Damned If One Does And Damned If One Doesn't Meaning

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

Example:   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.