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.

Oakland Hebrew Day School is a Modern Orthodox school that draws from a wide range of religiously diverse families. With our enrollment coming from (and relying on) a diversity of affiliations, our commitment to maintaining our Modern Orthodox identity sometimes creates complications, particularly in the realm of our tefillah practices. Many parents don’t have personal prayer practices, and for parents who do, some use liturgy or have traditions from different denominations. Like many schools, we have a siddur ceremony in the 1st grade in which students receive their own siddurim. As an Orthodox school, we distribute Orthodox siddurim (we have been using the Koren Youth Siddur).

When addressing morally complex Tanakh texts, middle school educators face the dual challenge of maintaining textual integrity while fostering meaningful student engagement. To meet this challenge, we have introduced “Communities of Inquiry” (CoI), a pedagogical approach rooted in the Philosophy for Children (P4C) movement. These collaborative learning environments allow students and teachers to explore ideas, questions, and ethical dilemmas that arise from complex Tanakh passages. In this framework, students engage in “doing philosophy”—not as an academic discipline, but as a way of thinking that deepens their connection to Tanakh and to the broader human experience.This approach emphasizes philosophy as an active, practice-based discipline.

Over a delectable meal during Hanukkah in 2012, Professor Gerald Bubis told me about a sermon he had heard at Valley Beth Shalom in Los Angeles. In it, Rabbi Harold Shulweis passionately insisted that kashrut practices must be rooted in ethical consciousness. “The Jewish theology of kashrut is not pots and pantheism,” Shulweis poetically preached from the bimah in 2009. Jerry spoke to me not only as a budding Jewish educator, but also as a future family member, encouraging me to balance halakhic rigor with spiritual depth. He railed against mechanical or performative acts, in all arenas. This was one of our earliest and most memorable conversations. Thirteen years later, while teaching a capstone course in modern Jewish thought to high school seniors at Rochelle Zell Jewish High School, I found myself reflecting on that encounter.