1. Family … the ties that bind

man stress money family
ESB professional | Shutterstock
Set your boundaries.

My worst financial decision?

Keeping my brother, his wife and their two kids afloat for six months while he looked for his "dream job." What a waste of money.

What was his dream job?

To be honest I don't even remember. He couch-surfed the entire time.

| demonbadger

2. More family matters

empty wallet
Blood is thicker than water, but sometimes they'll bleed you dry."MemoriesStocker | Shutterstock

I would say my biggest financial mistake was agreeing to help support someone else and her children when I wasn't in a position to do so.

Letting someone else have control over your finances is a terrible idea.

Watch out for yourself first before you agree to help anyone else.

My credit tanked by nearly 200 points and I'm still working daily to recover from “trying to help.”

| therealmvpisyou

3. Bringing down the house

woman collecting rain from leaky house
Andrey_Popov | Shutterstock
Is it a house or a sinking ship?

I bought a home in 2006 that was in severe need of repairs.

In retrospect it was probably a tear-down, but I didn't realize that until I had dumped a ton of money into the house for nearly a decade.

In the end, the house was worth less than I owed. Normally real estate appreciates (grows in value).

I bought it for $170,000, but the market crashed, making the house worth $130,000. Even with all the repairs, I couldn't sell it and had to put renters in.

Eight years later, I finally owed less on the mortgage than the house was worth and could sell it.

| ch3000

4. That’s gotta hurt

man pain stomach
Bannasak Krodkeaw | Shutterstock
That hurts way more than a bellyache.

I accidentally used an emergency room instead of urgent care.

Walked into a clinic, the receptionist said it was closed, and that I had to go through the “other door.”

I walked through the door without thinking about it. Turns out it was the ER.

I was on a long hike and contracted a giardia infection (that’s a parasite that causes bowel infections).

Anyway, it was $500 for a doctor to write me a prescription for Flagyl and a nurse to take my vitals.

If I had just waited a few more hours, the visit would have been free at the clinic. Pharmacy wasn't open until the morning too.

| wholeroll

5. Too good for little green trees

little green tree air freshener
Benedek Alpar | Shutterstock
Would you spend $300 a year to make your car smell like pine?

I work at a car dealership as an apprentice mechanic.

I've seen many examples of people wasting their money, be it on car parts, flashy but useless accessories, gaudy decals and so on and so forth.

There is one guy that I'll never forget, though. He comes in every three months and spends literally $75 on a very specific car air freshener.

What's worse is that he brags about it, constantly. He puffs himself up and claims he's "elite" because he afford to buy a $75 piece of scented cardboard. It's ridiculous.

I don't know what goes through his mind every time he buys one.

| bigjo101

6. Need an army of lawyers

divorce proceedings
Elnur | Shutterstock

I gave my now ex-wife power of attorney while I was deployed (while we were married).

Came home to an empty bank account and a house in [a bad part of town] that she had paid cash for. Her deadbeat dad was living there and was acting as the “property manager.”

He didn’t pay the mortgage, but cashed the rent checks. I ended up with a foreclosure and a divorce.

| beachkilla

7. Math was not her strong suit

cheating love triangle
271 EAK MOTO | Shutterstock
A love triangle. Or square. Or... hexagon.

I watched a friend of mine give his wife of one year power of attorney right before he was deployed.

He came home eight months later. She was six months pregnant.

Also, she had maxed out three credit cards in his name.

| k33p4lv3

8. Hindsight is 20/20

house homebuyer
nednapa | Shutterstock

[My worst financial decision?] Not buying a house when I was younger.

My wife and I could easily afford one but our credit score wasn't over 700 at the time and the housing bubble bursting made it super difficult to buy a home.

We just continued to rent houses for eight years and flushed all that money down the drain.

| sickranchez87

9. Pyramid schemes

at home sales pitch avon lady
DGLimages | Shutterstock
Beware the friendly Avon lady.

I watched a sorority sister sink thousands of dollars into an multilevel marketing scheme (also known as a “pyramid scheme”).

When that one flopped and left her with 5,000 unsold leggings, she took out a loan to invest in yet ANOTHER multilevel marketing scheme to "recoup" her losses from the first one.

I guess that counts as two extremely poor decisions.

| joeyjojojnrshabadu

10. Feeling buzzed

cheers champagne
Liliana Kieler | Shutterstock
That's one heck of a hangover.

My brother graduated from law school, and we were having lunch at a fancy restaurant before the graduation event.

My grandpa ordered a $500 bottle of Champagne for my brother and his wife to enjoy.

The waiter mistakenly thought my grandpa meant he wanted a bottle for the entire table of nine people.

The waiter then brings out a $4,000 dollar magnum bottle of Champagne and pops the cork off.

