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Blessed Are They That Mourn (Matthew 5:4)
I. Grieving Will Lead Us To Confess And Repent From Our Sins
II. Grieving Is The Work Of The Holy Spirit
Transcript:
Today we will consider the second blessing in this series of messages about the Beatitudes. Matthew 5:4: "Blessed are they that mourn, for they shall be comforted." The title of our message is "Blessed Are They That Mourn."
The desire to escape / to be spared from sorry and pain
But before we consider this verse, allow me to read for you Psalm 55:4-8. This was a Psalm of David. The psalmist David said, "My heart is sore pained within me: and the terrors of death are fallen upon me. Fearfulness and trembling are come upon me, and horror hath overwhelmed me. And I said, Oh that I had wings like a dove! for then would I fly away, and be at rest. Lo, then would I wander far off, and remain in the wilderness. I would hasten my escape from the windy storm and tempest." That was a picture of a man facing great sorrow and pain.
Have you ever faced great sadness, discouragements, perhaps even tragedies, disappointments? Surely you have. When you encounter such experiences in life, isn't that what you would wish for? Like the psalmist, I want to escape. If only I could have wings like a dove and fly away. If only I could wander far off and remain in the wilderness. If only I could be like a boat to sail away from the devastating storm or troubles. The greater our pain and sorrow, the greater our desire to escape. Right?
We would have expected Jesus to say, "Blessed are they that are free from troubles, pain, and sorrow." But instead, He said, "Blessed are they that mourn." It is the exact opposite of what the world would desire. The world wants to escape from all kinds of sorrow and pain. Do you realise that all the pleasures of this world, the amusement, the entertainment, the fashion and the enjoyment are meant to help the people avoid and numb the sadness and grief. That is why people would say, "Don't worry, just be happy."
But Jesus teaches the opposite. In the Gospel of Luke chapter 6 verse 25 He said, "Woe unto you that laugh now! for ye shall mourn and weep." Does that mean we cannot be happy and laugh? There are things in life that make us happy and laugh. When people are married, when children are born, when we purchase our first house, or we have a family gathering, those are happy occasions. As Ecclesiastes 3 verse 1 and 2 said, "To every thing there is a season, and a time to every purpose under the heaven: a time to weep, and a time to laugh; a time to mourn, and a time to dance." The problem with man is that he always wants to be happy. He does not want to grieve. And when the time comes for him to grieve, he will do everything he can to avoid it.
As you and I live our lives in this world, we must understand that this is a life of tears, a life of sorrow, a life of pain, especially when we live in the last days. Remember what Jesus taught His disciples about the last days in Matthew chapter 24. When the disciples asked Him, "When is the end of the world?" Jesus said in Matthew 24 from verse 4 to 8: "Take heed that no man deceive you. For many shall come in my name, saying, I am Christ; and shall deceive many. And ye shall hear of wars and rumours of wars: see that ye be not troubled: for all these things must come to pass, but the end is not yet. For nation shall rise against nation, and kingdom against kingdom: and there shall be famines, and pestilences, and earthquakes, in divers places." And take note of the last phrase there: "All these are the beginning of sorrows."
Can you imagine living in such times in these last days? And Jesus had already warned us all these are the beginning of sorrows. In other words, when you and I see deceptions, sicknesses, illnesses like the recent COVID-19, the economic downturn, wars and rumours of wars, the chaotic situations happening all around the world, this is just the beginning. We have not seen anything yet. And here we are. We always want to be happy. Don't worry. Just be happy. Can you see how wrong men can be?
Indeed, there's a time for everything. When the time comes for you to be happy, and there's a legitimate reason to be happy, by all means, be happy. When the time comes for you to grieve, and there is a legitimate reason to grieve, but you do not want to grieve, something is very wrong.
Blessed are they that mourn. What does it mean? In the original Greek language, there are about nine different words used in the New Testament for the word "mourn" which means to grieve or to weep. Here this word is the strongest of the nine different expressions. It is the most serious kind of grief. You see there are different kinds of grief. By the way, grief is a wonderful gift of God. It is a part of human life. Even the ability to cry is a gift of God. When you bottle up all the pain and anxiety in your heart, it is most detrimental to your emotional system. But once it is released in tears, your body will begin to heal. That is why being able to grieve, to cry, to weep is a wonderful gift.
