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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.

Rabbis Shai Held and Tali Adler explore one of the most provocative images in rabbinic tradition: that at Sinai, God held a mountain over the Israelites’ heads and threatened them into accepting the Torah. What does this say about the nature of faith, agency, and obligation? In this episode, Rabbi Shai Held and Rabbi Tali Adler explore deep questions about obligation, autonomy, commitment, and love. What does it mean to choose God in a world where God so often feels hidden? And how do commitment, tradition, and personal relationships shape a life of religious meaning?

Can we really judge everyone favorably? Rabbis Shai Held and Steve Greenberg dive into this Jewish idea, exploring how a generous outlook can transform relationships, personal healing, and even our view of God. But where do we draw the line? Tune in for a candid conversation that gets real about the power – and potential pitfalls – of seeing the best in everyone.

Rabbi Shai Held returns with a new cast of guest for another season of Answers WithHeld, the podcast where we confront big questions with bold thinking and honest searching. Every week, Rabbi Shai Held invites a leading thinker or teacher to explore one powerful Jewish idea or the life and legacy of a great Jewish thinker: Can We Really Judge Everyone Favorably? Is Torah Study the Highest Value? Is There Choice in Accepting the Torah? No pressure.   Together, we wrestle with timeless questions, uncover new insights, and model what it means to take Torah and Jewish thought seriously. 

In this special season finale, R. Shai Held welcomes his two oldest children to model a genuine conversation about God, experiences, belief, and doubt. Lev and Maya share some of the biggest questions on their minds as well as offer sage advice to grown-ups about how to have meaningful and impactful conversations with kids.

Questions surrounding our own mortality are some of the hardest to ask, and certainly some of the hardest to answer. What happens when we die? What does it mean to have a soul? R. Sharon Cohen Anisfeld joins R. Shai Held for a deeply meaningful exploration of these profound questions.

R. Aviva Richman joins R. Shai Held to discuss one of the most difficult moral and religious questions - why do bad things happen? Where is God when they do? Personal childhood memories of confronting this question lead them to explore how being present might mediate God's presence, to appreciate petitionary prayer in nuanced and sophisticated ways, and to wonder about God's role of holding loss in times of tragedy.

What if I don't believe in God? What if I'm not sure? Rabbi Dr. Leon Wiener Dow joins Rabbi Shai Held to reflect on the importance of doubt and continuing to question. They identify some of the straight-jackets that we put on our thinking about God and explore the possibility of being open to a spiritual life with or without a belief in God.