Have you ever ended a conversation with someone and walked away feeling empty? You both had showed up and talked, yet afterward you somehow felt just as lonely as if you’d never gotten together at all. It happens to all of us—conversing without connecting. There are times and places for that: transactions at the grocery store or hurried small talk in the breakroom at work, for example. But when we can’t satisfy the deeper sense of connection we crave, or when we can’t be fully present for a friend who desperately needs our companionship, that’s when it’s time to do something different.
Illustrations by Steve Scott
You may think you already know how to have a meaningful conversation—but research suggests otherwise. Most people, in this age of one-sided dialogues via message boards, social posts, and other digital media, struggle to converse in a healthy way. For many of us, skills are rusty, and this comes in an age when loneliness is at an all-time high. People need genuine connection, and as believers called to bear each other’s burdens, we should be willing and able to provide it.
In this guide, we hope to help you connect with whoever is in your presence—family, longtime friends, coworkers, neighbors, strangers, or even enemies. The goal is not to turn every conversation into an agenda or therapy session but to create a space where both parties can be seen and cared for. We want to offer tools that help you know what to do when someone you care for seems burdened or when there’s something a loved one is afraid to say. No one can force a meaningful conversation to occur, but creating the right environment makes it more likely.
Conversational Connection: The Four Mindsets
How are warm, meaningful connections with others formed? We start with the Four Mindsets of a Loving Conversation*:
Be curious.
Believe the best.
Express concern.
Share your life.
When all four approaches work together in a conversation, people are able to form what social scientists call “a warm connection.” However, most of us have a hard time with at least one. We might hesitate when it comes to being curious about others and asking about their life, because we’ve been taught it’s rude. Maybe we feel suspicious of neighbors who vote for a different political candidate or have social views that don’t match ours; then, assuming they can’t teach us anything, we fail to believe the best. Or perhaps expressing concern about others’ problems makes it feel wrong to share anything about our own.
But if we look to Jesus, we see these mindsets are key to meaningful connection. He was a master of curiosity, and the New Testament accounts show Him asking question after question. But why, if He already knew how people would answer, did He still ask? Because being curious facilitates open and genuine conversation.
Jesus dined and fraternized with sinners because, despite their failings, He valued them as people and viewed them with compassion, as people worth saving. He also shared His life with the disciples—eating, resting, and traveling together—and they witnessed some of His darkest moments. Perhaps more importantly, Jesus shared His own life with us. It's one of the ways He expressed concern for every person on earth. And He calls us to do the same by loving our neighbors—something Scripture says fulfills the entire law (Matt. 22:36-40; Gal. 5:14).
We don’t have to be perfect like Jesus to incorporate these four mindsets into our relationships. In fact, you’ve likely experienced them while talking with a friend. Take a few moments to ask yourself these questions:
When was the last time you had a meaningful conversation with someone?
How did you feel during the interaction? And after?
What stands out to you about the exchange?
Ask the First Question
Sometimes the hardest part of a conversation is getting started. We all know to ask, “How are you?” but that inquiry doesn’t always propel dialogue in a meaningful direction, as it’s vague and open-ended. Instead, when we want to connect with someone, we could say, “Hello! It’s so good to see you!” and then ask a question from one of the following areas of life*:
Social (people and pets): “Who have you been spending time with lately? How is _________ doing?”
Emotional (feelings): “How are you feeling about that [sports team, event, or story in the news]?”
Physical (spaces, bodies, the five senses): “Are you working on any home renovation projects? Tried any new restaurants? How are you sleeping?”
Cognitive (thoughts): “What have you been focused on lately?”
Volitional (decisions): “How did you make up your mind to___________ ?”
Spiritual (religious life and ideas): “Are you celebrating any upcoming religious holidays?”
Make Meaning
As your conversation partner answers questions, you can then move into meaningful connections by expressing concern and sharing your life.
