How to Deepen Your Conversations

If you’re like me, you really don’t like small talk. You want to get below the surface, to learn about a person’s heart. Their dreams, fears, favorite animal, memories, music taste, insecurities, childhood, and what keeps them up at night. Not the spiel we would all benefit from wearing a nametag for (i.e. name, school, job, etc).

“A deeper conversation is all I want from you. I want the words you’re afraid to say, the lonely ones you keep hidden in between the folds of your heart.”


Now, there is a need for some small talk. At the beginning of one friendship, I was delighted to find my new conversation partner skipping all the get-to-know-you questions and going straight to the heart of an issue.

Abundant miscommunication later, I realized we wouldn’t have tripped up so much during those first few conversations if we knew the background polite small talk establishes. To understand one’s perspective, you must understand where they’re coming from.

Once we backed up and learned about the other’s education, work, and family, we were then able to return to our pursuit of intellectual conversation with much greater success.

“I have the deepest affection for intellectual conversation. The ability to just sit and talk about love, about life, about anything, about everything. To sit under the moon with all the time in the world, the full-speed train that is our lives slowing to a crawl. Bound by no obligations, barred by no human limitations. To speak without regret or fear of consequence. To talk for hours and about what’s really important.”


This love of mine vexed my soul in college. I was trudging through the darkest two years I have yet to face, yet there was no rock in the flood of small talk rushing through academic circles on which I could have raw conversations about what was crushing my heart.

People would casually ask how I was doing, but what could I say? “Good” wasn’t accurate, but the emotions were too much to unpack and the story was too complicated. So I said, “God is good.” Regardless of everything I didn’t know how to say, I could hold on to that truth.

Perhaps that is the best that can be done for a three-second exchange in the hallway during a hard season, but what about elsewhere? When you have the time, setting, and mental capacity to dive deep, how do you help another make that leap into soul-revitalizing conversation?

#1 — Have deep conversations with God

Our relationship with God ripples out into our relationships with others. If want to have deep conversations with others, we need to be having real talks with the friend we have in Jesus. It also works the other way.

If we aren’t talking to others about what’s on our hearts or asking for prayer, we’re probably not doing that with God. What happens in our relationships with people reflects what our relationship with God is like.

So pray, “God, help me talk to You.” Confess your sin to Him, pour your heart out. Speak about the things that seem impossible and end with thanks. Always come back around to who He is. Tell Him you love Him every day. Talk to Him like He is your best friend (see point two here).

#2 — Don’t settle

You know the greeting: “How are you?” “Doing good! How are you?” “Good.” Five seconds or less while passing someone in a hall or on a sidewalk. We don’t actually want to know how the other is doing, we’re just being polite. Don’t settle for that.

If such an exchange occurs with another, don’t let the interaction end with their “good.” Ask them, “What makes it good?” By doing so, you’re opening a door to talk about some of the joy that is foreign to our dark and broken world.

Then listen. Love prefers the details. Do you know enough to pray for them, to feel their hurt? Come up under the burden they are bearing and take mental notes of things to follow up on the next time you see them. Love remembers.

#3 — Share your story

If you want people to share their heart, you also have to share yours. Your joys and burdens. Relationships are two way streets. It shouldn’t be one person doing all the talking and the other doing all the listening. They should both be pouring in and receving from the other.

The depth of what you share will depend on who you’re with, as only your inner circle and a counselor/mentor should be presented with advice-seeking situations. But there are multiple levels of soul-sharing above the darkness you are trying to grapple with.

Tell anyone about what God is showing you and listen to how God has made Himself real to them. That’s true koinonia, sharing about your deepest most intimate relationship with another. Run after Him and invite others along as you pursue the Source that makes healthy human interaction possible.

Of course, these points will be dependent on who you’re talking with. Some people are so accustomed to surface-level conversations they don’t know how to follow your lead. They may even be scared. So be considerate and discerning.

Encourage and invite others to be open and honest with you, but recognize when they are unprepared to move further. Sometimes it takes a few exchanges to build a relational bridge strong enough to carry truth over. Sometimes you’re not the kind of person they’d be comfortable talking to.

Regardless, don’t stop pursuing the heart of others. Love relentlessly. With some, this may be through soul-probing conversation. With others, it may be an encouraging smile. Apply your knowledge and love as fitting to each individual.

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