The Bible records for us different examples of grieving and weeping. Let me give you some examples. When Abraham's wife Sarah died, he was grieved and he wept. That was a natural way for him to deal with his loss. In Psalm 42, when the psalmist was away from Jerusalem and not being able to worship God together with God's people, he felt as if God was so far away from him. And he cried out, "As the hart panteth after the water brooks, so panteth my soul after thee, O God. My soul thirsteth for God, for the living God: when shall I come and appear before God?" (Psalm 42:1-2). When young Timothy faced very devastating discouragements and disappointments in the ministry, he cried desperately. That was why Paul said in 2 Timothy 1:4 that he greatly desired to see Timothy because he was mindful of his tears and he wanted to encourage the young man. When God called the prophet Jeremiah to warn Israel of the coming judgment, he preached with much tears. So much so he was known as the weeping prophet.
In Mark chapter 9, when the father brought his demon-possessed son to Jesus and the tears were running down his face and he cried, "Lord, I believe; help thou mine unbelief." What kind of tears was that? Those were the tears of a father's love for his son. Then in the Gospel of Luke chapter 7, when a woman came into the Pharisee's house where Jesus was visiting, she brought along with her an expensive box of oil and she stood at Jesus' feet. She washed His feet with her tears and then wiped them with her own hair. When the Pharisees questioned, "Why would Jesus allow this sinful woman to do that to Him?" Jesus taught them the lesson of how people who have been forgiven much were most grateful. What kind of tears was that? Those were tears of devotion, tears of worship and tears of heartfelt gratitude.
So you have people who grieve for their loved ones who have passed away like Abraham. You have people who cried for the worship of God like the psalmist, for discouragement and disappointment like Timothy, for the love of the people like the prophet Jeremiah, for the love of their children like the man—the father—whose son was demon-possessed, or for heartfelt gratitude like the sinful woman. But there are also those kinds of grief that are wrong and sinful. For example, Amnon, he wept and grieved until he was sick. Why? Because he wanted to defile his sister Tamar and later on he assaulted her. That was a sick kind of grief. And then we have Judas Iscariot who wept and grieved when he realised that he had betrayed the Lord Jesus Christ. He took the thirty pieces of silver and threw them into the temple. But instead of repenting from his sins, he went and hanged himself. So you can see there are so many different kinds of grief. That is why the Bible has so many different words to describe the different expressions of grief.
But the word used here in Matthew 5:4 is the strongest kind of grief. It is a word used for grieving the dead. For example, in Mark 16:10, after Mary Magdalene saw the resurrected Jesus Christ, she went and told the disciples. And the Bible said, "They mourned and wept." They were weeping for someone whom they loved greatly. Now it is not so much an external weeping but an inner agony. It is a deep, intense pain.
In the first Beatitude we have learned: "Blessed are the poor in spirit: for theirs is the kingdom of heaven." There was a reference to the believer because only the believer would belong to the kingdom of heaven which is synonymous to the kingdom of God. So in this whole Beatitude Jesus was speaking about the believer. The believer would know and understand his spiritual poverty. He was desperately poor, begging poor. Remember the image of the beggar with one hand covering his face in shame and the other hand reaching out for help. He recognised that he had no capacity or capability to help himself. He could only cry out to God for grace and mercy. Now, this is the same person who knows and understands his spiritual condition which would lead him to grief in the deepest sense. Here it is not just grieving because of disappointment, discouragement, sadness or even out of a grateful heart. It is to grieve because of sin. That is the main thrust of this verse.
I. Grieving Will Lead Us To Confess And Repent From Our Sins
Our first point is: grieving will lead us to confess and repent from our sins. In other words, blessed are they that mourn for their sins, for they shall be comforted. The blessedness or happiness does not come in the grieving. It comes when God responds to the grieving. You see, this is how we must deal with sin. When we try to cover our sins or we try to deal with our sins by ourselves, we will be destroyed. We will never be comforted. But when we confess our sins to God and repent, that is when we will be comforted. That is why it is a blessing.