Ask About Stress. One of the best ways to begin relating on a deeper level, even if you start with a question about sports or the weather, is to ask something that expresses concern. A great opening question is, “What are your major stressors this week?” or some variation about worries or thoughts keeping the person up at night. When we ask about these things, we’re inviting people to unburden themselves. Then we practice carrying someone else’s load by offering encouragement, helping out where we’re able, and pointing our conversation partner to God’s presence and care.
Listen for Core Values. Another way to make a conversation meaningful involves using active listening skills. When someone answers our conversation questions, we can listen for core values. Telling people what we’ve noticed about their dearly held priorities communicates understanding and love in a conversation more quickly than almost anything else.
For example, if we ask about major stressors and hear how upset the person is about a change of plans, delayed flight, or uncertain meeting date, we learn he or she prizes an orderly, predictable schedule. You might say, “As you’re talking, I can tell your schedule is really important to you, and it’s a struggle when things become unpredictable.” At first, identifying core values can be difficult, and repeating them back to others might feel awkward. But with practice, this will come more easily. And the more you see a positive response, the more you’ll be encouraged to keep trying.
Consider this list of answers to the question, “What happened over the weekend?” If people talk about the following categories, you can guess what they might value:
Whom they spent time with (Relationships)
What projects they finished (Productivity)
What they read or discovered (Learning)
What new thing they experienced (Adventure)
Whom they helped (Generosity and Service)
What they did on their own (Independence)
What they overcame (Courage and Resilience)
What they wore or how they looked (Aesthetics and Design)
What they did at the gym or in the kitchen (Health and Well-being)
Reflecting back core values helps a person to feel seen, heard, and most importantly, safe to share more—perhaps what’s really on his or her heart.
Keep track. Have you ever shared something personal or important, and then the other person completely forgot? That kind of experience can make you feel insignificant and hesitant to be transparent in the future. Since we want our conversation partner to feel safe and comfortable, let’s look at a couple of ways to maintain trust and connection, even after the conversation ends.
Use a journal (or a note app on your phone) to jot down keywords from your conversation. This doesn’t have to be neat or perfectly organized—just clear enough to jog your memory before your next conversation.
Did the person mention an important date coming up, like a doctor’s appointment or interview? Put this event or occasion in your calendar so you’ll remember to check in about it afterwards.
Share your life. Another way to make a conversation more meaningful is by talking about what’s going on in your own life. When the timing is right, try sharing what’s on your mind. For example, you might tell the person what you’ve been struggling with lately or what you’re worried about this week. When we share something difficult, it helps create a safe environment, where others feel comfortable being themselves and speaking honestly. Opening up communicates that we trust our friends—and that they can trust us, too.
Talk to God. Perhaps the most important thing we can do for our relationships is ask God to help us become good listeners. If we’re honest, we often end up half hearing the other person while we think of what to say next or anticipate sharing a story. But truly hearing someone requires humility. It’s a matter of the heart, and something for which we need God’s help.
Consider using this prayer before you meet up with a friend: Lord, I want to truly hear others. Help me become a good listener and humble friend. In Jesus’ name, amen.
Not every conversation has to be life-changing, but when we do need to connect with someone, it’s important to know how. So the next time a conversation stalls, a friend seems deeply burdened, or you’re feeling especially lonely, try out a suggestion from this guide and realize that you are equipped to move forward and connect. Conversation is one way we “bear one another’s burdens, and thereby fulfill the law of Christ” (Gal. 6:2). It’s also one way—perhaps the best way—we become fully human. God knew it wasn’t good for Adam to be alone, and that is true for every person made in the image of God (Genesis 2:18)—in other words, all mankind. We’re built for community and designed for togetherness, whatever form that may assume. And through the delightful give-and-take of conversation, we help to build much-needed bonds.
*This is a concept from the author’s most recent book, The Six Conversations: Pathways to Connecting in an Age of Isolation and Incivility.
