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.

Every other Friday, the 9th grade Jewish Studies classes each sit in a circle in the middle of the room. At the front of the room, a neatly pressed white cloth neatly covers a table with two Shabbat candles and two snacks. We start the period with a song and then dive into the heart of the student-led activity. This is what the kids have come to know as “Jewish Journey Friday.”  After lighting candles and distributing snacks, the two students hosting that week each ask a carefully constructed question. The questions are designed to elicit a specific and personal story that will reveal some element of a person’s Jewish Journey. “Tell a story about a particularly memorable Passover experience.” “When was a time when you felt particularly proud to be a Jew.” “Tell about a specific way in which you see your Judaism differently today than you