When the "Woes" turned to "O"

August 23, 2019 Preacher: Gareth Franks Series: Hypocrisy & Grace

Topic: Christian Living Scripture: Matthew 23:34–39

Home Group Study - Sermon Date: 23 August 2019

Text: Matthew 23:34-39

Opening Discussion: Part of growing up is learning the hard truth that we don’t always know everything. Can you remember as a child an instance when you did not heed your parents warning because you thought you knew better and more than they did? Share your story.


This "generation" that Jesus addresses in Matthew 23:35 lived in what the New Testament called "the fullness of the time" (Galatians 4:4). Those were the days that, as Scripture says, were "foretold" or "proclaimed" by the prophets of old (Acts 3:24). They were the very times about which "the prophets who prophesied about the grace that was to be yours searched and inquired carefully, inquiring what person or time the Spirit of Christ in them was indicating when he predicted the sufferings of Christ and the subsequent glories.” (1 Peter 1:10-11)

This particular generation, to whom Jesus spoke, lived in those rarest of times! They were among the most remarkable and exciting days to be alive! And yet, it was to them that our Lord spoke the strongest and harshest words of condemnation that any other generation has ever received!

Why? It was because their "religious hypocrisy" enabled them to covered-up their sin and conceal a heart of rebellion against God’s will for their lives in those very times. And their religious hypocrisy in those ‘outstanding’ times made them ‘outstandingly’ guilty.

In Matthew 23:34-36, we see the prophecy of their guilt. In Matthew 23: 37-39, we see Jesus’ anguish over their guilt.

Investigation & Interpretation:

  • Read: Matthew 23:34-39
  1. How does the word “Therefore”(v.34) connect our passage in v34-39; to the previous passage?
  2. In verse 34 Jesus is prophesying that even though he would send the Isrealites “prophets and wise men and scribes, some of whom [they] will kill and crucify, and some [they] will flog in [their] synagogues and persecute from town to town. Why would they do this?
  3. Jesus prophesied judgment on these Israelites in verse35. When did “all these things…come upon this generation? (v.36)
  4. Why do you suppose the word Jerusalem is mentioned twice in verse 37?

Application - How must I change?

  • Is there a Truth to be believed?

John Cooper, the lead singer of SKILLET, said; “I’ve been saying for 20 years, that we are in a dangerous place when the church is looking to 20 year old worship singers as a source of truth. We now have a church culture that learns who God is from singing modern praise songs rather than from the teachings of the Word.” Is this an accurate or inaccurate assessment of our modern day churches? Explain your answer?

  • Is there an Attitude to be fostered?

The incarnate Word of God wept over Jerusalem. God’s terror was accompanied by God’s tears, and so it always is. Bible commentator W. Cadman, once wrote, “Like Christ, Christians should desire and seek the salvation of men.” Sometimes Christians can become cold and indifferent to those who are unbelievers. What are some of the reasons people have for not weeping over the lost?

  • Is there a Behavior to be changed?

A time is coming when ethnic Jews, in large numbers, will welcome Jesus. A day of repentance is coming. At that time, Israel’s reprobation will turn to restoration. There is coming a day when bride and Groom will be reconciled. How should this truth – of God’s final return – effect our hope as well as our behaviour?


Let us remember that Matthew 23 is our Lord’s final public preaching. These are the last words the scribes and Pharisees and people of Jerusalem will hear from the lips of our Lord. As Matthew 5-7 introduced our Lord’s public ministry to Israel, so Matthew 23 concludes it.

The faithfulness of God should motivate us to faithful Christians living, instead of hypocrisy. God made promises to Israel and, as the faithful, covenant-keeping God, He will fulfill those promises. He is faithful, gracious and all-powerful to fulfill His Word.

Let’s not look at other people—or even other generations—and judge ourselves on how we compare to them! Genuine favor from God comes through looking at just three things—(1) the majesty-holiness of our righteous God, (2) the terrible sinfulness of our own sins in the light of His righteousness, and (3) the greatness of the mercy He has shown us in sending Christ to pay for those sins.


Prayer Points:  

  1. Pray we would be people willing to allow the Holy Spirit to convict us of our sins. 
  2. Pray we would never justify our sin and make excuses for them.
  3. Pray we would love the lost and love the glory of God.

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