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There are 8 clues with the answer 'DAREIASK'
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CLUE
1.
Trepidatious query starter
2.
"Might really regret this question, but . . ."
3.
"Might regret knowing the answer, but ..."
4.
"This may not be an appropriate question..."
5.
Hesitant start to a question
6.
"Might deeply regret this question, but . . ."
7.
"Mightdeeply regretthis question,but..."
8.
"Maybe it's better not knowing, but . . ."