Some Jewish texts are difficult to teach because they demand so much from us and, even more challengingly, our students. They present moral tensions, portray uncomfortable ideas, or raise questions about our faith that sit uneasily with younger thinkers trying to reconcile earlier voices with contemporary values when they feel most comfortable in a space of clear definition. Avoiding these texts can feel easier, but doing so undermines an opportunity for meaningful engagement. When we engage them honestly—balancing yirat shamayim and intellectual integrity—we offer them opportunities for deep learning, not just of content, but of character.

I teach both English and Limudei Kodesh at a Modern Orthodox high school. My students encounter Shakespeare, modern poetry, Nevi’im, and rabbinic commentaries all in the same week, and I see a value in bringing these voices into conversation with one another. In fact, some of the most honest and transformative conversations emerge when Torah and literary texts are placed in dialogue. My goal is not to flatten one into the other, but to let each illuminate aspects of the other: to help students ask better questions, explore competing truths, and wrestle with discomfort without shutting down the conversation. This approach takes different forms.

Jane Austen and Teshuvah

One of my first attempts at this intertextual method came during the Yamim Noraim, when I paired Jane Austen’s Pride and Prejudice (along with Sense and Sensibility) with Jewish texts on teshuvah. At first, the link seemed tenuous: a Regency novel and the mahzor? But the deeper we went, the more the connection resonated. At the heart of both lies the question: can we really come to know ourselves? We focused on Elizabeth Bennet’s turning point: “Till this moment, I never knew myself.” This moment of anagnorisis (a literary term for sudden recognition) mirrors the personal reckoning demanded in Maimonides’ Laws of Repentance and reads like vidui (the confession, which plays a central role in the prayers of Yom Kippur). According to Rambam, true repentance requires not only behavioral change but a direct confrontation with one’s flaws and motives. Teshuvah begins when self-perception shifts.

What made the attempt especially powerful was that neither text made this transformation simple. Elizabeth’s self-awareness is hard-won, and even then, incomplete. Rambam’s standard for teshuvah gemurah (complete repentance)—to face the same situation again and choose differently—is equally daunting. The discomfort in both texts is the point: they show how difficult, how unflattering, and how essential it is to reflect deeply and change honestly. We examined biblical passages speaking about self-reflection and sections from Pirkei Avot on self-scrutiny. We considered Mr. Darcy’s letter as a kind of vidui: part confession, part rationalization, written in hopes of being understood. This raised questions that felt familiar: Is defensiveness always a flaw? What makes an apology feel real? Can growth coexist with pride? Far from softening the Torah’s demands, the novel helped students encounter them more vividly. When read together, Pride and Prejudice and the various Yamim Noraim texts showed how painful, complex, and transformative it is to admit that we were wrong and to begin again. For many students, this was an encounter with teshuvah not as intangible concept, but as narrative of an emotional process. And for me, it confirmed that literature could be a gateway to the most serious kinds of religious conversations that shed light on texts that leave us troubled.

A Christmas Carol and Jonah

In other cases, the Jewish text serves as an anchor. In trying to grapple with the Book of Jonah, for instance, we look at Dickens’s A Christmas Carol to help students track the emotional and moral arc of a character struggling to change. Jonah’s story is famously ambiguous. He runs from his mission, is swallowed by a fish, prays, follows orders, and then ends the book angry under a withered plant. For students used to clearly defined Torah personalities, like certain prophets, this presented a challenge.

We began by examining the story’s structure: the downward spiral into the fish, the turning point of the prayer in the second chapter, and the unresolved ending. We discuss the interpretation that the fish’s belly was a space beyond time, where it is neither night nor day (much like the setting of Scrooge’s transformation), and an idea that reframes the “punishment” as a sacred space for reflection. Jonah’s anger, in turn, becomes more complex. As Erica Brown explores in Jonah: The Reluctant Prophet, his resistance is perhaps not personal stubbornness but theological protest. He cannot accept a world where repentance can erase injustice so easily. This is where A Christmas Carol is further developed. Scrooge, like Jonah, begins in resistance. He is closed-off and indifferent. But unlike Jonah, he is transformed by fear and vision. His teshuvah is public, joyful, and redemptive.

Martin Sable has written about how Scrooge’s journey reflects the Jewish framework of teshuvah: recognition, remorse, restitution. Comparing the two figures helps students explore whether teshuvah must be wholehearted to be valid, and what emotional costs come with accepting mercy. The contrast between the characters also opens up wider questions: What do we do with partial repentance? What is the emotional cost of mercy? And can transformation be authentic if it is incomplete? These are questions many of our students feel in their own lives, and when texts give them room to voice that uncertainty, real learning begins.

