How Jesus Engaged the Lost

Entire books have been written about the interaction Jesus had with the woman at the well in John 4. Let’s look at it with this question in mind: How does Jesus engage a person who is far from God? 

As you start reading, consider: Who is someone in your life who is far from God? 

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It could be a close friend or family member, or maybe a coffee shop barista or neighbor. As we see how Jesus engaged this woman, I want you to consider what parts of Jesus’s methods you might be able to take and apply in your own life.  

#1 Look for God to show up when you are weary.

If you already know the story from John 4, you may be thinking about verse 17, where Jesus omnisciently knew about the woman’s past. And since you have never been omniscient, you think that the rest of this passage doesn’t apply to you. 

You are correct about one thing: You and I aren’t omniscient. But in the rest of this story, Jesus actually functioned out of His humanity in a way that most of us can also do. In fact, some of them I can readily relate to. Like this one for starters:

“Jesus, tired as he was from the journey, sat down by the well.” (John 4:6, NIV)

Jesus was weary from a journey. The sixth hour means that it was the middle of the day. I don’t know about you, but when I’m weary, I’m at my worst. I stop listening to God. I stop focusing on obeying Him. I definitely stop thinking about others. And I put myself first. I do not do what Jesus did here.  

Jesus, in His humanity, was weary, but He used that weariness to engage someone in a conversation.

Perhaps those moments when we feel weak, tired, and completely worn out are the moments we should sit up, look around, and ask: Who has God brought across my path? 

It might be our own family. It might be a neighbor or a co-worker. Feeling crummy or tired wasn’t an excuse to get out of engaging people for Jesus.  In fact, He used that specific weariness as a way to enter the conversation.

“When a Samaritan woman came to draw water, Jesus said to her, “Will you give me a drink?” (His disciples had gone into the town to buy food.)

The Samaritan woman said to him, “You are a Jew and I am a Samaritan woman. How can you ask me for a drink?” (For Jews do not associate with Samaritans.)”

Jesus initiated contact across ethnic lines and social norms. In his book What Jesus Started, Steve Addison says this about what Jesus was doing here:

“Village women avoided the heat of the day by going to the well early in the morning and just before sundown. They normally went as a group. Yet one woman arrived at the well in the middle of the day. She was alone. Middle Eastern culture dictated that as she approached, Jesus should withdraw to a distance of at least twenty feet. Only then could she move to the well [and get water]...

A Jewish rabbi would not even talk to his wife in public, let alone a woman he’d never met. Jesus ignored those customs along with 500 years of hostility between Jews and Samaritans”


We know this was out of the norm, because the woman immediately took notice. But even more importantly, if we look back a few verses, we can see that this was more than a spontaneous cross-cultural response. 

#2 Intentionally cross social and cultural norms. 

It says in verse four that Jesus “had to pass through Samaria.” During those days, Samaria was the most direct route between Judea and Galilee, but it was very rarely taken by Jews because of their contempt for Samaritans. 

Jesus did not have to pass through Samaria; He chose to. Even before He met this woman, Jesus was taking intentional steps to connect with people who were far from God and who were very different from Him.

We could make an application to moving to the bad part of town or across the ocean, but before we do that, let’s make one closer to home:

Today, depending on your neighborhood, it might be crossing cultural norms just to meet your neighbors. And because it’s not socially normal, most of us just don’t do it. 

For example, I have 11 immediate neighbors. I have had to initiate the first conversation with 10 of those 11 neighbors. That’s 91% of the time. Am I willing to continue to do so as people move away and new neighbors move in?

#3 Humble yourself enough to ask for help.

How did Jesus start His conversation with the woman? 

Notice that He did it humbly. Sometimes when we cross social norms, we do it to talk down or belittle someone. We have a message and we’re going to share it whether that person likes it or not.

Instead, consider what we can learn from Jesus’s example. Without a way to get water on His own and being weary, He humbled Himself and put Himself at her mercy. He needed a drink, so what did he do? He asked for one. If the Son of God, who could create sustenance from nothing, put Himself in debt to this Samaritan woman, how much more should we as Christians stop playing the game that we have it all together?

Think about this: When was the last time you asked someone outside the church for help? Our American value of self-sufficiency gets in the way of our witness to the world. Played out to the end, it may mean we never interact with people outside of the church.  

