A Diplomacy game board is basically a map of World War I era Europe. Ideally you play with seven players, though you can easily play with as few as five. Each player controls one of seven European powers: Austria, England, France, Germany, Italy, Russia, or Turkey. The countries are more or less evenly balanced in relative strength. Each player begins with at least three "supply centers" (though Russia begins with four), and several neutral territories are supply centers as well. The first player to control half of the supply centers on the board wins.

Two major catches set Diplomacy apart from other strategy games like Axis & Allies or Settlers of Catan, however:
1) The game features no element of chance: no dice and no cards, simply set rules and pieces, like in chess.
2) Although each player plays for himself or herself, it is impossible to win without teaming up with other players.
The second catch is the kicker. Each round of the game features a period of discussion, followed by each player writing his or her moves down on a paper. These moves are then read aloud and resolved on the game board. Basically, this means lying and stabbing others in the back are essential to gameplay.
For example, the player controlling Germany can convince France to help him go up against England, then go behind France's back and team up with England instead. The German player must exercise caution, however, because for all he knows the French player might backhandedly team up with the English player instead. The game becomes a study in psychology, and success is determined largely by knowing how long to work with another player before almost inevitably turning against him or her and some point during the game. You wager whether or not you can trust someone against whether or not you want others to think they can trust you.
This leads to an often chaotic game that usually takes all day and frequently results in hurt feelings and annoyed friends. Almost every time I've played some poor sap gets teamed up against by every other player in the early rounds and wiped out before he or she can make any realistic attempt to win; usually this target is whoever is hosting the match, so it often pays to be a guest.
It's amazing to me how real some of our Diplomacy fights would get - particularly in the latter rounds shouting matches might erupt and people would storm out of rooms. This is ridiculous because the backstabbing is integral to the gameplay. You can't justifiably get angry at someone for throwing you under the bus in Diplomacy because sooner or later you'd have do the same to them. This isn't because you don't like them or want to hurt them; it's because that's what you have to do the win the game. Lying to someone about an alliance in Diplomacy is no different than setting up a hotel on Boardwalk in Monopoly and cackling with glee when an opponent lands on your property and starts mortgaging. Yet I admit I've been the guy who got upset and took it personally during some of these games.
Now, I'd hate to leave you with the impression that Diplomacy is merely fuel for broken friendships. Clearly, I played with the same group of friends multiple times, so somehow we found a way to continue despite the fights. That's because these arguments happened in the heat of the moment, but generally subsided very quickly. The person on the losing end of the deal would then usually resort to making bizarre moves just to mess with other players and/or doodling on the sheets where everyone writes their orders. I think I remember one game where an Italian fleet ended up in Iceland and just kind of hung out there for the rest of the game - I'm still not sure how that one happened.
Weirdly, I suppose that's what makes Diplomacy fun - my friends and I can act out aggression and subversion toward one another, and though we'll be frustrated at each other for an hour or so we always end up laughing about it in the end. In the end, that progression of conflict toward resolution is a mark of a true friendship. Our board game days just represented a microsm of that.
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