Taylor isn’t just my daughter; she’s my princess.

I knew it the day she was born. I took her in my arms and rocked her. I looked into her eyes. And in that nanosecond, I knew I’d do anything and everything I could to protect her. Always.

I was the first man in Taylor’s life, and over the years we’ve experienced plenty of firsts together: her first birthday party, her first bloody knee, her first day of school, her first heartbreak. I’ve watched my little princess grow into a beautiful, godly young woman. And then, before I knew it, I was faced with another first: A young man asking me if he could make my princess his queen.

Caleb asked for my permission before he even proposed – a wonderful gesture. But when he asked me, I was filled with a jumble of emotions: happiness and gratitude and, yes, a little sadness. But I also felt the same overwhelming sense of protectiveness I had felt from my very first moment with Taylor. I knew I needed to ask Caleb some tough questions.

What should you ask when a young man wants to marry your daughter? It’s not like fathers are given a set of instructions in the Bible for this important moment. Even before having this critical conversation with a young man, you should – if possible – talk with three people:

Your daughter

Make sure that she has a peace about the young man. Does she want to marry him? Does she have any concerns? Does she feel tense, confused, uneasy or pressured to become engaged? You want to know that she is paying attention to her gut and feels that getting married to this young man is the right decision.

If she feels that she’s ready to marry, ask her to put those feelings to paper and write a blessing letter to her boyfriend.

Taylor’s letter to Caleb unpacked her journey from being a prayerful little girl to a purposeful young woman – one who spent years wondering what her future husband would be like. “You were and still are so much more than I could have ever hoped for or imagined,” Taylor wrote.

She continued:

I fall in love with you more and more with every day I get to spend with you. I am constantly finding out new things to love about you, and it is just the most incredible gift to get to be loved in return by my best friend. I want to live every day of this crazy life with you by my side. I have never been so sure about anything else . . . Thank you for being the future husband of my dreams.

Your daughter’s mother

Many women seem to have an incredible intuition for reading people and sensing underlying issues – especially when it comes to someone’s character and maturity. It’s uncanny how they can discern deception and manipulation in ways that men often fail to notice. What does your wife think about this young man? Does she support this engagement? Does she have any concerns? Accept her influence, and if she raises some issues, talk them over with the man when you talk with him.

Ask her to write a letter of blessing, too. My wife, Erin, wrote one to Caleb, offering her unconditional support:

I wanted you to know that I 100% give you my blessing in asking for Taylor’s hand in marriage. I see what a good fit you are for our daughter and that not only are you good for her – but she is also good for you. I love how you care for each other and how you love each other. I love your sense of humour and that you fit right into our family. I especially love that you have loved not only our daughter, but also our entire family.

His parents

Even if your family is on board, is his? You want to confirm that this young man has sought his parents’ and his family’s blessings and that they are completely supportive of this marriage. What do they think of your daughter? Do they support this engagement? Do they have any concerns? If they do, pay attention and discuss these issues with your daughter’s potential fiancé.

If his parents are not in the picture, ask him for the name of his pastor, mentor or a close friend – someone he has turned to for advice and someone who knows him well.

Armed with the blessings from your daughter, her mother and his parents, you’re ready to have the conversation with the young man.

The questions

When Caleb asked for my blessing, he was living in a different state. So I had him fly to meet me at a marriage seminar that I was teaching. This conversation was too important to have over the phone.

Caleb and I talked several times that weekend. One night we went out to a local restaurant and I ordered some Cajun fried oysters for us. When I was slurping down an oyster, however, the mollusk got its revenge.

Crunch!

I cried out in pain. Turns out a pearl was hidden in the oyster.

Was it foreshadowing of things to come? Did it mean that Caleb was a pearl of a future son-in-law? Or that he might cause my daughter pain, like the pearl caused me pain?

I decided that how Caleb dealt with my questions – 12 big, important, overarching questions – might hold the answer. So once my tooth stopped throbbing, I started asking the questions

1. Are you united spiritually?

God isn’t a matchmaker. He doesn’t oversee the e-Heavenly dating service. There is no such thing as a soul mate or the one – the ideal person God picked just for you. Although 1 Corinthians 7:39 is talking about second marriages after a woman is widowed, it suggests we have free will when selecting a mate. But that verse also goes on to say, “He must belong to the Lord.” In 2 Corinthians 6:14, Paul stresses this again – that marriage partners must be “equally yoked.” In other words, God expects Christians to marry other Christians.

