damned if I do and damned if I don't Every possible action (or inaction) would result in a negative outcome or cause me trouble; there is no course of action that does not have a drawback. damned if you do, damned if you don't Every possible action (or inaction) would result in a negative outcome or cause you trouble; there is no course of action that does not have a drawback. So your boss will be mad if you miss the work event, and your husband will be disappointed if you skip your anniversary dinner.

My boss will be mad if I miss the work event, and my husband will be disappointed if I skip my anniversary dinner. Yep, I'm damned if I do and damned if I don't!
Damned if i do, damned if i don't definition at Dictionary.com, a free online dictionary with pronunciation, synonyms and translation.

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