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While making the excruciating trip up the Via Dolorosa on the path to the Crucifixion, Jesus noticed a great company of women following sorrowfully. Jesus took time to stop and declare:

Daughters of Jerusalem, weep not for me, but weep for yourselves and for your children. For, behold, the days are coming in the which they shall say, "Blessed are the barren and the wombs that never bare, and the paps which never suck.
Then shall they begin to say to the mountains "Fall on us," and to the hills, "Cover us." For if they do these things in a green tree, what shall be done in the dry?" (Luke 23:28-31)

Is this the same announcement made a few hours earlier to the disciples in the Olivet Discourse? (Matthew 24; but also read chapter 23 for context.) But in a summary form? So, not only the men folk (apostles), but the women also, were warned about the coming disaster upon the City and its Temple?

As a corollary, would this have opened up urgent conversation between the men and women on this matter? Would the Christian families, then, "be on the same page" in preparing for escape? Was this a thoughtful, intentional act on the part of Jesus?

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This passage does not seem to be a summary of Olivet Discourse - at least not intentionally so. The most direct connection to Matthew 25 is the emphasis on those who do not marry being better off than those who do. In Luke, those who do not give birth are blessed. In Matthew the wise virgins who stay alert receive the Bridegroom while the foolish ones who leave their posts are rejected. But in fact, these two passages carry different messages. In Luke, virginity itself results in being blessed. In Matthew virginity has to be coupled with wisdom, which means staying alert to receive the Bridegroom.

Matthew 24-25 presents an apocalyptic vision of the end times covering two chapters. It has been called Matthew's "Small Apocalypse." Luke 23 barely touches on this theme in the verses cited by the OP. A better parallel to Matthew's treatment of it in the Olivet Discourse is found in Luke's "Little Apocalypse" found in Luke 21:5–19.

The OP also asks about what kind of discussions Jesus' statement would have stimulated between men and women. That is hard to tell. I tend to think it was directed to women, not men. It harkens back to another saying reported only by Luke:

Luke 11:27-28

While he was speaking, a woman from the crowd called out and said to him, “Blessed is the womb that carried you and the breasts at which you nursed.” He replied, “Rather, blessed are those who hear the word of God and observe it.”

Few of Jesus' male followers seem to have been present (see vs. 27). But it is true that Paul advises this readers in 1 Cor. 7 to prefer virginity. Whether this is based on a tradition arising from from what Jesus said here is impossible to say.


ADDENDUM:

This link compares Luke's small apocalypse to that of Matthew. It notes that while there are many parallels:

  • Luke omits the Jewish eschatological language of the ‘birth pangs’ of the new age, the kingdom of God, breaking into this age (Matt 24.8, Mark 13.8).
  • There is no mention of testifying ‘to the Gentiles’ (Matt 24.24, also mentioned in the parallel in Matt 10.18) or being hated ‘by all Gentiles’ (Matt 24.9).
  • There is no mention of ‘false prophets’ (Matt 24.11), a concern echoing the history of Israel.
  • Where Matthew and Mark allude to the ‘abomination that brings desolation’ of Daniel 9.27, 11.31 and 12.11, Luke 21.20 makes a more prosaic allusion to the Roman armies besieged then destroying Jerusalem, something Jesus has already alluded to in Luke 19.43–44.
  • He omits the allusion to Zech 12 in Matt 24.30 that ‘all the tribes of the earth will mourn’.

This particular author believes that Jesus' teaching in here is not eschatological but predicts the events that would happen in Jerusalem around 70 c.e.

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  • @ Dan Fefferman - "Matthew 24-25 presents an apocalyptic vision of the end times covering two chapters." (?) This could not be so! Jesus Himself said that most of Matthew 24 would happen within that "generation" of time. (Events leading up to and including the Destruction of Judea.) Whereas Matthew 25 dealt with the "unannounced" Second coming: a stark contrast. The Second Coming at the "Last Days" of the world (or End times) would be totally secret. We have Jesus word on this. Hardly an "apocalypse"!
    – ray grant
    Commented Jan 3 at 21:57
  • @ Dan Fefferman - I realize some call this using the word "Apocalypse." But this is misleading, causing people to skip over the immediate import of Jesus's warning right then. This is why Psephizo.com added: "All this confirms that the content of our reading is not about 'distant end times' but was going to be immediately relevant to Jesus's audience in the period up to the fall of Jerusalem." --- The main topic, then, to the women was not marriage or virginity, but coming tragedy to all the women in the near future, no matter their situation. It must have broken Jesus' heart to know it!
    – ray grant
    Commented Jan 6 at 21:32

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