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A person flirts with dangerous ground, when he or she consciously puts him/herself in a dangerous situation.
When your friend holds onto the Rook in the game of Rook, a natural reaction would be to say, "WOAH! You're flirting with dangerous ground here missy!"
"WOAH! You should have played the rook! You're flirting with dangerous ground here missy!"
A friend - "I don't agree with your definition of that idiomatic expression."
Me- "You'd better back off; you're flirting with dangerous ground."
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