In the discussion of Yom Kippur that appears in The Human and the Infinite, a compendium of translated essays by the late Rav Shagar (Rabbi Shimon Gershon Rosenberg z”l), Rav Shagar describes the difficulty of truly feeling awe during the Days of Awe. A serious attempt to grasp the Absolute during this time-period will, according to Rav Shagar, invariably lead to a kind of anxiety. This anxiety, which may at times be confused with piety, is not actually religiously productive. It can even cause deep despair: “there is an essential paradox in the attempt to understand the Holy with the limited faculties at our command – words, deeds, etc… This paradox, then, fuels despair in the believer.”

The solution to this despair, for Rav Shagar, is a healthy dose of irony. Irony, he reminds us, should not be confused with cynicism: “Cynicism ridicules its subject, presenting it as pathetic. Irony, on the other hand, is a delicate instrument able to grasp two different sides of an issue at once. It can understand the true gravity of a subject, while at the same time showing up its limitations.” Rav Shagar explains that “[i]rony emphasizes new and different possibilities – even for those subjects that are seemingly absolute. The reflectivity of irony can breathe a new spiritual life into the stolid…. The ironic stance adds a lighter side to the religious act and so enlivens it. The religious can no longer stay fixed and see itself, as it were, as its own absolute. The ironic allows the religious to become what it should be.”

This spiritual interpretation of irony may come as a surprise to anyone who is familiar with irony in its contemporary guise, as a form of hipster detachment. Yet for Rav Shagar, irony may be one of the deepest avenues we have for connecting with God in a world where it’s impossible to escape our questions and doubts. Irony allows for the expression of two things at once – reverence as well as a sense of distance. The playfulness and fluidity associated with irony are also healthy in order to maintain a sincere religious disposition in a postmodern world. For Rav Shagar, the progenitor par excellence of this ironic mode is Shmuel Yosef Agnon, the great Israeli writer and Nobel laureate, whose stories and novels engage with religious life in a way that is impossible to characterize as either “religious” or “secular.” Agnon’s writings radiate sincerity as well as doubt, and while Rav Shagar suspects that Agnon’s “ironic gaze” prevented him from being “counted among those in true awe of judgment,” Rav Shagar still believes that this irony is a positive thing from a religious point of view. The ironic gaze that Rav Shagar identifies here, to me, seems connected to the broader notion of a literary sensibility more generally – but to explain this would require a longer discussion.

Around this time last year, Tablet magazine published a beautiful Yom Kippur story by Agnon, which was written in 1951 but was recently translated by Rabbi Jeffrey Saks. The original Hebrew title for the story was “Pi Shnayim,” translated as “Twofold.” As the title indicates, the story is filled with doublings, or repetition: the narrator vacillates between the Yom Kippurs of his past and his present, between his dreams and his reality. He considers the Yom Kippur of the heavens and that of the earth, and he even contemplates keeping Yom Kippur for a second day, as some Chasidim were rumored to have done. The main doubling of the story occurs in the form of two tallitot that the narrator holds dear, one tallit that was wrapped around a Torah scroll that was sent to him from his native Germany, and one that he purchased when he moved to Jerusalem, to better fit in with the people around him. He loves these tallitot so much that is he is unable to choose which one to wear, and as a consequence of reminiscing upon his memories that he associates with these tallitot, he misses neilah on Yom Kippur.

There is a dimension of the story that evokes the “Before the Law” parable from Franz Kafka’s novel The Trial. Agnon’s narrator keeps trying to enter the synagogue on Yom Kippur, but something inscrutable prevents him from doing so, until it is too late. Yet the fundamental sense of despondency that is present in Kafka’s parable is missing from Agnon’s story. Agnon’s sense of paralysis stems from feelings of love for his two tallitot, from a kind of nostalgic affection for his tradition. His memories of Yom Kippur are filled with sublime beauty, at the same time as he explores his inability to connect with the service, or even physically enter the sanctuary. He reflects upon his experience in the following manner:

“The synagogue was jam-packed. Even people who do not attend all year long came and stood, with tallit around their necks and machzor in hand, and the reflection of the holiness of the day shone in their faces. Standing next to them were their sons and daughters. The hearts of the children were still pure – this thing we see, what is it? Pleasant or unpleasant?”

The speaker is not sure to what to make of his Yom Kippur memories, are they pleasant or unpleasant? There are times in the story when his sense of the limitations of the day is manifest more strongly, for example: “from inside the synagogue one could hear the chazan’s melodies, those melodies that do not penetrate one’s heart.” At other times the narrator is bowled over by the power of Yom Kippur and its symbolism, “How I loved the night of Yom Kippur! The Gates of Heaven are open and God Himself, as it were, bows down to hear the prayers of Israel. He needn’t bow, since He knows the heart of every man, but out of affection for the Jewish people, He bows down, like a father who inclines his ear to his little boy.” Yet much of time, Agnon’s narrator integrates these two sensibilities of skepticism and sincerity, with the precise kind of ironic vision that Rav Shagar describes.

In reflecting upon Agnon, Rav Shagar confesses that he believes Agnon’s connection to Judaism to be mostly “aesthetic,” that it is not dependant upon belief in God as much as a heightened perception of beauty and symbolism that enhances his appreciation of humanity and the Jewish people. Yet Rav Shagar still sees spiritual significance in Agnon’s ironic mode, and he believes that the way in which Agnon can convey competing visions at the same time has great religious value. Perhaps Rav Shagar’s interpretation can even help us make sense of one enigmatic passage toward the end of the story:

“If a person has two of the same thing, while taking one he thinks of the other, while taking the other he thinks of the first, and his heart is split and his mind confused. But I, in His blessed mercy, when I wrap myself in one tallit, my mind is at peace.”

The reason these two sentences are confusing is because in fact, the narrator of “Pi Shnayim” is torn between the two tallitot that he owns, and between all sorts of poles. Repeatedly throughout the story we are shown how he is two (or even more) things at once. He says that he is at peace when he wraps himself in one tallit, but how is he meant to get to that point if even he can’t even make a decision of which one to wear in the first place? It is all very ironic. Yet for Agnon, this conflict does not leave the speaker mired in anxiety but instead, a light touch of irony can actually move the story, and the religious experience, forward, allowing him to be “at peace” in his tallit even while choosing between the two is impossible.

Agnon’s story, “Twofold,” is available here in English translation.