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We all make mistakes. That said, some are definitely more costly than others — sometimes in literal dollars.
AskReddit users discussed their most expensive mistakes of all time, from college to petty crime.
1. Not saving bitcoin.
“Spending all my bitcoins back in the days way before they went through the roof.
I bought a box of mixed tea for 2,5 million dollars.”
2. Skipping class.
“My fair share of failed college classes.”
3. Forgetting to fix the company website.
“I asked for a dev to make a change on our website to test something. Forgot about the test as things got hectic.
Turns out that dropped the lead count by 60% for about a month. Cost the company well over 200k.
Nobody knew it was me :)”
4. Swapping price tags.
“I swapped price tags on a video game at Walmart to try to save $20.
Never was arrested but the county had to come out to talk to me so they filed a civil suit. Probation cost me over $4k and shoplifting on my record cost me some opportunities.
Worst part about the situation was I had plenty of money at the time but I was young and really dumb..”
5. Selling my condo to move in with my ex.
“Selling the condo I owned outright with no mortgage and putting it all towards a new life with my ex long term relationship partner who later cheated on me and left me after 9 years.
He got the house. I left with a quarter of the money I sunk into it. Lesson learned for me.
I’m a dumbass.”
6. Star Wars movies.
“When I was seven, I accidentally brought $800 worth of Star Wars movies. I kid you not, when my father finished scolding me, he stormed into the living room, sat down, turned on the TV and started watching The Clone Wars.
I did not know I was spending money at the time, I just thought I was turning the movie on. It charged $50 for each movie, then I purchased the bonus features for each movie.”
7. Doing drugs.
“Drugs and the purchases I made while using.
When I was 17 I received an inheritance. Not huge but enough to party on pretty good for a few years. Blew it all by the time I was 20. What a waste. Honestly, nearly a whole lifetime later still one of my biggest regrets.”
8. Napping while drunk.
“Telling my wife that it’s fine if she wants to go sleep in the car, while she was drunk and tired at a house party. Not even super-drunk, just drunk enough to be like “Fuck this, I’ve been up since 6am and I’m done.”
Several thousand dollars to fight that non-DUI. Learned about “operating” the hard way.
The mistake was that the headlights were set to auto and it was winter/night time, so that was the giveaway.”
9. A custom night guard.
“I got scammed by a dentist for a custom mouthpiece to help stop grinding my teeth at night.
She said my insurance would cover it, got a bill for $3000. The piece doesn’t fit in my mouth anymore because my teeth have shifted.
It’s been 5 years I try not to think about it, but it comes up in the back of my mind randomly.”
10. Leaving my car unlocked.
“Leaving my car unlocked back in 2013.
“I was just starting my career as a photographer/photojournalist. After work one day I went on a date with a girl I met. I didnt want to carry my camera with me so I left my gear in the car and went hiking with her. In my nervousness I forgot to lock my doors.
Came back and someone opened my car door and stolen all my camera gear and laptop. Almost $10,000 in gear gone. Couldn’t go through insurance because the car wasn’t ‘broken into’ and the police couldn’t do anything.
I had to leave my job at the newspaper I worked for after that because they didn’t have any camera equipment of thier own for me to use. Completely stopped my career and I was stuck in a dead end town working temp jobs to scrape by for the next 4 years until I met my ex and we managed to save up enough together to get out of that town.
I finally bought myself a cheap DSLR last year and have started to pick up photography again. I often wonder how different my life would be if I had just remembered to lock my car door that day.”
11. Missing my flight.
“Missed an international flight home and had to buy a second ticket.”
12. Keychains.
“This was the most expensive relative to the amount of money I had at the time: in middle school, my family went to Niagara Falls.
I spent all my money (that I’d saved from birthdays and the paper route) on keychains from that one place. It was over $50.
It still haunts me today.”
13. Fancy skincare.
“Bought a ton of expensive skincare and it didn’t suit my skin.
Had a bad reaction to it and had to toss it all in the bin.”
14. Broke my glasses and laptop at the same time.
“Wouldn’t seem that expensive now But when I was 16 I was laying on my back with my laptop propped up on my legs. It slipped and landed on my face. Snapped my glasses in half and caused the laptop screen to crack and black out.
My parents gave me the option to pay my laptop in full and they’d buy my glasses Or I could pay half of both.
I don’t remember which I did but it was a few hundred dollars either way.”
15. Taking my cat to the emergency vet.
“Idk if it’s a mistake, but when a guy found a kitten near where I worked at the time, there was no humane society or anywhere we could take him nearby so I took him home.
He was on death’s door so the next day I took him into an emergency vet. Got a bunch of useless tests back only to tell me he was a boy, he hadn’t peed for 3 days and other than that they didn’t know what was up.
Paid $900 for useless tests only to find out he just needed some milk and rest.”
16. Forgot to put the cap back on.
“Forgot to put the cap back on after filling up the coolant in my car. Then boiling my engine on the highway…
5000$ for a new engine, just because of a f**king cap…”
Sometimes the most expensive mistakes are the ones you can never forget, even decades later.
Have you had even fiscal mishaps that sting? Let us know in the comments!
