The Ugh and Ahh of Repentance

Almost everything about Jesus’s encounter with the Samaritan woman is unexpected. That Jesus, a Jewish male, is engaging a Samaritan woman in conversation is unexpected and unthinkable. That Jesus, a Jewish teacher, wants to offer eternal life to this religious polyglot is bewildering. That Jesus, holy and sinless, spends time with a woman with as much relational baggage as she has betrays a significant but veiled moment in the making.

There are countless treasures and puzzling questions tucked away in the fourth chapter of John’s Gospel. But for now, let’s consider this one question: “Why did Jesus bring up the Samaritan woman’s sin in the following manner?"

“Jesus said to her, ‘Everyone who drinks of this water will be thirsty again, but whoever drinks of the water that I will give him will never be thirsty again. The water that I will give him will become in him a spring of water welling up to eternal life.’ The woman said to him, ‘Sir, give me this water, so that I will not be thirsty or have to come here to draw water.’ Jesus said to her, ‘Go, call your husband, and come here.’ The woman answered him, ‘I have no husband.’ Jesus said to her, ‘You are right in saying, ‘I have no husband’; for you have had five husbands, and the one you now have is not your husband. What you have said is true.’”

Few who read this passage would be eager to imitate Jesus’s evangelistic method with the Samaritan woman; but, Jesus has done what He has in order to convince this woman of her own need and emptiness. She’s being prepared for the spiritual metaphor of eternal life described as "living water." Many would like this to be the place for Jesus to say, “Woman, your sins are forgiven.”--but He doesn't. So, why press in on this woman’s rocky past and current messy home-life? Why point out her specific sins? The answer reveals the genius of the grace of God in Christ. In order for us to get there we must first pass through the doctrine of repentance.

Generally General Repentance

Repentance is a two-edged sword. That we should be able to bring our sins, rebellion, and failings to God and receive full pardon through Jesus is an amazing gift. On that proposition, one might think that repentance is an easy and painless process, a sort of daily verbalizing of a laundry list of omissions and commissions. But herein lies the problem, the pain of sin remains and is magnified even after conversion. John Owen made this point so well in his excellent book,The Mortification of Sin. There, Owen observed that our knowledge of the sinfulness of sin only grows after conversion.

There we have the problem before us. On the one hand, we have the offer of repentance from a God who has proven his love to us in the most extreme way possible—the crucifixion and resurrection of His Son. Who would pass on a repentance like this? Yet on the other hand, there remains the deepening pain and understanding of the heinousness of sin. Who would want to dwell on such dark and gory details? What are we to do?

The common solution is for us to repent generally. We are tempted to believe that we can have the pleasure of forgiveness without the pain of repentance--the crown without the cross. So we may at times, under a general weight of guilt or even reflexively, pray general prayers of repentance like:

  • Lord, have mercy on me a sinner.
  • Father, I have sinned against you, please forgive me.
  • Lord, today I did things I shouldn’t have done and the things I should’ve done I didn’t do.

Even a novice student of the Bible can pick up the biblical echoes in those prayers. And none of them are inappropriate prayers. It is an excellent practice to pray for general repentance as long as our prayer diet also includes prayers of repentance for specific sins.

Specific Repentance Specifically

We find the answer to our question, “Why did Jesus point out the Samaritan woman’s specific sins?” here: In part, Jesus wanted this woman (and all of us) to know that as He offered her eternal life He wasn’t overlooking sins that may come back later to haunt her. It was an amazing act of pastoral care and concern that, on the surface, appears to be unfeeling and insensitive.

Imagine for a moment that Jesus hadn’t asked about her husband, hadn’t delved into her sordid past. Imagine that he had simply steered the conversation to a short description of Samaritan-Jewish temple theology culminating in his self-designation as the Messiah. We most certainly wouldn’t have considered this passage to be missing anything.

But the Samaritan woman would’ve gone home. She might’ve waved to Jesus when he left Sychar a few days later. She might even have joined the church that Philip planted there after Jesus’s resurrection.She certainly would’ve repented generally for her failings and claimed the promise of eternal life offered to her in person by Jesus. But somewhere in the back of her mind there would be lurking this insidious question, “When Jesus offered me forgiveness, did he know about my five marriages and my live-in boyfriend? If he did, would he still have offered me eternal life?” Unanswered questions like these over a few specific sins are enough to shake any believers faith. But Jesus, in love, wanted to guard her against that. He probed her past to provided her with the knowledge of his grace that covers even specific sins, bad sins, particular sins, embarrassing sins.

This is why specifically repenting for particular sins is so crucial. When we confess our specific sins to our forgiving Lord we deprive our future unbelief of ammunition. When we confess our specific sins to our forgiving Lord we’re depriving our future unbelief of ammunition. We are keeping a short account of sin with the Lord and a long account of His grace. Every time we confess a specific sin and claim God’s promises of forgiveness we are declaring loudly that Jesus is not just a general savior for general sinners but our savior for our particular sins.4

So how do we do this?

  1. Pray for God to reveal your sins to you. As the Psalmist writes, “Search me, O God, and know my heart! Try me and know my thoughts! And see if there be any grievous way in me.”5 Pray in sincerity and think over your recent past, looking for unconfessed sin.
  2. As sin comes to mind, be honest with God about it. At it’s heart, repentance is a Holy Spirit honesty before God about your sin and unbelief.
  3. Prayerfully claim the promises of the gospel, that sin confessed to God in faith is forgiven sin. Confess the truth of Jesus’s sacrifice for your particular sins. It might be particularly useful to pray through 1 John 1:8-9 at this point.
  4. Thank God for the mercy you’ve received in reference to your particular sins and ask him to help you to live a life of increasing holiness.


Further Resources


The Westminster Confession of Faith, chapter 15 - Especially see XV.5 on confessing particular sins

The Mortification of Sin, John Owen

Repentance, Jack Miller

The Doctrine of Repentance, Thomas Watson

1. Luke 7:48

2. Acts 8:4-8

3. 1 John 1:8-9

4. Galatians 2:20

5. Psalm 139:23–24



Joe Holland