My grandpa, not wanting to be embarrassed, accepted it. It was too much, even for nine people. We all drank what we could and he had the rest sent up to his room.

It was about a $6,200 lunch.

| eatgulp

11. Always read the fine print

reading fine print with magnifying glass
Tiko Aramyan | Shutterstock
Grab a magnifying glass.

Not touching my 401(k) for a year. I had a summer internship through most of college at a firm that offered 401(k) matching — even for interns.

I set it up, contributed to it for three summers and then wound up not working there during my last semester of college.

I thought, "No big deal, I'll just start contributing again at my new job."

Thing is, I didn't read the fine print and didn't know that after one year of no contributions, my 401(k) would automatically cash out and get sent to me as a check.

On top of that, I got dinged a 20% tax penalty for withdrawing the funds early.

| metrogdor22

12. Shopping addiction

shopping addiction
pixelrain | Shutterstock

My dad saved his entire life. Staunch minimalist. Had about $1 million saved by his 60s when my parents divorced.

My mom (a shopaholic) fought him in court and received $800,000 from him, which he just let her have.

All he wanted to do was spend the remainder of his years living in a tiny house he already owned outright.

He’s still self-sufficient to this day at age 75 and has been to 45 countries.

My mom, on the other hand, spent the $800,000 in less than five years. She bought nothing but garbage. Collectible angels, a bedroom suite from Ikea and a house she couldn’t afford.

I'm paying her electric bill because she can't afford it.

| franticshouting

13. Blown inheritance

woman hands choosing credit card
Bacho | Shutterstock

Had an unemployed friend inherit a ton of money when her dad died.

Instead of investing it and getting a job, she took it easy for 10 years and lived off the money.

She was homeless and living in a van when the money ran out.

| abaeternonomo

14. Just what dad would have wanted

make it rain money
Africa Studio | Shutterstock
Watch out for when that honeypot runs dry.

A girl I know burned through her inheritance money in less than a year.

She spent her father’s life insurance policy on a nose job and a BMW 7 series. She also gave a lot of money to help her deadbeat boyfriend’s “rap career.”

Now she's no longer with the boyfriend, she lives paycheck to paycheck and she had to trade in the car due to high maintenance costs.

| iheartcrack666

15. All bets are off

gambling loss
G-Stock Studio | Shutterstock
No one but yourself to blame.

I know of at least one guy who lost absolutely everything at the casinos in Atlantic City.

I was just hanging out with my girlfriend when we spotted this dude who had MONSTER stacks of chips at the roulette wheel.

They were worth at least $100,000 to $500,000. He had stacks of them.

I went to the bathroom, when I came back out five minutes later, the guy was holding no chips.

I kid you not. This guy lost a literal fortune in five minutes.

My girlfriend said he lost everything in one spin and we watched him cry his eyes out in the aftermath.

| atheistcomic

16. Father doesn’t know best

car loan
muk woothimanop | Shutterstock
Daddy dearest didn't know a thing about cars.

My friend was told by his dad to always replace his used car every three years, even if it is still working just fine (WHY?).

Now, because of the constant trade-ins, new loans stacking up and poor credit, my friend currently owes $35,000 and drives a 2009 Toyota that needs a lot of repairs.

His first car was a perfectly fine Honda in perfect condition that, I believe, he could have paid off easily and would still be driving today.

This friend also put his dad's name on his saving account with the full awareness that his dad is not trustworthy, and now that account has been emptied and given to his dad's mistress.

| handbooksoncork

17. Married and buried (in debt)

unhappy bride and groom
Moshbidon | Shutterstock
Not a great way to start a life together.

I know a couple who spent $125,000 on their wedding.

Their marriage lasted less than four years. They ended up arguing over who had to pay which part of the debt ("I didn't want the flowers in the first place!") during their divorce settlement negotiations.

They were each still paying for the first wedding when they married their second spouses.

| craicd

18. Flown away

expensive wedding money
zimmytws | Shutterstock
Remember that a wedding only lasts one day.

I went to a wedding that chartered everyone from a hotel in Auckland [New Zealand] to a venue two hours away in HELICOPTERS.

Yup, there was a parade of like 30 helicopters taking people to a wedding.

$100,000+ outfits, multiple for different events throughout the day, booking A-list celebrities to sing, 20-foot ice sculptures, flown in chefs and top shelf open bars.

It was absolutely gorgeous, but that wedding had to have cost the family at least $5 million.

| raj96

19. Arrested development

man playing with toys
AJR_photo | Shutterstock
This man-child loved his toys.

One of my college roommates would constantly come home with toys. Literal toys. Like for children.

Toy dinosaurs, cap guns and army men. For himself. Then he’d play with them twice and forget about them.

Then he had to borrow money to pay our bills.

