Help! I Don’t Know How to Initiate Meaningful Conversations

This article is part of the Help! series.

Steering Small Talk

Imagine you’re sitting in the middle seat of row 18 on a full airplane. As the plane lifts off the ground, the twenty-something young man next to the window pulls down the shade, slips on his earphones, and slouches to his left for a good, long nap. Sitting on your right is a woman we’ll call Chatty Cherry. Middle-aged and dressed in business casual, she’s pleasant enough. But a few minutes after her courteous introduction, you realize she doesn’t plan to stop talking until the plane lands.

As your conversation with Cherry moves from where you’re both traveling and why, to where you work and for how long, to basic details about your families, this thought comes to mind: God has me sitting here for a reason. How am I going to move into a meaningful, spiritual conversation with this woman? I don’t want to waste this opportunity, but I don’t know what to say.

When Words Matter Most

Cheryl Marshall, Caroline Newheiser

In When Words Matter Most, Cheryl Marshall and Caroline Newheiser encourage and guide women to discover that they can make a difference in the lives of those they love who are worried, weary, wayward, and weeping.

We’ve all been there. We’ve had small talk with a stranger on a plane, in a doctor’s waiting room, or at a park playground. We’ve talked about common interests with acquaintances at church, at work, and in the neighborhood. We’ve even shared the ins and outs of our daily lives—the mundane tasks and the significant events—with family and long-time friends. And in all these relationships, even with those dearest to us, we often find ourselves wading only in the shallow end of the conversational pool.

Whether speaking with strangers, acquaintances, or those we dearly love, we sometimes realize that we and they would greatly benefit if we would only dive deeper into our conversations and talk about God—who he is, what he’s like, what he’s done, and how those biblical truths intersect with our lives.

But how can we initiate those meaningful conversations?

3 Reasons for Deeper Conversations

Before we answer that question, let’s consider three reasons that deeper, God-centered conversations are needed in our lives. The first reason is that as image-bearers of God, we desire to know and to be known. God is perfectly known within the Trinity, has infinite knowledge of all his creation, and has revealed himself to us through his word and his Son. He is the God who knows and is known. He created us to interact with others—to know, understand, and appreciate our fellow human beings—and this reflects the image of God: “God designed us to be relational—it is our very nature, and it is one way in which we reflect the image of God. And only when we live in community do we fully reflect the likeness of God. Relationships are not optional!”1

Second, meaningful conversations are needed because without them we can’t share the gospel. Building a bridge into an unbeliever’s life through acts of service and casual conversations has its place, but something eventually must cross that bridge: the spoken gospel of Christ. Paul wrote to the Corinthians, “For I delivered to you as of first importance what I also received: that Christ died for our sins in accordance with the Scriptures, that he was buried, that he was raised on the third day in accordance with the Scriptures” (1 Cor. 15:3–4). We must also deliver—with our words—the gospel to the unbeliever. We must purposefully speak of Christ. Before Jesus ascended into heaven, he said to his disciples and to us by extension, “Go therefore and make disciples of all nations . . . teaching them . . .” (Matt. 28:19). Christ’s call to speak to the lost drives us to deeper conversations.

Third, meaningful conversations are necessary because they are a primary way for us to love fellow believers. Christ expressed the priority of love among his people when he said, “A new commandment I give to you, that you love one another: just as I loved you, you also are to love one another” (John 13:34). We fulfill Christ’s law of love when we bear one another’s burdens, but that requires proactive conversations. Paul referenced these types of conversations when he wrote to “admonish the idle, encourage the fainthearted, help the weak” (1 Thess. 5:14). Love within the family of God—for the sake of our mutual spiritual good—moves us beyond surface conversations and into deeper matters.

