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Answer:
NOWIN
Possible Questions:
Hopeless
Like some situations
Kind of situation
Like a hopeless situation
Type of situation
Sure to end badly
Lose-lose
Like hopeless situations
Hopeless, as a situation
Beyond help
Bad kind of situation
Unsalvageable
Unprofitable, as a situation
Sure to end in failure, as a situation
Like an impossible situation
Like a frustrating situation
Like a choice between evils
Like a Catch-22
Impossible, and hint to this puzzle's theme
Impossible
Hopeless, as situations go
Having only unfavorable outcomes
Grim, as a situation
Futile, as a situation
Darned-if-you-do, darned-if-you-don't
Certain kind of situation
_____ situation