100 Questions to Ask Before You Get Engaged
One hundred questions for couples talking seriously about getting engaged, grouped by subject: what marriage means to each of you, money, children, families, home and work, conflict, sex, health, and the lines neither of you has named.
The questions
Open any question for the note
What do you think will actually be different about our life once we are married?
Why ask it
A gentle opening that shows whether they expect a change or a formality. Answers about security, children, or family recognition all point at what the marriage is really for.
Why now, rather than in two years?
Why ask it
Timing is usually driven by something unspoken: an age, a lease, a parent's health, a visa, a sibling's wedding. Better to know which pressure is setting the date than to discover it afterwards.
What does being engaged mean to you in practice, and how long should it last?
Why ask it
People treat engagement as anything from a private agreement to a year of public planning. A mismatch here produces the first fight of the engagement, usually within a month.
Whose marriage do you admire, and what specifically about it?
Why ask it
Look for a real couple and a concrete detail rather than an idea. Admiring how two people argue is a very different model from admiring how comfortable they are.
Whose marriage would you not want ours to resemble?
Why ask it
This is where the honest fears live, and they are usually about a specific relative. Ask what they think went wrong there, because they will be watching for it in us.
What did you learn about being married from watching your parents?
Why ask it
Everyone learns something and few people have said it out loud. Whether they describe a partnership, an arrangement, or a warning tells you what they will treat as normal.
What do you want the wedding day to feel like, and who is it for?
Why ask it
Weddings go wrong over ownership rather than taste. If the answer is largely about what other people expect, the negotiation ahead is with families rather than with each other.
What do you want us to promise each other out loud?
Why ask it
Vows are a rare chance to hear what someone thinks they are committing to. What they leave out, faithfulness, honesty, staying through illness, is as informative as what they include.
Can we sit down this week and show each other every account, debt and obligation we have?
Why ask it
This asks for an action rather than an opinion, which is why it works. Reluctance, delay, or a partial disclosure now is the most reliable predictor of money trouble later.
What is the largest amount you would spend without checking with me?
Why ask it
Couples rarely agree on this figure and almost never state it. Naming a number prevents the specific argument that follows the first unexpected purchase.
Do you want our money pooled, kept separate, or split in some proportion?
Why ask it
All three arrangements work. What causes damage is one partner assuming pooling while the other quietly keeps a separate account, so get the arrangement said plainly.
How much has to be in savings before you would feel safe?
Why ask it
Financial anxiety is set by upbringing more than income. A partner who needs six months of expenses banked will read your spending as risk-taking unless this is understood.
Who do you expect will handle the bills, the taxes and the paperwork?
Why ask it
Somebody always ends up doing this and it is rarely discussed. The person who does it holds more information about the household than the other, which matters if things go wrong.
What should a wedding cost, and who is paying for it?
Why ask it
The gap between two answers here is often a factor of five. Parental contributions are the part to pin down, because money from families usually arrives with expectations attached.
How would you feel if I earned a great deal more than you, or a great deal less?
Why ask it
Ask about both directions. Resentment about earning less and resentment about carrying more are both common, and people can usually predict which one they are prone to.
What happens to our finances if one of us stops working for a year?
Why ask it
Illness, redundancy, study, and a new baby all produce this year. Whether the answer treats the household income as shared or as belonging to whoever earned it is the thing to listen for.
Are you likely to be supporting a parent or a sibling financially at some point?
Why ask it
This is a common and legitimate obligation that couples discover late. What matters is whether it is expected, roughly how much, and whether you are being told or consulted.
What do you spend money on that other people think is a waste?
Why ask it
A lighter question that gets an honest answer, and it identifies the purchases you will be tempted to criticise. Everyone has one, and marriages do better when it is agreed rather than defended.
How were money conversations handled in your family when you were growing up?
Why ask it
Silence, arguing, or open accounting all leave a mark. This explains behavior that will otherwise look irrational, such as hiding a purchase or refusing to look at a statement.
How would you feel about being asked to sign a prenuptial agreement?
Why ask it
The reaction matters more than the answer. Someone who hears the question as an insult rather than a practical matter will hear other practical questions the same way.
What does retirement look like to you, and when?
Why ask it
You are asking about decades of small decisions. A partner planning to stop at fifty-five and one who expects to work indefinitely need to know that about each other now.
