Red Letter Conversations - Discussion 8

Discovering life in the words of Jesus

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The Woman at the Well

Christ Speaks to the Problem of a Guilty Past


Pray together for the group meeting, and any pressing needs within the group.

Mission Talk

Each week you’ll spend some time sharing about the previous week’s mission. What was your mission, what were your results, and what did you learn from it?


Watch the following discussion-starter video. It’ll set the topic of discussion for the group.

Read John 4:1-30

  1. One person will first read the scripture selection in the King James Version.
  2. Next, another person will read the same passages in a modern language or amplified version for more clarity such as the New Living Translation (NLT), Message Bible (MSG), New English Translation (NET), Amplified Bible (AMP), etc. We recommend using the YouVersion Bible app.


  1. One person will begin retelling the scripture passage in their own words (a new person to start each week is great!) Then…
  2. As a group, work together to fill in gaps and build the story. This will help us internalize and own it. Be sure everyone participates.


Together, share around the group how the topic and scripture setting applies to your life personally. Here are some thoughts to consider for discussion… don’t let the discussion stop here, though… what questions can you ask that will help uncover God’s message?

The Contact- verses 1-8

  • To get from Judea to Galilee, there were multiple routes to take… to the east, to the west, or straight through Samaria. Which way did Jesus take?
  • The Bible says he, “must needs” or “had to” go through. What does this mean?
  • The Jews would rarely go through Samaria. Why was this?
  • Note: Samaritans were a mixed Gentile race that settled near Jerusalem in the Old Testament after the Jews and other nations were defeated by Assyria. These non-Jews adopted some of the Jewish religious beliefs and mixed them with their Pagan beliefs… these people were eventually called Samaritans and were despised by the Jews as both racial and religious half-breed heretics.
  • Did Jesus know the woman would be coming to the well at precisely the time she did?
  • Was the woman expecting Jesus to be there? 
  • What was she hoping to find at the well?
  • How would you define the idea of, “divine appointments”?
  • Can you describe a time when God made a divine appointment for you?
  • When you’re reaching someone for Christ, what obstacles or inconveniences might you encounter?
  • The woman came to the well at noontime when most people would come in the morning or the evening. Why do you think she came now?
  • What was the question Jesus asked her?
  • Each of them were thirsty, but for different things. What were each thirsty for?
  • What does this encounter with Jesus tell us about racial prejudice?

The Challenge – verses 9-15

  • How might the woman have known Jesus was Jewish?
  • Note: There were three issues here: 1) Jesus was a Jew (racial issue), 2) Jesus was a man talking to a woman (gender issue), and 3) Jesus was willing to drink from a Samaritan’s cup (religious issue).
  • Where were Jesus’ disciples at this time?
  • What was the woman’s response to Jesus’ request for water?
  • How did Jesus begin to make her see her need?
  • How did he begin revealing to her who he was?
  • What did Jesus mean when he told her about “living water”?
  • What might the woman have thought “living water” was?
  • How does Jesus compare “worldly water” to “living water”?
  • Describe a time when the world left you thirsty.
  • What was Jesus referring to when he spoke of water “springing up into everlasting life”?
  • What was the woman’s response to his offer now?
  • Did she at this time fully understand what he was offering?

The Confrontation – verses 16-18

  • Why might Jesus have confronted the woman about her living situation?
  • How did he coax the truth from her?
  • Was this part of the conversation comfortable for her? What can this tell us about our approach to Jesus?
  • Describe a time when you had a painful medical procedure that resulted in better health.
  • Did the woman tell Jesus the truth? Did she tell him the whole truth?
  • What was Jesus’ response? Why was it important for him to describe her reality to her?

The Conversion – verses 19-26

  • Who did the woman now think Jesus was?
  • Why did she engage Jesus in a debate about beliefs?
  • What two things did Jesus tell her were most important about worship? 
  • From this passage, what things are not important about worship?
  • Did the woman know that Jesus was the Messiah?
  • What is significant about Jesus’ declaration that “I… am”?

The Changed Life – verses 27-30

  • How did his disciples react when they saw Jesus talking to her?
  • What does the woman now do with her new-found knowledge?
  • When she began reaching people about Jesus, how knowledgeable was she?
  • What is required in order to be an effective witness?
  • In what ways can this woman’s experience change your approach to witnessing to others?

Bonus – Verse 42

  • After the woman shared her faith with others, it was still important for them to come and go through the same process she had gone through. There’s no such thing as second-hand faith! After they heard him, they could say personally that he was, “indeed the Christ, the savior of the world.”


    In light of what we now know about this passage, what is God calling you to do this week? As a group, take just a couple of minutes to silently pray to God asking, “Lord, what do you want me to do this week because of what I’ve seen today?” Briefly write this down as a personal mission statement for the week,

    “Lord, this week, I will __________________________.”

    A possible suggestion:

    • Lord, this week I will go out of my way to share my faith with someone else.
    • Lord, this week I will work to tear down walls between myself and others.
    • Lord, this week I will turn away from my reliance on the world’s value system, and trust in you.
    • Even better, write your own!