August 25, 2023 at 3:41 am

What’s the Worst Financial Mistake You Saw Someone Make? People Responded.

by Matthew Gilligan

ARFinancialMistake What’s the Worst Financial Mistake You Saw Someone Make? People Responded.

It’s always terrible to hear stories about folks who had it all and then it came crashing down in an instant.

Because finances can be a game of inches and you never know when one little mistake is going to ruin someone’s life.

AskReddit users shared stories about the worst financial decisions they ever saw someone make.

Take a look!

That’s bad.

“I knew someone who got a loan for their wedding, but decided to blow it all at a casino.

Now they have a loan for 20k to pay off and nothing to show for it.”

Water woes.

“A friend of mine who is very bad with money and his girlfriend bought some sort of water filtration system from a door to door salesman.

He has to pay something like $300/month for this filtration system. He was all stoked because it came with a free set of pots and pans.

Fast forward a year and his girlfriend has broken up with him, moved out of the house, and he’s had to sell his home because he can’t afford to live there.

The water filtration system is now sitting in a storage unit where he still pays $300/month for it because he’s on a 2 or 3 year contract (sorry the details are fuzzy).

We have great water quality in my area.”

That sucks.

“A coworker I used to have worked every second of overtime he could for several years to save up for a house.

When he applied for the house loan, he based his mortgage payment on all of the overtime he had been working. I tried to tell him that wasn’t a good idea but he didn’t want to hear it.

He ended up divorced a few years later because his wife got tired of him always working.”

All in.

“A guy in my fraternity got 30k for an undisclosed reason, I’m guessing a family d**th or something and he bet it all on the Yankees winning one game.

They lost.”


“A dude who owned a small convenience store in our town spent like $20,000 on fidget spinners.

He was posting for like a year begging people to buy them as he would lose his business and his marriage was falling apart due to it.”


“My maternal grandmother bought an 8-plex to avoid capital gains when she sold her large house.

The apartment complex was in the red and needed a lot of repairs. She hired my father to do them and be on-site manager. The place started making money.

My mom (divorced from my dad) was mad that my grandma bought it in the first place, then hired my dad, then was proved wrong because it was making money. My grandma was in her 90s and my mom pressured her for years so my grandma finally sold it.

That place is in a high market area and is now worth millions. My mom made a poor financial decision based on petty spite.”

Oh, my…

“My supervisor took out a loan against their 401k to pay their rent because “their credit cards were maxed.”

Two weeks later, they bought a brand new 60k Lincoln with basically nothing down because “her daughter just had a baby and I need a bigger car for that.””

Bad news.

“Ran up credit card debt requiring bankruptcy.

Once they were able to build credit again (7 years later) they proceeded to run up a massive amount of debt again, but couldn’t go bankrupt again, so they used “debt consolidation.”

The debt didn’t come from sudden expenses. They just needed to buy things to feel better.”


“Had a co worker with 5 kids who could all go to USC for free once he has worked there for 15 years (even if he quit).

He quit at 14.5 years for a job that barely paid more than he made at USC.

Cost all 5 kids a free education at a top school since he couldnt wait 6 more months.”

The runaway.

“Put everything in his gf’s name to hide assets as he owed the IRS, the gf sold his business, cashed out his accounts and ran.”


“My brother’s ex fell for a Craig’s list scam.

She found a motorcycle and the guy “needed money up front to pay bills” before she even saw it. We told her don’t do it, it’s a scam. She said she already sent $1000.

Of course, he was never available to show her the bike and we found out from my brother after they broke up she actually continued sending him money in hopes of getting the motorcycle. I think she was out $3,000 by the end.”