The days of destruction are days of weeping – "She weeps bitterly in the night and her tear is on her cheek; she has no comforter." Even the Holy One, Blessed be He – who generally weeps only in His inner chambers, while outwardly "strength and joy are in His place" – weeps openly on the day of destruction (Chagigah 5b). On one hand, the weeping comes as a result of the destruction, but on the other hand, it is itself the cause of the destruction: "'And the people wept that night [following the words of the spies]'… The Holy One, Blessed be He, said to them, 'You wept a gratuitous weeping, and I will establish for you a weeping for generations.'"
But will weeping be eliminated from the world with the coming of Mashiach, may it be speedily in our days? Weeping is a deep and internal experience – its place is in God’s inner chambers, and also in the inner chambers of the Jewish heart, whose personality is composed of weeping and joy (in the language of the Zohar: "Weeping is fixed in my heart on this side, and joy is fixed in my heart on that side." Weeping even has its root in the yechidah of the soul, above the root of joy in the chayah of the soul). The inner weeping and longing are also a source for the infinite wellspring of Torah innovations – "The secrets of Torah are only given to one whose heart worries within him." Therefore, it seems that the inner point of weeping will remain even in the redemption. How so?
Knowing How to Weep
Weeping expresses a non-acceptance of the existing situation, and indeed, "The righteous have no rest, neither in this world nor in the World to Come" – there is always room for progress, and one can always weep over the present state. To illustrate: The Lubavitcher Rebbe wept and cried out "Ad mosai?!" ("Until when?!"), and demanded vigorous progress towards redemption. Will a personality like the Rebbe 'transform' into a calm and complacent one during the time of redemption? On the contrary! The Rebbe always reiterated that "One who has a hundred wants two hundred" – one should never be content with what exists and should always aspire for more.
Weeping is a point of inner discontent and criticism that always pushes forward – even if everything is good, it can be even better. From this, we can also understand who is permitted to weep – weeping is justified only when it is accompanied by a vision of the hoped-for goal. On one hand, the future vision evokes weeping in the face of the lacking present, and on the other hand, it guards against weeping of despair and discouragement. The rectified weeping 'dissolves' the present for the sake of a better future.
The "gratuitous weeping" in the desert was not accompanied by a vision of a good future, but rather the opposite – it caused entrenchment in the present and fear of progressing towards the future. Positive "weeping for generations" after the sweetening of redemption, is weeping that advances from generation to generation, from the present generation to another, more wondrous generation of Mashiach and redemption. It evokes the revelation of ever deeper layers of "secrets of Torah" in the "new Torah that will come forth from Me."
Dissolving the Present
This perspective also explains the true role of weeping during exile, and in essence, the role of the destruction and exile themselves: Just as weeping is meant to dissolve the present for the sake of a better future, so too the destruction itself is actually "demolishing in order to build" – to rebuild the kingdom of Israel and the Holy Temple in a much more redemptive and complete manner.
Indeed, in exile there is a difficult and sad time gap between destruction and rebuilding (and only in the most hidden point of the soul does the weeping unite with the sharp and primordial point of joy). In the soul, exile is a state of pride and self-importance, where the destruction of one's present state hurts and causes difficult and bitter weeping. But for the righteous, who have no rest neither in this world nor in the World to Come, this movement is smooth – the weeping is an inner nullification, a nullification of the 'form of the righteous' in the present in order to progress to a more illuminated and clear 'form'.
Thus in redemption – and this is how one should live as we approach redemption – the weeping over the present merges with the revealed joy over the wondrous future that arrives immediately (without an intermediary crisis period), until it becomes difficult to distinguish between tears of sorrow and tears of joy: "With weeping they shall come, and with supplications I will lead them; I will cause them to walk by rivers of waters in a straight way, wherein they shall not stumble."

