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I am really interested in trying this game with one of my friends. I just read the rules and there is one thing I am not sure of. After the GM and player do the opening questions is the GM supposed to send the first letter detailing a bit about the situation and asking for help?

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Thank you for checking out my game! While this is up to exactly how you'd want to run the game, I think the player & GM should talk through the rules of the game (making sure the player understands how to play), decide the relationship between writer and player and why they can't leave the location and then discuss safety. Then the GM should be free to send the first letter, starting the game off and asking for help.