Student loans for an extra degree you don't need or from a school a bit out of your price range? A car which has too much horsepower or renders you too many speeding tickets? A house you bought at the height of the bubble? An item of clothing with a prestigious tag which you find you never wear? The last fast food visit which turned into an ER visit? Tell us your stories or show us pictures. Mine is an ER visit from the sour cream nachos after I found out the hard way that I was lactose intolerant so I won't show pictures. Doc said I didn't have food poisoning because I was in too much pain and this type of pain accompanies lactose intolerance not food poisoning...gee thanks, Doc. I did buy the below pair of ultra weather proof hiking boots for $190. I don't hike anymore and I live in a drought area where it rains very little. Stupid purchase for a nice item with no context in my life. I used to collect guitars and had 60 over the years and that was money truly wasted, and when I reverted to one or two, I actually focused on playing and became a decent guitar player. Almost every collector of guitars either does not play, and if they do, they suck. I would read about rock star collections, and I knew something was off when I found I had more than them.