Questions to Ask Before Engagement
Twenty-one questions for two people thinking about getting engaged, working from easy ground to the harder subjects: children, money in detail, in-laws, sex, illness and what either of you would consider a dealbreaker.
The questions
Open any question for the note
What did marriage look like in the house you grew up in, and what do you want to copy or avoid?
Why ask it
This is an easier way into everything that follows, because people describe their parents' marriage more freely than their own expectations. Listen for what they take for granted: who handled money, whether anyone shouted, whether affection was visible. Those defaults tend to reappear in your marriage unless someone names them.
When you picture us in five years, what does an ordinary Wednesday evening look like?
Why ask it
Ask about a Wednesday rather than about goals, because the answer exposes the texture of the life they are imagining: who cooks, whether the television is on, whether anyone is still working at nine, whether children are in the picture. Two people can share every stated ambition and be picturing completely different weeks.
Where do you want to be living in ten years, and what would make you move?
Why ask it
Geography ends more marriages than anyone expects. What you want to know is whether they are anchored to a place or to a career, and how they would weigh a promotion in another city against your job, your friends and an ageing parent nearby. Vagueness now becomes a crisis later when a real offer arrives.
What kind of wedding do you actually want, who is paying for it, and what are we willing to spend?
Why ask it
This is the first joint financial decision you will make and it is a fair rehearsal for the rest. Watch what happens when parents are contributing, because money from family usually comes with opinions attached, and how the two of you handle that says more than the guest list does.
Do you want children, how many, and by roughly when?
Why ask it
Ask for a number and a rough timeframe rather than a feeling. Someday is not an answer two people can plan around, and one partner quietly meaning never while the other means within three years is the single most common serious mismatch found late. If the answer is uncertain, ask what would make it clearer and when.
If children turned out to be hard for us, how far would you want to go?
Why ask it
Treatment is expensive, invasive and repetitive, and couples who have not discussed limits in advance end up negotiating during a difficult year. Ask about how they feel about fertility treatment, adoption, fostering, and about stopping. Also ask how they would feel if the answer eventually became no children at all.
If we have children, who cuts back at work, and for how long?
Why ask it
Most couples agree on wanting children and have never said this part out loud. Ask who they picture handling nights, who takes leave, whose career absorbs the interruption, and what they think that costs. An answer of we will work it out usually means the default arrangement they grew up with.
How much do you earn, what do you owe, and what does your credit look like?
Why ask it
Ask plainly and answer plainly, then look at the actual documents together, including credit reports. Undisclosed debt is a common shock in the first year of marriage, and in many places marriage makes your finances jointly consequential whether or not you merge accounts. Reluctance to show numbers is itself information.
Do we pool our money, keep it separate, or run some mix?
Why ask it
There is no correct arrangement, but there is a wrong process, which is drifting into one without discussing it. Ask what feels fair if your incomes are very different, who pays for what, and how each of you would feel asking the other for money. Also ask how you would each want it handled if one of you stopped earning.
What is the most either of us should be able to spend without checking with the other?
Why ask it
Naming a figure turns an abstract value into a working rule, and the gap between your two numbers is usually the interesting part. It also surfaces attitudes to secrecy: whether a partner has ever hidden a purchase, and whether they would consider that a small thing or a serious one.
What am I like to argue with?
Why ask it
Asked seriously and answered honestly, this is one of the most useful questions on the list. You are looking for something specific and slightly uncomfortable: you go quiet for days, you bring up old material, you make jokes to escape. Nothing comes to mind is either a very easy relationship or an unfinished conversation.
What is the argument we keep having, and what do you think it is really about?
Why ask it
Every couple has one recurring fight, so it is a bad sign if neither of you can name it. Compare your two accounts. If one of you thinks it is about dishes and the other thinks it is about being taken seriously, you have found the thing worth working on before adding a marriage to it.
What did you learn about apologizing growing up?
Why ask it
Repair matters more than the fight itself, and people learn wildly different lessons about it: that apologies are humiliating, that they are automatic and meaningless, that nobody in the house ever gave one. Ask what a real apology looks like to them, since a partner who cannot apologize makes every future disagreement permanent.
Which of my family members do you find hardest, and what do you want me to do about it?
Why ask it
Ask this before the wedding, because weddings put family friction in a room together. The important part is the second half: they may want you to intervene, or simply to be believed. Resentment about in-laws is usually less about the relative than about a partner who never took a side.
How much time with your parents feels right to you, and what happens if one of them needs to live with us?
Why ask it
This is where expectations from different families collide, and the second half is not hypothetical for long. Ask what they would consider their duty, what caring for a parent would mean practically, and how decisions and costs would be shared. Couples who discuss this early handle it far better than those who improvise during a crisis.