But what does it mean to be comforted? Again, turn with me to Psalm 32:1 and 2, another Psalm of David. Let me read for you. Psalm 32:1: "Blessed is he whose transgression is forgiven, whose sin is covered. Blessed is the man unto whom the LORD imputeth not iniquity, and in whose spirit there is no guile." When David confessed his sins, how was he comforted? He was forgiven. For the rest of the world, the unbelievers, they have to live with the guilt of their sins—with no forgiveness, no relief, no escape. But for the believers who grieve for their sins, they who confess and repent from their sins, they would experience the comfort of God because they are forgiven.
Throughout David's life, he had experienced much tears. If you are familiar with his life, he had experienced tears of rejection, tears of frustration, tears of discouragement and disappointment, tears of betrayal. Can you imagine being betrayed by your own son Absalom who wanted to kill you? How painful that would be. But it was the tears over the guilt of his own sins that broke David's heart. Remember when the prophet Nathan confronted David of his sins of committing adultery with Bathsheba and then murdering her husband Uriah? He did not defend himself. He did not try to justify his actions. He was so totally broken and overwhelmed with sorrow that the only thing he said was, "I have sinned against the LORD." It was that broken and contrite heart that led David to cry out in Psalm 51:12, "Restore unto me the joy of thy salvation." Notice David did not say, "Restore unto me thy salvation," but "the joy of thy salvation." Which means the true believer will never lose his salvation, but he will lose the joy of his salvation because of sin.
Have you ever considered what it means to be forgiven of our sins? According to Ephesians chapter 2 verse 1 and 2, we were once dead in sins. We were walking according to the course of this world, according to the prince of the power of the air, that is Satan. We were the children of disobedience, the children of God's wrath. And because the wages of sin is death, one day we will be sent to the lake of fire. A million upon a million years we will be tormented in eternal hell. That was our most pathetic situation. Do we really believe that? If we do, and then to know that all that had changed, our most pathetic situation had changed, all our sins have been forgiven, we are safe to go to heaven—how do you explain that kind of joy?
Dear friend, if there is one emotion, one word for you to use to express how you feel when you know that your sins have been forgiven, what is that word? Someone said it is the word "relief". Like when you were driving home and you saw fire and smoke coming up in the direction of your house. You saw fire engines rushing to your house. People were screaming, shouting and crying. All kinds of thoughts ran through your mind. What about my dad? My mom, my brother, my sister, my children? They may be caught in the fire and burned to death. You were trembling with fear. And then you turned around the corner and you saw your entire family standing there. All of them were saved. How would you describe that emotion? Relief, right? Thanks be to God. I should be dead, but I am alive.
A man can try to deny his sin and ignore it. Or he can admit it and try to change it by himself. Or he can admit it and sink into despair. Or he can admit it and turn to God for His grace and mercy. Only the last option can bring him comfort because only the last option can bring the forgiveness of his sins. That is why it is such a blessing to grieve for our sins because it is the only way you and I can be comforted. It is the only way you and I can be forgiven.
II. Grieving Is The Work Of The Holy Spirit
Our second point is: grieving is the work of the Holy Spirit. Perhaps you may say, "I've already confessed my sins and believe in the Lord Jesus Christ. My sins are forgiven. I have been comforted. That is something that happened in the past. So how does this verse apply to me now?" Today when you ask someone who professes to be a believer, "Are you a Christian?" he or she may say yes. "How do you know you are a Christian?" Most of the time they will say, "I remember the day when I professed my faith" or "the day I said the sinner's prayer" or "the day I was baptised" or "the day I spoke to the preacher who explained to me about sin and salvation." Notice they are always talking about the past. Can you imagine the whole basis of their assurance of being a Christian is based on something in the past?
When it comes to the assurance of our salvation, the Bible always talks about the present—the evidence of the present. The Bible says, if you have salvation, Romans 8:9, then you have the indwelling of the Holy Spirit in you. It is the evidence of what you have at this moment. If you have salvation, 1 John 4:20 says you will love your brother. Anyone who says he loves God but does not love his brother is a liar. Again, it is the evidence of what you have at this moment. It is not something in the past, something that is happening now.
