Questions to Ask Before Getting Engaged: A Christian Checklist

By Pastor Mega Philip Mega, author of Dating on Purpose.

The best time to ask the hard questions is before the ring, not after. Engaged couples often say, “I just knew.” That makes a nice story, but feeling certain is not the same as being ready. This checklist gives you real conversations to have, real markers of readiness to look for, and a way to involve your church well, so that you choose each other with open eyes.

It is not a romance-killing interrogation. It is the ordinary due diligence that any serious, lifelong commitment deserves.

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Why count the cost first?

“For which of you, desiring to build a tower, does not first sit down and count the cost, whether he has enough to complete it?” (Luke 14:28, ESV)

Jesus was speaking about discipleship, but the wisdom travels: anything worth building needs honest accounting before commitment, not after. Picture a couple sitting across from a premarital counsellor three weeks before the wedding, discovering for the first time that one of them assumed they would live near his parents and the other assumed they would never live in the same city as either family. It is a strange but common story. Two people spent a year building deep romantic intimacy while quietly avoiding the practical conversations that would decide whether a shared life was possible.

The prophet Amos asks, “Do two walk together, unless they have agreed to meet?” (Amos 3:3, ESV). Marriage is a lifelong walk, and it helps to know early whether you are heading the same way. Have these talks kindly and honestly, “speaking the truth in love” (Ephesians 4:15, ESV).

Question group 1: conflict

How you each handle disagreement will shape your marriage more than almost anything.

When we disagree, do I need space, or do I need to resolve it straight away? What about you?
Have either of us seen healthy conflict modelled, or only avoidance and blow-ups?
What is the hardest thing for you to say to me when we are upset?
How do we each apologise, and how do we each forgive?

Question group 2: money

Talk in specifics, not vague values.

What are our actual financial habits, debts and expectations?
Who will manage what? How were we each raised to think about spending, saving and giving?
Is there any significant debt, obligation or financial commitment the other person should know about before we go further?
How do we want to approach generosity and tithing?

Question group 3: family

How close do we each expect to live to our extended families?
What do we expect about holidays, visits and obligations to in-laws?
What boundaries do we each want with family, and how will we support each other in them?
What wounds or patterns from our families of origin are we still carrying into this relationship?

Question group 4: calling

What is each of us pursuing, vocationally and spiritually?
How do those callings fit together in practice, geographically, financially and in time?
Whose career will flex for whose season, and how will we decide?
Do we want children, and what do we each assume about raising them and about faith at home?

None of these conversations guarantees agreement. Some will surface real incompatibilities that deserve to be taken seriously, rather than assumed away by the hope that love will sort it out later. Having them before engagement means you are choosing each other with open eyes, not discovering your future spouse’s real expectations once the wedding is being planned and momentum has made honest reconsideration feel impossible.

Beyond “being in love”: signs of readiness

Scripture describes marriage this way: “Therefore a man shall leave his father and his mother and hold fast to his wife, and they shall become one flesh” (Genesis 2:24, ESV). Leaving and holding fast assume maturity, the ability to form a new primary loyalty and keep it through real difficulty. Strong feelings alone do not produce that. Character, tested over time, does.

Ask honestly whether these are true of your relationship:

The hard conversations have happened. You have talked about conflict, money, family and calling, and found workable alignment, not just avoided the topics.
You have seen each other under pressure. Not only in curated, easy moments, but in stress, disappointment, correction and ordinary life logistics.
Trusted people have had honest access. Family, friends or mentors have spent real time with you both, and any concerns they raised were heard and addressed, not dismissed.
You are each prepared to build a shared life. Not perfectly, but honestly, without hiding significant debt, unresolved trauma or patterns that will predictably return under marriage’s pressure.
Your motive is right. You genuinely want to build a life with this specific person, not out of fear of losing them, social pressure or tiredness with waiting.

Readiness is not perfection. No couple checks every box completely. It means enough honest groundwork has been laid that you are choosing each other with real information, and are prepared to keep doing the work marriage will keep asking of you. Waiting for perfect certainty is its own kind of avoidance.

Involve your church well

Some couples treat their pastor as a final exam to pass: attend the required sessions, say the right things, get the signature and move on. Others avoid pastoral involvement entirely, as an intrusion into a private decision. Both miss what the church offers: not a gatekeeper to satisfy, and not an intrusion to avoid, but a genuine resource most couples underuse.

“Where there is no guidance, a people falls, but in an abundance of counselors there is safety.” (Proverbs 11:14, ESV)

Good premarital preparation covers the same ground as the four question groups above, with a trained third person asking harder, more specific questions than you might ask each other alone. It should surface family-of-origin patterns, examine expectations about roles and responsibilities, and give both of you real space to voice doubts without fear of derailing a wedding that is already planned.

Choose wisely. Look for someone with real experience and spiritual maturity, not just whoever is convenient. A good mentor will ask uncomfortable questions, welcome honest answers without judgment, and be willing to say plainly if they see a serious concern, while still respecting that the decision belongs to you and your partner before God. Treat their counsel as input to your discernment, not a decision handed to someone else.

A foundation, not a fairytale

Many cultures tell the same story: two people meet, fall in love, overcome an obstacle, and the story ends at the altar. It is beautiful, and it is also quietly one of the most dangerous lies a couple can carry into marriage, because it makes the wedding the finish line when it is really the starting line. “Unless the LORD builds the house, those who build it labor in vain” (Psalm 127:1, ESV). A wedding is one afternoon. A marriage is the decades of ordinary Tuesdays that follow, and they are built well or poorly based largely on the foundation you lay now.

Questions to ask yourself first

Which of the four question groups have I never discussed in detail with my partner?
What one financial habit or expectation have I never said out loud to someone I am dating seriously?
Have I seen my partner’s character under real pressure, or mostly in easy moments?
What is my honest motive right now for moving toward, or away from, engagement?
Where might momentum be pushing me toward a decision before I have honestly counted the cost?

Frequently asked questions

How long should we date before getting engaged?

There is no biblical number. What matters is not the length of time but what has happened in it: whether you have had the hard conversations, seen each other under pressure, and involved wise people.

Is premarital counselling necessary?

The Bible does not command it, but Scripture strongly values wise counsel. Premarital counselling or mentoring is one of the most practical ways to add wisdom you cannot generate alone.

What if we disagree on something big?

Do not assume love will resolve it later. Take it seriously, talk it through honestly, and seek wise counsel. Some differences can be worked through, and some are serious enough to change your decision. It is better to know before the wedding.

What if one of us has doubts?

Doubts are worth listening to, not hiding. Name them honestly, and bring them to God and to a trusted mentor. A good preparation process gives you both space to voice doubts without fear of disappointing everyone.

Should we talk about past relationships and our pasts?

Yes, in the right way and at the right time. Significant matters that will predictably affect a marriage, such as debt, health, children or past harm, should not be hidden. A wise counsellor can help you decide how and when.

A prayer

Lord, give me courage to have the hard conversations now, honestly, rather than discovering the cost only after I have committed. Give me discernment that goes deeper than feeling, humility to receive real counsel, and a foundation only you can lay. Not a fairytale, but a real covenant, honest, tested and yours from the very beginning. Amen.

This article is drawn from chapters 6, 9, 10 and 11 of Dating on Purpose: Courtship, Boundaries, and Discerning God’s Will Before Marriage. Related reading: Emotional and spiritual readiness for Christian marriage and Is dating biblical? Courtship vs dating for Christians.

9 min read Questions to Ask Before Getting Engaged: A Christian Checklist