When do we move from light topics to serious ones, and how should the conversation deepen from date to date?

The intermediary dates, in his scheme, are for moving from everyday topics to personal ones, including attitudes to money, wishes and spending priorities. Once it is clear that the person is pleasant, he suggests checking shared goals, expectations of a spouse, ideas about the home, and the ability to support each other in hard times. Emotional questions should come up as things progress, including what genuinely struck you in the other person's words. The goal, as he puts it, is to reach a decision knowing the person and feeling a connection.

“The intermediary dates are the time that the conversation graduates from mundane to more serious”

Her questions for deeper acquaintance are meant for the stage when you already like the person but have not yet decided on marriage. She distinguishes this getting-to-know stage from the final compatibility check before an engagement.

“These are the kind of things that you ask a person you like but haven't decided to marry, yet.”

She expects the conversation to become a little more personal on the second date, and around the third or fourth the discussion of views on family and religious life to begin. Her examples include children's schools, the community, tznius, technology in the home, davening and learning. When in doubt whether a topic is appropriate, she suggests first checking with the shadchan after the date.

“Usually on the third or fourth date, the couple begins to discuss hashkafa”

Her sequence of deep questions calls for an already serious stage of the relationship and a setting free of judgement. She advises giving explicit permission to skip any uncomfortable question, and moving in the suggested order from the less deep to the more personal. The goal is an honest conversation, not getting the right answer.

“The goal isn't to get the 'right' answers but to create an open environment”