Probably one of my most stupid gaming moments was in the Rayearth RPG game. There was this one boss that you were supposed to lose to(I was unaware that the battle was utterly unwinnable). However, I refused to do so. I fought that guy for a total of SEVEN hours(save states helped here) before I finally decided to google why the smurfing hell this guy would not drop dead! Talk about wasting expendable items and several hours of my life.