Pray, Prepare, Practice

So how can you initiate meaningful, spiritual conversations with both strangers and acquaintances, friends and family, believers and unbelievers? Here’s some practical advice we’ve gleaned after years of riding on airplanes, taking our kids to parks, visiting in church foyers, and talking over shared meals:

1. Pray.

First, pray for God’s help. Apart from the work of the Lord in your life, you won’t be able to bear this beautiful fruit. When Moses complained about his inadequacy to speak, the Lord responded with a powerful promise to come to his aid: “Who has made man’s mouth? . . . Now therefore go, and I will be with your mouth and teach you what you shall speak” (Exodus 4:11). God promises us his wisdom today: “If any of you lacks wisdom, let him ask God . . . and it will be given him” (James 1:5). We can’t count the number of times we’ve prayed for wisdom in conversations and God has granted it! Pray for opportunities and Spirit-empowered skill to speak his truth in love.

2. Prepare.

To engage in meaningful conversations, your love for others may need to be strengthened. If your mind is full of concerns and your calendar full of responsibilities, it’s easy to become self-focused at the expense of caring about the spiritual needs of others. You may need a change of heart, conforming your thoughts to Christ: “Let each of you look not only to his own interests, but also to the interests of others. Have this mind among yourselves, which is yours in Christ Jesus” (Phil. 2:4–5). To prepare yourself to initiate spiritual conversations, evaluate your attitude toward others. Is it Christlike? If not, confess and repent of indifference and selfishness, and follow Christ’s example of sacrificial love from the heart.

With a prepared heart, now give thought to preparing questions to ask others when you want to direct conversation toward more meaningful matters. The questions can be very simple: Where do you attend church? What does your church teach about . . . ? Have you read a good book or seen a good movie lately? What do you think its message was? What has God been teaching you lately? How can I pray for you? These are just samples, but you can tailor your list of pre-planned questions to the people and experiences you encounter in your daily experience. The key is to proactively prepare both your heart and your questions.

Pray for opportunities and Spirit-empowered skill to speak his truth in love.

3. Practice.

You may think you lack the communication skills or personality to move a conversation to a deeper level. Or, you may believe you have the ability but you’re afraid that you’ll come across to others as too bold or invasive. Whatever your personal concerns may be about initiating meaningful conversations, those concerns can be put to rest with practice. In your daily conversations, begin practicing these suggestions and you’ll see improvement with time:

  • Ask open-ended questions. Avoid questions that can be answered with only “yes” or “no.” Pose questions that can lead to further discussion.
  • Listen intently to gain understanding and ask follow-up questions. For example, Why is that? Could you explain what you mean? That’s interesting; can you tell me more about . . . ? Don’t rush the other person’s answer or be quick to jump in with your own experience or comment.
  • When appropriate, share your own thoughts and experiences. Mention what you read in your devotions and explain why it gripped you. Ask your friend to pray for you. Reveal how the Lord has answered your prayers or convicted you of some weakness.
  • Speak words of hope. Give encouragement beyond simply complimenting someone’s shoes or hair. Share Bible verses and scriptural truths that have upheld you in your own time of need.
  • Carefully watch those who are skilled at caring for others spiritually. What do they say and how do they say it? Observe their intentionality, the questions they ask, the ways they listen and respond—and how others feel loved. Follow their good example.

“The purpose in a man’s heart is like deep water, but a man of understanding will draw it out” (Prov. 20:5). Jesus was the perfect man of understanding. Once after a day’s journey, he wearily sat beside a well in Samaria and spoke to a woman. Their conversation began with his simple request for a drink of water. Soon they were discussing true worship. And by the end of the conversation, Jesus had dipped into the well of her soul and she never thirsted again.

Seek to speak like Christ. Take the steps to initiate meaningful, eternally profitable conversations. Pray, prepare, practice—and then dive into the deep.


  1. Timothy S. Lane and Paul David Tripp, Change and Your Relationships: A Mess Worth Making (Greensboro, NC: New Growth Press, 2009), 11.

Cheryl Marshall and Caroline Newheiser are the authors of When Words Matter Most: Speaking Truth with Grace to Those You Love.

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