The most stupid way you've lost money?

[Albert]

There is already a thread about the most antimustachian thing you've done, but that thread is more about mistakes made which didn't seem to be mistakes at first. Here about wasting money simply by not thinking things through. 

My story: few years ago I was on vacation with my girlfriend in Madeira. We were there for five days and thought ok we rent a car for four days to drive around the island and stay our last day in Funchal (biggest town) without one. Around 6 pm on our fourth day we filled the tank and arrived at airport to return the car, but turns out we had forgotten car documents in our hotel room (no idea why we brought them there in the first place) and had to drive back to retrieve them to avoid 200 euro fine. It took us about hour to make this completely unnecessary return trip to our hotel. After returning the car we found out that the last bus (3 euros) has already left and our only option is taxi costing 35 euros. In addition our flight back to Lisbon was Sunday early morning before public buses start to operate thus we need a taxi again. It would have costed only extra 30 euros to have a car for extra 1 1/2 days, instead we spent closer to hundred + all the stress.

The amount of money wasted was inconsequential, but I felt so stupid...

[Megatron]

timing the market.

[ketchup]

Five figures of loaning out money to people.

[hybrid]

Gambling.  Fortunately I hate losing more than I enjoy the thrill of winning so I've not done it often, but playing poker with people who are better than me was a great way to lose both time and money.

[matchewed]

A "debt service" company. I was broke and living on more than I was making. I don't recall where I heard of the company but I contacted them and sen them a check for $200 to help me not be so bad with money. When their package came in with the vouchers looking like they came off the copier at work and some other less than legitimate looking promises contained in the envelope I knew i was the sucker. At that point I flew into a mild rage and cancelled the "service" I believe I used some phrases such as "couldn't be more disgusted if you had actually mailed me an envelope full of shit."

Still took several years to get my finances under control but I can say I haven't screwed up that bad so far.

[Posthumane]

I lost $400 in what seemed to me to be really stupid, although I still feel a bit cheated by it to this day. A few years back when I bought my house with an at-the-time-GF (which was a bad move as well) my dad decided to buy us a new battery powered lawn mower as a house warming gift. We picked one out at home depot - black and decker brand. Home Depot had a deal on at the time where you got a 10% discount on your first purchase if you signed up for the credit card, so we decided that I would get the card (since I shop at home depot sometimes) and put the lawnmower on it, and then my dad would pay it off with cash at the register right away. A few days later I discovered that the charger that came with the lawnmower was not working and had to take it back. They could not replace just the charger but would have to exchange the whole lawnmower package, except they didn't have any left in stock. Alternatively, I could return the mower for a full refund. I took them up on the latter option, got the refund, and bought the same mower at walmart for the same price. However, since it had been bought with the Home Depot credit card, the refund had to go back on that card which resulted in me having an extra $400 pre/overpayment on that card. Or so I thought...

A couple years later I realized that I still had that card with what should be $400 of prepaid credit on it, so I used it to buy a bunch of paint for a project (about $180 worth). I thought everything was good until a few months after that I got a notice that I had $180 overdue on the card (plus interest) and they would send collections after me. I called them up wondering what this was about since it should have been covered by the $400 that was available on there, and they told me they had no record of that transaction. I argued up and down, but they said I would have to go into the store with my receipt showing the refund. The receipt was long gone by that point (it had been several years, after all), and so it would seem that the money was gone. Poof. Apart from that, it also affected my credit rating.

[michael]

Bought my ex-fiancee a $600 first guitar, which she played maybe three times. Young and in love... ugh!

[Skinnyneo]

Loaned $500 to a boyfriend.

And if you're a comic geek, this will make you cringe... I also gifted him the comic Hulk #181. And we broke up shortly after.

Very very stupid, past me.

Oh man!  First Wolverine!  That really sucks!

[jfer_rose]

This may not be the stupidest way, but it is stupid and also very fresh. I procrastinated on submitting my travel request for a work-related conference I need to attend this fall. Yesterday I received an e-mail at work saying that there is a travel freeze effective immediately. This means I'll have to pay to go out of my pocket for something I could have easily had work pay for had I simply submitted the forms. I had all the information I needed to do that in May. Face punch.