Likewise, "Blessed are they that mourn, for they shall be comforted." The words "mourn" and "comforted" are both in the present tense. In other words, blessed are they that are continuously grieving for their sins and they shall continuously be comforted. The believer will grieve for his sin because he knows and understands what it means to lose the joy of his salvation. As mentioned a while ago, the true believer will never lose his salvation. No man can snatch the believer out of God's hand. Once saved, always saved. But what he will lose is the joy of his salvation. So he knows and understands what is missing in his life because of sin: the joy of worshipping God, the joy of serving God, the joy of Christian fellowship, the joy of prayers, the joy of studying God's Word, etc. Therefore, he will grieve for his sins. He will be sorrowful. He will be repentant. And he will be restored the joy of his salvation. Isn't that a blessed thing?
Most certainly the believer will grieve for his sins because he knows and understands the spiritual struggle in his heart. On one hand, he wants to glorify and honour God, but on the other hand, he fails to do it. As the Apostle Paul said in Romans chapter 7, there is always this spiritual struggle within his heart: the things I should do I do not do, and the things I should not do that I do. The believer will grieve for his sins because he not only knows what sin is—sin is a transgression of God's law—but he also knows that it was because of sin that Jesus Christ was crucified on the cross of Calvary and shed His precious blood. And only His blood can wash away all our sins. Therefore, he is sensitive to sin. And whenever he sins, he will be grieved in his heart. He will confess. For he knows, "If we confess our sins, He is faithful and just to forgive us our sins, and to cleanse us from all unrighteousness" (1 John 1:9).
Dear friend, pause for the moment and consider this. Why do we miss the joy of our salvation? Why is there this spiritual struggle in our hearts whenever we sin? Why are we so sensitive to sin? There are sins we have committed that no one in this world would ever know. There are sins we have committed and have gotten away, so to speak, or at least we think we have gotten away. Why do we still grieve in our hearts over those sins that no one in this world would ever know and we have so-called gotten away? It is because to grieve is a conviction of the Holy Spirit. So whenever we sin there is grief. We know that this is the working of the Holy Spirit and we know that we are God's children.
Now whenever we sin and there's no grief, what does it mean? There are only two possibilities. It could be because we are rebellious. We are backsliding. It is a time of our disobedience. We are grieving the Holy Spirit and the day will come when the Holy Spirit will convict our hearts. But it could also be that we do not have the Holy Spirit in the first place. In other words, we were never a believer in the first place because the Holy Spirit will always convict our hearts of our sins. So why is there no grief? Can you see how serious it can be?
And also what a blessing when we have this conviction of grief. It is such a blessing because when we are grieved in our hearts because of our sins, it means that the Holy Spirit is working in us. The Holy Spirit is convicting us. The Holy Spirit is in us. We are a child of God. And God loves us. He wants us to confess and repent from our sins that we can be comforted, that our sins will be forgiven. No one may know what we do, but we know it. And the Spirit of God that dwells in us knows it as well. And when there is this conviction, there's this grief, this mourning, which will then lead us to confess and repent. It is the wonderworking of the Holy Spirit. And for us to know that—what a blessing—I am a child of God. God is working in me through His Spirit, enabling me to grieve for my sins as our Lord Jesus has taught us. "Blessed are they that mourn: for they shall be comforted."
So dear friends, if you have forgotten whatever I said, it is such a great blessing because to grieve will lead us to confess and repent from our sins, and to grieve for our sins is the evidence of the Holy Spirit's work, which means you and I are the children of God. That is why Jesus says, "Blessed are they."
Let us pray.
Closing Prayer
Our Father in heaven, we come before Thee and we give Thee thanks for every opportunity for us to learn Thy precious Word. And as we study the series of messages on the Beatitudes, we have come to the second blessing: "Blessed are they that mourn, for they shall be comforted."
And we know that we are to continuously mourn for our sins, and we shall also continuously be comforted. For as long as we live our lives on this earth as fallen men, though we are new creatures in Christ, we are living in this old body, we are still capable of sin. So whenever we sin, we grieve because we know what it means to lose the joy of our salvation. We will never lose our salvation as true believers, but the joy of Thy salvation.
