Luke 21:23 says, “But woe to those who are pregnant and to those who are nursing babies in those days! For there will be great distress in the land and wrath upon this people.” Now let’s read Luke 23:28-29, “But Jesus, turning to them, said, ‘Daughters of Jerusalem, do not weep for Me, but weep for yourselves and for your children. For indeed the days are coming in which they will say, Blessed are the barren, wombs that never bore, and breasts which never nursed!”

I’m glad to see you making a connection between these two passages, for in them the Lord Jesus is speaking prophetically of Jerusalem being invaded by Roman armies and the terrible destruction (to property and human life) that would take place because of their rejection of Him as the Messiah. In Luke 21:23 He says, “in those days” and in 23:29 He says, “the days are coming.” Those “days” were fulfilled in 70 A. D. when the Roman armies, under the leadership of General Titus, besieged the city, killing many and leading others into captivity. In Luke 21:20-22 they are warned of this siege and what they were to do, “But when you see Jerusalem surrounded by armies, then know that its desolation is near. Then let those who are in Judea flee to the mountains, let those who are in the midst of her depart, and let not those who are in the country enter her. For these are the days of vengeance, that all things which are written may be fulfilled.” It is reasonable to assume that many took these warnings to heart and thus they did attempt to “flee to the mountains” for protection. This escape would be very difficult for pregnant women and nursing mothers and thus the Lord pronounces a WOE on them (in 21:23) and a BLESSING on those women with barren wombs and with breasts that never nursed (in 23:29).

We could end our meditation there, but I want to point out something in Luke 21:24. The Lord goes on to say, “And they will fall by the edge of the sword, and be led away captive into all nations. And Jerusalem will be trampled by the Gentiles UNTIL THE TIMES OF THE GENTILES ARE FULFILLED.” Jesus is obviously teaching them that Jerusalem will suffer again in the future from Gentile armies “until the times of the Gentiles are fulfilled.” What is meant by “the times of the Gentiles” and when will those times be fulfilled? It is a fact that Jerusalem (and the whole nation of Israel) has been under some kind of Gentile rule since the invasion of Jerusalem in 586 B. C. by the Babylonians. They too besieged the city of Jerusalem, killing many and taking others into captivity. I believe the “times of the Gentiles” began then. Many invasions of Jerusalem have taken place and the Jews have been governed by Gentile rulers. The siege that occurred in 70 A. D. is a foreshadowing of another siege which will occur during the future seven-year Tribulation Period when Jerusalem will be attacked again and its residents will be warned to flee to the mountains (see Matthew 24:15-22 along with Zechariah 14:1-2). Yet this will be the LAST INVASION OF JERUSALEM, for at the end of Tribulation the Lord Jesus will return in power and glory to destroy the invading armies and to rescue believing Jews who are waiting for His coming (see Zechariah 14:3-4; Matthew 24:29-31; 25:31-32; Revelation 19:11-21). His glorious coming and deliverance will bring the “times of the Gentiles” to an end, for He will smash to smithereens their kingdoms and establish His own kingdom in peace and righteousness (see Daniel 2:34-36 where Nebuchadnezzar was given a vision of the end of the “times of the Gentiles” and Daniel interpreted it in verses 44-45).  (DO)  (509.1)