He demanded answers to questions that one would hesitate to put to one's intimate friends
问题描述：
He demanded answers to questions that one would hesitate to put to one's intimate friends
答
这句话这样子你就清楚了：He demanded answers to questions,while one would hesitate to put THESE QUESTIONS to one's intimate friends.
中文意思就是：他想得到这些问题的答案,而每个人在将这些问题交给知己时自己都会再三犹豫.（言下之意是：他想得到答案的这些问题,会让知己很为难.）
愚见,仅供参考.