What part should faith play in our home, and in raising children if we have them?
Why ask it
Ask about practice rather than belief: what happens on a Sunday, what holidays look like, whether children are raised in a tradition, and how each set of parents would react. People who describe themselves as not especially religious sometimes discover strong feelings at a baptism, a bar mitzvah or a funeral.
What do you need from sex in a marriage, and how would you tell me if that changed?
Why ask it
The second half is the part people skip. Frequency, illness, medication, pregnancy and stress all change this over decades, so what matters is whether you have a way of raising it. Ask what they would want you to do if one of you lost interest for a long stretch, since silence is what makes that damaging.
What do you need for yourself, alone or with your friends, to stay recognizably you?
Why ask it
Ask for specifics: a Saturday morning ride, a weekly evening with old friends, a room with a closed door, a trip once a year. Marriages get into trouble when one person quietly gives these up and cannot say why they feel diminished. Naming them now makes them easier to protect later.
How do you want us to handle it if one of us gets seriously ill, or loses work for a year?
Why ask it
You are asking how they behave under sustained strain, not whether they love you. Listen for whether they have thought about savings, insurance, who they would tell, and how much help they could accept. Someone who cannot imagine needing care, or giving it, is telling you something worth knowing.
What are you hoping will be different about me once we are married?
Why ask it
Everyone has an answer and almost nobody offers it unprompted. Anything about behavior, less time at work, more planning, is negotiable. Anything about temperament, wishing you were more outgoing, more ambitious, calmer, rarely changes, and marrying in the hope that it will is a reliable source of long term resentment.
What would make you want out of a marriage, and what would you want us to try first?
Why ask it
Say your own list too. Naming what each of you considers unrecoverable, and what you would want attempted before anyone leaves, whether counseling, a separation, a specific conversation, is a serious commitment rather than a pessimistic one. A partner who refuses to discuss it at all has answered a different and important question.
How to actually have these conversations
Practical guidance for the conversation itself
Running the conversations well
Spread them over weeks, not one long evening
Two or three questions at a time, when you are both rested and not about to go out. A single marathon session turns into an interview, and the answers get shorter as the night goes on. Long drives, walks and washing up together are better settings than a table with a list on it.
Both of you answer everything
These are not questions to put to a partner while you assess them. Answer first when you can, and answer at the same length. If one person is doing all the disclosing, you learn less and you set up a dynamic that will show up again during the marriage.
Ask the follow up, then stop talking
The useful material is usually one layer down: why that, since when, what happened the last time. Ask, then leave silence rather than filling it. If an answer surprises you, resist arguing with it in the same conversation. Say you want to think about it and come back another day.
Look at documents, not just intentions, for money
Sit down together with pay figures, debt balances, credit reports and any support obligations. This is not distrust, it is the same diligence you would apply to a lease. Doing it now also makes it far easier to discuss a prenuptial agreement, which is best raised long before a wedding date and with separate legal advice.
What to do with what you hear
- Sort disagreements into three piles: things you can compromise on, things you can live with by taking turns, and things where one of you would have to give up something they would grieve. The third pile is the only one that matters.
- Children, geography, money and faith are the four that most often sit in that third pile. A vague agreement in any of them is worth reopening rather than banking.
- Notice how disagreement itself goes. A partner who can hear a difference without punishing you for it is better evidence of a workable marriage than agreeing on everything.
- Take an evasive answer seriously the second time it happens. People who deflect a direct question about money, an ex, or their family usually have a reason, and it rarely improves with a wedding.
- Distinguish a habit from a temperament when you catch yourself hoping for change. Habits move with effort, temperament mostly does not.
- If a conversation keeps ending badly, that is a reason to see a couples counselor now rather than a reason to stop having it. Premarital counseling is ordinary, often available through a religious community, and cheaper than the alternative.
- If any part of this makes you afraid of your partner's reaction rather than merely uncomfortable, that is the most important answer you have gathered.
The practical business nobody mentions
- Marriage changes your legal and financial position: tax filing, debt exposure in some places, next of kin status, inheritance and benefit entitlements. Find out what it changes where you live.
- Talk about wills, beneficiaries on retirement accounts and life insurance, and who each of you would want making medical decisions. These are quick to arrange and awkward to be without.
- Agree what you will each tell your families and when, particularly if either family will have opinions about the engagement itself.
- Decide whether either of you is changing a name, since it has practical consequences for work, passports and professional records.
- If either of you has children already, discuss what role the other will have, and get advice about anything legal that follows from marriage.
- If either of you has significant debt, a business, property or expected inheritance, get independent legal advice before the wedding rather than after.
- Set a date for a check in a year into the marriage, in the diary, to go through the same subjects again. Most of the answers above change with circumstances.