Damned-if-one-does-and-damned-if-one-doesn-t Definition

adjective

(idiomatic) A dilemma where either choice results in a negative outcome.

If John leaves for New York to follow his career, his father will disinherit him. He's damned if he does and damned if he doesn't.
Damned if I do and damned if I don't.
Damned if you do and damned if you don't.
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