It turns out, this struggle is ancient. The Yalkut Shimoni, a compilation of rabbinic interpretations of the Bible, preserves a powerful midrash—an interpretive story—on the verse "Comfort, oh comfort My people" from Isaiah 40:1. (We're looking at section 443 from the collection on Nakh, that is, the books of the Prophets and Writings). And it reveals a profound truth about grief, trauma, and the very nature of divine comfort.

The midrash begins with a question: Who is truly in need of comfort? Is it the husband who lost his wife? The text suggests it’s deeper than that. Zion, representing the people of Israel in exile and mourning, is likened to someone dwelling in darkness, "like those long dead," as Lamentations 3:6 puts it. But the Yalkut Shimoni asks, isn't it God who we should be comforting?

The text then unfolds through a series of analogies, each more poignant than the last. It’s like a person whose children are taken captive, or whose house has burned down, echoing Jeremiah 10:20 and Kings II 25:9. It's like a person whose vineyards have been cut down (Isaiah 5:7), or a shepherd whose flock has been ravaged by a lion, as Jeremiah 50:6 describes. In each case, the question remains: to whom do we offer comfort, if not to the one who has suffered the greatest loss? In this case, according to the midrash, that's God.

But here's where it gets really interesting. God sends the prophets to comfort the House of Israel. One by one, Hosea, Joel, Amos, Micah, Nahum, Habakkuk, Zephaniah, Haggai, Zecharia, and Malachi approach her, each bearing a message of hope and restoration.

But Israel rejects them all.

Each prophet offers a vision of future redemption, quoting their own prophecies, but Israel throws their words back at them, saying, "Yesterday you told me one thing, and now you say another – which should I believe?" It's a powerful indictment of empty promises and the difficulty of accepting comfort when the pain is still raw. As Job 21:34 says, "Why then do you offer me empty consolation? Of your replies only the perfidy remains." Ouch.

Then comes a series of attempts by our great ancestors: Abraham, Isaac, Jacob, and Moses, to comfort Jerusalem, as well. But these attempts also fail. Abraham reminds her of the binding of Isaac, saying: “On the mount of God there is vision” (Genesis 22:14)? Isaac reminds her of Esau's wickedness. Jacob reminds her of his vision of the ladder, saying, "'This is none other than the abode of God' (Genesis 28:17)?" And Moses reminds her of the curses in the Torah, as it is written: “Wasting famine, ravaging plague” (Deuteronomy 32:24). She rejects them all, saying their actions or legacies have contributed to her suffering.

Finally, the prophets cry out to God, "Master of the Universe—she does not accept our comfortings!"

And God responds with the most profound statement of all: "I and you shall walk to comfort her." God recognizes that only the one who has shared in the suffering can truly offer solace. "Comfort O comfort my people," God says, "Comfort Her, O comfort her, my people."

The midrash then delves into a remarkable self-indictment by God. God says it is not fitting that anyone other than God should walk to comfort Jerusalem, because God transgressed what is written in the Torah: "you must not work your firstling ox” (Deuteronomy 15:19) and Israel God called “My first-born son” (Exodus 4:22).

God acknowledges having seemingly violated God's own laws: hating kinsfolk, selling the people into the hands of idol-worshippers (Deuteronomy 32:30), and venting anger upon them (Lamentations 4:11). God even acknowledges igniting the fire that consumed the Temple, referencing Lamentations 1:13, but promising a future fire of protection, as described in Zechariah 2:9.

God asks Jerusalem, "My Daughter, why all of this anger?" And Jerusalem responds, "Is it not justified that I be angry? You dispersed me among the nations, cursed me, and whipped me… and despite all of this, I sanctified Your great name!"

The dialogue continues, with God acknowledging Israel's transgressions as well, citing Ezekiel 22:7, 22:9, and Hosea 4:2. But ultimately, God assures Jerusalem that redemption is at hand, promising to avenge her oppressors in front of her very eyes, as Isaiah 49:26 prophesies.

The midrash concludes with a powerful analogy: God's comfort will be like that of Joseph towards his brothers, who had wronged him so greatly. Despite their betrayal, Joseph reassured them, speaking kindly and providing for them. “And so, fear not. I will sustain you and your children.” Thus he reassured them, speaking kindly to them” (Genesis 50:21).

Finally, the text draws a parallel between the prophecies of Jeremiah and Isaiah: where Jeremiah lamented, "There is none to comfort her" (Lamentations 1:2), Isaiah heals with the promise: "Comfort, oh comfort My people" (Isaiah 40:1).

So, what does this all mean for us today?

Perhaps it's a reminder that true comfort isn't about offering quick fixes or empty platitudes. It's about acknowledging the depth of the pain, validating the anger and grief, and offering a presence of shared suffering. It's about recognizing that sometimes, the one who needs comforting the most is the one who feels responsible for the pain in the first place. And it's about the long, slow, messy, and deeply human process of healing, a process that requires both divine compassion and the courage to confront our own shortcomings.