Ten Questions to Ask Before Getting Engaged

I am in the question business when it comes to weddings and premarital counseling.

During a wedding ceremony, I ask questions. In a traditional ceremony, one of the first things I ask is directed to the father, mother, parents, or whoever walks the bride down the aisle: “Who presents this woman to be married?” Later in the service, I may ask questions of the families or the congregation. Then, eventually, we come to the big question. “Do you take this person?” or “Do you promise?” or “Will you love, honor, and cherish?” Every ceremony says it a little differently, but the question is always there.

You cannot have a wedding without asking a question.

That is worth thinking about. Weddings are marked by questions, but the process leading up to the wedding should also be marked by questions. The whole relationship likely began when someone asked a question. Someone asked someone to go out, hang out, get coffee, grab lunch, have dinner, meet up, take a walk, or spend time together. A question opened the door.

That first question began the movement through the three major phases of a relationship: dating, engagement, and marriage. Dating starts with a question. Engagement begins with the big question: “Will you marry me?” Then, at the wedding, I am legally and pastorally obligated to ask an “I do” question.

Those are big moments, but between “Do you want to go out?” and “I do,” there are dozens of questions to ask. Some are romantic. Some are practical. Some are awkward. Some are deeply personal. Some may be the very questions that save a couple from rushing into something they are not ready for, or help them move forward with greater confidence.

Before a couple moves from dating to engagement, or from engagement to marriage, I want them to ask better questions. I hope every couple reading this chooses a premarital process, whether it is with me, another minister, a counselor, a mentor couple, or a structured assessment like SYMBIS. There is no substitute for a thoughtful marriage preparation process. Still, wherever you are in the process, these ten questions are worth asking before you get engaged.

1. Why are you marrying your fiancé?

This is one of the first questions I ask when I meet with a couple, and it tells me a lot.

It should be easy to answer, though sometimes couples have to think longer than they expected. I am not looking for a perfect essay or a Hallmark movie speech. I want to know what you see in the other person. I want to know what has made you believe this is the person you want to marry. I want to know whether your answer is rooted in character, friendship, shared faith, shared values, trust, love, calling, compatibility, and a realistic picture of who this person actually is.

There are weaker answers. “She is beautiful” is true and wonderful, but beauty alone cannot carry a marriage. “He makes me happy” may be honest, but no spouse can carry the burden of keeping another person happy every day. “We have been together forever” may explain history, but history alone does not equal readiness. “It just feels right” may be part of the answer, but feelings need wisdom around them.

A good answer does not need to sound impressive. It needs to be true. Why this person? Why marriage? Why now?

2. Why do you think your fiancé is marrying you?

The second question is harder. Most people can eventually explain why they want to marry the other person. It takes a different level of reflection to ask, “Why do I think this person wants to marry me?” That question requires you to step outside your own feelings and consider the relationship from your partner’s perspective.

What does your fiancé see in you? What do they trust about you? What kind of life do they think they are building with you? What do they believe you bring into the marriage? What makes them feel safe, loved, chosen, and hopeful?

This question can expose something important. Sometimes one person has a clear and thoughtful answer, while the other person is vague. Sometimes a person knows why they want the marriage, but they have never really considered what the other person is receiving. Marriage is mutual. It is not only about what you want. It is also about what you are offering. If you cannot answer this question, it may be time for a deeper conversation.

3. Are you sure?

Before the proposal, before the ring, before the pictures, before the social media post, before the venue tours, before the dress appointments, before the guest list, and before everyone in your world starts asking questions, there is one deeply personal question.

Are you sure?

Once you get engaged, the relationship goes public in a new way. People will ask your story. They will want to know how you met, when you knew, how the proposal happened, and whether you have a date. Some people will ask sincerely, and some will ask jokingly. Guys often hear some version of, “Are you sure you are ready to settle down?” or “She is the one, huh?” Those questions can be annoying, but they point to something real.

Engagement is a public declaration of private certainty. It does not mean you know everything. It does not mean you have no fears. It does not mean the future is completely clear. It means you have done enough honest reflection to say, “I am ready to move toward marriage with this person.”

If you are not sure, slow down. Uncertainty is not always a stop sign, but it is always worth noticing. Ask why. Talk it through. Pray. Seek counsel. Give the relationship enough honesty to answer the question before you ask the question.

4. Have you been together long enough to see the relationship clearly?

Relationships need time to breathe and mature. My general recommendation is that couples date long enough to see each other in more than one season of life. For many couples, that means dating for at least two years before getting engaged. I know there are exceptions. I have seen couples date for a short time and go on to build beautiful marriages. I have also seen couples date for years and still avoid the real questions. Time alone does not guarantee wisdom, but time gives wisdom room to work.

