Is it possible to win this thread?
Because my worst purchase ever, is the Magic The Gathering computer game from, I dunno, 1998, or something.
I'll just throw it out there: I was a little shit back then. I regularly stole hard-earned money from my dad's wallet. He's always been a shit too, but that doesn't make the money less hard-earned.
It started out with small amounts, but it was so easy, I got cocky. It was of course stupid to think he wouldn't start to miss sums of sometimes up to 2000 Belgian francs (which is about 50 euro). And 2000 francs was how much most new games costed back then.
My parents were divorced, I lived with my mom, and that evening I visited him as I often did, took 2000BEF when he wasn't looking. When I got home, the money was still in my pocket when the bell suddenly rang. My dad was at the door, furious, and he demanded I emptied my pockets, took off my pants, everything. He was sure he'd find the cash on me, and the cash totally was on me, so I was in a pickle. I played a guilt trip. I played being severely hurt at such accusations, and my mother defended me, she got angry at my dad. He'd probably spent the money on booze and then forgot about it, or something. I fled "furiously" to another room, emerging about two seconds later, but that gave me ample time to quickly shove the banknote under a loose end of the fixed carpet. I "angrily" emptied my pockets, and took off my clothes. He was sure I'd got rid of it somehow (my ruse was transparent as hell to him, of course), but he knew he'd lost and he went home.
Trust between me and my father was forever destroyed and we've spoken maybe three times since then.
With that money I bought the freshly released Magic: The Gathering, of which I knew next to nothing, only that I'd started to feel interest in the card game, and played it for about half an hour, then never touched it again. Never even found out if it was a good game or not. I wasn't aware of it back then, I thought I'd just lost interest really quickly, but now I'm sure it was the guilt that just completely killed it for me.