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damned if I do, damned if I don't

A situation in which one can't win. For example, If I invite Aunt Jane, Mother will be angry, and if I don't, I lose Jane's friendship—I'm damned if I do and damned if I don't. Eric Partridge suggested this idiom may have come from the emphatic I'm damned if I do, meaning “I definitely will not do something,” but despite the similar wording the quite different meaning argues against this theory. [Colloquial; first half of 1900s] Also see catch-22.

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The American Heritage® Idioms Dictionary Copyright © 2002, 2001, 1995 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company.