The most expensive and useless thing I've ever spent money on was an ex-wife.

Ever few months or so I give online dating a try.

A pair of gold shoes which don't even fit me, but they were reduced in a sale and I like having them just to look at

I spent 600 dollars on a couch I have never used

I bought a vacation condo which i rarely used. It's sold now. But when I thought about it I should have just been staying at 5 star hotels ....it would have been cheaper.

I sent quite a lot of money to girls in the Philipines back when I had a softer heart and a thicker skull. I am not holding my breath waiting for any of it to be returned.

Ex wives!

All the DLC for Cities: Skylines. Now, this is an awesome game, and I love it. What's stupid is that I bought the DLC as a bulk buy, the day before a sale would have allowed me to get them for a third of the price. Since then, I've been very careful to wait until sales to buy anything I might desire.

Looking through some of these answers, I realise that my problems are not really problems.

California Psychics. Readings are5 dollars a minute!

A $70,000 sports car

Clothes & shoes worn once.

Depending on the knife, it may have been a good deal. A professional Chef's knife is worth that much or more.

I got several, most recent is a new 3 speed turntable, haven't hooked it up yet, had to have it. Ping putter, 2 sets of clubs, haven't golfed in 17 years... I might. Several rare and vintage records to play on my new turntable... a tuxedo... hiking boots, don't ask... the list goes on n on n on.

I don't consider the money I spent on drugs and alcohol dumb. There are plenty of other things I bought that were dumb, a gun in my 20's, a couple of cars, and a Propeil slicer and dicer, but not the drugs and alcohol.

A $1200 Military Macaw.

Eye surgery last year. eye tests show no improvement, to me my vision seems worse, and eyes feel unco, oh, and did I mention PAIN of the surgery? Lots of pain.

Does it slice clean?

A TIC - tenants in common. I own a piece of a shopping center. It performed beautifully until the financial mess several years back. Now, there are many empty stores, and new tenants are hard to come by, and I can't get rid of my share ... live and learn !

I spent over $500 for a barbie doll. Then exposed it to ciggarette smoke.

Been at least 20 years but I still have it. I should check it's value

I bought a smart phone and accessories, but never used it, and finally gave it away, continued using a cheap nonsmart cellphone.

I hate being on the phone, so only use it for emergencies.

I spent $300 on computer software, specifically for writing a book, that I couldn't figure out how to use and ended up writing my book in Microsoft Word.

My second partner. she was dumb as fuck.

Bought a business, that drowned the day I walked in due to the previous owner.

300 dollar kitchen knife is not dumb as long as it’s not a Cutco knife.