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Summary: In one of the most profound, and paradoxical texts in the Bible, Jesus declares in Matthew 5:4: “Blessed are those who mourn; for they will be comforted.”

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The Gladness of Sadness

I like to begin my messages with something that makes us laugh when I can (though some of you probably wouldn’t necessarily call it humor). As we approach the second Beatitude however, I realize that frivolity isn’t called for today. In fact, this character quality is no laughing matter. In Luke’s reporting on the Messiah’s message from the mount in Luke 6:25, Jesus says: “Woe to you who laugh now, for you will mourn and weep.”

Have you noticed that our culture embraces entertainment and pursues pleasure at all costs? Most of life is spent avoiding sorrow and pain. Even when we get bad news on TV, the newscasts often conclude with a funny story or something designed to make us smile. The mantra of many today is something like this: “Blessed are those who laugh their way through life.” Some of us will do almost anything to stifle our sadness and turn away from tears. And yet, if we were honest we’d have to admit that we sometimes feel like Proverbs 14:13: “Even in laughter the heart may ache, and joy may end in grief.”

I walked a mile with Pleasure, she chatted all the way

But left me none the wiser for all she had to say

I walked a mile with Sorrow and not a word said she

But oh, the things I learned when sorrow walked with me

In one of the most profound, and paradoxical texts in the Bible, Jesus declares in Matthew 5:4: “Blessed are those who mourn; for they will be comforted.” This startling paradox could be put this way: “Happy are the unhappy” or “The gladness of sadness” or “God applauds you when you’re in agony.” As we’ve been learning, God is much more concerned with our character than He is with our temporary conditions. This Beatitude flows from the first one: “Blessed are the poor in spirit; for theirs is the kingdom of heaven” because spiritual bankruptcy should always lead to spiritual brokenness. As John Stott says, “It is one thing to be spiritually poor and acknowledge it; it is another to grieve and to mourn over it…confession is one thing, contrition is another” (“The Message of the Sermon on the Mount,” Inter Varsity Press, Page 41). The haughty heart and the tearless eye should be foreign to the Christ follower.

Of the different words that can be translated, “mourn,” Jesus is using the strongest one available. It means, “to grieve or wail” as when a loved one dies. It is deep sorrow that causes the soul to ache and the heart to break. Jesus is not talking about complainers or moaners, but about those who are gripped by grief as seen in Psalm 34:18: “The LORD is close to the brokenhearted and saves those who are crushed in spirit.”

I’d like to suggest that there are four arenas in which this Beatitude can be lived out.

1. Lament the losses in your life. This first area might be the easiest in the sense that we all have experienced excruciating pain at some point in our lives, and if we haven’t, we know its coming. 1 Peter 4:12: “Dear friends, do not be surprised at the painful trial you are suffering, as though something strange were happening to you.” Some of you have gone through, or are going through right now, some health issues that make you afraid about the future. Perhaps you’ve experienced a relational rupture with someone and it’s eating your heart out. Can you relate with the words in Psalm 6:6? “I am worn out from groaning; all night long I flood my bed with weeping and drench my couch with tears.”

Maybe you’ve lost a loved one through death and you still cry yourself to sleep at night. You can relate to how David felt when his son Absalom died in 2 Samuel 18:33: “The king was shaken. He went up to the room over the gateway and wept…’” When Abraham’s wife Sarah died, we read in Genesis 23:2 that he “came to mourn…and to weep for her.”

Remember, that since Jesus wept when His friend Lazarus died, its OK for you to cry as well. Ecclesiastes 7:2-4 says, “It is better to go to a house of mourning than to go to a house of feasting, for death is the destiny of every man; the living should take this to heart. Sorrow is better than laughter, because a sad face is good for the heart. The heart of the wise is in the house of mourning, but the heart of fools is in the house of pleasure.” It’s better to go to a funeral than to a party because sadness is actually good for us, especially if it helps get us ready for our own death and enables us to live like we should now.

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