And we are also grieving because we know and understand this spiritual struggle in our hearts: things we ought to do, we do not; things we ought not to do, that we do, said the Apostle Paul. And we are also sensitive to our sins because we not only understand what sin means but it was because of sin that our Lord Jesus came and died on the cross of Calvary. Therefore, we will grieve in our hearts whenever we sin.
And this is the evidence and assurance of our salvation. It is something happening at this moment—the wonderworking of Thy Spirit. And Thou wouldst want us to know and to repent so that we will be comforted. And Thou wouldst also want us to know and be assured in our hearts that we are truly the children of God. Because as long as there is this grief, it is the Holy Spirit that is working in our lives. It is the evidence of what we have at this moment.
So we pray that the Holy Spirit will continue to convict our hearts each time we sin against Thee through Thy Word. May Thou open our spiritual eyes and touch our hearts in such a way that we will grieve for our sins, all to the glory of Thee. We pray all this in Jesus' name. Amen.
Sermon Breakdown
1. Introduction
- Opening Scripture: Matthew 5:4 – “Blessed are they that mourn, for they shall be comforted.”
- Title: “Blessed Are They That Mourn”
- Supporting Scripture: Psalm 55:4-8 (David’s desire to escape sorrow like a dove flying away).
2. The Human Desire to Escape Pain
- Everyone experiences sadness, discouragement, tragedy, and disappointment.
- Natural human reaction: want to escape (wings like a dove, wander in the wilderness, sail away).
- The greater the pain, the greater the desire to escape.
3. The World’s View vs. Jesus’ Teaching
- World expects: “Blessed are those free from troubles.”
- Jesus says: “Blessed are they that mourn” – the opposite.
- World uses pleasure, amusement, fashion, and entertainment to numb sorrow.
- World’s motto: “Don’t worry, just be happy.”
- Jesus’ warning: Luke 6:25 – “Woe unto you that laugh now! for ye shall mourn and weep.”
4. A Time for Everything (Ecclesiastes 3:1-2)
- There is a time to weep and a time to laugh, a time to mourn and a time to dance.
- The problem: man always wants to be happy and refuses to grieve when grief is legitimate.
5. The Last Days and the Beginning of Sorrows (Matthew 24:4-8)
- Jesus warned of deceptions, wars, famines, pestilences, earthquakes.
- These are “the beginning of sorrows” (Matthew 24:8).
- Examples: COVID-19, economic downturn, chaos worldwide.
- We have not seen anything yet – yet people still say, “Don’t worry, just be happy.”
6. Defining “Mourn” – The Strongest Greek Word for Grief
- Nine different Greek words for mourn/grieve/weep.
- The word in Matthew 5:4 is the strongest – the most serious kind of grief.
- Grief is a gift from God; the ability to cry is healing.
7. Biblical Examples of Grief and Weeping
- Abraham – grief over Sarah’s death (natural loss).
- Psalmist (Psalm 42:1-2) – grief over distance from God’s worship.
- Timothy – grief over discouragement and disappointment (2 Timothy 1:4).
- Jeremiah – grief over Israel’s coming judgment (the weeping prophet).
- Father in Mark 9 – grief over his demon-possessed son: “Lord, I believe; help thou mine unbelief.”
- Sinful woman (Luke 7) – tears of devotion, worship, and gratitude.
- Wrong grief: Amnon (lust and assault), Judas Iscariot (remorse without repentance, suicide).
8. The Main Thrust: Grieving Because of Sin
- The deepest grief is not over circumstances but over sin.
- The believer knows his spiritual poverty (first Beatitude) and therefore grieves over sin.
- Point 1: Grieving leads us to confess and repent from our sins.
- Blessedness comes not from the grief itself but from God’s response – comfort through forgiveness.
9. The Comfort of Forgiveness (Psalm 32:1-2)
- “Blessed is he whose transgression is forgiven, whose sin is covered.”
- David’s comfort: forgiveness.
- Unbelievers have no forgiveness, no relief, no escape.
- Believers who grieve for sin experience God’s comfort because they are forgiven.
10. David’s Example: Brokenness Over His Own Sin
- David’s tears: rejection, frustration, discouragement, betrayal (Absalom).
- But the deepest tears came over his own sins (adultery with Bathsheba, murder of Uriah).
- Nathan’s confrontation: David said, “I have sinned against the LORD.”