[Forcus]

Loaned money and bought things for relatives in an "emergency". Yeah I'll never see any of it.

[AlmostIndependent]

Paid off $16k of my (then) wife's student loans. She decided she didn't want to be married 3 months later.

[rebel100]

One word....Starbucks....nuff said! :)

[Hugh H]

Paid off $16k of my (then) wife's student loans. She decided she didn't want to be married 3 months later.

I almost did this with my ex-wife… except I was ready to plunk down 50k on her loans. Whew!

[AlmostIndependent]

Paid off $16k of my (then) wife's student loans. She decided she didn't want to be married 3 months later.

I almost did this with my ex-wife… except I was ready to plunk down 50k on her loans. Whew!

Yeah, and its pretty sweet how my savings get split 50/50 but never mind that debt that she brought into the relationship that I paid off. That counts for nothing. Live and learn I guess.

I helped her buy a condo as a rental (in an advisory sense, no financial help) and she managed to get it foreclosed on within a year of us splitting up. It was rented the whole time and making money. I still have no idea how she managed that.

[workathomedad]

I'm currently down over 100k in some investments

[ncornilsen]

The stupidest way I've lost money recently was as on a home improvement project... it's chump change but I felt so dumb about it.
I needed to have counter-flashing installed on my chimney after replacing the roof (Did the roof myself at least!)  A few mortar joints needed repaired too. I got a quote, $300 to have it done. I thought, hell, for $25 in tools and after watching some vids, and practicing on scrap bricks, I could do that myself!

Nope. I jacked up the flashing, the joints looked like ugly and don't match colorwise, and ended up having to have the guy come do the work anyway. Except now it cost $400 to fix the damage I did.

Whoops.

[lifejoy]

$800 loan to ex bf

~$1000 spent on piercings that I have since taken out (face punched myself already)

[SaveALLTheThings]

Booked a hotel with Hotwire's no refund hot deal system for this Thanksgiving weekend before being 100% sure I can take the week off for $550.  With persistence I was able to rebook with Hotwire and pushed the trip to late March, but since I'm new on the job I'm waiting to settle in before asking for that week.  I'm also annoyed at myself for not thinking to make my rebook a 1 night purchase to minimize my losses if it doesn't work out until it was too late (since I can always book with the hotel directly for the rest of the week anyway).  I won't know if it's a total fail until I make the request.

Lesson of the week: The stress induced by a no refund purchase is not worth the savings if you can't be 200% sure it'll pan out.

[Forcus]

I was going through some old papers this weekend and found some bank CD release forms from 2000ish (I would have been 19). My grandparents gave me 3 CD's, which I promptly cashed. The interest rates were 6-7.5%!!!! Man, wish I knew more way back when.

[AlmostIndependent]

The interest rates were 6-7.5%!!!! Man, wish I knew more way back when.

I hear ya brother.

[yahui168]

This was about 15 years ago. Graduated college making 55k/yr and financed an Audi A6 for $45k and then trading it in for $12k four years later. Taking the Bad out of Badassity.

[iris lily]

Yesterday we went to the casino. I lost $2.

That's the stupidest way to lose money, throwing it at slot machines. It's not even fun.

[avonlea]

I lost my wedding ring.  That doesn't get just a face punch, but a heart punch as well. :( 

[savingtofreedom]

Approximately $2,000 or so by not submitting receipts or using the FSA credit card - what an idiot (this is before 2011).  I have since taken over responsibility of this from my husband and am actually utilizing the funds set aside.

I can only view this as a donation to the government to feel a little better.....

[Hugh H]

I'm currently down over 100k in some investments

Stocks I'm guessing? Care to elaborate?

[AccidentalMiser]

I think I’ve got most of you beat.

May, 1992 - Started an ice cream business in a strip mall.  Closed it in September, 1992.
2000 – Quit my job, drew all my money out of retirement savings, day traded it all away.
2006 – Bought the most wonderful house in the world for 160k.  Sold it in 2012 for 140k.
2008 – Started a computer repair and IT services business with my last dime.  Closed it in 2009.

Fortunately, was fairly young when I did these dumb things. 

