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My finest moment in a role-playing game had to be the night we played a one-shot session of Dungeons and Dragons that I called, "At the table of peace in a world of war." This particular gaming session was extremely enjoyable and, while as a Dungeon Master I worked my butt off, it was totally worth it.
The premise of this particular game was that each of the players would run a character that represented a different faction from the Warcraft setting. This game was run prior to the release of the MMORPG World of Warcraft, and so many of the elements of our session may not have been necessarily true to what the "real" Warcraft world, but that didn't really matter.
At any rate, the idea was that these faction leaders were meeting to try to form a peace treaty of some sort. There were several issues at stake, including territorial disputes, access to an archaeological site, and protection of a sacred grove. Each faction had some common goals with some other factions, and some opposed goals. Each character also had certain special abilities at their disposal, such as spies that could listen in on conversations and such.
Most of the session was spent with everyone around the table, essentially negotiating. There were scheduled breaks, during which the players would leave the table and try to negotiate in private with members of other factions in order to accomplish their particular goals. These in-between times were among the most interesting, and gave players an opportunity to really get into their character.
At the end of the evening, each player received a certain number of points, based on which goals they achieved, and which objectives of others they prevented. It was an all-around great session, and even now, several years later, everyone in our gaming group points to that night, affectionately, as the "night the stars were aligned."
This was, indeed, my finest moment in a role-playing game. As a Dungeon Master, everything seemed to go off without a hitch, everyone had a good time and, interestingly enough, the outcome of the actual storyline was very different from what I had envisioned when I originally planned the game.
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