I will surely hide My face in that day for all the evil which they shall have wroughtWhat does the verse mean "I will surely hide My face"? Doesn't that undermine the sense of connection and relationship we hold with Hashem? There is no worse punishment that a Jew can face than not feel the closeness of Hashem.
הַסְתֵּר אַסְתִּיר פָּנַי בַּיּוֹם הַהוּא, עַל כָּל-הָרָעָה, אֲשֶׁר עָשָׂה
Devarim 31:18
Dwells In Our Impurity
The Slonimer Rebbe explains that this is not a dire warning, but more of a test, that a Jew must believe that EVEN a wall of iron does not stand between us and our father in heaven, for HaKadosh Baruch Hu evens dwells in our impurity.
A Jew is elevating and there is no power that can disconnect us from our father in heaven, as long as we don't want to disconnect. Rather all these mentions of 'hiding' they are only metaphorical, like the father that sometimes distances himself from his son, but never abandons him even for a moment, and constantly watches over him.
This is only to test his son, that without thinking, his son may believe that his father has abandoned him. Rather the smart son knows that there's no way that his father would abandon him, and truly knows that his father will always watch over him.
This is the essence of the idea that a Jew who has even committing the most dire prohibition, should he not be able to open his heart and pour out his thoughts and prayers to Hashem? A Jew must always believe that HaKadosh Baruch Hu always is accepting of us.
The Slonimer Rebbe brings an allegory from the Baal Shem Tov to help explain this concept.
The King's Illusion Walls
"A king, by magic, surrounded his palace with many walls. Then he hid himself within the palace. The formidable walls were arranged in concentric circles, one inside the other, and they grew increasingly larger-- higher and thicker-- as one approached the center. They had fortified battlements and were manned by fierce soldiers who guarded from above; wild animals-- lions and bears-- ran loose below. All this was so that people would have proper awe and fear of the king and not all who desired to approach would be allowed to do as they pleased.
"The king then had proclamations sent throughout the kingdom saying that whoever came to see him in his palace would be richly rewarded and given a rank second to none in the king's service. Who would not desire this? But when many came and saw the outer wall's awesome size and the terrifying soldiers and animals, most were afraid and turned back. There were some, however, who succeeded in scaling that wall and fighting past the soldiers and animals, but then the second wall loomed before their eyes, even more imposing than the first, and its guards even more terrible. Seeing that, many others turned back.
"Moreover, the king had appointed servants to stand behind the walls to give money and precious stones to whoever got beyond each wall. Those who had crossed one or a few walls soon found themselves very rich and satisfied with what they had gained from their efforts; so they too turned back. For one reason or another, either from fear at the increasing obstacles or satisfaction with the accumulated rewards, none reached the king ...
"Except for the king's son. He had only one desire: to see the face of his beloved father. When he came and saw the walls, soldiers, and wild animals, he was astonished. He could not understand how his dear father could hide himself behind all these terrifying barriers and obstacles. 'How can I ever reach him?' he thought. Then he began to weep and cried out, 'Father, Father, have compassion on me; don't keep me away from you!' His longing was so intense that he had no interest in any rewards. Indeed, he was willing to risk his life to attain his goal. By the courage of his broken heart, which burned to see his father, he ran forward with reckless abandon and self-sacrifice. He scaled one wall and then another, fought past soldiers and wild animals. After crossing the walls, he was offered money and jewels, but he threw them down in disgust. His only desire was to see his father. Again and again he called out to him.
"His father the king, hearing his son's pathetic cries and seeing his total self-sacrifice, suddenly, instantaneously, removed the walls and other obstacles. In a moment they vanished as if they had never existed. Then his son saw that there were no walls, soldiers, or animals. His father the king was right before him, sitting on his majestic throne, while multitudes of servants stood near to serve him and heavenly choirs sang his praises. Gardens and orchards surrounded the palace on all sides. And the whole earth shone from the king's glory. Everything was tranquil, and there was nothing bad or terrible at all. Then the son realized that the walls and obstacles were a magical illusion and that his father the king had never really been hidden or concealed, but was with him all the time. It was all just a test to see who truly loved the king.
Walls of This World
This allegory comes to describe the world we live in, that everything we encounter is like a wall - all the distractions of this world standing between a Jew and Hashem. Yet none of these walls are as strong as the wall that is formed in the heart of Jew that feels far from Hashem.
When the Yetzer Hara acts to seduce a Jew, the Yetzer Hara is not interested in the Jew committing the specific indiscretion, but rather bringing the Jew to a state of feeling hopeless. This is worse than the sin itself, for there is a way to recover from the action, but the state of hopeless leaves one disconnected from Hashem, without a feeling that there is a way back.
Day of Judgement
This is the main preparation for Rosh Hashana and Yom Kippur. For not only does a Jew need to recognize his sins, and how large they are, but also to truly believe that even an iron wall can not stand between him and Hashem. For a Jew is never lost, for we are Hashem's children.