So in the last SoK episode (Congratulations on the 50 btw!!!) Jeff goes into the story of how he killed his wife's beloved vampyre character 20 minutes into a 2 year campaign. The game setup sounded cool with a supernatural vampire hunting swat team and lots of goodness, but the result...ouch. My wife's not a gamer, and now I'm thinking that might not be such a bad thing.
Anyway, the episode made me think of one of my GMing fiascos back when I was playing with my brothers and some friends. They were a bunch of kids from a farming village, one of whom was unbeknownst to them, the descendant of the ancient High King of legend. A Viking attack on their village had swept them into greater happenings as they begin to discover a great evil is working against the land, raising a monster invasion horde. At one point they step into the otherworld and are confronted by the King of Faery, who will bestow "items" upon them that will help them defeat the Dark Lord, but they can take no "gifts" from under the hill. They must win them by a challenge of...wait for it....Chess!!!
In my defense, I was really into chess at the time. OK, that's not a defense. Somehow I had forgotten how long and devastatingly boring a game of chess can be to those who are watching. One of my brother's friends rose to the challenge, we were both very deliberate (read "slow") players and the agony was drawn out as the entire game ground to a halt. Maybe if I had given the King of Faery a two minute chess clock the hell could have been over faster. Once the game began, I knew I had a problem because how do you speed up a chess game? Looking back with hindsight, I could have just pushed pieces out quickly, I mean it wouldn't be me losing it was the King of Faery...but if I had been that wise, I wouldn't have started the game in the first place.