This is the reason you want to understand the young man’s relationship with the Lord. Has he accepted Christ as his Saviour? Is he pursuing a daily relationship with Christ? Is he a Christian but has fallen away from his faith? Don’t be afraid to ask deep, even nosy, questions: “Have you had times where you felt distant from God? How did you handle that season?” “What has God been teaching you lately?” “Where do you plan to attend church once you’re married?”

Don’t panic if the answer isn’t just what you’d like to hear. When I asked Caleb this question, his answer shocked me initially.

“Taylor and I really haven’t developed a spiritual relationship,” he said.

Excuse me?

In my best therapist voice I said, “How interesting. Please elaborate.”

“I believe that having a spiritual relationship is one of the deepest, most intimate experiences that we can have together,” Caleb continued. “I was concerned if we really nurtured this aspect of our relationship that it would lead us to want to be fully intimate.”

“We’re now talking about sex, right?” I smiled at Caleb.

“Yes.” Caleb said. “And I really didn’t need that added temptation. So, early on in our relationship, Taylor and I agreed to wait until we were married to fully develop our spiritual intimacy.”

I sat there staring at Caleb, looking for some sign that he was feeding me a line – like a new-generation Eddie Haskell. But he was sincere. It was really hard not to like this kid!

If the young man who wants to marry your daughter isn’t a Christian, tell him that you have serious concerns about the two of them being unequally yoked. If it’s a big deal to God, it should be a big deal to you.

2. Are you ready to make a lifelong commitment?

Again, God isn’t a matchmaker, and you should emphasize that to the man who’s interested in marrying your daughter. He is freely choosing your daughter, and because it’s his decision, your prospective son-in-law needs to be prepared to do whatever it takes to make it work. You want to be sure that he believes that marriage is for a lifetime – that the word divorce isn’t in his vocabulary. You want to be certain that he understands he is making a covenant before God.

Ask questions like, “What does it look like when things get hard?” “Are you willing to get help from a mentor, pastor or counselor when your marriage gets difficult?” and “Are my grandkids going to be raised in an intact family?”

3. What do you see in my daughter that makes you want to marry her?

You want to know that he is drawn to your daughter’s inner character traits (such as integrity, generosity, kindness and loyalty) over shallow or superficial things like her looks, her taste in fashion or a shared love of a particular sports team. You want to know that he values your daughter’s unique personality traits; her gifts and talents; her passions, dreams and aspirations.

Make sure he knows that your daughter – as wonderful as she is – isn’t perfect, and he should know that from the start. You want to make sure that he values their differences and sees how their individual strengths and weaknesses complement each other.

4. Do you agree on core values and big dreams?

What are the man’s most important values? Does he value honesty? Commitment? Generosity? Sacrifice? Do he and your daughter agree on the “big stuff,” such as children, career goals and the like? Do they both generally want the same things out of life? Ask if they’ve talked about each other’s passions, hopes and dreams for what the future might look like. Make sure they’re both heading in the same direction.

5. How do you plan to financially support my daughter?

Biblically speaking, a man must be able to support and provide for his family (1 Timothy 5:8). And as your daughter’s first protector, you owe it to both of them to get a sense of the fledgling couple’s financial landscape. What is the man’s job situation? What are his career goals? Is he bringing debt into the relationship? If so, what are his plans for getting out of it? Is he financially independent now, or does he have plans to be soon? 

Newlyweds should be financially independent from their parents. An important part of marriage is God’s command to “leave your mother and father” (Genesis 2:24). A newly married couple cannot “leave” Mom and Dad if the couple is still depending on them for housing or financial support. If the husband and wife can’t financially support themselves or live at their own place, I would question their readiness for marriage.

When I talked with Caleb, he still had one year left in college as an engineering major. I made it clear to Caleb that if he couldn’t financially support my daughter, then he wasn’t ready to get married. Caleb assured me that he and Taylor had put a lot of thought into their financial plan for the time when he would be finishing his degree. As he explained the details, I felt comfortable with their plan.

6. Would you marry you?

I loved the surprised look on Caleb’s face when he heard this question. Like studying for the SAT or ACT, Caleb had tried to prepare for our meeting. He read some of my online articles and perused a book that Erin and I had written for engaged couples called Ready to Wed. But he hadn’t anticipated this.

