What happens when you test an AI version of a rabbi—live on camera—against the real thing? Host Shabbos Kestenbaum pulls out his phone mid-conversation and puts Rabbi Simon Jacobson's own AI chatbot to the ultimate test. First, he asks the real rabbi. Then he asks the AI. And the room goes completely silent. The AI's answer is so precise, so theologically rich, and so unexpectedly humble—Rabbi Jacobson can't believe it. And then comes the moment nobody saw coming: "Does this count as complimenting yourself?" This clip covers: Can an AI fulfill the ancient Jewish obligation to "make for yourself a rabbi”? The live on-air test: real rabbi vs. AI rabbi—who answers better? The AI's stunning answer on idolatry, digital gods, and human…
Did the Exodus really happen? Can religion be pick and choose? And is Conservative Judaism dying? In this episode of Theological, Shabbos Kestenbaum sits down with Rabbi David Wolpe, rabbi emeritus of Sinai Temple and Shabbos’s former professor at Harvard Divinity School, for a serious and respectful debate about faith, history, Torah, sin, prayer, and the future of American Judaism. In this episode, Shabbos and Rabbi Wolpe also explore: Orthodox vs Conservative Judaism: Do Jews have to keep kosher, Shabbat, and other biblical commandments? Is Judaism meant to change? Rabbi Wolpe argues that Judaism is an interpretive tradition and an ongoing dialogue between God and the Jewish people. What is sin in Judaism? Is sin simply breaking a…
Beginning at sundown on Thursday, May 21, 2026, Jews around the world will welcome Shavuot, the festival that commemorates the giving of the Torah at Mount Sinai.