Great guy, and he's since gotten better, but wow that was baffling at the time.

| stumplestiltzkin

20. A big whoopsie

closed sign
Claudio Divizia | Shutterstock
You can't run a business on confidence alone.

I cashed in my retirement savings and opened a business in a field and market that I knew nothing about.

Basically I had a consumer mentality, I saw the potential for profit and thought of it like an investment that I assumed would net huge gains.

I also naively assumed that because I'm a smart guy, I could easily run a business.

| flexmohomo

21. Send to junk mail

closed sign
fizkes | Shutterstock
This prince was actually a toad.

A 43-year-old woman I know got hooked by an actual “Nigerian Prince” email scam.

Not only did she send this guy all her money, she actually flew to Nigeria and married him.

He's 21 years old.

Her intention is to bring him back to the USA, but he really has no intention of leaving. She funnels all of her money to him, which in turn helps him scam other women. He's living a pretty sweet life.

She went from living a decent life to moving into her grandmother's basement with her daughter, just so she could send all of her money to him.

| pennyxroyalty

22. Alternate reality

video games play
korobskyph | Shutterstock

My friend had more than $5,000 worth of gaming purchases. Not even tangible things, mind you, but virtual purchases.

Things like armor, weapons or finishes that you can buy inside the game.

He got banned for cheating. When you get banned for cheating in a game, your inventory of items for that game becomes locked.

Meaning the $5,000 he could have invested or used for literally anything else was rendered totally useless.

| maximus125

23. Frustrated salesman

car salesman
SeventyFour | Shutterstock
He's seen it all.

I've been working in the car industry for 10 years.

I see horrible decisions being made on the daily.

96-month loans on Dodge Caravans with $10,000 worth of negative equity rolled in at 10% interest.

$30,000 for a used BMW SUV with an 84-month loan term.

I have no idea how people sign up for these loans without reading what they have gotten themselves into.

| nuttydave127

24. Feline finances

Alena Ozerova | Shutterstock
Your landlord doesn't care how adorable Biscuit is.

Getting a cat when our apartment lease said no pets.

It started my husband and I on a long spiral downward that took a long time to get out of.

We were young and dumb. While the lease said “no pets,” we could see other people in the building had them.

When we asked the manager, she said it was ok. Everything went fine for awhile, until the actual owner drove by one day to check on the property, and saw a bunch of cats in windows and heard dogs barking.

Soon we all got notices that the pets had to go, or we'd be evicted. My husband and I found another apartment nearby that took pets, and moved before the eviction date instead of fighting it.

The new apartment was a lot more expensive and ate up a much higher percentage of our income.

| msspentmiddleage

25. Fast food, fast money

junk food eating
Syda Productions | Shutterstock

In college I would easily spend $50 a week (approximately $200 a month) on takeout and fast food.

I don’t eat fast food as often anymore, and I'm too broke to eat the way I used to, but it's so shameful.

Not only did I waste literal thousands on excess food (this was in addition to my regular food budget) but I also made myself unhealthy.

I'm still struggling to get my health back under control, years later. If I had to give advice it would be DON'T give into comfort eating. Moderate yourself.

Be very mindful when using food as a reward.

I think there are definitely ways to do it and be healthy but when you're poor — and going for the cheap relief of $30 on a Big Mac meal and nuggets every other night — it's not as harmless as you think.

| Anonymous

26. Watch yourself

smart watch
Twin Design | Shutterstock
Hey Siri, what are some good money management websites?

My boyfriend’s dad owns seven different Apple Watches because he doesn’t want to change the bands out.

| handsomecolon

27. Disney economics

mickey and minnie
George Sheldon | Shutterstock
$7,000? Now that's just straight up Goofy.

I'm a VIP tour guide at Walt Disney World.

Each guide costs $600 per hour and charging starts when you ask us to meet you, whether you're there or not.

A family booked two of us multiple days in a row and were at least three hours late each time.

They paid an extra $7,000 for tour time they didn't use. Didn't care at all.

Take into account that I make roughly 2% of that, or $12 an hour.

| gatejejf

28. Wasteful weddings

bride with lots of money to spend
ViDi Studio | Shutterstock

I work as a freelance musician and often work weddings. Some families have crazy money, and burn through it like it’s nothing.

One thing I always see at fancier events without fail is a ton of amazing, fully prepared food and expensive drinks being thrown away at the end of the night.

When I asked about it once, I was told by one of the staff that a lot of catering companies are trained to prepare enough of every menu option so that if everyone orders the same thing, they have enough.

What happens in reality is they make enough food to feed the wedding party (often comprised of 200+ people) another two times over.

It’s particularly annoying when the band are served cold fries as their “evening meal” because "we couldn't stretch the budget, sorry."

| solidsizzle

29. Walking on sunshine

stylish woman sunglasses
Jacob Lund | Shutterstock

I work at a five star beach resort in our luxury gift shop.

