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I wasn’t really sure how to address this question, mostly because no examples sprung to mind, but also because it could be interpreted in a variety of ways. ‘Tricky’ could mean difficult or complicated RPG experiences where success was far from certain, but I’ve talked about challenges I’ve faced as a GM elsewhere. It could also be an experience that had the potential for emotional conflict or feelings OoC, or something that was difficult to negotiate. In all honesty, the chances that I would have enjoyed an experience like that are very low! My last post discussed a situation that was fraught and involved some outcomes I found difficult to take (as well as how they turned out better than expected), so I don’t really want to go over that again. I suppose the only thing I can think of was one of my early tabletop games where I, as the GM, was the one who made the game jump the shark, and both regretted and enjoyed it.
One of the early campaigns I ran (the second one, in fact) was Witch Hunter: The Invisible World 1e. I might have talked about it before in my thoughts on tackling player and GM expectations before a campaign. It was meant to be a horror game where the swashbuckling action didn’t stop the threats from being genuinely hair-raising and serious. For the most part, I succeeded, but then I managed to torpedo my own tone with a dissonance the game never recovered from. I decided to run a Christmas special. I ran a game about a village where people’s hearts were being stolen and it turned out to be an evil baker with the power of cakeomancy. He had tiny hoards of gingerbread men, hulking gingerbread golems powered by human hearts, and pastry tentacles. It was very silly, and afterwards, I didn’t understand why the tone didn’t go back to serious horror. Little did I realise that I’d jumped the shark all by myself, and now we could never go back. I still managed to give the players some horror moments (when they tried to ride horses to outpace a Patch Jack and then realised it was keeping up with the horses) but I lost any control over how wacky the game got after that.
While that experience was difficult, the thing I learned from it was that it didn’t matter. It was fine. I could still run a game people enjoyed, and they hadn’t even noticed the tonal shift. It was a good learning experience, to find that even if my perfect concept of what the game could be didn’t survive contact with the players, what did survive was still worthwhile, fun and fulfilling. And that was what mattered, after all.