5 Questions to Ask to Make Conversation Last Longer, Go Deeper


When we have people over, my favorite part of our time together comes after dinner has been eaten, when the kids are playing independently, and we have all gotten comfortable on the couches. Wives kick off their shoes, husbands put away their phones, and everyone has a full glass of lemonade. That’s when the real stories come out. That’s when connections are made. As C. S. Lewis wrote,

“Friendship is born at that moment when one person says to another: ‘What! You too? I thought that no one but myself . . .’”

We have to allow enough time for those connections to happen though.

After our guests leave, Lee and I often talk about how we think the evening went. We noticed a pattern forming. We were most satisfied with our time with friends when the conversation lasted longer and went deeper. So, I came up with five open-ended questions we ask our guests as they are telling stories to help them know we really are interested.


  1. When did you realize … (you wanted to marry her? you had found the right job? it was time to move on?)
  2. How did you feel when … (you went through that trial together? you heard he had gotten into that school? you realized everyone was safe?)
  3. What did you learn from … (the job you just left? the book you read? having dinner at your grandma’s every Sunday night?)
  4. Who helped you … (feel comfortable at that church? realize your gift for teaching? learn how to make that dessert?)
  5. Why did you … (make that change? want to go back there? decide they would be your favorite team?)

We don’t use these like a questionnaire; we use them to continue the conversation that’s already happening. I like to hear what was happening in their heads when they are describing situations they went through. I don’t just want the facts, but the feelings.

People want to be heard and understood. They want to know their friends (or, often in our case, their friends who are also their pastor & pastor’s wife) value what they’ve been through and all the stories that make them who they are now.

What’s your favorite part of spending time with friends? How do you make conversations last longer and go deeper?

8 thoughts on “5 Questions to Ask to Make Conversation Last Longer, Go Deeper

  1. I LOVE these questions. Thanks for reminding me of simple ways to encourage those at my table to go a little deeper in conversation. Grateful!

  2. You are so right…friendship starts when we feel connection with another person.

    I’ve always struggled with conversation topics, and a while ago, much like you, made a list of some topics that I thought might be helpful in the future if I ever got to talking and couldn’t think of a question to prompt a great conversation.

    If you ever have a moment check out http://deepconversationtopics.com/ and let me know what you think. It’s come in handy for me on more than one occasion.

    “People want to be heard and understood” – I couldn’t have said it better myself.

  3. I struggle with this and these sound very practical. shallow relationships are just exhausting, depth is fulfilling.

  4. These are really helpful as our church is changing its vision for small group ministry, and we’ll *hopefully* be spending more
    time in deep conversation with our brothers and sisters in Christ and our neighbors. Thanks!

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