If we lost everything financially, what would you want us to protect first?
Why ask it
Answers tend to be the house, the children's schooling, or independence. It is a hypothetical that gets at what they consider non-negotiable more directly than asking about values.
How many children do you picture, if any?
Why ask it
Ask for a number, not a sentiment. Two answers of some day and a few can hide a difference between one child and four, which is a difference in the shape of a whole life.
How would you feel in five years if we did not have children?
Why ask it
This separates a real wish from a default assumption. A partner who would be relieved, or devastated, is telling you something the general question about wanting children does not reach.
What would you want to do if it turned out we could not conceive?
Why ask it
Difficulty conceiving is common and the disagreement it causes is usually about how far to go, not whether to try. Having the conversation before the disappointment is much easier.
How do you feel about fertility treatment, adoption, or fostering?
Why ask it
Views on these differ sharply and are often rooted in faith or in family history. You want to know now which routes are open to both of you and which are not.
At what age do you want to start, and what would you do if it took years?
Why ask it
A specific age forces the timing conversation that engagement usually postpones. It also reveals whether they have thought about the medical realities or simply assumed it will be straightforward.
Who would look after them day to day when they are small?
Why ask it
The honest options are a parent at home, family, or paid childcare, and each has a cost. Vagueness here nearly always resolves into whoever earns less doing it by default.
Would you want to work part time, stop working, or continue as you are?
Why ask it
Ask them to answer for themselves and then for you. The second answer is where the assumption sits, and it is often one neither of you has said out loud.
How were you disciplined as a child, and what would you repeat?
Why ask it
Parenting style is inherited unless it is examined. This is also the safest way to find out whether they were hit as a child and what they now think about it.
Would you want children raised in a faith, and whose?
Why ask it
This is one of the few genuinely structural disagreements. Couples routinely defer it and then discover at a christening or a school application that nothing was actually agreed.
What would you do if one of us wanted another child and the other did not?
Why ask it
A question about the process rather than the outcome. Whoever answers that the person who wants one should win, or should lose, is describing how all deadlocks will be handled.
What role would our parents have in our children's lives day to day?
Why ask it
Answers range from childcare four days a week to strict distance. This is also the moment any concerns about a grandparent's drinking, health, or behavior should be said.
What would you want our children to be able to say about us as parents?
Why ask it
A softer close to a hard section. The answer usually describes what they felt was missing in their own childhood, which is useful to know long before there are children.
How often do you want to see your family once we are married?
Why ask it
Get a frequency, not a sentiment. Weekly Sunday lunch and twice a year are both normal, and the difference is a decade of small negotiations if it is not agreed.
Where do the main holidays happen, and who decides?
Why ask it
Holidays are the recurring flashpoint of married life. A rule agreed now, alternating years or splitting the days, is worth more than goodwill in December.
What is the most difficult relationship in your family, and how do you handle it?
Why ask it
Every family has one, and you are marrying into it. What they do about it, avoidance, management, or confrontation, is what you will be asked to join in with.
What do you tell your family about us, and what do you keep private?
Why ask it
Couples get into trouble when one treats a parent as a confidant. Find out now whether your arguments and your finances are being discussed elsewhere.
Is there anyone in your family you would not leave a child alone with?
Why ask it
A plain question that gives permission for a serious answer. Silence or hesitation here is worth returning to gently and privately, and it should never be dismissed.
Would you move to be near a parent who needed care?
Why ask it
Care for ageing parents arrives in most marriages, often suddenly. Whether they would move, and whether they expect you to, is a decision better previewed than discovered.
What does loyalty to your family mean when it conflicts with me?
Why ask it
You are asking where you rank when it matters, which sounds harsh and is worth knowing. Someone who cannot imagine the conflict has probably never been asked to choose.
Which of your relatives will find our marriage difficult, and why?
Why ask it
If the answer is nobody, ask again. Naming the objector, and the reason, whether it is faith, money, background, or a previous partner, means you meet it as a couple.
If we needed help, whose family would we ask first, and for what?
Why ask it
Practical and revealing. Being willing to take money from one family and not the other, or from neither, tells you about pride, obligation, and where the debts will be felt.
What did your family teach you about how to argue?
