Said when one is faced with two undesirable options. I'm damned if I do and damned if I don't—if I confess that I broke the vase, then my parents will be mad, and if I don't, then I'll feel guilty about it.A: "Katie found out that I also asked Colleen to prom. Should I come clean with her?" B: "Man, you are damned if you do and damned if you don't!"