101 Questions to Ask Before Getting Engaged
Twenty questions to settle before an engagement rather than after it: whether you both want this now, what the wedding costs and who pays, actual figures for income and debt, children, whose career gives way, both sets of parents, faith at home, and what each of you would call a deal breaker.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
Do we both want to be engaged this year, or is one of us being carried along?
Ask it first and ask it plainly. A hesitation here is worth more than every other answer combined, and the common pattern is one person treating engagement as the obvious next step and the other treating it as a decision they have not made.
- 2
What does being engaged change for us, apart from the ring?
If neither of you can name anything concrete, you are describing a status rather than a plan. Good answers involve moving in, merging money, telling an employer, or starting a visa or property process.
- 3
How long an engagement are we picturing, and who is that timeline for?
Timelines are usually set by a venue, a visa, a parent's health or a lease rather than by the couple. Naming whose clock it is prevents a year of pressure that neither of you chose.
- 4
What do we each want the wedding to be, and who is paying for what?
The size disagreement is really a family disagreement. Ask specifically whether either set of parents is contributing, because money from a parent almost always arrives with an opinion about the guest list.
- 5
Who has to be told first, and who is going to be difficult about it?
Every couple has one relative who will make the announcement about themselves. Deciding the order and who makes which call stops the first week of an engagement becoming damage control.
- 6
What do we each earn, owe and own, to the nearest thousand?
Not a feeling about money, a figure. Undisclosed debt is the most common financial surprise in the first year of marriage, and student loans, family loans and credit cards all need saying out loud.
- 7
Do we combine our money, keep it separate, or run something in between?
There is no correct model, but there is a wrong outcome, which is one of you assuming a joint account and the other assuming independence. Ask how bills, savings and gifts each work under the model you pick.
- 8
What is the largest amount either of us can spend without telling the other?
Set a number. Couples who never set one argue about a purchase rather than about the principle, and the argument repeats because the principle was never agreed.
- 9
Children: how many, roughly when, and what if one of us changes their mind?
Agreeing on children in the abstract hides a lot. The number and the timing are where couples turn out to disagree, and the change-of-mind clause is the part almost nobody asks about in advance.
- 10
If we could not have children, what would we do?
Treatment, adoption, fostering or a life without children are four different answers, and they cost different things emotionally and financially. This is a question to have answered before it is urgent, not during.
- 11
Whose career gives way if the two of them conflict?
The default is that the lower earner's career yields, which is a decision made by nobody. Ask what would make the person yielding feel it was chosen rather than assumed, and what they would want in return.
- 12
Would either of us move cities or countries, and for what?
Ask for the conditions rather than a yes or no. People who say never usually mean not for a job, and people who say anywhere usually have one parent they will not leave.
- 13
What faith or practice do we want in the house, and at what volume?
Mixed households work when the expectations are explicit: what happens at holidays, what a wedding ceremony looks like, and what children are taught. Vagueness here gets resolved later by whichever family pushes hardest.
- 14
How much time do we owe each set of parents, and who enforces it?
Holiday arrangements are the recurring version of this and the one that causes the most repeat arguments. Agree that each of you handles your own parents, because the alternative is one person always cast as the difficult one.
- 15
What happens if one of our parents needs to live with us or needs care?
For many couples this arrives before children do. Ask about money, space and who does the day-to-day work, since willingness in principle and willingness in a spare room are different things.
- 16
How do you argue, and what do I do that ends the conversation?
You are asking for a behaviour, not a personality trait. Common answers are walking out, going silent, bringing up old material, or getting so reasonable that the other person cannot continue.
- 17
What does sex look like for us in a normal month, and what would you change?
Ask about frequency and about initiation, because a mismatch in who initiates causes more quiet resentment than the number does. It is much easier to raise now than three years in.
- 18
What counts as cheating, and has either of us come close to it?
Couples often have unmatched definitions covering messaging, old partners and what is acceptable on a night out. Establish the definition before you need it, and treat a vague answer as an answer.
- 19
Do we want a prenuptial agreement, and who is going to raise it with the families?
Raising it is uncomfortable and easier before a proposal than after. What such an agreement does, and whether it holds where you live, is a question for a family lawyer in your jurisdiction rather than something to settle between you.
- 20
What is your deal breaker, said out loud?
The right closer, because it is the only question where the answer needs no negotiation. Anyone who says they have none has either not thought about it or is not saying, and both are worth another conversation.
Before the proposal
Practical guidance for the conversation itself.
How to work through these
How to work through these
- 1Answer separately in writing first, then compare. Answering together produces agreement that was arrived at by whoever spoke first.
- 2Do the money questions with documents open: payslips, loan balances, credit card statements, and anything owed to family.
- 3Split them over several evenings. Money and wedding in one, children and careers in another, families and faith in a third.
- 4Note anywhere your answers differ by more than a little. Those are the conversations to return to, not the ones to resolve in the moment.
- 5Redo the ones about children and money if a year passes before anyone proposes.
Where couples find real differences
Where couples find real differences
- Debt that one person has been managing alone and has never named a figure for.
- Whether an engagement is a commitment to marry within a period or an open-ended state. Couples routinely mean different things by it.
- How much of the wedding either family expects to control in exchange for paying.
- Whether a partner who says they are relaxed about faith stays relaxed about it once children are involved.
- How much contact with parents counts as normal. This varies enormously by family and neither person thinks their own version is unusual.
Reading the answers
Reading the answers
- A partner who will not give a figure or a date is giving you information. Repeated vagueness on money or children is rarely accidental.
- Watch for answers that arrive as reassurance instead of content. We will work it out is not a plan, and it is the most common substitute for one.
- Disagreement is not a reason to stop. Discovering a disagreement now, when nothing has been announced, is the cheapest version of finding it out.
- If the same argument keeps recurring in the same shape, that pattern will still be there after the wedding. It is a reasonable point to see a couples counsellor.