Why ask it
Shouting households and silent households produce partners who misread each other completely. Naming the pattern now shortens the first year of arguments considerably.
Which family tradition do you want to carry on, and which would you drop?
Why ask it
This lets each of you keep something and let something go on purpose. The traditions people cannot drop are usually the ones tied to a person rather than to the occasion.
Is there anywhere you would refuse to live, and why?
Why ask it
Refusals are more informative than preferences. A city, a country, a distance from parents, or somewhere with a history behind it will constrain every job decision you make together.
Would you move for my job, and on what terms?
Why ask it
Ask for the conditions, not a yes. Whether the answer includes their own career, their family, or a time limit tells you how a real offer would actually go.
How many hours a week do you honestly want to work?
Why ask it
The honest number is often well below what they currently work, or well above what you assumed. It sets the expectation for evenings, weekends, and who is at home.
What would you do if your job asked for three weeks of travel a month?
Why ask it
A concrete scenario beats a discussion about work-life balance. It also tells you whether they would treat it as their decision or as a joint one.
How would you feel about one of us going back to study?
Why ask it
Study means lost income, changed hours, and a period of self-absorption. Enthusiasm in the abstract often shrinks when the fees and the lost salary are named.
What does a good weekend look like to you?
Why ask it
A light question with practical consequences, because weekends are most of the shared time a marriage has. Mismatch between plans and rest is a very common quiet resentment.
What do you need after a bad day: company, quiet, or to be left alone?
Why ask it
Getting this wrong is one of the most frequent ways couples hurt each other with good intentions. Ask for the instruction rather than guessing for the next thirty years.
Who do you think should notice when the house needs cleaning?
Why ask it
Sharper than asking who does what, because the work of noticing is the part that goes uncounted. A partner who happily helps when asked is still leaving that job to you.
How tidy does a home need to be before you can relax in it?
Why ask it
Two different thresholds mean one person is always the enforcer. Saying the standard out loud lets you agree a shared one rather than defaulting to the stricter person's.
Do you want pets, and who looks after them?
Why ask it
Pets are a fifteen-year commitment with real costs, and the walking and the vet bills tend to land unevenly. It is also a useful rehearsal for the childcare conversation.
What would you want us to do if one of us came to hate where we lived?
Why ask it
This happens after a move for a job or for family. Whether the answer is that we would move again, or that we would have to make it work, tells you how much weight your unhappiness would carry.
Which of your ambitions would you be sad to give up for this marriage?
Why ask it
A generous framing, and the thing they name is what to protect. Ambitions given up quietly are one of the main sources of resentment at forty.
How do you know you are getting angry, before you say anything?
Why ask it
You are asking for self-knowledge rather than manners. A partner who cannot describe their own build-up cannot warn you, and you will be left reading the weather.
What do you do when you are hurt and do not want to talk about it?
Why ask it
Withdrawal, sarcasm, tidying, silence, and leaving the house are all real answers. Knowing which one you are seeing prevents years of misreading it as indifference.
How long can something stay unresolved before it starts to bother you?
Why ask it
One partner needing it settled tonight and the other needing to sleep on it is the most common conflict pattern there is. Naming the mismatch is most of the fix.
What is the fastest way for me to make an argument worse?
Why ask it
They will know, and telling you is a gift. Expect specifics: raising your voice, bringing up the past, being reasonable in a particular tone, involving your family.
Is there anything I have said in an argument that stayed with you?
Why ask it
This is an invitation to give evidence, so brace for it and do not defend yourself in the moment. What you hear here is the material of the next ten years if it is not addressed.
Which argument do we keep having in different forms?
Why ask it
Most couples have two or three recurring arguments and rarely name them. Naming the pattern turns it from a fresh betrayal each time into a known problem to be managed.
At what point would you be willing to see a counselor with me?
Why ask it
The point is whether outside help is available at all. Ruling it out now, while things are good, is far more significant than most people realize when they say it.
How do you want to be apologized to?
Why ask it
Words, time, a change in behavior, or being left alone for a day are all different requirements. Apologies that do not land are usually the right sentiment in the wrong currency.
Is there anything you are still holding against me?
Why ask it
Ask it plainly and then be quiet. An immediate no from a partner who has been distant is worth revisiting another day rather than accepting with relief.