This question gets at maturity level. Obviously, you’re not looking for perfection. He’s probably pretty young and still has to mature. Instead of perfection, you want to see if he’s aware of his weaknesses and areas of potential growth areas. You want to better understand how he has dealt with his personal “junk.” (We all have junk.) Is he growing and moving forward in dealing with his weaknesses? What are his experiences with pornography, alcohol, abuse or any other sensitive issues that many of us grapple with? Is he still emotionally entangled with a past romance? Does he have children from a previous relationship?

Help him understand that the question of whether he’d marry himself isn’t “pass” or “fail.” You aren’t looking for him to defend or rationalize his past mistakes. You aren’t going to judge him or repeat what he shares. He needs to feel safe in order to open up and deal with this question honestly and directly. To help facilitate that safe space, I’d encourage you to first share some of the struggles that you were dealing with at his age.

Be respectful.And then, when that safe space is created, start asking him those difficult questions: “What area of your life needs the most improvement?” “What are some of your weaknesses or growth areas?” “What are some ways that you frustrate my daughter?” “What do you two fight about?”

7. What do you like about your relationship with my daughter?

Obviously, you’d like to assume that your daughter and the man who wants to marry her like each other and that they like spending time together. But why? Ask him if your daughter is one of his best friends. Ask if they allow each other space to be individuals – to be sincerely transparent with each other and reveal who they are inside.

8. Do you have meaningful communication?

Communication is the lifeblood of a marriage. How well do your daughter and her prospective husband communicate? Ask him what they talk about. Is it mostly “to do” lists and schedules? Or do they talk about deeper emotional issues?

Focus on whether he’s committed to being open and known. Are there off-limits topics that they can’t talk about? If they can’t talk about certain things (past relationships, personal struggles, finances, etc.) that might be a red flag.

9. How do you manage conflict?

Before we’re married, some of us imagine that marriage will be a fairy tale. But that’s a lie, and the Bible tells us so: “But those who marry will face many troubles in this life” (1 Corinthians 7:28). Does he understand this? More importantly, how do he and your daughter manage conflict? Is he respectful and loving when they disagree? Does he value her point of view and emotions? Are they able to repair their relationship in a reasonable amount of time after a fight? Do they find solutions that feel good to both of them – as teammates?

There is no such thing as a win-lose situation in marriage. You will either win together or lose together. Your goal is to better understand how your daughter and her prospective husband function as a team and to encourage your future son-in-law to always treat your daughter as an equal partner.

10. Do you and my daughter agree on biblical roles and responsibilities?

When I talked Caleb through this question, I pointed to Ephesians 5:22-33, and the 214 words Paul uses in it. Of those words, Paul spends 162 of them – 76 per cent – on a husband’s responsibilities to his wife. And his main message is that a husband needs to love his wife as Christ loves the church. A husband’s role is all about sacrificial leadership. But what does that really mean?

As the husband, what does it mean to be the “leader” of the family? Do your daughter and the young man both agree on the wife’s role within the potential marriage? What does biblical submission mean to them? In Ephesians 5:22-33, Paul instructs a wife to follow her husband’s lead in response to her commitment to the Lord. She is accepting her husband’s role as the leader of their family; it isn’t mindless obedience.

It all gets back to the concept of being a relational team. The husband may lead, but that never means that he unilaterally makes decisions for his family. This would be a gross misuse of biblical leadership. Yes, husbands and wives have different roles and different gifts. But they were created as equals – both made in the image of God and joint heirs in the gracious gift of life (1 Peter 3:7).

11. Have you had a range of experiences together?

Experience is an important key to navigating anything life throws at you. To truly see how a couple works together, they need to see each other handle a variety of experiences and challenges, which allows the couple to see each other as real individuals and to learn how they cope with stress and crises.

Has the man seen your daughter when she’s stressed? Has she seen him when he’s grieving or frustrated? Ask if they’ve had a wide range of relationship experiences – if they’ve seen each other around family and friends, during day-to-day errands or big nights out, at weddings and funerals and just sitting at a dinner table. Are they compatible in all those various situations?

I personally witnessed this compatibility in Caleb and Taylor’s relationship. When my dad was in hospice, Caleb drove Taylor from Arkansas to Texas so that she could say goodbye to her grandfather. I’ll never forget something that Caleb did for me during this painful time: I was sitting on my dad’s bed. Dad was struggling to breathe, and I knew that it wouldn’t be long until he would go home to be with his heavenly Father.

