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My favourite was in Japan when I was trying to tell our hosts that my friend left his job because he had a bad boss, but did so by saying that his "oyaji" was "aku", thus unintentionally implying that he worked for the Mafia. They spent the rest of the evening cracking Godfather jokes ;)

For his part, he was trying to talk more masculine, avoiding the feminine air that polite forms cause, but took it too far, and kept calling us "aitsu", not realizing how harsh that was. Which we took great fun at throwing back at him as though we were deeply offended - "Aitsu?!??"