Got into commodities trading with $6000. Actually had some good trades. Pretty exciting to make a couple of grand on that investment in a month. The stress though was incredible. With commodities, you can lose more than your investment.
I ended up losing $4000. Gained getting sleep at night.
Those things are effing money pits. I paid $14K over the years for crap that wasn’t worth a thousand. Did the math & dumped it.
Just found out today that I ordered about $100 worth of books sent to an address I haven’t lived at for five years.
Not a huge amount of money, and I might still be able to recoup it, but goddammit.
In 1972 I left college and signed on as an apprentice carpenter. Times were hard and, as it turned out, the leadership of the local union were corrupt. The year I signed on, the electricians took on fifteen or twenty guys. The plumbers about the same. My apprentice class was about two hundred guys. Work was spotty, and it was hard to hang on. Six years later I had my Journeyman’s card, but no union work in well over a year. When I finally gave up hope, I added up all of the pay stubs from union jobs and the money I had laid out in union dues and fees. The union came out way ahead.
Ok you win
Not a huge amount of money compared to other amounts in this thread, but when I was in college I lost $100 to what in retrospect was an obvious con. A man approached me in a shopping center parking lot and told me his car had a dead battery, and the gas station up the street wanted a $100 deposit to let him borrow their jumper cables, but they wouldn’t take a $100 bill and that was all he had on him. But if I went to an ATM and withdrew $100 in twenties and gave it to him, he’d give me the $100 bill. And he had some excuse as to why the jumper cables I had with me in my car wouldn’t work, his car needed special high current cables or something. So long story short he took my $100 and walked away never to return.
Was in Jerusalem with a tour, and the tour leader took us to a shop his ‘friend’ owned (that’s expected guided tours anywhere in the world). End up spending $4,000 on a sword and dagger set that I never have had mounted/framed or costed. Told my friends that anytime I entered a store like that again to drag me out if it looked like I was interested in anything.
I’d post, but wouldn’t want my wife to find out. 
Getting married
Hmm so it seems divorce, bad investments and gambling are the main culprits for a lot of people.
Those two posters who lost their money simply by leaving it out in the open and walking away - ouch. It hurt a bit to read it.
I hired someone to do some work on my barn. I paid him all the money upfront ($2300). Stupid. :smack: He took off with the money.
Bought a holiday home in Southern Italy for 80,000 euros. Spent about 30,000 euros on purchase taxes, legal fees and renovations. Sold it ten years later for 80,000 euros.
Italy, the one damn country where property is NOT a reliable investment.
200 plus Euros on a family tour of the Alhambra (Granada, Spain), then I took us there the day after our tickets were actually valid
I got taken in by a traveling contractor, the “Hey, we were doing work up the street and noticed your driveway and had some extra materials…” type of thing. Paid $225 or so to have them basically spray some oil on the driveway to darken it. Cash, of course, so there’s not a check to stop payment on. Mostly, I felt dumb because that sort of thing is such an obvious scam but I guess scams only work because everyone assumes they’re too smart to fall for them.
Ironically, they DID do a nice job of trimming the grass off the sides and and weeds coming through the cracks.
Damn. I’ve wondered around the casino trying to find my table in situations like that, but I’ve never just left.
Off topic anecdote:
The defense contractor I worked for made aircraft computers. The software was classified much higher but the hardware, with no program in it, was Confidential. As such they could be shipped around via DHL, FedEx or UPS so long as they were double wrapped, a box with the classified stamps on it within a plain ol’ shipping box.
One time one disappeared; the box was heavy for it’s size and we figured it had attracted the wrong kind of attention. About nine months later a fisherman snagged it out of a reservoir. Doubtless, the thief saw all the inner stamps and panicked, probably imagining the FBI knocking on his door.
20+ years ago for back taxes. I worked in a different state from where I lived, and the employer withheld state tax was about 1/3 less than my home state. Ended up having to pay back about 1800 dollars. Hard to come by as I was barely getting by as it was. They let me pay it back by monthly installments.
More recently: just spend 16 dollars on a Blueray DVD movie that will not play in my region.
The dumbest way I ever lost money was in the hours after I first landed in the USA, jet lag and growing up with differently coloured currency lead to me tipping $100 on a $2 taco.
Got a tip on a biotech stock from someone online, and bought some without bothering to do any research. It went from a few dollars a share to zero in under a year. Lost a couple of thousand dollars.
Four years ago I sold some stocks to buy a property. Knowing that the capital gains tax rate is 15%, I set aside $X for paying that.
When tax time came, I found out that 15% is the starting tax rate, and it goes up if you have a lot, and that when you have a lot the Alternative Minimum Tax was triggered.
So instead of $X, I needed to set aside $X plus $23,000. Had I known to look out for that, I could have structured it over a couple of years.