10 Breakthrough Conversations for Your Friendship

10 Breakthrough Conversations for Your Friendship

We’ve all seen them. We’ve maybe even looked at them with a bit of awe and a hint of longing. They don’t mean to evoke such bittersweet feelings in us, but their presence can sometimes make us wish we had what they seem to so easily share.

They are at the gym, in the office, at the bookstore, at church, and in your favorite restaurant. There is always that little group of them cozily burrowed into the booth at the café with their heads drawn toward one another, pouring their hearts out faster than the server can pour coffee into their cups. There’s also the team of them gathered purposefully around the picnic table at the park who are communing over the deepest details of motherhood, marriage, and family while their children chase one another around the playground.

Friends. And, not just the kind of casual friends who stick to superficial, everyday chatter. These kinds of friends are real friends. They are deeply invested in one another, know one another well, and seem to be really connected on a different level.

Photo Credti: Getty Images/Antonio Guillem

  • Deep Connection Takes Deep Determination

    Deep Connection Takes Deep Determination

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     We were created for that kind of rich, deep, and authentic community. God intends for us to pray together, to encourage one another, to partner in accountability, and to do life together.

    It is evident throughout the Bible when you look at people like Ruth and Naomi, Moses and Aaron, Elijah and Elisha, Paul and Timothy, and Jonathan and David. You even see it as you consider God and the community He has within himself as the Trinity.

    While there is nothing quite as beautiful as these deep friendships, it can often be challenging to move from casual acquaintance to the rich and authentic relationship that we really desire. The best way to build that kind of connection is by engaging in heart-felt, vulnerable, intimate, and honest conversation.

    If you’re looking to take your friendships to the next level, be willing to ask questions that engage the heart of your friend and help you get to know them better. Then be willing to share your heart, as well.

    10 Breakthrough Conversations for Your Friendship: Questions to Build Connection

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  • #1: What is your story?

    #1: What is your story?

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    Our past doesn’t define us, but it does shape us. Ask your friend if they’d be willing to share their story with you. Remind them that you stand by the truth in Romans 8:1 that says there is no condemnation in Christ Jesus. Be willing to go first, if necessary, and share yours.

    Photo Credit: Unsplash/Priscilla Du Preez

  • #2: What are you most passionate about right now and why?

    #2: What are you most passionate about right now and why?

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    We all have something that sets our souls on fire and makes us want to get out of bed in the morning. Invite your friend to tell you what that is for them and then invite them into your life by sharing your passion.

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  • #3: What are your goals in this season?

    #3: What are your goals in this season?

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    Knowing what is important to your friend in this season of life will help you to journey with them and to support them in their goals. It will also help them do the same for you.

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  • #4: What are your dreams and aspirations for the future?

    #4: What are your dreams and aspirations for the future?

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    Sharing our hopes with one another is a way to invest in one another and in the relationship. It shows that we are willing to journey with one another and care about being a friend to one another now and in the future.

    Photo Credit: Pexels/Luis Quintero

  • #5: What are your fears?

    #5: What are your fears?

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    We all want someone safe that we can share our hearts with. Opening up about the things that we fear takes vulnerability and bravery. Lead by example, if it makes your friend feel more comfortable sharing their fears with you.

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  • #6: What challenges are you currently facing?

    #6: What challenges are you currently facing?

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    Life is full of challenging situations. With a friend by our side, the challenges seem less daunting. Invite your friend to share the hard parts of life with you and do the same with them.

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  • #7: How has God been revealing himself to you?

    #7: How has God been revealing himself to you?

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    Conversations like this one allow you to share your faith walk together, open the door to connecting spiritually, and help you to see how your friend experiences God.

    Photo Credit: Getty Images/Alessandro Biascioli

  • #8: How can I pray for you?

    #8: How can I pray for you?

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    Knowing how to pray for your friend and telling your friend how they can specifically pray for you will create a strong spiritual bond and will draw your hearts closer to one another.

    Photo Credit: Getty Images/Wavebreakmedia

  • #9: What do you value in a friend?

    #9: What do you value in a friend?

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    Being aware of what you each value in a friend will help you to know the kind of characteristics that you both look for in a friend and to be intentional about being that kind of a friend to one another.

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  • #10: How can I be a good friend to you in this season?

    #10: How can I be a good friend to you in this season?

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    In different seasons of life, we need different things. Ask your friend how you can be a good friend to them right now, and let them know how they can be a good friend to you.

    We don’t have to long for the kinds of friendships that we see others having. We were created for that kind of beautiful, intimate community and we can move our relationships from superficial to deep and rich.

    Inviting our friends to share their authentic hearts with us and then being willing to share ours with them is one of the best ways to build connection. These kinds of breakthrough conversations draw us into the richer, deeper, and more meaningful friendships that we all long for.


    Bobbie Schaeperkoetter is a writer, speaker, community builder, and an encourager of women at http://www.bobbieschae.com. She’s doing her best to honor God in the craziness of everyday life and she’d love to walk alongside you as you do the same. You can connect with Bobbie through her website or on Instagram at http://www.instagram.com/bobbieschae or on Facebook at http://www.facebook.com/bobbieschae

    Photo Credit: Unsplash/Kevin Laminto