The conversations to have before you get engaged
Not a generic list of a hundred questions. Answer a few things about your situation and this builds the shorter list that actually applies to you.
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Why a tailored list beats a long one
Lists of “100 questions to ask before marriage” get shared constantly and completed almost never. They are too long, most of the questions do not apply, and the ones that would have mattered are buried among the ones that would not.
This asks five things about your situation — whether either of you has children, whether there is a meaningful difference in observance, whether you live in the same city, whether either of you has been married before, and how involved your families are — and then builds the list that fits.
The areas it covers
Money, children, the Jewish home you want, work, conflict, family, and health. Every couple gets those. Depending on your answers it adds specific questions about step-parenting, whose practice sets the standard at home, who is relocating and what they are giving up, ongoing obligations from a previous marriage, and what happens when family and marriage want different things.
How to actually use it
Not in one sitting. Take one area at a time. Both of you answer before either of you responds — otherwise the second person calibrates to the first, and you will both believe you agree more than you do.
And when a question produces a strong reaction, that is the one to stay on. The reaction is the finding.