Questions to Ask When Courting
Questions for two people who are dating with marriage in view: what an ordinary week looks like, money and debt, how each family expects to be involved, children, how each of you argues and recovers, physical boundaries during courtship, and the history worth telling each other early. Ordered so the lighter ones come first.
The questions
Open any question for the note
What made you want to date with marriage in mind rather than casually?
Why ask it
Worth asking out loud, because two people can use the same word for very different intentions. Listen for whether the reason is their own or borrowed: a person repeating what their community expects will describe rules, while someone who has thought it through will describe what they are hoping for.
What does a good ordinary week look like for you when nothing special is happening?
Why ask it
Courtship tends to happen on the best days, dressed up and out of the house, which hides the thing you would actually be living in. The answer tells you the pace of their normal life, and whether it resembles yours on a wet Tuesday with nothing planned.
How much time on your own do you need in a normal week?
Why ask it
A mismatch here causes more day-to-day friction in early marriage than almost any disagreement of principle, and it rarely comes up while you are still living apart. Someone who has never considered the question is usually about to discover the answer at your expense.
What part does faith play in your ordinary week, not just in what you believe?
Why ask it
Shared beliefs and shared practice are different things, and the gap between them is where couples argue later: attendance, giving, prayer at home, how children would be raised. Ask about the week rather than the doctrine, since the week is what you would actually share.
Who do you go to when something is going wrong?
Why ask it
The answer tells you whether they have anyone at all, and whether that person is a friend, a parent, a pastor, or nobody. It also tells you what you would be taking on: a partner with no one else to lean on will lean entirely on you, which is heavier than it sounds at this stage.
What did watching your parents' marriage teach you, for better and for worse?
Why ask it
Most people repeat or deliberately invert what they grew up with, and both are worth knowing. The most useful answers name something specific their parents did well and something they intend not to repeat; an answer with no criticism in it at all often means they have not looked yet.
How involved do you expect your family to be once you are married?
Why ask it
Expectations about Sunday dinners, holidays, money, and advice are set long before anyone discusses them, and each person assumes their own arrangement is the normal one. Ask for concrete numbers: how often you would see them, and who gets told about a problem first.
Where do you expect to be living in ten years, and how tied are you to being near your family?
Why ask it
Geography quietly decides careers, childcare, and how often you see relatives, and it is often the first real conflict a couple hits. Someone who says they are flexible is worth testing gently, because flexibility usually has a limit that only becomes visible when a job offer arrives.
What are you like when work gets hard?
Why ask it
Everyone is pleasant on a good week. What matters is the pattern under pressure: longer hours, short temper, silence at dinner, or work that never comes home. Their honest self-description here is a preview of your worst months together, and vagueness is worth following up with an example.
If we were living together a year from now, who cooks, who cleans, who handles the bills?
Why ask it
Far more revealing than asking about roles in the abstract, because it forces specifics. Notice whether their answer is a plan or an assumption, and whether the tasks they hand you are the ones they simply have never had to think about.
How do you keep track of money, and is there debt I should know about?
Why ask it
Two separate questions, and both matter: the system tells you their habits, the number tells you what you would be marrying into. Reluctance here is common and worth being patient with, but a refusal to say anything concrete before an engagement is itself the answer.
What do you imagine us earning and spending, and would either of us stop working if we had children?
Why ask it
This is where assumptions about income, ambition, and caregiving all collide, and they are best surfaced before anyone has quit anything. Listen for whether their picture depends on you doing something you have not agreed to.
Do you want children, how many, and how soon would you want to start?
Why ask it
The three parts are separate and people often agree on the first while differing sharply on the other two. Timing is the one that ends engagements, so ask for a year rather than a sentiment, and say your own answer plainly instead of testing theirs.
How were you disciplined as a child, and what would you keep or change with your own?
Why ask it
This gets at parenting in a way that abstract questions about values cannot, because it starts from something they experienced. Wide differences here are workable if both of you can talk about them now, and much less so once there is a toddler in the room.
When you disagree with someone you love, what do you actually do?
