How to Have Deeper Conversations Today

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We all engage in conversations on various levels. We know the light and airy conversations of the weather, the funny antics our children did last week, the novel we just started reading, and brainstorming new meals to feed our families.

In some relationships, we easily sink into deeper conversations. I think of my sister-in-law, my friend Michelle, and a pastor’s wife I know. Within a few visits together, we swim through the surface-level conversations of dirty diapers and streaky floors and, without noticing, we tread into the deeper and sometimes murkier places of life. We move from giggling about the silly things our husbands did on our first dates to the arguments from the previous night. We may start by rolling our eyes at the unreal number of dishes we wash each day to sharing the fearful thoughts for our children that come to mind as we washed those dishes yesterday.

There are some women I sit down with whose kind eyes and gentle questions seem to uncork my heart and lead me to pour out my honest questions, past hardships, and current struggles with sin. Others, though I still enjoy their presence, stay within unspoken boundary lines of wall colors, water bottle choices, and tips on how to hide vegetables in our children’s food.

What makes these conversations so different? How can we dive beyond the surface of our relationships and encourage deeper conversations?

They were willing to initiate.

Few people want to be the first one to share. I like to wait and listen to how others respond and then gauge how I should frame my response. I often do the same in conversations. If they discuss the recent snowfall, I’ll reply with how my son and I share a distaste for the cold weather. But if they share about how postpartum depression nearly debilitates them in the winter months, I may feel the nudge to tell them how my depression is likewise worse when snowstorms and snowbanks keep me trapped inside.

Those who engage us in deeper conversations are willing to go first and share their pain. They don’t over-share for sake of gasps—they want to go beyond the shallow end. They want to know us. They want friendship, a companion to shoulder suffering with. They want to know they aren’t alone. And they in turn are willing to take the risk of vulnerability so we won’t feel alone either.

Being proactive: What are some ways we can steward our stories well? Who is going through a similar experience as you that you could share your story with to encourage them? 

They asked better questions.

Those who have engaged in deeper conversations with me didn’t allow the hard question to stew in the silence. They asked them with tender, focused eyes, slightly perched forward and ready to listen. 

“How are you doing, Lara? How is your grief since the miscarriage?”

“How has your postpartum depression been since we last talked?” 

“What does a hard day look like for you? What does your grief feel like?”

“How can I pray for you this week?” 

These women weren’t satisfied with my usual response of, “I’m not too bad!” They asked pointed questions to reach my heart. They weren’t prying to ease a nosy itch. Rather, they wanted to make sure that beyond my smiles I was well—and if not, find a way to support me.

Being proactive: How can we engage one another with better questions? How can we press beyond the usual, “I’m good, you?” questions and answers?

They welcomed the hard conversations and listened.

Sometimes when we share with others, we’re shut down. The subject abruptly changes. Perhaps they make light of our hard topics to avoid the awkwardness of it. The shutters of their heart slam together in our faces and fasten tight.

Meanwhile, others welcome these difficult conversations. While I’ve felt the abrupt ending of my attempt to start conversations on difficult subjects, I’ve likewise felt the warm, opening arms towards me and my pain. I’ll never forget these words written on a card after our miscarriages: “I’m so sorry for your loss, Lara. I too know this private pain. If you ever want to talk, I would love to be a listening ear.”

These people often don’t come with promises of fixing our pain. They probably can’t. Yet, they welcome the conversation with words of acknowledgement and questions to prompt our own thoughts. They aren’t seeking to serve their own curiosity. They are willing to back away from raw wounds if we are hesitant to share, while assuring us they will be a listening ear if we ever want it. They don’t flinch at the painful conversations, nor do they express an air of awkwardness around them. Instead, they grieve with us and listen to us.

Being proactive: How can we become better listeners? How can we push past the awkwardness of another’s tears? How can we ignore the pressing desire to just fix it and instead simply listen?

We need to strive for a helpful balance when it comes to having deeper conversations.

The surface-level conversations about fashion, housekeeping, weather, diapers, and the like are still good. They encourage friendship as we share interests, experiences, and laugh together. We shouldn’t exhaust ourselves by feeling like we must always produce deep and meaty conversations. Sometimes we can simply laugh about the silly stories the children in our Sunday school class told us. 

It becomes unbalanced when we always remain in the shallow end. It’s important that we go beyond those conversations every now and again to truly seek to know the person across the table—and to open ourselves up for them to know our hearts. Friendship isn’t formed only on these surface-level conversations but instead on the weightier ones of life, hardship, anger, battles, confessions, and questions. We’ll never be able to minister to one another in our fights with sin and suffering if we never answer truthfully, “How are you today?” It’s impossible to bear one another’s burdens without first reaching the heart and earning trust.

Not every relationship will be worthy of deeper conversations. Some people have proven themselves to be unreliable and untrustworthy in providing safe spaces to share our hearts. Others might still be in the growing process, on their way to becoming a person who can engage in deeper conversations. If we persevere in both being better listeners and better sharers, we are likely to find relationships where deeper conversations can flourish. 

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Lara d'Entremont

Lara d’Entremont is first a wife and a mom to three little wildlings. While the wildlings snore, she designs websites and edits for other writers, but her first love is writing—whether it be personal essays, creative nonfiction, or fantasy novels. She desires to weave the stories between faith and fiction, theology and praxis, for women who feel as if these two pieces of them are always at odds. You are welcome to visit her online home at laradentremont.com.

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