What to discuss from the third date on: home, money, Torah, parents, children

On the second date the talk gets a little more personal; usually on the third or fourth date the couple begins to discuss hashkafa (religious outlook): schools for the children, the community, tznius (modesty), technology at home, davening and learning.

If you are not sure a topic is appropriate, ask the shadchan after the date.

Date conversations must progress from the mundane to the deep, from the obvious to the private: your circle, beliefs, motivation, formative experiences, core values.

That is how you let the other person see who you are inside.

Ask concretely, not in generalities: how should a husband and wife resolve an argument; where will you never compromise; a shiur or the parent-teacher meeting; what do you expect of me as a spouse.

Different people have very different ideas of what marriage is and how to raise a family.

The most obvious things go unasked: do they plan to live in Israel; if the goal is kollel, for how many years, and do both sets of parents agree; does the person drive; does yichus (family lineage) matter.

You need to know whether there are circumstances that would surely keep the shidduch from happening.

Discuss household roles directly and test compatibility by actions, especially where the family backgrounds differ a lot: these feelings come out once you marry.

In her story the husband's stated flexibility did not match his expectation of the care he was used to in his parents' home.

If your marriage is a house, lifestyle values are the foundation: what you spend your time on — religious practice, health, travel, family, work. Don't settle for agreement; look for alignment.

Agreement is answers to questions; alignment is deeper: how you see the world and where you are heading when no one is watching.

Do not mistake understanding the other's opinion for agreement: really listen and clarify views, so that you see common goals and mutual respect.

In her example, hours of conversation did not prevent a bad engagement; she does not suggest arguing over detailed plans for years far ahead, such as where to live in retirement.

Ask why each of you wants marriage and children, what place religion, community and helping others will have — and keep asking "why" until you get to the real why.

The repeated "why" takes you past the usual answers.

Introduce a sensitive topic as it applies to you or the people around you — that leaves the other person room to respond without a direct interrogation.

In her example, talk of his sisters' struggle with clothes in the heat opens a discussion of tznius standards.

Once the shidduch looks positive, check the plans: where do you want to live, are you buying or renting, what chinuch options do you have in mind for the children.

Sketching life out in practical terms has very serious consequences.

Financial arrangements should be spelled out clearly before the shidduch's conclusion.

Leaving the subject for later is not an option.

Go down the list directly: is each of you employed; does each have the education or potential to find employment; do both plan to be in the workforce; do parents help financially; are there savings.

The answers give the real picture instead of assumptions about it.

Start by asking how the person would describe his own spending habits — and know that he is about to ask you the same thing.

Asking about the role in the family income — that is, whether you will work — is fine; demanding a ten-year plan and specific salaries is not.

To one who was not going to learn in kollel: continue the shidduch, but first have a realistic notion of "with what," "how," and "in what manner" he will earn a living.

The work need not start immediately, but there must be a practical plan: a realistic assessment of where and how you intend to earn.

Learning in kollel after the wedding must have the full and joyful consent of the prospective wife: the decision touches the family's standard of living.

The decision implies certain concessions on the family's side, so the consent must be informed and sincere.

Did he learn in kollel: if not, does he want to; if yes, where and for how long; is he interested in kiruv, does he plan to do it, and when.

She asks women not to skip this topic: listen, learn, and love.

Ask how he would describe his level of emunah, whether others see it in him and whether they tell him so. Discover the connection with Hashem before marriage.

Then in marriage you will be on the same page and able to grow together.

Whether a man stays in kollel depends on what he harbors in his own heart and soul, not on his wife and not on the promised support of a father-in-law.

A condition of ten years of learning cannot be demanded of one side without taking on an obligation of your own.

He grants the merit of such a choice but describes the disappointment of some women a few years on, when life with several children proved harder than expected: "This is not really what I anticipated."

He also warns of conflict if the wife sees the husband as achieving nothing while he values his learning differently; these are risks he describes, not the inevitable outcome of every kollel.

Ask what his father loves most about his mother and what his mother loves most about his father — and how close his family is to the parents of his married siblings' spouses.

That shows which model of marriage the person takes as normal, and how his family gets along with mechutanim — that is, with your family.

Asking directly whether his family is normal will not get an honest answer: share a story about a family you admire and ask whether theirs is similar.

Listen for the shades — hesitations, a change of tone, evasiveness; trust builds gradually.

In the parents' home, observe the parents: do they speak politely to one another, do they respect each other's opinions, is there laughter in the house or an air of resentment.

And a question to yourself: does either parent have a trait you would not want to find in a spouse later.

Before the engagement, discuss family-planning expectations: just because both people are religious does not mean they share the same values. The specific halachic questions are for a rav.

Her pre-engagement list also includes where to live, the length of the engagement, health, and existing study or career plans.

Do the two of you share a common approach to chinuch — and is Torah study at the expense of a wife or children justified? The questions are meant to reveal views, not to supply ready answers.

Among his topics: the place of learning in the home and the example the children see in their father.

Once you picture life together: does the person hold unusual views on marriage; does he like being in charge or is he more comfortable assisting; what responsibilities does he carry at home now.

Her section on family ties, money, kids and managing everything else that comes up.