That feeling, that journey, is at the heart of a beautiful passage from Shir HaShirim Rabbah (Song of Songs Rabbah) 5, which opens with the evocative line: "Who is that ascending from the wilderness, leaning upon her beloved?"

This verse from Song of Songs 8:5 becomes a springboard for exploring Israel's relationship with God, the giving of the Torah, and the ever-present tension between promise and failure. It’s quite a journey, so let’s dive in, shall we?

The text immediately grounds us in the stark reality of the wilderness. "Who is that ascending from the wilderness?" It reminds us that Israel's ascent, decline, and even death, are all intertwined with this desolate space. As it says in Numbers 14:35, "In this wilderness they will expire, and there they will die." The wilderness isn't just a physical location; it's a metaphor for the trials and tribulations that shape a nation’s destiny.

But there’s hope! The verse continues: "Leaning upon her beloved." What does it mean to lean? Rabbi Yoḥanan offers a beautiful interpretation: it's about resolving sections of the Torah and issues of the kingdom in the future. He cleverly points out that the Hebrew word for "leaning" – mitrapeket – can be rearranged to suggest matir perek, "resolving a section." The idea is that Israel, in its relationship with God, will ultimately resolve all the questions related to Torah and reestablish its monarchy. It’s a powerful vision of restoration and renewal.

Then comes the image of the apple tree: "Under the apple tree I roused you." Pelatyon of Rome, in a fascinating exposition, equates the apple tree with Mount Sinai. He says that Mount Sinai was detached and positioned in the supernal heavens, and Israel was situated beneath it, as it says in Deuteronomy 4:11, "You approached and stood beneath the mountain." Why an apple tree, though? Well, just as an apple tree produces fruit in the month of Sivan, so too, the Torah was given in Sivan.

There’s another, even more profound reason why an apple tree is used. Most trees grow leaves before fruit, but the apple tree is unique – it produces fruit first. This is seen as a parallel to Israel's declaration at Sinai: "Na'aseh v'nishma" – "We will do and we will hear" (Exodus 24:7). They committed to performing God's commandments before even hearing them. That’s faith! And, according to the text, God was so impressed that He essentially said, "If you accept My Torah, great! If not, I’ll drop this mountain on you." Talk about high stakes!

The passage then takes a poignant turn with the line, "There your mother was in travail with you." Rabbi Berekhya offers a moving analogy: Imagine someone who barely survived a dangerous ordeal. A friend might say, "Wow, you went through so much! It's like you were just born, a new creation." Sinai, in this light, wasn't just a moment of revelation; it was a rebirth, a moment of intense spiritual and national formation.

Rabbi Abba bar Kahana delves deeper into the idea of trauma and consequence. He connects "travail" (ḥibela) with "collateral taken from her" (ḥubela). The "travail" occurred when the Israelites said, "Everything that the Lord spoke we will perform and we will heed" (Exodus 24:7). But the collateral was taken when they turned to the Golden Calf, proclaiming, "This is your God, Israel" (Exodus 32:4). It's a stark reminder that even after a profound spiritual experience, we are still vulnerable to making mistakes, and that those mistakes have consequences.

Rabbi Shimon ben Yoḥai adds another layer: the weapon given to Israel at Ḥorev, he says, had the ineffable name of God etched upon it. But when they sinned, it was taken away. Rabbi Aivu and the Rabbis debate whether the name simply faded on its own or if an angel had to remove it. Regardless, the message is clear: sin diminishes our connection to the divine.

The text concludes with a series of lamentations. Rabbi Shimon ben Ḥalafta cries, "Wretched is the bride who sins under the wedding canopy!" Rabbi Yoḥanan mourns that they lost the good counsel given at Sinai, citing Proverbs 1:25, "You hollowed all my counsel." Rabbi Yehoshua of Sikhnin, in the name of Rabbi Levi, recalls Deuteronomy 9:8, "At Ḥorev you provoked the Lord." He says God came to bless them but found their palate pierced and unable to hold the blessing. Rabbi Levi adds that they made God mourn over them.

So, what are we left with? This passage from Shir HaShirim Rabbah isn’t just a commentary on a verse from Song of Songs. It’s a meditation on the complex relationship between God and Israel, a relationship marked by moments of profound connection and heartbreaking betrayal. It’s a reminder that the journey through the wilderness is ongoing, that we are constantly being tested, and that even after moments of great inspiration, we must remain vigilant in our commitment to Torah and to one another. And perhaps, most importantly, it teaches us that even in our moments of failure, the possibility of renewal and restoration always remains.