In the instruction of Biblical or Rabbinic texts, it is quite common for teachers to experience apparent conflicts between the values arising from the texts and the prevailing values of their students. Teachers may feel torn between their loyalty to Jewish tradition that they are expected to impart and their personal and/or cultural identification with the students entrusted to their care. It is my contention and experience that the sharper or more painful the apparent conflict between the values of a text and the values of students, the greater the educational potential. However, teachers need to carefully consider how their own value-orientational ambivalence is playing a role in the educational dissonance—are we really dealing with “troubling texts,” or are we dealing with troubling troubles with texts?

I’ve been teaching for forty years, mostly to day school graduates. And I’ve noticed something surprising: very few of them have had real educational experiences exploring who God is—or what kind of relationship we’re meant to have with Him. They’re taught about Judaism, Torah, Halakha—but not God.

I won’t explore why that’s the case here, but I do want to talk about the consequences.

We live in a world shaped by beliefs. Beliefs build our reality. They can uplift and energize us—or drain and depress us.

Many people view traditional religious and modern critical orientations to Tanakh study as mutually exclusive… Yet, presenting these two approaches as oppositional, with only one holding a claim to the “real” truth, forces students to choose between the curiosity of their minds and the yearnings of their souls, rather than cultivating and nourishing both aspects of their personhood as fully committed Jews living in the modern world. In its best form, Jewish education should involve teaching critical academic and traditional religious perspectives alongside one another, so that students can see the value of both approaches in uncovering the Tanakh’s multivalent meaningfulness and come to embrace the texts of their heritage “with all their hearts, minds, and souls.”

In my mid to late teens, I became very attached to the study of Gemara. That passion continued for me until, as a twenty-something, I began teaching it to high school students. I soon came to the realization that I did not understand the Gemara in a way that allowed me to successfully transmit its meaning to others. My cultural and religious connection to Gemara had been strong, but not because its contents were fully clear to me. In fact, coming to this realization, I stopped teaching Gemara for a while.Years later, I fell in love with Gemara again. Now, I love learning difficult segments in the Gemara. These are not necessarily morally or ethically disturbing texts. For me, difficult texts are those where meaning-making is not simple; where, as a learner, I will ask: ”What is this Gemara trying to say and why is it here at all?”

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.

On 22 July 1946, a massive explosion ripped through the King David Hotel in Jerusalem, leaving 91 people dead, dozens injured, and significant damage to the building itself. Although all three paramilitary organizations operating in the Yishuv had known about this event beforehand, the Irgun was solely involved in planning and executing the attack. This bombing is a critical moment in the history of modern Israel, exemplifying the desperate lengths to which Jews in Palestine were willing to go to confront the British through increasingly military means. At the time, the bombing of the King David Hotel was condemned by many, including the international press and even prominent figures such as Chaim Weizmann.

For the final unit assessment of our 12th grade Jewish Studies elective called “Love, Gender, and Relationships,” students had to address the prohibition of same-sex intimacy found in Leviticus 18:22. They could either explore the inclusion of this text in the Yom Kippur Minha Torah reading or respond to a (fictional) friend’s request for advice regarding Jewish practice and same-sex relations. Gabby—a dedicated student who had never missed a deadline—requested an extension because she cried every time she sat down to write.

This article is neither a record of success nor of unmitigated failure. It is a reflective description and evaluation of my experience, which I see as part of my own professional growth and which I share in the hope that it will be of help to other teachers. I should add the caveat that this reflection is happening much too soon for reliability. My standard line to students is that I judge my teaching by the condition of their souls ten years afterward (and I love it when they call to let me do that).Nearly three decades ago, I taught the book of Jeremiah in a Modern Orthodox high school. I identified ways that the text might challenge my students and planned my teaching around them.

It is impossible to learn and teach Torah without encountering texts that relate to women in challenging ways. Contemporary conceptions of women’s roles and rights chafe against stories and laws in the Tanakh and Talmud, the historical development of halakha, normative prayer practices, and underlying assumptions in philosophical works. In this brief article, I do not attempt to soothe these tensions—that is far too great a task! Rather, I seek to offer the reader three conceptual frameworks—hashkafot, if you will—through which we tend to approach this tension in Orthodox day schools. Each hashkafa is described in the full-throated voice of a proponent of that lens. Then, I discuss some potential tradeoffs of using each conceptual framework in a Judaic studies classroom.

Teachers of Torah texts in the day school setting are bound to encounter a text that contains content that is difficult to teach. It can be especially difficult when the text seems to be working from a framework of values or interests that are distant from the current moment. Or, it may just be too heavy a lift to explain to students what a particular text or story was trying to accomplish when the students only notice a bothersome turn of phrase. With attention paid to context and subtext, a text that initially seems troubling may show depth that makes teaching it not only possible, but essential. An example of this can be found on Kiddushin 49a-b. The Gemara begins a discussion about how to make sure a man has fulfilled a condition he set regarding his own character traits in order to accomplish the transaction of kiddushin.