I agree completely with you that "how some roleplaying nerd thinks you should pick up wenches" bears no meaningful relationship to real social dynamics, so it's all password-guessing.

From my perspective, the same thing was true of slicing swords through armor, raising allied morale, casting spells, praying for divine intervention, avoiding diseases in the swamp, etc. None of those simulated activities bore any meaningful relationship to the real thing they ostensibly simulated.

But I'll grant that in the latter cases, there were usually formal rules written down, so I didn't have to guess the passwords: I could read them in a book, memorize them, and optimize for them. (At least, assuming the GM followed them scrupulously.)