What would count as crossing a line during a fight?
Why ask it
Names, threats to leave, involving families, going through a phone, leaving for the night. Agreeing the boundary in a calm moment is what makes it hold in an angry one.
Do you tell me when something is wrong, or wait for me to notice?
Why ask it
Someone who waits to be noticed is running a test you cannot see. Knowing that about each other converts a lot of resentment into a straightforward request.
What have you been meaning to raise with me and keep putting off?
Why ask it
Ask this in a calm week rather than after a row. Whatever has been waiting is usually small in itself and has been growing for months.
When our appetites do not match, what would you want us to do about it?
Why ask it
Mismatch is normal in every long relationship, so the question is procedural rather than romantic. Couples who have never discussed it tend to treat the difference as rejection.
What do you want more of, and what would you rather we stopped?
Why ask it
Both halves matter and the second is much harder to say. A partner who cannot name anything to stop may be tolerating something they have never mentioned.
How comfortable are you talking about sex out loud?
Why ask it
This is the question that determines whether the rest of the subject can be discussed at all. Discomfort is workable; a refusal to ever discuss it is a decision about the next thirty years.
What would you want if one of us lost interest for months at a time?
Why ask it
Illness, medication, new babies, and grief all produce these stretches. Agreeing now that it is a shared problem rather than one person's failing is worth a great deal later.
Where is the line for you between a friendship and something you would not want me to see?
Why ask it
Definitions differ far more than people assume, particularly about messaging and old partners. Agreeing the line now removes the later argument about whether one existed.
Is there anything in your sexual history you want me to know before we marry?
Why ask it
This is about health, about past experiences that shape the present, and occasionally about people you are likely to meet. Ask it once, calmly, and do not interrogate the answer.
How do you feel about porn?
Why ask it
Views range from indifference to a serious objection, and both are worth knowing before they surface as a discovery. What matters is whether you can discuss it without either of you lying.
What does affection look like to you outside of sex?
Why ask it
Hand-holding, sitting close, being brought a cup of tea. Couples with different vocabularies here can each feel unloved while both are trying, which is worth catching early.
What would you need during a stretch without physical intimacy, such as an illness or a new baby?
Why ask it
Asking about a foreseeable period rather than a hypothetical crisis gets a practical answer. Reassurance, other kinds of touch, honesty about frustration: it helps to know which.
Have you ever felt pressured by me, and did you say so at the time?
Why ask it
A hard question that has to be asked calmly and answered without defence. If the answer is yes, the conversation stops being about the wedding for a while, and it should.
What should I know about your health that has not come up?
Why ask it
People omit chronic conditions, old injuries, and medication out of habit rather than secrecy. Marriage makes each of you the other's first responder, so the omissions should be closed now.
What is your relationship with alcohol, and would you change it if I asked?
Why ask it
The second half is the real question. Willingness to look at it plainly, without justification or a joke, tells you more than the number of drinks a week.
Have you ever had treatment for your mental health, and what helped?
Why ask it
Common, treatable, and better understood before a crisis. What helped is the practical part, because it tells you what to reach for when it recurs.
What do you need from me when you are very low or very anxious?
Why ask it
Ask for instructions while they are well, because nobody can give them while they are not. Practical answers, food, company, no questions, a phone call made for them, are the useful ones.
Who would you want making medical decisions for you, and what would you want them to decide?
Why ask it
Marriage usually makes each of you the default decision maker. Hearing the answer once, in an ordinary week, is what makes it possible to act on it later without guessing.
Do you have a will, and does it need to change?
Why ask it
A calm administrative question that people avoid. If either of you has children, property, or a business, the answer affects them directly and should not wait for the wedding.
How do you feel about life insurance, and who should it cover?
Why ask it
Straightforward and worth settling early, particularly if one of you would be left with a mortgage. Reluctance to discuss it is usually discomfort with the subject rather than with the cost.
What would you do if one of our parents had to move in with us?
Why ask it
This arrives in many marriages, often with little warning. Whether the answer assumes a spare room, a care home, or a fight is something to know before the phone call comes.
What would you do if I lost my job for a year?
Why ask it
Listen for whether the answer is about the money or about you. A partner who describes practical adjustment and a partner who describes disappointment are telling you different things.
What is the hardest thing you have been through, and what did you need from people then?
