Craziest things you have spent money on.

Heck. I spent that much on my first computer in 1984. I did get the external floppy drive so that I would have enough storage (400K isn’t a lot when you have to store the application on the floppy as well).
The original Macintosh.

Oh, and the original MonsterBoard for another $1000 when it came out. That boosted me up to (just) over 1 meg of ram!

I spent about $3000 on a Thinkpad around the same time…I was in high school and paid for it with my own money (I worked a lot). 486DX2, ran Win3.1 (IIRC) and had, I think, about 640 megs of hard drive space, more than both the hard drives put together in my family’s desktop.

But I didn’t consider that crazy, I was a ‘computer guy’, it was a pretty natural purchase for me.

I spent a lot of time playing Chip’s Challenge on that computer.

My wife. 'nuff said.

My ex-wife. Ditto.

My second ex-husband. He cleaned me out but good.

Sex toys.

I won’t go into details.

My love of music has cost me a bloody fortune over the years, and sadly, it’s not just buying new music. No, I’ve bought the SAME music over and over and over again because the format keeps changing. First I bought the vinyl record. Then I bought a new round of cassette tapes so that I could listen to them in the car. Then cassette tapes went bye-bye and I bought a new round of CDs, which I thought would last forever. Then iTunes came out and I bought a new round of digital copies. Just today, I spent $25 to convert all the songs I’d downloaded from the CDs to the new iTunes Plus format.

And this doesn’t include the gadgets - the Walkmen, the CD players, the iPods, the Sonos, Bose speakers, headphone number 1, headphone number 15…headphone number 300.

I’m pretty sure that “Comfortably Numb” has cost me around $75 per listen.

Well worth the money! I gave this serious consideration since many of the great players didn’t come over for the match that was in my area, but I couldn’t get away from work. Have a great time!

I did a return Sydney/Rome/Sydney trip once over a long weekend to attend a friend’s wedding. It was great fun, but I spent most of the flight home wondering if I’d just done something completely insane.

I wouldn’t call it crazy because I still use and enjoy it after seven years, but definitely my most frivolous purchase to date was $110,000 for a 35-foot Four Winns 328 Vista cruising yacht. I have spent time on it every weekend this season so far.

My second most frivolous purchase to date was $22,000 for a 10-day Hawaii vacation for me and my wife a few years ago. I didn’t intend to spend that much but, in the end, that’s what it came to. We had an absolute blast. Vacation of a lifetime.

I saw this hanging in a local gallery window one day. A rather large embellished print in a thick, heavy frame. Had to have it, $2700 later it was hung at the head of my bed. Still there 14 years later.

I spent $500 on a suit so I could have something nice to wear at an upscale restaurant I went to with some friends.
Wore the damn thing once and it has been sitting in my closet ever since. And NOW it’s too small to wear. (I’ve gained weight) I still refuse to give it away because… Well because reasons!

About 1988 or s I bought a 486 computer and a lazer jet printer with font cartridges that cost me a total of around $8,000. All I used it for was book keeping.

When my old beagle developed a bad back (degenerative disc) I bought her a doggy stroller. Looks like a baby stroller, but just has a clip in it for the leash.

I took her out in it a number of times.

I was feeling sort of proud of myself that I haven’t made any frivolous purchases, and then I got to this. :o O, the dresses I’ve worn once.

As a dog owner who appreciates the quality time a nice walk gives me with my dog, I wouldn’t consider that a crazy purchase, more like a nice thing to have for enjoying your dog’s later years.

I paid $15 for a membership here once.

My wife recently spent $189 on a vibrator she used exactly one time. It didn’t get her off so she’ll probably never use it again. However, the one I bought her for Christmas a few years ago as a stocking stuffer for $9.99 at Brookstone induces wild orgasms. Go figure.

I just spent $8 for WiFi on a Southwest flight. So slow that I couldn’t really stream or download anything.

I’m going to Vegas this weekend, so I’m sure I’ll make several purchases this weekend. The girl I’m going with wants to rent a Lamborghini.