The first several months of dating can be wonderful. The other person seems perfect. You tell your friends and family how amazing they are, and your friends and family smile and say, “We are happy for you. Give it time.” They are not trying to be negative. They know that early attraction can make everything shine.

Over time, the shine gives way to reality. You begin to see habits, patterns, weaknesses, strengths, wounds, preferences, family dynamics, and conflict styles. Ideally, the more you see, the more you love. You are not discovering a flawless person. You are learning whether two flawed people can build a healthy life together.

Time allows you to see each other at work and at play, with friends and family, in celebration and disappointment, when things are easy and when things are hard. A relationship that cannot withstand the test of time may not be ready for engagement.

5. Have you dated longer than you have been engaged?

I like to see couples date for a while before getting engaged because engagement changes the relationship.

Technically, someone could say, “What is the difference between dating for two years and being engaged for one year, or dating for one year and being engaged for two years?” In both cases, the relationship has lasted three years. On paper, that may seem the same.

In real life, engagement often shifts the focus. Once the proposal happens, the couple can easily move from relationship development to event planning. The conversation turns toward venues, dresses, photographers, flowers, invitations, guest lists, budgets, colors, playlists, seating charts, and family expectations. Those things matter, but they can pull attention away from the relationship itself.

That is why I prefer that couples have a solid dating foundation before the engagement begins. Date long enough to know each other. Then, once you are engaged, do not stay engaged forever. A long engagement is sometimes necessary because of school, military service, finances, family circumstances, or venue availability. Still, engagement should be a bridge toward marriage, not a holding pattern that never becomes anything else.

The point is not to create a rigid rule. The point is to ask whether the relationship has had enough time to develop before the wedding planning takes over.

6. Are you close to 25?

Age matters more than most couples want to admit.

I know that can sound frustrating, especially to a couple in their early twenties who feel deeply in love, fully committed, and ready for marriage. I also know that age by itself does not make someone wise. We all know people in their forties, fifties, and sixties who still struggle with basic maturity. We also know young couples who married early and built beautiful, faithful, lasting marriages. Still, age is worth paying attention to.

SYMBIS uses two numbers that I think are very helpful. The first is whether the couple has been together for at least two years. The second is how close the individuals are to the age of 25. Those numbers matter because they give a couple something more objective than emotion. When a couple has had enough time to know each other and is closer to the mid-twenties than the teenage years or early twenties, the risk factors begin to shift in a healthier direction.

Recent studies have shown that the human brain does not reach full developmental maturity until around 25. One study suggests three developmental categories:

·Adolescence (generally defined as puberty through age 18)

·Young Adulthood (generally defined as 18 to 22 or 18 to 25)

·Later Adulthood (generally defined as the mid-20s and older)

So, the human brain reaches full maturity at least in the mid-20s. Researchers have said, "The rental car companies have it right." The brain isn't fully mature at 16, when we are allowed to drive, or at 18, when we are allowed to vote, or at 21, when we are allowed to drink, but closer to 25, when we are allowed to rent a car. Those who marry before 25 face a higher divorce rate. The divorce rate after ten years is 48% for those who marry before age 18. However, the rate is just 25% for those who marry after age 25. For people who marry between the ages of 20 and 25, there is a 44%-60% chance of the union ending in divorce. These statistics confirm that the couple's age at the time of marriage impacts subsequent divorce rates.

That does not mean 25 is magic. It does not mean everyone under 25 is unready. It does not mean everyone over 25 is ready. But it does mean that age and time together should be taken seriously.

So the question I ask is not simply, “Are you mature enough?” Most people think they are. The better question is, “Are we giving this relationship enough time, and are we close enough to 25 to make this decision with wisdom?”

If you are younger than 25 and considering engagement, slow the process down enough to ask serious questions. Have you been together for at least two years? Have you seen each other under stress? Have you dealt with conflict well? Have you talked about money, family, children, faith, sex, work, expectations, and the future? Have trusted people around you confirmed that this relationship seems healthy? Have you gone through a premarital process that helped you see both strengths and risk factors clearly?

Young love can be real love. It still needs time, wisdom, counsel, and preparation.

7. Are your parents still married?

Your family of origin has a powerful impact on your marriage.

Out of all the factors that shape you as a person, your parents or primary caregivers leave one of the deepest marks. Whether the story is good, painful, complicated, or somewhere in between, your family has given you a template for what marriage looks like, how conflict works, how affection is expressed, how money is handled, how holidays are celebrated, how apologies are offered, and how people stay or leave.

No one has ever told me, “I want a marriage exactly like my aunt and uncle’s,” or “I definitely do not want to do marriage the way my coworker did.” Those people may influence us, but most people eventually say some version of, “I want a marriage like my parents had,” or “I do not want a marriage like my parents had.”

When I push on it a little, I ask, “What exactly did your parents do well?” or “What exactly do you want to do differently?” Sometimes people are not sure. They have a strong emotional reaction to the family they grew up in, but they have not examined the details.

