For many of us, confronting death raises urgent questions of faith, doubt, and the meaning and purpose of our lives. Yet we live in a culture that avoids talking about death, let alone the existential challenges it raises. Physician and ethicist Lydia Dugdale, author of The Lost Art of Dying, joins Rabbi Shai Held to draw on ancient and contemporary wisdom about mortality and meaning. Recorded in Fall 2025. 
This conversation is part of the Faith WithHeld series, generously sponsored by the Schiller family.

Want the full Q&A? Catch the video version here: https://youtu.be/i1ktCH7ISoE

When the unthinkable happens, what remains of faith? Journalist Sarah Wildman, who lost her young daughter, joins Rabbi Shai Held in a searching conversation about grief, love, and the struggle to go on. They will probe how mourning collides with meaning-making, and how faith might fracture, endure, or be remade in the wake of devastating loss. Recorded in Fall 2025. 
This conversation is part of the Faith WithHeld series, generously sponsored by the Schiller family.

Want the full Q&A? Catch the video version here: https://youtu.be/YNZb_AkS7Ec

Was Rabbi Kook a mystic, a radical, or a realist? And what did he really believe about redemption?
In this season finale, Rabbi Shai Held is joined by Professor Yehudah Mirsky to unpack the bold and complex messianic vision of Rabbi Abraham Isaac Kook and the ways in which this vision still reverberates today. Together, they explore Kook’s hopes for a transformed humanity, his belief in the spiritual potential of the Jewish people, and how his messianism shaped (and was shaped by) the politics of his time. 

Is studying Torah really the most important thing a Jew can do? Or is that just something rabbis say—because they're the ones doing the studying? In this episode, Rabbi Shai Held talks with Rabbanit Devorah Zlochower about the value and limits of Talmud Torah. Together, they wrestle with classic rabbinic sources, the meaning of learning as a spiritual practice, and how Torah study connects (or sometimes disconnects) from justice, action, and everyday life. If you’ve ever wondered what makes learning holy—or whether it's enough on its own—this conversation is for you.

Is lighting candles, giving tzedakah, or saying a prayer enough if your heart’s not in it? Rabbis Shai Held and Josh Feigelson sit down to explore what it means to live a heart-centered Jewish life—and why it matters more than we often think. Together, they reflect on the perceived split between "the duties of the limbs" and "the duties of the heart," wrestle with the legacies of thinkers like Yeshayahu Leibowitz, and examine how cultivating the heart can help us live less reactive, more compassionate lives.

What does it mean to embody God’s love in a world where God sometimes feels absent?
In this episode, Rabbi Shai Held is joined by Christian biblical scholars Dr. Judy Fentress-Williams and Dr. Ellen Davis to explore what the Book of Ruth reveals—not just about loyalty and love, but about God’s subtle presence in human lives. Together, they ask: What does it mean for God to work through ordinary people? Can human faithfulness reveal divine faithfulness?

What do we do with the questions that have no answers? How does Jewish faith confront suffering, loneliness, and finitude? And how did Soloveitchik's own life—marked by grief, tradition, and the tension between reason and revelation—shape his unique theological voice?
In this episode, Rabbi Shai Held and scholar Arna Poupko Fisher explore the life and thought of Rabbi Joseph B. Soloveitchik, one of the most important Jewish thinkers of the 20th century. Together, they examine Soloveitchik’s vision of a religious life, one that doesn’t solve every problem, but gives us the language to live with our questions—and find meaning in the asking.

What if God isn't just the one we seek—but the one who seeks us? In this episode, Rabbi Shai Held is joined by Rabbi Dr. Michael Marmur for a profound and passionate exploration of the theology of Rabbi Abraham Joshua Heschel—one of the most influential Jewish thinkers of the 20th century. Together, they unpack Heschel’s daring idea that God is not a distant, unmoved mover, but a personal, passionate presence—a God of pathos who longs for humanity’s response. What does it mean to say that God is “in search of man”? Why was Heschel so critical of a purely rationalist or philosophical picture of God? And what kind of life are we called to live if we truly believe that God cares about justice, compassion, and the vulnerable?

Warning: This episode includes discussion of suicide.

What does it mean to truly meet another person—or even God—as a “Thou” and not an “It”? In this episode, Rabbi Shai Held and Dr. Arnie Eisen dive into Martin Buber’s transformative philosophy of relationship. They explore how Buber’s I and Thou challenges us to encounter others with presence and vulnerability, how this vision shapes prayer and ethics, and whether such deep connection is possible—or sustainable—in everyday life. Along the way, they reflect on love, loneliness, and the sacred potential in human encounter.

Can we really describe God—or does every word fall short? In this episode, Rabbis Shai Held and Jason Rubenstein explore the bold theology of Maimonides, who argued that the only true way to speak about God… is not to speak at all. Together they unpack why saying “God is loving” might actually be misleading, what it means to worship a God beyond human understanding, and how silence, awe, and mystery can shape a meaningful spiritual life.