Use the material below to lead a small group in a discussion pertaining to the content of Pastor Darren’s message, “ONE MOMENT WITH JESUS: the woman at the well.”

Small Group Guide

“One Moment With Jesus: The Woman at the Well”

Based on John 4:1-7 and the Full Passage

BEFORE YOU BEGIN

Open your time together in prayer. Ask God to soften hearts, open minds, and allow each person in the room to hear what He specifically has for them in this passage. Remind the group that this is a safe space — what is shared here, stays here.

CONTEXT OVERVIEW

In John 4, Jesus makes a deliberate journey through Samaria — a route most Jews avoided entirely due to deep cultural and theological tensions. There, at an ancient well, He meets a Samaritan woman who has lived a life marked by rejection, shame, and repeated heartbreak. Rather than avoiding her, Jesus initiates a conversation that changes her life forever. What begins as a request for water becomes one of the most profound personal encounters recorded in all of Scripture.

KEY TAKEAWAYS

  • Jesus moves with divine purpose. The Greek word “dei” — translated “had to” in John 4:4 — indicates divine necessity. Jesus was not simply taking a shortcut. He was following the Spirit’s leading to a specific appointment with a specific person.
  • Jesus sees past the surface. While the woman came to draw physical water, Jesus addressed the deeper spiritual and emotional emptiness she had been trying to fill for years through relationships, routine, and survival.
  • Shame does not disqualify you. This woman was among the most marginalized people in her culture — a Samaritan, a woman, and someone with a painful relational history. Jesus chose her anyway, spoke to her directly, and revealed His identity to her before almost anyone else.
  • Worldly solutions are temporary. Everything this world offers to fill our internal voids — relationships, possessions, substances, status — provides only momentary relief. Jesus offers living water: a permanent, soul-deep solution.
  • An encounter with Jesus leads to testimony. The woman did not leave the well the same way she arrived. She left her water jar behind — a powerful symbol of her old emptiness — and ran back to her community to tell everyone what she had experienced.

DISCUSSION QUESTIONS

Opening Questions

Use these to warm up the group and ease into the conversation.

  1. Have you ever taken a route somewhere — literally or figuratively in life — that felt uncomfortable or unusual, but turned out to be exactly where you needed to be? Share that experience with the group.
  2. The sermon points out that the woman likely came to the well at noon to avoid people. Have you ever rearranged your life or your schedule to avoid shame or judgment? What did that feel like?

Digging Into the Text

  1. The pastor highlighted the Greek word “dei” — meaning divine necessity — used in John 4:4 when it says Jesus “had to” go through Samaria. What does it mean to you personally that God sometimes leads us through difficult or uncomfortable places with a specific purpose in mind? Can you think of a time in your own life when a hard season turned out to have a divine purpose behind it?
  2. Jesus opens the conversation by asking the woman for something — a drink of water. But the pastor notes this was merely the starting point, because Jesus already knew He was there to give, not to receive. What does this tell us about the way Jesus initiates relationship with us?
  3. The woman had been through five marriages and was now living with a man outside of marriage. The pastor emphasizes that in her cultural context, she likely had little power to prevent these rejections. How does understanding her circumstances change the way you read this story? How does it change the way you think about people in your own life whose histories are complicated?
  4. Jesus does not ignore the woman’s past, but He also does not condemn her for it. He names it, acknowledges it, and then moves past it to offer something better. What does this approach reveal about how Jesus deals with the painful and broken parts of our lives?
  5. The sermon draws a strong parallel between the physical water jar and our spiritual emptiness — the things we keep returning to for temporary relief. What are some of the “water jars” that people in our culture carry today? What are some you have personally carried?
  6. The pastor notes that even in all her pain and rejection, the woman had not lost her faith — she still believed the Messiah was coming. Why do you think faith is often one of the first things we are tempted to abandon when life becomes painful? What does her example teach us about holding on?
  7. After her encounter with Jesus, the woman left her water jar at the well and ran to tell her entire community about what she had experienced. What is the significance of leaving the jar behind? What might it look like for you to symbolically leave your “jar” behind today?
  8. The pastor points out that this woman — a Samaritan, a social outcast, someone living in shame — became the first evangelist for Jesus in Samaria, and that many believed because of her testimony. What does it say about God’s character that He would choose her for this role? What does it say about how He might want to use your story?

Personal Reflection Questions

These can be discussed as a group or used for quiet individual reflection before sharing.

  1. If Jesus sat down with you today the way He sat down with the woman at the well, what do you think He would gently name in your life — the thing you have been trying to fill with temporary solutions?
  2. The sermon asks directly: “What has robbed you of your identity in Christ? What has stolen your joy? What is stealing your self-worth?” Take a moment to sit with those questions. Is there anything you feel led to share with the group?
  3. Jesus revealed Himself to this woman and then waited for her response. He does the same with us. Is there any area of your life where you have been resistant to fully accepting what Jesus is offering you? What is holding you back?

PRACTICAL APPLICATIONS

This Week, Choose One or More of the Following:

1. Identify Your Jar
Spend time in quiet prayer or journaling this week asking God to reveal what “water jar” you have been carrying — the thing you keep returning to for temporary relief. Write it down. Name it honestly before God. Then ask Him to replace it with something from His living water.

2. Revisit the Well
Read John 4:1-42 in its entirety on your own this week. As you read, place yourself in the woman’s position. What do you hear Jesus saying to you personally? Write down any words, phrases, or moments that stand out.

3. Share Your Story
The woman at the well did not wait until she had everything figured out before she testified. She ran and said, “Come see a man who told me everything I ever did.” Think of one person in your life who needs to hear about your encounter with Jesus. It does not have to be polished. It just has to be true. Pray for the courage to share it this week.

4. Practice the Presence of Living Water
Each time you drink water this week — whether from a glass, a bottle, or a cup — let it serve as a reminder of Jesus’ offer of living water. Use that moment to pause, pray, and ask God to fill whatever feels empty in you that day.

5. Extend Grace to the Marginalized
The pastor noted that we as Christians can be quick to blacklist and slow to extend grace. This week, identify one person in your life, your church, or your community who may feel socially discarded or shamed. Ask God how you can reflect the same posture Jesus showed this woman — seeing them, valuing them, and treating them as worthy of a divine appointment.

CLOSING THOUGHT

The pastor closed the sermon with this observation: the most significant detail at the end of this story is not what the woman said, and it is not the number of people who believed. It is what she left behind. She came to the well carrying an empty jar, representing every void she had tried to fill on her own. And she walked away without it. She no longer needed it. Because she had found the One who could fill what nothing else ever could.

Whatever you are carrying today, Jesus already has His calendar circled. He sees you. He knows you. And He has exactly what you need.

CLOSING PRAYER

Close your group time by inviting members to share one specific need or area of emptiness they would like the group to pray over. Then pray together, asking God to meet each person at their own well this week — just as He met the woman at hers.

“Come, see a man who told me everything I ever did.” — John 4:29