12 questions worth asking before you say yes

Most first meetings cover the same ground: education, job, family, expectations about where you will live. Useful, but none of it tells you how the two of you will handle a bad year.

Money

1. How are financial decisions made in your family right now?
2. Do you expect to pool income after marriage, or keep things separate?
3. What financial responsibilities do you already carry — a loan, a sibling's education, parents' medical costs?

Family

1. Where do you expect us to live in the first two years?
2. What does your family expect from a daughter-in-law or son-in-law, in practice and not in theory?
3. How are disagreements handled in your house — discussed, or avoided?

Work

1. If one of us gets a good opportunity in another city, what happens?
2. Do you expect me to continue working? Under what circumstances would that change?

Children

1. Do you want children, and roughly when?
2. Who do you imagine doing the day-to-day care?

Faith and practice

1. Which observances actually matter to you, as opposed to which ones your family keeps?
2. How would you want to raise children with respect to religion?

None of these have a right answer. What matters is whether the two of you can have the conversation at all without it becoming a fight — because you will be having versions of it for the next forty years.