Back to my neighborhood as a modern-day example: The neighbors we have the best and ongoing relationships with (and as such have had the most spiritual conversations with) have done more for our family than we have done for them. 


#4 Intentionally move conversations into spiritual topics.

“Jesus answered her, ‘If you knew the gift of God and who it is that asks you for a drink, you would have asked him and he would have given you living water.’” (John 4:10, NIV)

Jesus didn’t waste words in small talk. He didn’t outright share the truth of the Gospel with her … yet (we’ll see that happen in verse 26). But He quickly moved the conversation to a spiritual topic.

Often evangelism gets talked about in two extremes: relational evangelism and confrontational evangelism.

Relational evangelism is the idea that you invest in a relationship over the long haul, slowly building a strong friendship so that when you bring up spiritual conversations, maybe years later, you have the relational capital to stay friends even if they disagree with you.

Confrontational evangelism is the idea of walking up to someone you’ve never met and confronting them with the Gospel. 

Yes, I’m speaking about both of these negatively, because I’d like to give you the best option: biblical evangelism. 

If you built your evangelism methods on what Jesus and the Apostles did, I don’t think you’d end up with a purely relational or confrontational evangelism, but instead an effective method for engaging lost people with the Good News.

It may be very direct and upfront at times. But it will also be very personal and caring. 

We need to pursue biblical evangelism. This story is one of many examples where the spiritual conversation goes upfront, not at the end, and the personal and spiritual nature of the conversation leads to a fast building of relationships.


#5 Keep the focus on God and Jesus.

In verses 19 through 24, Jesus engaged in religious conversation without losing focus or direction. Jesus brought the conversation back around to God and the truth of who He is and how we relate to God. He did not get bogged down in religiosity. While it’s fine to use religion as a bridge to the Gospel, be sure to keep the focus on God and the Bible. And, most importantly, keep the focus on Jesus.


#6 Present Jesus as a decision.

“The woman said, ‘I know that Messiah’ (called Christ) is coming. When he comes, he will explain everything to us.’

“Then Jesus declared, ‘I, the one speaking to you—I am he.’” (John 4:25-26, NIV)

This woman, being a Samaritan, already had a background knowledge that God had promised a Messiah. And what did Jesus do? He cut directly to the heart of the matter by claiming: “I’m the Messiah … I’m the guy that you are claiming to look for.”

In doing so, He forced her to make a choice about Him. She already said that she would believe the Messiah, and then He gave her the truth that it is Him.  

Don’t miss this: At some point, we need to present a choice to people when it comes to Jesus. 

“Evangelizing is not simply a matter of teaching and imparting information to the mind. There is more to it than that. Evangelizing includes the endeavor to elicit a response to the truth taught. It is a matter, not merely of informing, but also of inviting.” – JI Packer in Evangelism and the Sovereignty of God 


Too often our evangelism is only having a spiritual conversation but taking it no further. We can be glad we got into any spiritual topic and we leave it there. 

While I do think we need to celebrate baby steps, let’s look to Jesus as our example: He did not shy away from a direct message and a direct question. He left her with a choice to make …  a decision to make about who He was.

As we engage the lost, we haven’t fully shared the Gospel until we’ve presented Jesus as a decision. Yes, He is a historical person. Yes, He is God. But there are many people who are far from God that won’t argue with either of those. At the end of the day, everyone has to make a decision to follow Him or not.

This story has some clear examples of how Jesus moved a conversation to spiritual things and a call to repentance in a relatively short amount of time.

What are we going to do with this example that Jesus set?  

It is your turn to take a cue from Jesus and put it into action. Which one will you do today?

Whatever you feel like God is prompting you to do, do it. Write it down. Step out in faith and obedience and see what God does. 

Look for God to show up when you are weary.

Intentionally cross social and cultural norms. 

Humble yourself enough to ask for help.

Intentionally move conversations into spiritual topics.

Keep the focus on God and Jesus.

Present Jesus as a decision.

Peter Lindell

Peter Lindell does a lot of things. It might be masonry one day and ministry to Muslims the next. Along the way he keeps a podcast and blog going and seeks to serve the Great Commission community however God leads. He and his wife live in central Illinois with their 7 kids.

https://ontheroad.link/
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The Pattern of Jesus