doomed if you do, doomed if you don't

damned if one does and damned if one doesn't

Of a situation where either choice results in a negative outcome.

in a bind

In a difficult situation, usually of one's own making; having a dilemm…

on the horns of a dilemma

Facing a choice between two equally undesirable alternatives.

death by a thousand paper cuts

An ultimate negative outcome, such as the failure of a project, brough…

the joke is on someone

Someone is the butt of a joke or is experiencing a negative outcome, e…

make the best of

To derive what limited advantage one can (from an unpleasant outcome o…