Questions to Ask for Engagement
Twenty questions to work through with your partner before you get engaged. They cover children, money and debt, where you will live, careers, in-laws, faith, conflict, and the things people usually leave until after the wedding.
The questions
Open any question for the note
What made you decide you wanted to be married, rather than carrying on as we are?
Why ask it
The answer separates people who want a marriage from people who want a wedding, a visa, a baby, or an end to being asked about it. Listen for whether they describe something they want to build or something they want to settle.
What does being married mean to you that being together does not?
Why ask it
Couples often discover here that one of them sees a legal formality and the other sees a change in obligation. Neither view is wrong, but discovering the gap three years in is expensive.
What kind of wedding do you actually want, and who is paying for it?
Why ask it
Wedding plans are where family expectations and money collide first, so it is a useful rehearsal for later negotiations. If either of you cannot say a number out loud, that is the finding.
Where do you expect us to be living in five years, and what would have to happen for that?
Why ask it
One of you may be assuming a move home eventually, or a house in a place the other has no intention of living. Asking what would have to happen turns a daydream into a plan you can check.
Do you want children, how many, and roughly when?
Why ask it
This needs a specific answer rather than an agreement in principle, because someday means different decades to different people. The timing matters as much as the number.
If children turned out to be difficult or impossible for us, what would you want to do then?
Why ask it
Fertility treatment, adoption, and choosing to stop are all decisions couples make under pressure and grief, and it helps enormously to know each other's instincts beforehand. A refusal to consider the question is itself worth noting.
How would we divide the work at home, and what does an even split look like to you?
Why ask it
Write down separately who currently does what, then compare the two lists. Both of you overstating your own share is extremely common, and the gap between the lists is the argument you will be having in five years.
If one of us had a chance that required moving, whose career gives way?
Why ask it
You are looking for a decision rule rather than a promise to work it out, because in the moment there will be an offer with a deadline. Ask whether the answer would be the same in both directions.
What do you earn, what do you owe, and what is your credit like?
Why ask it
Marriage merges financial reality whether or not you merge accounts, and student loans, tax arrears, and a poor credit history will shape what you can rent or buy. Exchange actual figures, not ranges.
Would we combine our money, keep it separate, or do something in between?
Why ask it
Any of the three can work; what causes trouble is each of you assuming a different one. Work through a concrete case, such as who pays what if one of you earns three times the other.
How much can either of us spend without checking with the other?
Why ask it
Naming a number now prevents the argument that starts with a purchase neither of you thought needed discussing. Notice if your figures are an order of magnitude apart.
What do you expect us to give to or do for our parents as they get older?
Why ask it
Money sent home, a spare room, or moving to be nearer a parent are commitments that arrive without warning. Cultural and family expectations here often go unspoken until they are urgent.
How much time with your family is normal to you, at holidays and the rest of the year?
Why ask it
Every family has a default that its members consider unremarkable, and yours are probably different. Get specific about which holidays are non-negotiable for each of you.
What did you take from watching your parents' marriage, and what do you want to do differently?
Why ask it
This is the most revealing question in the set for most people, because the model each of you grew up with is the one you will fall back on when tired. Vagueness usually means the subject has not been examined rather than that there is nothing to say.
What does faith or religion need to look like in our home, and for our children?
Why ask it
Couples often settle the adult version of this question and skip the part about children, which is where it resurfaces years later. Include weddings, funerals, and schooling in the answer.
When we fight, what do you need from me, and what makes it worse?
Why ask it
One of you may need to resolve it that night and the other may need an hour alone, and both of you reading that as rejection is how a small argument becomes a long one. Ask for the specific move that helps.
What is something I do that you have decided to live with?
Why ask it
There is always something, and hearing it now is better than hearing it in year four as evidence. If the answer is nothing, ask again after a day of thinking about it.
Is there anything you would consider a reason to end a marriage?
Why ask it
You are asking where each of you draws lines: infidelity, addiction, violence, or the slower kinds of neglect. Knowing the answer is not planning for failure, it is knowing what you are promising.
What do you need from our sex life over the long run, and how do you want to raise it when something is wrong?
Why ask it
Frequency, illness, pregnancy, and stress will all change this over decades, and the durable question is how you talk about it rather than how it is now. Couples who cannot discuss it while things are good tend not to manage later.
Is there anything about your past, your health, or your finances that I still do not know?
Why ask it
Asked plainly and once, this gives an opening for the thing someone has been waiting for the right moment to say. Hesitation is not proof of concealment, but it does mark where to go next.
Working through these before you get engaged
Practical guidance for the conversation itself
How to run these conversations
Spread them over weeks, not one evening
Twenty questions in one sitting turns into an interrogation and produces the answers that end the evening fastest. Two or three at a time, on a walk or over dinner, gets better material.
Answer first, then ask
Going first on the hard ones, particularly money and family, makes it much easier for your partner to be specific rather than diplomatic. It also stops the conversation looking like an assessment.
Get numbers where numbers exist
Income, debt, credit, savings, and what a wedding would cost are facts, not feelings. Write them down together in one place; the exercise itself often changes the plan.
Notice the questions that get deflected
A joke, a change of subject, or an answer about principles when you asked about practice is information. Come back to it another day rather than pressing in the moment.
When the answers do not match
- Separate the differences that need a decision now, such as children and where you live, from the ones you can manage as you go.
- For each real disagreement, ask what would have to be true for you to be at peace with their answer.
- Beware of assuming someone will change their mind after the wedding. Most people do not.
- Premarital counselling exists mainly to make these conversations survivable, and a few sessions is a small cost against the alternative.
- If a topic ends the same way three times, it needs a third party rather than a fourth attempt.
Practical items to settle alongside
Names, documents, and next of kin
Decide about surnames, and update wills, beneficiaries, and emergency contacts. These are small tasks that carry weight when they matter.
Prenuptial agreements
If either of you has a business, property, children from a previous relationship, or family money, raise the subject early and calmly rather than weeks before the wedding. It reads very differently at six months than at six weeks.
Health and insurance
Compare coverage, discuss known conditions and family history, and agree who handles what. Some couples find it useful to have this conversation with a doctor rather than only with each other.
Common pitfalls
Treating agreement as the goal
The point is an accurate picture of what each of you wants, not a set of matched answers. Two honest and different answers are more useful than one comfortable consensus.
Asking during the proposal window
Once a ring is bought or a date is set, both of you have an incentive to give the answer that keeps the plan intact. Have the hard conversations before that momentum exists.
Skipping money because it feels unromantic
Debt and spending habits do not stay private after a marriage, and the discovery version of this conversation is much worse than the planned one.