Why ask it
The second half is the point, because it tells you how to be useful in the next hard thing. Some people need company, some need to be left to get on with it.
What would you want us to do if one of us became seriously ill in our forties?
Why ask it
A plain question about a real possibility. Answers about who would work, who would care, and what they would want said to family are all worth hearing once.
How do you want to be looked after when you are old, and by whom?
Why ask it
Expectations differ, particularly across cultures and families: children, a care home, or staying at home with help. It is also the point at which retirement plans meet reality.
What would you consider unforgivable in a marriage?
Why ask it
Everyone has a line and most people have never said theirs out loud. Hearing it is not a threat, it is being told what you are each promising to stay clear of.
What would you want me to do if you were the one who broke a promise like that?
Why ask it
This asks them to set the terms for their own accountability while nothing is at stake. The answer is worth remembering, because people rarely offer it later.
What are you hoping I do not ask you tonight?
Why ask it
A direct question that works surprisingly often, because it names the avoidance rather than the subject. Whatever surfaces is usually the most important thing in the whole list.
What are you not telling me because you think it might change my mind?
Why ask it
Ask it once, gently, and then wait through the silence. A long pause followed by nothing is itself worth returning to on another day.
What do you think I am wrong about that you have never said?
Why ask it
This invites the criticism they have been managing on their own. A partner who has been holding something for years will usually take the opening if you stay calm.
What part of this still worries you?
Why ask it
Some doubt before a marriage is normal, and naming it is generally a good sign. What would be worth pausing for is a worry that has been carried privately for months.
What do you need from me before you would feel ready to marry?
Why ask it
This converts vague hesitation into a request you can act on. If the answer is that you need to change fundamentally, that is important to hear now rather than at an anniversary.
If nothing about our relationship improved from today, could you marry me as we are?
Why ask it
The hardest question here, because most engagements rest on a private assumption that something will improve. Anyone marrying a plan rather than a person should know that before the wedding.
What do you want to still be true about us in thirty years?
Why ask it
A closing question that lets both of you say what you are actually aiming at. Small, specific answers tend to be more durable than grand ones.
Working Through a Hundred Questions
Practical guidance for the conversation itself
How to Get Through It Without a Fight
Take one subject per sitting
Money one evening, children another, conflict another. Mixing subjects produces short answers, because nobody stays open across four difficult topics in a row, and the last one always gets the worst of it.
Write your answers separately before you compare
Particularly on money, children, and housework. If you talk first, whoever speaks sets the answer and the other one agrees in order to keep the evening pleasant, and you learn nothing.
Stop when either of you is tired
The aim is the conversation, not finishing the list. A tired yes to something neither of you has thought about is worse than leaving the question for next week.
Write down what you actually decide
You will remember the big agreements differently within a year, especially about faith, money, and where you will live. Two lines in a note on the day settles arguments you have not had yet.
Answers That Need a Second Conversation
- We will cross that bridge when we come to it, applied to children, money, or location. That is a delay dressed as an agreement.
- A partner who agrees with every one of your answers. Ask what they would say if you wanted the opposite, and see whether the answer moves.
- Debt or income given in round numbers. The round number is usually the flattering version.
- A whole subject one of you will not discuss. The refusal is the finding, whatever the subject happens to be.
- Answers about who you are both going to become rather than who you are. People do change, slowly, and marriage does not speed it up.
- Anything either of you needed a drink to say. It still counts, and it is worth returning to sober.
- Agreement reached in the last ten minutes of a long evening. Check it again on a different day.
When You Disagree
Sort disagreements into three piles
Things you can live with, things you can negotiate, and things that are structural, such as children, faith, and where you will live. Only the third pile should affect whether you get engaged, and most couples treat all three as equally alarming.
Do not trade concessions late at night
Swapping a holiday compromise for a money compromise at eleven at night produces agreements neither of you honours. Note the difference, sleep, and come back to it as two separate questions.
Take the stuck subjects to someone else
Premarital counseling exists for the two or three topics that stall every time you try. A few sessions before an engagement is ordinary, and considerably cheaper than the alternative.
Watch the pattern rather than the topic
If the same person concedes every time, that is the finding, whatever was being discussed. Unnamed, it repeats for decades and turns into resentment neither of you can trace.