I only said Monopoly because HPLovecraft said not to. Most Monopoly games I've played have involved excessive arguments over whether profit sharing agreements are legal or someone making a bad trade that screws everyone else over.
My actual favorite is Settlers, although the bad trade scenario can definitely occur in that one too. I also enjoy Scrabble, but it's a bit different in that your opponent really has to be at the right level to make it a good game as it requires a lot of specialized knowledge.
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