Last week, we talked about having simple conversation starters—or “handshakes”—ready in your back pocket to break the ice. This week, we’re focusing on the next step: “bridge” questions—the kind that help move a conversation from surface-level to something deeper and more meaningful.

I’ve found that bridge questions tend to fall into three helpful categories:

1) Personal Bridges – Invite someone to share more of their story.

“What’s the best thing about you?”

“What do you believe is your purpose in life?”

“What are you living for right now? How’s that going?”

2) Spiritual Bridges – Create space to talk about faith and the gospel.

“Can I ask what your church or religion teaches about how someone gets to heaven?”

“Is there anything I could pray about for you?”

“Has anyone ever shared with you the main message of the Bible?”

3) Worldview Bridges – Explore beliefs and perspectives on life’s bigger questions.

“Do you see yourself as a seeker of truth? What has that looked like in your life?”

“In all of history, who do you think has had the greatest impact on the world? Why?”

“Where do you think pain and suffering come from?”

“What gives you hope?”

These kinds of questions can help turn a casual encounter into a meaningful conversation that might even open the door for gospel conversations. But sometimes it’s hard to know how to get from small talk to a deeper place—that’s where transition questions come in.

Here are two transition questions I often use:

“Can I ask you a question I enjoy asking people?”

“My church has challenged us this year to really notice people and listen to their stories. Would you mind if I asked you a question or two to learn a bit of your story?”

If none of these questions feel natural to you, that’s okay! The point is to have something ready that fits your personality and helps you overcome the awkwardness of not knowing what to say next.

If you come up with a handshake, bridge, or transition question that works well for you, I’d love to hear it! It might just help others in our church take a step toward Knowing Their Story too.

May God bless you this week with conversations that go deeper, as you listen well and reflect His love.