If your parents are still married, what have you learned from their marriage? What do you admire? What would you repeat? What would you change? If your parents divorced, what did that teach you about trust, conflict, commitment, pain, forgiveness, or fear? If your family story is complicated, how has that shaped the way you approach love? You cannot choose the family story you came from, but you can choose to understand it.

8. What have you learned from your siblings and extended family?

If you or your partner has siblings, I am interested in their stories about their relationships, too.

Are they married, single, divorced, remarried, dating, or avoiding marriage altogether? If your partner comes from a family where the parents divorced, have the siblings married? Have any of them divorced? Did the family become more cautious about marriage, more eager for stability, or more skeptical of commitment?

Siblings do not determine your future, but family patterns matter. Sometimes one sibling becomes determined to create a different story. Another repeats what they saw. Another avoids marriage because they are afraid of pain. Another rushes into marriage hoping to build the family they always wanted.

Extended family can also shape expectations. Grandparents, aunts, uncles, cousins, and family stories all contribute to the picture of marriage a person carries. Some families celebrate marriage with deep joy. Some tolerate it as a practical arrangement. Some joke about it constantly. Some treat divorce as failure. Some treat divorce as inevitable.

Before getting engaged, pay attention to the stories around you. They may be shaping you more than you realize.

9. Do your parents approve of you both?

Parental approval is not the only factor in deciding whether to get engaged, but it should not be dismissed too quickly.

In reality, if your parents do not like your partner before the wedding, they will probably not magically like them after the wedding. If they believe you need more time, if they are concerned about the relationship, or if they see something you are ignoring, pause long enough to listen.

Parents can be wrong. Families can be controlling. Some parents have unhealthy expectations, unresolved wounds, or unreasonable standards. Their approval does not automatically mean the relationship is wise, and their disapproval does not automatically mean the relationship is wrong. Still, when people who love you have concerns, those concerns deserve a hearing.

Romeo and Juliet and West Side Story are romantic tragedies about star-crossed lovers. They are romantic and tragic. Rushing into marriage to avoid disapproval rarely fixes anything. You might get married, and the marriage may be legally binding, but the wedding will not automatically change hearts, opinions, family tension, or long-term relational strain.

Ask your parents what they see. Ask trusted friends what they see. Ask mentors what they see. Listen without becoming defensive. Then bring those concerns into prayer, conversation, and premarital counseling.

Love should be strong enough to receive wise questions.

10. Are you stable financially and relationally?

Financial stability does not mean you have to be wealthy. No one is ever fully financially prepared for marriage, and certainly no one is fully prepared for children. Many couples begin marriage with student loans, starter jobs, small apartments, old cars, tight budgets, and a lot to figure out. That can be normal. The question is whether you are stable enough to build together.

If finances are already a major issue, they usually do not disappear quickly after the wedding. Money pressure can reveal deeper issues connected to trust, honesty, planning, family history, spending habits, debt, generosity, control, fear, and responsibility. Couples need to talk honestly about income, debt, savings, credit cards, school loans, spending expectations, financial goals, and how decisions will be made.

Relational stability matters too. Have you broken up repeatedly? Has there been betrayal, secrecy, manipulation, or ongoing mistrust? Are you constantly fighting about the same issue without resolution? Are you trying to use engagement to stabilize a relationship that has been unstable for a long time? A proposal does not repair what a couple refuses to face.

Before getting engaged, ask whether the relationship has enough trust, honesty, responsibility, and maturity to carry the weight of marriage. If the answer is uncertain, do not panic. Slow down and get help. The goal is not to create a perfect relationship before engagement. The goal is to enter engagement with enough clarity to keep moving toward a healthy marriage.

Final Thoughts

Every wedding is built around questions. Who presents this person? Will you take this person? Will you promise? Will you love? Will you remain faithful? Will you build a life together?

The questions asked at the ceremony matter, but the questions asked before the ceremony may matter even more.

Before you ask, “Will you marry me?” ask whether you are ready for the life that question begins. Ask why you want to marry this person. Ask why this person wants to marry you. Ask whether you are sure. Ask whether the relationship has had enough time to mature. Ask whether your age, family story, support system, finances, and relational patterns are moving you toward wisdom.

If you are already engaged, these questions still matter. Bring them into your premarital process. Talk them through together. Let them become part of your preparation, not a source of fear.

Good questions do not weaken love. Good questions strengthen it.

Sources and Notes

This article draws from my work with engaged couples through WeddingChaplain.com and Marriage Boot Camp. The section on age and maturity reflects general research on brain development into the mid-to-late twenties and the broader relationship between age at first marriage and marital stability. These issues should be treated as wisdom factors rather than rigid rules. Every couple has a unique story, and premarital preparation helps couples discern that story with honesty and care.

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