- Psalm 51:12 – “Restore unto me the joy of thy salvation” (not lose salvation, but lose the joy of it).
11. The Reality of Our Sinful Condition (Ephesians 2:1-2)
- We were dead in sins, walking according to the world and Satan.
- Children of disobedience, children of wrath.
- Wages of sin is death – eternal hell.
- To know that all our sins are forgiven and we are safe – that brings relief.
12. The Analogy of Relief
- House on fire, family feared dead – then found alive.
- Emotion: relief.
- Only turning to God for grace and mercy brings forgiveness and comfort.
13. Point 2: Grieving Is the Work of the Holy Spirit
- Many base assurance of salvation on past events (prayer, baptism, profession).
- The Bible speaks of present evidence: indwelling Holy Spirit (Romans 8:9), love for brother (1 John 4:20).
- “Mourn” and “comforted” are present tense – continuous grieving and continuous comforting.
14. The Believer’s Continuous Grieving Over Sin
- True believer never loses salvation (once saved, always saved).
- But he loses the joy of salvation – joy of worship, service, fellowship, prayer, Bible study.
- He grieves over sin because of the spiritual struggle (Romans 7): what he should do he does not, what he should not do he does.
- He grieves because sin caused Christ’s crucifixion.
- He confesses: 1 John 1:9 – God is faithful and just to forgive.
15. The Conviction of the Holy Spirit
- We grieve over sins no one else knows – this is the Holy Spirit’s conviction.
- That grief is evidence that we are God’s children.
- If there is no grief after sin, two possibilities:
- Rebellion/backsliding – grieving the Holy Spirit.
- Never had the Holy Spirit – never truly a believer.
16. Conclusion: Why Mourning Is a Blessing
- Grieving leads to confession and repentance.
- Grieving is evidence of the Holy Spirit’s work.
- Therefore, mourning proves we are children of God.
- That is why Jesus says, “Blessed are they.”
17. Final Prayer
- Thanks for God’s Word.
- Prayer for continuous mourning over sin and continuous comfort.
- Prayer for the Holy Spirit to convict hearts.
- Prayer for open spiritual eyes and tender hearts, all for God’s glory.
- Closing in Jesus’ name. Amen.
Sermon Context
This sermon is the second in a series on the Beatitudes from the Gospel of Matthew. The previous message covered the first Beatitude: “Blessed are the poor in spirit” (Matthew 5:3). Building upon that foundation of recognising one’s spiritual poverty, this sermon now examines the second Beatitude: “Blessed are they that mourn, for they shall be comforted” (Matthew 5:4).
The preacher addresses a common human struggle—the desire to escape pain, sorrow, and grief. He contrasts the world’s philosophy (“don’t worry, just be happy”) with Jesus’ teaching, which presents mourning not as a curse but as a blessing. The sermon carefully distinguishes between different kinds of grief (natural loss, disappointment, devotion, etc.) and focuses on the deepest kind: grief over sin.
Key biblical examples include David’s brokenness after his sin with Bathsheba (Psalm 51), the weeping prophet Jeremiah, and the sinful woman who washed Jesus’ feet with her tears (Luke 7). The preacher also addresses the role of the Holy Spirit in convicting believers of sin, the assurance of salvation, and the danger of having no grief over sin. The sermon concludes with the comforting truth that those who mourn for their sins will be forgiven and comforted by God.
Hook
“What if your deepest sorrow is actually your greatest blessing?”
Most people spend their entire lives running from pain. We numb our sadness with entertainment, escape our grief with amusement, and tell ourselves to “just be happy.” But then Jesus says something utterly shocking: Blessed are they that mourn.
Not blessed are the happy. Not blessed are the carefree. Blessed are the brokenhearted.
This sermon will challenge everything you think about grief, happiness, and the Christian life. You will discover why the ability to cry is a gift from God, why grieving over sin is the evidence of the Holy Spirit’s work in you, and why the only path to true comfort leads straight through the valley of tears.
If you have ever wondered why your heart still aches over sins no one else knows about—or worse, if you have stopped grieving altogether—you need to read this message. The answer may just save your joy, restore your assurance, and lead you to the only comfort that truly lasts.