I’ve never taught nor meditated on Jesus’ words to the women of Jerusalem. I don’t even remember hearing a sermon on this event, which is recorded only in Luke’s gospel:

And there followed him a great multitude of the people and of women who were mourning and lamenting for him. But turning to them Jesus said, “Daughters of Jerusalem, do not weep for me, but weep for yourselves and for your children. For behold, the days are coming when they will say, ‘Blessed are the barren and the wombs that never bore and the breasts that never nursed!’ Then they will begin to say to the mountains, ‘Fall on us,’ and to the hills, ‘Cover us.’ For if they do these things when the wood is green, what will happen when it is dry?” (Luke 23.27 – 31, ESV)

Let’s spread out Jesus’ words: But turning to them Jesus said,

• Daughters of Jerusalem, do not weep for me but weep for yourselves and for your children.
• For behold, the days are coming when they will say,
  • ‘Blessed are the barren and the wombs that never bore and the breasts that never nursed!’
  • Then they will begin to say to the mountains, ‘Fall on us,’ and to the hills, ‘Cover us.’
• For if they do these things when the wood is green, what will happen when it is dry?

First, and this is right before Jesus is nailed to the cross, Jesus expresses concern, not for himself, but for them.

And then he predicts tough times:

• “Blessed are the barren…” sounds like what he said to the disciples on the Mount of Olives just a few days before. Jerusalem will be destroyed by the Romans (happened in 70 A.D.), and things will be nasty:

When you see Jerusalem being surrounded by armies, you will know that its desolation is near. Then let those who are in Judea flee to the mountains, let those in the city get out, and let those in the country not enter the city. For this is the time of punishment in fulfillment of all that has been written. How dreadful it will be in those days for pregnant women and nursing mothers! There will be great distress in the land and wrath against this people. They will fall by the sword and will be taken as prisoners to all the nations. Jerusalem will be trampled on by the Gentiles until the times of the Gentiles are fulfilled. (Luke 21.20 – 24, NIV, emphasis mine)

• “They will say to the mountains, ‘Fall on us…'” sounds like Hosea 10.7, 8, a prediction of the Northern Kingdom’s destruction by Assyria.

Samaria’s king will be destroyed, swept away like a twig on the surface of the waters. The high places of wickedness will be destroyed— it is the sin of Israel. Thorns and thistles will grow up and cover their altars. Then they will say to the mountains, “Cover us!” and to the hills, “Fall on us!” (Hosea 10.7, 8, NIV)

Jesus seems sad because what his own people are doing to him (remember, it was the Jewish leaders that ordered the crucifixion) is going to result in severe hardship, not only for the perpetrators but also for ordinary women – believers.

He was in the world, and the world was made through him, yet the world did not know him. He came to his own, and his own people did not receive him. (John 1.10, 11, ESV)

[Jesus lamented, ] “Jerusalem, Jerusalem, you who kill the prophets and stone those sent to you, how often I have longed to gather your children together, as a hen gathers her chicks under her wings, and you were not willing.” (Matthew 23.37, NIV)