Wilfred Owen and Natan Alterman

Sometimes I let the literature lead. When in English lessons we study Wilfred Owen’s Dulce et Decorum Est, the poem’s visceral depiction of war grips students. His portrayal of suffering strips away all glory: a soldier choking on gas, the bitter irony of patriotic slogans. To deepen the conversation, we read Natan Alterman’s Magash Hakesef (“The Silver Platter”), a poem long associated with the founding and cost of the modern State of Israel. Where Owen deconstructs sacrifice, Alterman sanctifies it. The unnamed boy and girl in Alterman’s poem are offered to the nation like a korban (a sacrifice)—silent, nameless, holy. Here, it is Alterman who becomes the counterpoint. We ask: Is this poem glorifying martyrdom, or grieving it? Is the language of sanctity necessary, even dangerous?

Through comparison, students begin to see how national narratives about sacrifice are formed, resisted, cherished, or transformed. Owen mourns with outrage; Alterman with reverence. Both are powerful responses to loss, but their tone, structure, and aim differ sharply. The discussion becomes not just about the poems, but about the societies they speak to and the frameworks they establish.

A Broad Vision of Jewish Learning

These juxtapositions open space for a broader vision of Jewish learning, one in which Torah engages culture not as threat, but as partner. Rabbi Aharon Lichtenstein, in By His Light, models this approach powerfully. While he may not have used the phrase, he espouses something of a textured religious personality, his perspectives on integrating halakha, moral depth, and human culture encourage precisely that, a religious life marked by depth, dynamism, and intellectual honesty. In his essays, references to Yeats, Shakespeare, and Henry More are not ornamental, but essential: they expand the scope of religious imagination or indicate where Judaism goes beyond typical Western thinking.

This model continues to inspire my planning as well. I am currently developing an approach that pairs Shakespeare’s Othello with Jewish texts on lashon hara. In one of his essays on the parasha, Rabbi Jonathan Sacks describes Othello as a compelling literary illustration of the gravity of slander and lashon hara. He recounts how Iago, consumed by resentment, manipulates Othello into believing that his wife Desdemona has been unfaithful. The play unfolds as a slow unraveling of trust and perception, ending in death, grief, and irreversible regret. Othello enacts the teaching that lashon hara kills three: the speaker, the listener, and the one spoken about. Iago speaks carefully, often without direct accusations. His genius and villainy lie in implication and tone, which are no less lethal than outright lies. This offers a powerful entry point for discussing the emotional and communal consequences of careless or harmful speech. My hope is to pair excerpts from the play with suitable Jewish texts (among these the writings of the Hafetz Hayim), to help students explore how speech shapes moral reality. The goal, as always, is not to overlay Torah content onto literature or vice versa, but to allow literature to open new paths into Torah and to make halakhic and ethical questions visible through the human drama of literature.

This approach offers more than just a way to teach texts; it enhances opportunities for students to engage in different ways and contexts in moments of textual uncertainty. It allows us to acknowledge complexity without rushing to resolve it, and to explore difficult ideas with care and variety. When students sense that a question can be held, that certain questions are not just Jewish questions or that the Jewish question goes where the Western question does not, they may be more willing to enter the conversation. And when Torah is studied alongside literature that also asks hard questions, the learning feels both anchored and expansive. It’s not about having answers, but about creating space where serious engagement feels possible.

For educators interested in experimenting with this approach, it’s important to emphasize that you don’t need to be trained in literature to make it work. This is not about academic analysis, but it’s about fostering a conversation between texts. Begin with a Torah passage or episode that feels emotionally or morally complex. Identify the key question it raises: justice, failure, growth, speech. Then ask what other texts—from fiction, poetry, or film—might explore the same theme, whether it complements or contradicts your core text. You don’t need to teach a whole book. Some of the richest comparisons I’ve facilitated came from a single chapter, a soliloquy, or even a line. And you don’t need to provide the answers. Let students read across traditions and respond. Ask: What’s being asked of us here? Does our text demand the same? Where do we locate ourselves in the comparison? Some instances require careful curation and moderation to avoid straying too far from the lesson’s purpose, but others may need that exploration. It all depends on your goal.

Pairing Torah and literature does not weaken tradition, but reveals its vitality and proves how essential it is to engage it meaningfully. It teaches students that Torah can hold their questions, that discomfort is not a threat to faith but part of its growth. The classroom, after all, is not just a place to transmit knowledge. The classroom is a beit midrash which offers a place for both the mind and heart and a space where reverence and resistance can not only exist side by side, but mutually deepen one another. In this integrated space, students learn not only how to think critically, but how to experience Torah as both anchor and catalyst.