Gretchenfragen are mostly unpleasant and challenging, and look to elicit some kind of confession.
The term is extracted from Goethe’s Faust, in which Faust’s lover Gretchen asks Faust, who has secretly made a pact with the devil, what his opinion on religion is. In a narrower sense, a Gretchenfrage concerns religion, but can also be used in a more general sense.
The term can perhaps be translated as a pivotal, or crucial question, although these terms don’t quite convey the direct and disagreeable nature associated with a Gretchenfrage.
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Ich bin kaum überrascht, dass sie dich nicht klar antwortete. Du hast eine Gretchenfrage gestellt.
I’m hardly surprised she didn’t answer you clearly. You asked a very difficult question.
Der Pfarrer musste die Gretchenfrage bedenken.
The vicar had to consider the crucial question.
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