Why ask it
Ask for behaviour, not philosophy: raise your voice, go quiet, leave the house, apologise fast to end it. Everyone says they communicate. What you want to know is what happens in the first ten minutes, and whether anything they describe would frighten you.
How long do you stay upset, and what helps you come back?
Why ask it
Repair matters more than conflict style, since every couple fights and the difference is how long the cold lasts. A person who knows their own recovery time and can name what helps has usually practised it. Days of silence, described casually, is a warning worth taking seriously.
What physical boundaries do you want us to hold while we are courting, and how do we keep to them?
Why ask it
If you are courting within a tradition that expects restraint, the agreement needs to be explicit and mutual rather than assumed, including the practical parts: which places, which hours, who says something when a line is getting close. Silence on this tends to be read by each person as agreement with their own position.
What ended your last relationship, and what would the other person say ended it?
Why ask it
The second half is the whole question. Anyone can give a tidy version where they were the reasonable one, but being able to state the other person's account fairly shows they have absorbed something. If the ex is described entirely as a villain, you are hearing a pattern rather than a story.
Has anyone ever told you something true about yourself that was hard to hear, and what did you do with it?
Why ask it
This tests whether criticism can reach them, which decides how the next forty years of small corrections will go. A specific memory with a specific change is a good sign. Not being able to think of anything usually means it has been said and did not land.
Is there anything in your past you would rather I heard from you than from someone else?
Why ask it
Asked without an accusation in it, this gives someone a clear opening to say a hard thing while there is still time for it to be received well. It also sets a precedent that difficult news travels between the two of you first, which is the habit you want in a marriage.
What would make you decide this is not right, and how would you tell me?
Why ask it
Courtship carries real pressure to keep moving forward, so agreeing early on how either of you would stop makes it possible to be honest later. It also reveals whether they can imagine leaving at all, and someone who cannot may struggle to say no to anything, including the wedding.
Using these well over months, not one evening
Practical guidance for the conversation itself
How to pace it
- Two or three questions in a sitting is plenty. A list worked through in one night produces prepared answers rather than true ones.
- Answer first and answer fully. Anything you ask without being willing to answer yourself turns the conversation into an examination.
- Ask the same question again months later, especially about children, money, and where to live. Positions move, and the movement is the information.
- Save the heaviest ones for a walk or a drive rather than a table. Side by side is easier than face to face.
- Write down what you each said about timing and numbers. Memory reshapes these to fit whatever was decided later.
Ask about behaviour, not principles
Anyone can describe good values, because the vocabulary is public. What predicts a marriage is the specific: how much they have saved, how often they call their mother, what they did the last time they were embarrassed in public, how they treat a server on a bad day. If an answer arrives as a general commitment, follow it with the last time that happened. If a story cannot be produced, the commitment is aspirational, which is worth knowing but is not the same as evidence.
Bringing other people in
Spend time with each other's families
You will learn more from one weekend at their parents' house than from any conversation about family expectations, particularly about how conflict and money are handled.
Let a couple you both trust ask you both things
An older married couple, a mentor, or a pastor will ask what you have avoided. Choose people who will say something you do not want to hear, not only people who like the idea of the match.
Keep your own friendships in it
Friends notice changes in you that you cannot see. If several of them have gone quiet about the relationship, ask one of them directly and plainly what they think.
When the answers do not match
Sort the difference before you argue about it
Some differences are preferences that can be negotiated, some are timing that will resolve, and some are convictions neither of you will move on. Naming which kind you are dealing with prevents months of the wrong conversation.
Do not plan around a change you have been promised
Intentions about drinking, debt, temper, or wanting children later are common and are not commitments. Watch what happens over a year instead of building on what was said.
Notice pressure to hurry
Momentum, family expectation, and the wish to be settled can all push a decision that the answers do not support. A good reason to marry sounds like a reason about this person, not about the calendar.
Take the alarming answer at face value
If something you hear describes contempt, control, hidden debt, or a temper others have warned you about, treat it as information rather than as something your patience will fix.