Questions to ask your boyfriend before getting engaged
The pre-engagement conversation is the most consequential one in the relationship arc. The public conversation about it is dominated by either Christian-marriage-prep frameworks or Pinterest-bait listicles, and there is not much in between. The honest version sits somewhere quieter. There are eight load-bearing topics, every couple should have a serious conversation about each, and the answers do not have to align perfectly, but they have to align enough.
What follows is thirty-two prompts, four per topic, across the eight topics. Money in two layers, children, geography, in-laws and family of origin, faith and meaning, conflict patterns, sex over the long arc, and the practical layer of money. These conversations should happen across weeks, not in one evening. Some will surface friction. That is not a problem with the prompts, it is the work of the conversation.
Money, the values not the spreadsheet
The values layer of money. The spreadsheet conversation is on /the-money-conversation. This one is the bigger one.
What does enough money look like to you, when you imagine your forties?
Sufficiency-number. Worth naming in advance.
What would you do, in our marriage, if one of us out-earned the other significantly?
Earning-asymmetry. Often unaddressed until it happens.
What is the role you imagine money playing in our family, if we have one?
Money in family-system frame. Different from money in couple frame.
What is the financial value you would not compromise on, even in marriage?
Non-negotiable. Worth knowing the shape now.
Children
Timing, number, what if. The conversation that has to happen with weight, not in passing. Many couples avoid the specifics until the specifics force themselves.
Do you want children, and how sure are you?
Asked plainly. The percentage of his certainty is the answer.
When do you imagine wanting them, ideally?
Timing, named in years. Worth comparing your two answers honestly.
How many do you imagine, and why that number?
Number-and-reason. The reason is more revealing than the number.
What would we do if it took longer than we hoped, or did not happen?
Difficulty-conceiving conversation, in advance. Hard, important.
Geography
Where do we live. Whose career bends. Do we move for work. The most under-discussed topic in pre-engagement conversation, in our experience.
Where do you imagine us living in ten years, ideally?
Long-tense geography. Often surprisingly mismatched between couples.
Whose career, in a real conflict, would bend, in your honest view?
Career-priority. Worth naming before the conflict happens.
What is a place you would never want to live, even for love?
Limit, named. Specific. Worth surfacing.
How important is being near family, for you, in the long run?
Family-proximity weight. Often the deciding factor in geography decisions, often unspoken.
In laws and family of origin
How close is too close. How distant is too distant. Four prompts on the family system you are about to formally join.
How close to your family do you imagine us being, after we are married?
Closeness-frequency, in real terms. How often do we visit, how involved are they.
What is something about your family that I should know now, before we are formally joined?
Family-disclosure, in advance. Better said now than discovered at a wedding.
What would you want, if my family was harder to be around than yours?
Asymmetric-family. Most couples have one harder side. Worth naming the protocol.
How would we handle a family decision we disagreed with, if it involved my parents or yours?
In-law conflict resolution, mapped.
Faith, meaning, and worldview
Whether or not you are religious, the meaning-frame matters. Four prompts on what the world is for, in his view.
What gives your life meaning, in your most honest answer?
Open. The shape of his answer is the answer, more than the content.
How do you want to raise children, in terms of faith or meaning?
Best discussed before, not after. Often deeply inherited.
What is something you believe that I might not know about?
Hidden belief surfaced. Worth knowing.
What does a life well lived look like to you, when you imagine yours?
Big question. The right hour for it is unhurried, not the rehearsal dinner.
Conflict patterns and repair
How we fight, how we repair, what we do when neither of us is willing to bend. Four prompts that map the relational arc that will hold the marriage up.
What is our worst recurring conflict, named honestly?
Marriage will not erase the conflict. Knowing it now is worth more than hoping it goes away.
How do you know when our repair has worked?
Repair-marker. Worth aligning on what counts as fixed.
What is something you do, in conflict, that you would like to do less of?
Self-awareness. Most adults can name one if asked.
When we have been at our worst, what brought us back?
Recovery-pattern, named. Worth honouring.
Sex and physical intimacy
Over the long arc, not the immediate one. Four prompts on the sexual relationship as a thirty year question, not a tonight question.
What do you imagine our sex life looking like, ten years in?
Long-tense, asked plainly. Most couples never have this conversation.
What would you want from me, if our sexual relationship went through a hard stretch?
Hard-stretch protocol, in advance. Easier to set up now than mid-difficulty.
What is something you wish was different about how we talk about sex?
Communication audit, gently. Worth asking once a year.
What is a fear you have about long-term physical intimacy, if you have one?
Honest fear, named. Most thoughtful adults have one. Worth surfacing.
Money, the practical layer
Debt, savings, financial transparency. The spreadsheet, after the values. Four prompts to close the financial picture.
What is the full picture of your debt, accounts, and savings, that I would need to know?
Full disclosure, in advance. Should not be a surprise after the wedding.
How transparent do you want our finances to be, day to day?
Transparency-level. Mismatched expectations is the most common money fight in early marriage.
How would you want us to handle a major financial mistake, if one of us made one?
Mistake-protocol. Better named in calm than in crisis.
What would you want our financial life to look like, in twenty years?
Long-tense vision. Useful for aligning, even if both answers feel rough.
The eight-topic structure draws on the SMART Couples programme from the University of Florida’s IFAS Extension, which uses a similar load-bearing-topics framework, and on Mira Kirshenbaum’s pre-engagement assessment in her book Too Good to Leave, Too Bad to Stay. NPR Life Kit’s 5 Questions Before Marriage piece, with relationship therapist Eli Finkel, contributed the children, geography, and in-laws emphasis.
The conflict-patterns and repair section draws on John and Julie Gottman’s research on the four most predictive conflict patterns in long-term marriage and on their work distinguishing repairable conflict from non-repairable conflict. The Gottman Institute’s pre-marriage prep workbook is a more structured complement to this page.
The app has two hundred more for this stage, plus shuffle, save, and a paired mode where you both answer privately and compare.
It is not built yet. Tell me when it is ready, no email required, just a one click follow.
If the pre-engagement conversation surfaces something that needs more than these prompts, structured pre-marriage support is worth the cost. Lasting and Relish are both legitimate apps that pair couples with structured exercises, with or without a coach. Paired is closer to the ongoing-prompt model we are building toward, and the daily-prompt format is well suited to the post-engaged engagement period.
Disclosure, the links above are affiliate links. We earn a small commission if you sign up through them. We have used or trialled all three. A licensed couples therapist is still the better answer if there is something serious going on. More on our editorial line.