was eight. I was playing with a neighborhood friend on the street in my neighborhood. We were throwing rocks and were having a contest to see who could throw them farther. I remember I went, "I betcha can't throw it this far," and I threw it 45 degrees off from where I was aiming.

It went through someone's window shield. My family had to pay $400.

- RandomPenguiness

Murphy's Perfect Storm

As a lawyer I missed a court deadline. The court cleric told me the case was dismissed when it wasn't, and the letters to the contrary didn't reach me due to our mail room messing up. Perfect storm of Murphys law sht cost 80K. Oops. Thank goodness for appeal being a thing.

- shurdus

Clipped A Wing


Towing an airplane at work, there was a lot of noise on the ramp, and the guy watching the wing tip for obstacles wasn't paying attention. Backed the wing into and over a set of mobile stairs, did about $5 Mil of damage in parts alone. spent the next two weeks repairing it and the plane flys to this day. Government job, didn't come out of my paycheck.

- biorad1

Boring Old Man's Car

I'd saved up to buy this Lexus I've always wanted. Im not bragging the car was 15 years old and very cheap as it's a V8 and fuel is really expensive here in the UK. I'd wanted one for so long and now I finally had one. As soon as I got it I started putting money into it to make it as good as new, mostly preventative maintenance and a few little repairs. Me and a friend were planning a European road trip in it so I wanted to make sure it wasn't going to leave us stranded.

I had not long for the car in a good condition when I lost control on a corner and crashed sideways into a lamppost. The most important thing is that nobody got hurt, and I'm so grateful because it could have been so much worse.

All that money, down the drain. It may have seemed like a boring old man's car to others but I loved it. I don't treat myself to many luxuries as I try to be good with money, but that car was the one nice thing I allowed myself to have. I came to love my boring commute as I was in my favourite car. I looked forward to the end of the day as I got to drive it home. I offered to collect my friend at the airport a 5 hour drive away because it was an excuse to drive more. If I couldn't sleep, I'd go for a drive. And now she's gone.

I managed to scrimp and save and just recently got a replacement. It's a bit of a dog compared to the last one, but I'll get it there eventually. But because of my silly mistake having one of these cars had cost me at least twice as much as it should have.

- takeachillpilldude

Don't Ignore The Light

Ignoring the oil warning in my car for a few days thinking it was a "you are a bit low on oil, you should be adding oil soon" instead of "add oil NOW or you engine will break down beyond repair"

It ended up costing me 6k.

- -kobash-

A $3M Mistake

Ooh I might have the most expensive one in this thread.

Well, not me but my co worker. We work in a refinery. Part of where I work is offloading rail cars. We get a verification faxed that shows what's in each rail car. Co worker mixes up his tracks, offloads one side to tank A the other to tank B, when it should've been vice versa. The one he offloaded to tank B made its way through the plant, and destroyed the catalyst on two reactors. It's an expensive fucking catalyst.

Totals cost of replacement, labor, and reduced feed to the plants: around $3M.

He was not fired.

- Dances_With_Labias

A Paperweight

Be an orthopedic scrub nurse doing a total hip replacement (all scrub nurses and surgeons already know where this is going)

Get handed the acetabulum component by the rep and open it (the socket part of the ball and socket joint).

Drop it on the ground

$20,000 bounced across the floor and comes to rest at the surgeons feet.

Pure silence

No, it can not be re-sterilized or used.

I made a $20,000 paperweight.

- CreativeSun0

An Inch Of Water

I accidentally flooded my parents' upstairs bathroom. I used too much toilet paper and clogged the toilet. I tried to unclog it myself, and when I flushed, the pipe was still clogged and the water got everywhere. There was about an inch of water on the ground. Repairs cost us a couple thousand and took about a month.

- ChronicAwesome15

Threats Of Violence

Oh boy, an opportunity to highlight what a dumbass I am. I was a stellar student in high school, and my efforts paid off handsomely in the form of a full-ride scholarship to an expensive private University, the University of Chicago.

Unfortunately, the stress of getting to this point took a toll on me. My grades fell in my last semester, and I started having behavioral problems. I was told however that the only way to get your scholarship revoked was to do something monumentally stupid, like being arrested.

Well, I did something monumentally stupid, my first mistake. My vice principal threatened to flunk me out of all my classes and thus ruin my scholarship and graduation unless I stopped missing classes. I in turn sent an email threatening to be violent not only toward him, but toward anyone who got in my way, and toward humanity in general. (Delusions of grandeur.) Needless to say, the police got involved. I wasn't arrested because I was a white kid with a clean record, but I was placed in a mental institution for a week to sort out my problems.

Then came my second mistake. Despite not necessarily creating a record of this incident, I was open and honest with my admission counselors. Some of them sided with me, based on the account I was given, but a narrow majority did not. Thus, I lost a financial package worth roughly $280,000, and got blown back to reevaluate my life choices. Four years later, I'm still reeling a bit.

- CrystieV

You May Also Like
Hi friend— subscribe to my mailing list to get inbox updates of news, funnies, and sweepstakes.
—George Takei