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Last weekend my 18-carat gold bracelet worth somewhere around $3k decided to fall off and disappear. That is by far the most expensive and sentimental thing I have lost. It wasn't the value because I never planned on selling it, but I though it would have made a nice family heirloom to pass down later in life.
I have never totaled a car, but my wife did, so that's a pretty big loss too.
When I was 19 I bought a car that was very popular at the time, no longer being made, and it was stolen a week later. Never saw it again. That's a big hit to a 19 yr old male.
All the money that I lost gambling. I seldom lose much at one time, but it adds up over the years.
I don't think I ever lost anything valuable because I seldom bring anything with me since I fear losing it. I once lost a screwdriver in a junk yard and even though I found two others much better than mine I still spent over an hour looking for it. I felt miserable all the way home.
When I was a teen in the 80s I lost my wallet with around $15 in it. To a kid, in those days, that was a lot of money to lose. To this day I constantly check my pockets for my keys and wallet.
I lost my college sweetheart's high school ring. It happened 47 years ago, but I still feel guilty about it. I took it off to wash my hands in a shopping mall's public restroom and then forgot and went home. About a year and a half later, after we had gotten engaged and then broken it off, he asked for the ring back and I had to confess that I'd lost it. Even now I sometimes look for it on eBay.
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