One day, a rich 30-something-year-old mom comes in around 10 a.m. to buy sunglasses.

$500 Prada shades? No big deal. These people have money coming out of their ears, so I think nothing of it and ring up her purchase. She comes in ten minutes later.

She's lost the glasses in the ocean, so she buys another pair. She loses that pair, then complains that we won't give her the third pair for free.

So she pays for the third pair, and finally didn't come back.

This all happened before 3 p.m. $1,500 dollars spent on sunglasses in five hours.

| notyourdadsop

30. High roller

blackjack table closeup
juliannedev | Shutterstock

In Las Vegas in 2000, at the Bellagio, I watched a guy walk up to a high roller blackjack table.

He was being followed by a security guard and some guy in a suit carrying what I estimated to be at least $300,000 in chips.

He sat and played blackjack by himself.

My wife and I sat and watched him for about 45 minutes. He had been there for an hour and already lost over $150,000.

Never once showed any emotion.

No clue who the guy was, he was dressed like a stereotypical grandpa in jean shorts, a polo shirt and white New Balance tennis shoes.

| iyaayas

31. That’s not so neat

men cheers scotch
BATMANV | Shutterstock
Cheers to bad decisions.

It's definitely not the biggest sum of money ever lost, but I spent and wasted my money for a really silly reason.

I bought a $300 bottle of Scotch whisky when I meant to buy the $60 version from the same distillery (the boxes looked nearly identical).

When the cashier told me the price, I realized my mistake, but she and everyone behind me in line seemed really impressed that I was buying something so expensive.

I grudgingly handed her my credit card and walked out with my purchase.

So, now I own an unopened and very expensive bottle of single malt because of my social anxiety.

| drtribs

32. A well-traveled laptop

woman working on laptop concentration
G-Stock Studio | Shutterstock
This laptop has more travel miles than you.

This may not be the biggest waste, but it certainly is the weirdest one.

Around 2001, my wife worked for a national company, and her team was split between East Coast and West Coast.

There was no working from home on laptops.

Desktops were standard for them. If someone needed to work from home, they had a single laptop they could use. For the whole team.

So, if that laptop was in North Carolina, and someone in California needed to work from home, they had to box it up and ship it (with full insurance, rush shipping and a few days notice) to the other coast.

| roboninjapirate

33. Lost his appetite

supermarket produce
Rrrainbow | Shutterstock

I was an assistant manager at a grocery store and you wouldn't believe how much produce I threw out because it wasn't "pretty enough."

The district manager had crazy high standards for how the produce should look. If I didn't cull it correctly, he would write me up.

He came in three times a week, so I couldn't get away with not doing what he asked.

When I looked at our weekly waste reports, produce accounted for about $100-$200 dollars a week.

I asked him if I could donate the produce we throw out, but his response was, "That's theft."

I was so glad when this place went out of business.

| satankingofhell

34. Don’t toy around

cutest baby EVER playing with toys
Romrodphoto | Shutterstock
Think of my college fund, Mommy.

My biggest financial mistake was spending tons of money on baby toys.

I think lots of parents can learn from my mistake.

You spend hundreds on certain flashy, expensive gifts that just sit unused in the corner, and then your kids end up playing with that trinket you picked up from the dollar store.

I know it's a bit cliché, but my experience so far is that kids often just want to play with the cardboard box, so to speak.

You don't need to spend hundreds on a 1-3-year-old in terms of toys and games. Just get them a few nice toys and save the money for something more important.

| [mrbasilthebrush](mrbasilthebrush](https://www.reddit.com/user/mrbasilthebrush/)

35. They should teach this stuff in school

money to burn
emin kuliyev | Shutterstock
Financial illiteracy.

I had a fairly sizable inheritance waiting for me when I turned 18.

It was $70,000, after student loans.

I should have invested that, stuck $40,000 in some index funds and cashed out as I went through the rest.

Instead it just sat in a bank account accruing minimal interest. I've been living off it for the past few years.

I haven't wasted it at all, I live a typical frugal student lifestyle and still have $20,000 left.

Don’t get me wrong, I realize that is an amazing position to be in for a recent grad starting a career, but I wasted the potential the money had.

| nonprofaccount

36. Those golden handcuffs

man handcuff work
Elnur | Shutterstock
Time to deploy that golden parachute.

Years ago, I quit a commodities brokerage job at an enormous global commodities trading house for a brokerage job at an old European investment bank.

While my old job was making me miserable and draining my soul, the commodities firm ended up turning my old division into the largest macro commodities hedge fund in the world.

If only I'd stuck it out for another year or two.

My former colleagues went on to make their personal fortunes as global macro hedge fund traders, while I was still stuck at a dusty old bank.

I'm doing fine now, but sometimes I have to resist the urge to kick myself.

| *discardedideas