The Biggest 'Money Mistakes' People Have Ever Made

While there might be some financially savvy unicorns among us who just seemed to "get it" since birth, most of us have had some mishaps with our wallets.

And in some cases, those financial lessons have been pretty expensive.

Redditor The_guy321 asked:

"What is the biggest money mistake you have ever made?"

A Big Life Change

"I took a job way up North in Canada. I quit my old job, got rid of tons of stuff, had my dad help sell my house, etc. This was in 2019/early 2020 just before the pandemic hit big."

"I ended up hating the job up North; it was terrible. I went back home and somehow managed to get my old job back, but my house is gone, and I can’t afford a new one in the current market."

"Stupid, idiotic decision on my part, and it keeps me up at night. I hate where I am in life right now. A stupid, big, and expensive mistake that I’ll regret for the rest of my life."

- SaulWellAndGood

Sentimental Value and More

"My mom gave her original, 20+-year-old wedding ring to a jeweler to work it over and improve fitment (since it was too tight I think)."

"The jeweler f**king lost the ring in the mail. They sent it out without insurance and it never arrived at the place that was supposed to do the jeweler's work."

"She did not get her original wedding ring back, and all they offered her was 'a new one of equal worth.'"

"Honestly, that was the biggest f**k you to her. The best you can get in that situation is at least a ring visually similar to the original one, or one made to be identical to the original."

"Don't tell me 'copying an existing ring' is not possible, because the ring itself was very simple. Basically only metal, no diamonds or any other fancy rock, just metal with a groove in it and smooth edges."

"But no, their only offer to 'make up for it' was to choose a cheap looking one from their stock, basically saying 'we f**ked up but we won't put in any work to replace your ring; this is what we already have.'"

"Let alone the fact that the ring was 20+ years old and had a lot of sentimental value, because unlike my dad, my mom wore that ring all the time."

- GuyFromDeathValley

Student Loan Arrangements

"Spending all my student loan refund checks instead of saving those f**kers to, oh, I don't know, PAY OFF MY STUDENT LOANS."

- JanisRBoyes

Extra Funds Available

"Accepting larger loan amounts than I needed."

"Tuition, for me, was about $1200 a semester. But when you’re 18 and someone offers you $5,000 (which is more than you’ve ever had) and you don’t have to pay it back for years, you don’t hesitate to click accept the full amount."

"So yeah, I’m $20,000 in student loan debt when it could have been $10,000. Praying that student loan relief actually goes through but doubt it."

- TrueRusher

Attending College At All

"Going to college right out of high school. College is great if you know why you're there, but not for someone who isn't yet sure."

- Common-Actuary-2982

No Return on Investment

"I can't speak for everyone but when I was fixing to graduate high school back in 2000-2001, everyone thought college was the next step because literally no one ever told us anything different. Parents, teachers, school guidance counselors, and the culture. EVERYTHING was about pushing kids into the college pipeline."

"I literally thought everyone working trades were living in poverty until I was in like my mid-twenties because no one ever brought it up unless it was to disparage the whole idea of working for a living."

- Wolfbeckett

Collector's Investment

"Not my mistake, but my dad's. He bought like $500 worth of collectible Star Trek dinner plates in the 80s thinking they'd be worth a ton of money in a few years. They're not."

- Theareyj


"I was at $1800 per month for alimony and child support for six years, but it was more losing half of the assets (including retirement savings) that was the killer."

"Oh well. It's in the past now and I'm in a much better place and happy rather than resigned to being miserable like I was for quite a few years until I decided to go through with it. I'm just going to have a late retirement (most likely) instead of early like I had hoped."

- evilmonkey2


"As f**ked as it is, the financial expense is what got me to quit nicotine. I realized that I was spending $150 a month on disposable vapes and started comparing it to my other bills."

"I was paying more for my unhealthy addiction than my car insurance, or my utilities. Kinda hard to justify when you look at it like that."

- DabLord5425

Beyond Her Means

"My ex-wife was an expert at spending us into a black hole. She was a widow. We got engaged. The very next day, I told her to bring me all her debts, and then I wrote checks to pay them all off. $14,000."

"That became the pattern. She never saw a dollar she couldn’t spend before we earned it. She looked at things by what they cost each month and not by what they actually cost."

- TheMadIrishman327

Someone Else's Debt

"I agreed to take over my ex-girlfriend's bills so that she could pay off her debts. Five years and over $100,000 of my money later, she was in more debt than when we started, and she was cheating on me."

"Don't ever do this. Just make her be an adult or dump her. It's never worth it."

- Stoneluthiery

Just One More Semester

"I paid for my ex-girlfriend's college tuition for three semesters as she 'just one semester left'-ed me for all three."

"That was AFTER she got a letter stating she was no longer eligible for the Pell Grant or further loans. So, the banks said, 'No more,' but I paid for another year and a half, while also paying all the household bills and supporting her kid."

"We broke up, and she had the nerve to talk about what I supposedly OWE her."

- Suspicious-Self2067

Scammed by the Pound

"One of those Bootcamp-style gyms opened up within walking distance from our apartment. We wanted to get in shape and figured we'd check it out. It was run by a married couple who was really nice."

"Initial classes were very small but the exercise was great. The husband also did martial arts instruction so I was considering getting into that."

"They were doing a really reduced special to get a year membership so I went for it and paid half upfront. A few weeks later, I can't remember the conversation, but they asked for the remaining payment, and I said, 'Sure, why not?'"

"A little bit after that, they called and said, 'Sorry, but we opened the gym with a verbal agreement we would be getting a large number of karate students and that fell through, so we have to shut down. We will get your money back once we get settled after we move back home.'"

"I foolishly had paid for all this but never had even gotten a written contract or whatever. They just ended up ghosting me and stopped replying to everything."

- urchisilver

Buying the Wrong Home

"I bought a mobile home as a starter home. No one ever explained to me as a young adult the importance of investment and future planning."

"Mobile homes of course do not hold nor increase in value so you never build equity. It's akin to renting except you have to cover all your own repair costs too."

"Terrible financial decision. Don't buy mobile homes kids. Just don't do it."

- eatafetus632

Helping a Friend Out

"I let her move in with me and then covered all of her living expenses so she could pay off debt. It only cost me a little more money since I was already covering 100% of my living expenses. Some of my bills like water went up a little and I voluntarily covered most groceries."

"I told her upfront that there are no hard feelings if it doesn't work out in the long run (and it didn't). I would have done the same thing for any close friend."

"I suggested her first step should be to save an emergency fund to protect herself if we break up because I would expect her to get the f**k out. And if she cheats on me, her stuff will be on the curb the same day."

"I'm a practical person. We had been discussing moving into together anyway. This way we see how things work out and she ends up with less debt. But I didn't put any money directly towards her debt. That would have felt like I was being taken advantage of."

"This wasn't completely selfless on my part. It seemed like we may have been headed for marriage and in that case, I would want that debt gone. It didn't happen for us but I'm still glad she got a little further ahead in life."

- che-che-chester

While some might argue that each of these were learning experiences that were worth experiencing, there's no denying that they were expensive lessons.

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