5 Most Terrifying Money Stories on Reddit

Yahoo

01-08-2025

Reddit offers a veritable smorgasbord of wild stories. There are sweet, funny stories, like the girl who found the star of her favorite movie randomly sitting in her airplane seat. Then there are the tales of family drama that would make 'Game of Thrones' feel like 'Full House.' And the scary stories — oh yes, Reddit abounds in tales of terror in all areas of life. Money matters are no exception.
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GOBankingRates decided to spelunk into the deepest caverns of Reddit (well, within reason) to find spine-tingling tales of money woes and mismanagement. These stories will shock and amaze you — and if nothing else, they'll serve as cautionary tales while reminding you to be grateful for the money skills you've mastered.
1. $10K in Take Out
The pandemic was a hard time for everyone, some of us more so than others, obviously. People who weren't on the front lines had their own ways of coping, like picking up new hobbies and baking sourdough bread. So much sourdough bread. Well, for one Redditor in the Caleb Hammer community, the strain of lockdown led to a major penchant for DoorDash — to say the least.
Redditor Somnus Sampling spent a whopping $10,000 in savings on DoorDash, including tips, to 'cope with the stress and my family's situation.' To put things in context, it's actually possible to get a used car for that amount of money in some instances. You could also pay off a lot of debt, make significant investments in the market or even start a small business with that much cash.
Instead of being mired in their mistake, Somnus Sampling learned from it: 'Since the beginning of 2022, I stopped using any food delivery service apps.'
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2. The Dinner Out That Turned Into a Mad Search for Rent Money
When the Redditors of the Money Diaries community asked each other to spill their own scary money stories, user Mordecai_AVA_OShea spun a truly terrifying story of a night out gone terribly wrong.
Picture it: New Year's Eve brunch at a trendy DC establishment. Mordecai and their husband are both 'broke graduate students' visiting hubby's best friend from high school, who is now an attorney at a big DC firm. A meet-up with 10 of bestie's law school friends turned into a three-hour shindig with people ordering many bottles of Prosecco — to the tune of $300 per person.
'I was beside myself,' Mordecai said. 'We got home my husband and I went through our apartment and made a pile of anything we could live without and sold it on Craigslist to make rent. 15 years later and I'm still sad I traded a breakfast with strangers for my grandmother's rocking chair that my mom used to rock all her babies.'
3. A $25K Investment Tossed Out With the Trash
An engagement ring and wedding band represent investments in the strength of your love and your future as a happily married couple. Let's be real, though, it's also a major financial investment — one you'll want to get insured. Redditor Petite AC learned that lesson the hard way, when she lost her wedding band and engagement ring only three months after her wedding.
'I had planned on getting insurance after the holidays as it was a very busy time,' she wrote. '$25k gone. Pretty sure they were thrown away with our take out.'
4. Putting All the Eggs in One Basket
In a thread dedicated to how ex-millionaires lost their money, Redditor wishnana shared the gob-smacking story of a close friend's parents. They were frugal folks who worked hard at a well-regarded American company that was flying high back in the 2000s, eventually ending up in high managerial positions — as well as the perks that came with those positions. They put all their investments, from 401(k) funds to cash, back into the company — and only the company.
The Redditor guessed that, all in all, they'd probably invested close to $5 million to $6 million into the company. Just as they were about to pull that money out so they could retire, they found the rug pulled out from under them. That company's name? Enron. As in, soon-to-be-mired in scandal and go belly-up Enron. Their friend's parents lost those millions in savings.
5. The Hypothetical Millionaire
Fans of 'The Twilight Zone' could count on Rod Sterling to take them through alternative worlds, featuring protagonists whose one small move can bring about devastation — like the last man on earth, who was oh-so-happy to be alone with his books, until he broke his glasses.
One Redditor doesn't need to go to the Twilight Zone to imagine that kind of scenario: They bought $100 worth of Bitcoin when they were only $1 each. 'I sold them when they were about $2.50 each and was so happy I made money from 'internet coins,'' they wrote. 'As of the moment I am typing this, those coins would be worth $1,855,000.'
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This article originally appeared on GOBankingRates.com: 5 Most Terrifying Money Stories on Reddit
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