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Answer:
NOWIN
Possible questions:
Hopeless
we know 9 Answers
Like some situations
we know 2 Answers
Kind of situation
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Like a hopeless situation
we know 1 Answer
Type of situation
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Sure to end badly
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Lose-lose
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Like hopeless situations
we know 1 Answer
Hopeless, as a situation
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Beyond help
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Bad kind of situation
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Unsalvageable
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Unprofitable, as a situation
we know 1 Answer
Sure to end in failure, as a situation
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Like an impossible situation
we know 1 Answer
Like a frustrating situation
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Like a choice between evils
we know 1 Answer
Like a Catch-22
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Impossible, and hint to this puzzle's theme
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Impossible
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Hopeless, as situations go
we know 1 Answer
Having only unfavorable outcomes
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Grim, as a situation
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Futile, as a situation
we know 1 Answer
Darned-if-you-do, darned-if-you-don't
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Certain kind of situation
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_____ situation
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NORETURNOFPOINT
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