Historical clue formulations

• "Is this such a good idea?" — 2023-06-11
• "Is it worth the risk?" — 2023-02-02
• "Is this such a good idea?" — 2021-10-23
• "Is the risk worth it?" — 2019-04-21
• Timorous question — 2018-06-23
• "Is it worth the gamble?" — 2015-07-15
• "Is it worth the chance?" — 2011-09-16
• Hesitant question — 2005-11-18
• Risk-taker's self-question — 2001-09-08
• Risk-taker's self-question — 1999-07-16