What do we talk about once dating gets serious, and what must be covered before the engagement?ask your rav

He suggests moving on to goals, aspirations, character traits, and a shared approach to raising children. It matters to find out whether the real desire to build a home of Torah matches the familiar words used on the date. Among the topics he names for discussion are where learning will fit into the home, the example a father sets that his children will see, and how learning Torah is balanced against the needs of wife and children. The questions he raises are meant to clarify outlook, not to serve as ready-made answers to these obligations.

“Is learning Torah at the expense of one's wife or children justified?”

She suggests moving from the everyday to the personal: one's inner circle, beliefs, motivations, formative experiences, and core life values. This kind of openness should let the other person see the real person inside.

“Conversations on dates should move from the everyday to the deep, from the obvious to the personal.”

Her questions for a serious relationship touch on how first impressions have changed, the reasons for compatibility, and times a person felt truly understood. She also suggests discussing hardships weathered together, mutual support, ways communication could improve, things still hard to say, and expectations for a shared future. Among her closing questions: what main message would you want to leave the other person, if this conversation were the last one you'd ever have.

“If this were our last conversation, what's the one thing you'd want me to carry with me?”

She advises asking what triggers anger and stress, and discussing, before the engagement, where you will live, for how long, health, and any existing plans for school or career. She singles out expectations about family planning: shared religiosity by itself does not guarantee identical views. None of this discussion replaces a rav's ruling on specific halachic questions.

“The fact that both people are religious doesn't mean they share the same values.”

She suggests seeing each other in a variety of natural settings and getting to know each other's surroundings. Her benchmark is two or three meetings a week with short calls in between, so there is still room to evaluate. She advises paying attention to how someone reacts to discomfort, how they argue respectfully, how they take criticism, and how they treat other people. She suggests not making romantic settings the center of getting to know each other.

“A person's surroundings say a great deal.”

A caution: in her example, hours of conversation did not prevent a failed engagement, because the couple mistook understanding the other's opinion for agreeing with it. The author advises really listening and clarifying views, so as to see shared goals and mutual respect. Detailed plans for the far future, such as where to live in retirement, she does not suggest turning into an argument: outlooks can change, and paths to shared goals can be worked out within the marriage.

“You need to see shared goals and mutual respect.”