DOIDARE

Set to 2 different clues across 3 published puzzles, most often “Risk-taker's self-question” — The New York Times, Saturday, 8 September 2001.

7 letters

Every clue on record, most used first

Risk-taker's self-question2 times
The New York Times — Saturday, 8 September 2001
Hesitant questiononce
The New York Times — Friday, 18 November 2005