Clever and deceitful in a sneaky way, plotting or scheming secretly to achieve selfish goals.
From Latin 'connivere,' meaning 'to wink at' or 'to shut one's eyes,' which evolved to mean 'to deliberately overlook or cooperate secretly in wrongdoing.' The meaning shifted to describe someone who engages in that secret, winking-at-you deception themselves.
The original Latin meaning of 'connive' was actually innocent—it meant 'to close your eyes to something'—but by the 1600s in English it had darkened to mean deliberately helping someone commit a crime by pretending not to see it, and eventually came to mean the person doing the sneaky plotting themselves. Language often tracks the moral degradation of human behavior: words start innocent and gradually become darker as we find new ways to be devious.
Conniving carries stereotypical feminine deviousness coding in English literary tradition, often applied disproportionately to female characters in early novels and drama. The association reinforces the trope of women as manipulative, while male calculation is framed as 'strategy.'
Use the word neutrally when describing actual deceptive behavior regardless of gender; avoid applying it selectively by gender.
["scheming","calculating","manipulative","deceptive"]
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