I’d easily be FI by now if I hadn’t done these things.  Now, it’ll take me five or six more years.  Fortunately, DW and I have good jobs with good companies and have forsworn going into business for ourselves for the remainder of our lives.  I don’t have the self-discipline to work for myself.  The most important financial thing I’ve ever done is to realize that about myself.

[snellbert]

1. Declined the stock options offered to me when I started working with my old tech company. (I was very young, didn't understand the first thing about stocks and was terrified by the prospect of managing yearly taxes/vesting/etc.) Had I taken the stock, never bought more and not even reinvested dividends, I'd be up about $40k.

2. On a whim, sold and cashed out my company stock. For no particular reason other than I felt like reorganizing. Three days later it was announced that the company was bought out and all shares were closing out at a higher price. If I'd ignored my "whim" for three days, my stocks would have gone up about $50k. Blast!

[kms]

I've bought a brand-new BMW R1200GS Adventure in 2009 for 16,000€. Was so disappointed by the bike and BMW's behavior (the bike started rusting a month after I bought it, BMW's response was basically 'it's my fault, I should be cleaning it more often') that I've sold it a year later for 10k - lost 6k in one year, that really hurt. The replacement bike, a Yamaha, cost me 8k total -> Facepunch.

[BlueMR2]

I really don't know what the worst has been.  There's been so much sickening waste in my life that I don't know where to start!

To go on a slightly different route, here's one from last year that was a "everything went wrong and things got way more expensive than planned":

Grabbed the cheap club airplane (PA28, $85/hr fuel included) for a quick trip (just a little over 1 hour each way) to visit friends on the other side of the state.  Weather was looking rough for the flight out, but good for the return trip, so we didn't make the "go" decision until the last minute.  Definitely instrument conditions for the outbound trip, but was improving and was high enough that I could return to homebase in case of emergency.  So, off we go.  Had a wonderful day with friends.  Then the weather prediction completely broke down.  Instead of the completely clear flight home the forecast had shown, a monster line of thunderstorms popped up in the middle of the state, so wide it completely cut us off.

Having to be at work the next day we were forced to abandon the airplane down there.  Being Southern Ohio, practically *nothing* is open after 6pm on weekends.  Finally found a rental car place open on the other side of the city, got our friends to drop us off there.  Rented a car and drove home.  Got nailed for the 1 way charge on the rental, but at least was able to turn it in the next day near home and keep it to a 24 hour rental.  Was working all week so couldn't go get the airplane myself.  Had to pay for a couple other club members to fly another airplane down there and then fly both back.

Sometimes the $200 trip can turn into a $1000 trip despite proper planning.  The good news is that by that time I had greatly improved my frugality and the surprise expense was merely an inconvenience and not a major problem.

[geekette]

Minor, but stupid.  I fell on vacation - it just seemed like a badly skinned knee (on volcanic cinder - ouch!)  The whole vacation, I was slathering it with antibiotic ointment but it just wasn't healing.  I stubbornly refused to go to the doctor, even though we had trip insurance that would have covered it while we were traveling.

By the time we got home it was looking even worse, so I ended up spending over $500 for the doc, the x-rays, labs, antibiotics...  All went to the deductible, of course!

[AlmostIndependent]

Sometimes the $200 trip can turn into a $1000 trip despite proper planning.  The good news is that by that time I had greatly improved my frugality and the surprise expense was merely an inconvenience and not a major problem.

You're looking at this all wrong. You did exactly the right thing. $1000 is chump change. You could have ended up as the subject of an NTSB report. Never good but especially bad when the cause is "continued VFR flight into IMC." Translation: pilot made a very bad decision.

[Le Dérisoire]

timing the market.

Me too. Especially irrational because I believe in the efficient-market hypothesis.

[abuzzyisawesome]

I squandered a $57k settlement from a car accident on a house remodel, credit card repayment, lasik and laser liposuction. I still punch myself in the face, daily. I was young and dumb. Here I am back in debt again, in glasses and fat. Yep. *facepunch*

[mgreczyn]

As I posted in the other thread, the most anti-mustachian thing I ever did was become a professional pilot.

So happy I dodged that bullet...

[Bigote]

10s of thousand of dollars worth of cigarettes over the years. (Thankfully those days are well behind me)