A friend recently linked to a Grantland article about the board game Diplomacy; and this friend commented that the game sounded interesting, but also sort of horrifying. "But," I eagerly posted back to him, "if you never played it, you only get some idea of how horrifying it actually can be."
I've played Diplomacy a few times: with college friends, both in person and online; and online with some random and anonymous people. In fact, after that Grantland article, I decided to sign back in to my account at playdiplomacy.com and joined a few games.
Now, as with religion, how you approach a board game like Diplomacy has a lot to do with you. So here's my favorite way to play: back when I was playing online with college friends, I was playing Czar Nicholas (or Kaiser Wilhelm) and I kept up an elaborate correspondence with other players in character; I even researched and discussed what historical uniforms my soldiers would be wearing at the time. Right there, that tells you a lot about what I like: I like roleplaying, I like story-building, I like specifics.
One other benefit--and horror--of playing with friends is that you already have an existing relationship with them. You think you know them. Which of your friends will pull a fast one to get what he wants? Which of your friends will stick to a deal even if another opportunity comes up? Of course, this isn't serious: at the end of the day, you are playing a game, and no soldiers actually get pushed out of territory. So you can't entirely judge people by their private, non-board game lives.
(Much better to judge them according to the "Would they hide me from the Nazis?" sort of game that some people play.)
Now, after playing for a few days online this time around, I resigned all my games, whether I was winning or losing. (Curiously, the games where I was doing the best were the ones where I was Austria; which, if you don't know the game board, is significant because Austria is surrounded by potential enemies.) Why?
Because it wasn't any fun. Would anonymous-player-63 turn on me? Who cares! It wasn't an interesting question since I had no other relationship with these people. Could they trust me? Well, that's a slightly more interesting question, but still not all that interesting to me. Why would I betray an erstwhile ally? To win. Why? Uh, because... winning is good? So now I'm playing with strangers that I don't care about, playing a game that I don't really care about.
And on top of that, it takes a lot of mental energy to go through all the scenarios, trying to figure out the best move to make.
So, for me, Diplomacy is best played with friends, probably while being stuck in a small room.