Does G-d regret sending us into exile? And if he does, why doesn't He redeem us?
The “regret” is to remind us that exile is temporary and not our true condition.
According to a saying of our sages (Sukkah 52b) there are four things that G-d regrets having created. One of them is exile. However, as the verse states, “G-d is not a human being who regrets.” A human being does not know the future outcome of his actions and can thus have regrets when his actions bring unwanted results. However, G-d does not have this limitation.
We must interpret the word “regret” in a different sense. Exile is something that G-d created regretfully, reluctantly. It was never intended to be permanent, but was created with the intention of eventually being nullified completely. The exile is only a transition period leading up to a glorious future, in which the negative effects of exile will be erased completely. It is important for us to remember this constantly: Exile is not the true state in which G-d desires His people to be.
Our sages taught us about this regret for two reasons:
a) We should not come to be satisfied with the state of exile, but we should remember that it is not a positive state: “Because of our sins we were exiled from our Land”;
b) We should not be daunted by the darkness of exile, nor driven to despair. We know that the exile is not a substantial reality, and it will ultimately dissolve. At every moment, we should keep in mind that the exile is only temporary.
Especially in our time, we are already at the threshold of Redemption. Knowing that the exile is in its final moments gives us courage and strength to withstand the final challenges as we enter the era of Moshiach.
(Bamidbar 23:19. Sukkah 52b. Yerushalmi Taanit 3:4. Likutei Sichot vol. XXIV, p. 165. From Exile to Redemption, p. 27)