Taylor was sitting next to me and we were having a special moment alone with my father – or so I thought. As I wept, saying goodbye to my dad, I thought Taylor was gently rubbing my back. I suddenly noticed that both of Taylor’s hands were on her lap. My next thought was, Who’s rubbing my back? I turned my head and saw Caleb with his hands tenderly on my shoulders. I think that’s when I first thought, I love this kid. I’ll perform the wedding ceremony now if you want! (But I didn’t want to make it quite that easy for him.)

12. Are there any relational red flags?

Ask to hear their “love story” from his perspective. How did they meet and fall in love? This isn’t just an opportunity for your daughter’s possible fiancé to walk down memory lane. You’re looking for negative themes that might crop up. For instance: Have they broken up and gotten together multiple times? Has there been any abuse or violence? Do they live together? Are they simply sliding into marriage (because they feel like they should)? Is he trying to get away from his parents? Are they hiding a pregnancy? Does he think that marriage will fix the problems they’re already experiencing?

The list goes on. A proposal could hide any number of important issues. And while a red flag doesn’t necessarily mean a marriage is doomed before it even begins, it does mean that all parties should be extra cautious going forward. Encourage him to initiate individual or couples counselling before you give him your blessing.

Your blessing

At the end of the day, your daughter – not you – chooses her husband.

I’ve always told my daughters that I will walk them down the aisle and give them away to whomever they choose. They know that I’ll be honest about my concerns, and I hope they would accept my influence. But God has given them free will, and I would, and will, honour that.

But that doesn’t mean I’ll bless the union.

If I wouldn’t have been able to bless Caleb, I would have been honest with him. I would have explained the reasons and given him specifics. I would have encouraged him to get help to deal with any issues I noticed and told him that I’d re-evaluate my position if and when he took the necessary steps to correct those issues. I would hope that he would have believed that my daughter was worth fighting for and do whatever he could to win not just her love but mine as well. I would even have offered to mentor him if my daughter was open to that relationship.

But Caleb did earn my blessing. And while I had a good feeling about my son-in-law long before I asked him these 12 questions, his answers confirmed what I saw in his and Taylor’s relationship.

Remember, you’re not looking for perfection in the answers to these 12 questions. But you do want to see a young man headed in the right direction. And asking these questions should actually have a positive impact on your relationship with your future son-in-law. We can talk about anything, they tell him. This leads to open communication and discipleship.

I love how two years into their marriage, Caleb feels comfortable to call me about work issues or financial questions. I believe that our talk during the marriage seminar weekend paved the way for our relationship today.

Once your daughter, her mother and his parents have given their blessing, and you’ve worked through these 12 questions, if you have peace about giving your blessing, I encourage you to verbalize your affirmation or write your prospective son-in-law a letter. Here’s part of what I wrote to Caleb:

In you, I see a man who loves the Lord with all his heart – a man who will love God more than he will ever love my daughter.

In you, I see a man who cherishes my daughter and recognizes her tremendous value. You see in her what I’ve treasured since the day she was placed into my arms.

In you, I see a man who will love my daughter unconditionally for a lifetime.

In you, I’ve experienced a fun sense of humour. I know that my daughter’s life will be filled with laughter and joy.

I’ve been thinking about you for 22 years. And I can truly say that you’ve exceeded every one of my expectations. Thank you for preparing yourself for the role of a lifetime – a husband.

Today, I give you my blessing to ask Taylor for her hand in marriage. It’s an honour and privilege to welcome you into our family as my son.

I still mean those words today. Caleb and Taylor’s relationship is strong. My relationship with both of them is strong, too. And whenever they celebrate an anniversary, I get them something with a pearl in it.

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12 Questions Every Father Should Ask His Future Son-in-Law

1. Are you united spiritually?
2. Are you ready to make a lifelong commitment?
3. What do you see in my daughter that makes you want to marry her?
4. Do you agree on core values and big dreams?
5. How do you plan to financially support my daughter?
6. Would you marry you?
7. What do you like about your relationship with my daughter?
8. Do you have meaningful communication?
9. How do you manage conflict?
10. Do you and my daughter agree on biblical roles and responsibilities?
11. Have you had a range of experiences together?
12. Are there any relational red flags?

Dr. Greg Smalley is vice president of Marriage and Family Formation at Focus on the Family and the author or co-author of several books, including Crazy Little Thing Called Marriage.