Back in August, I released a conversation with Rabbi Yakov Horowitz about Orthodox parents whose children come out as LGBTQ. The feedback to that episode was intense. Some listeners wrote that they finally felt seen. Others said that they were deeply uncomfortable. Quite a few parents asked what they should actually do when their son or daughter comes out to them, and how they can respond with genuine love while remaining faithful to halacha.

Those questions are not theoretical. They are deeply personal, and they are coming from people who keep Shabbat, send their kids to day schools, sit in our shuls, and are trying to raise their families as loyal Torah Jews. Ignoring them does not make them go away.

Today I am speaking with two people who have decided not to look away. Rabbi Menachem Penner is the former dean of RIETS and currently serves as the executive vice president of the Rabbinical Council of America. Together with his wife Adeena he founded Kesher Families, an organization that supports Orthodox parents of LGBTQ children. Rabbi Yakov Horowitz is the founder of Project YES and a co leader of Kesher Families, and he joined me for that earlier conversation.

In this episode we talk about what moved the Penners to start Kesher Families, what it was like for Rabbi Penner to be a very public rabbinic figure when his son came out, and why they chose to share their family story with the broader community. We discuss the first things a parent should and should not say when a child comes out, the confusion that many young people feel as they try to understand their own sexual identity, and how parents can balance acceptance of what a child is telling them with the awareness that some parts of the story may still be unfolding.

We also look at how attitudes in the Orthodox world have changed over the past decade, what has improved, what remains painful, and whether it is really possible to increase compassion and understanding without abandoning our mesorah. And finally, I ask both of my guests what single message they most want the Orthodox community to hear about LGBTQ children and their families.

To learn more about all that Dreamearly does, go to https://dreamearly.co/. Make sure to check out the excellent recent episode of the Stream of Dreamearly Podcast with Dr. David Rosmarin.

To contact Kesher Families, click here.

Follow Rabbi Yakov Horowitz on Instagram - @yakovhorowitz and @brightbeginningsforum.

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

Zohran Mamdani - a politician who openly rejects Israel's right to exist as a Jewish state, yet insists that this has nothing to do with antisemitism - is now the mayor-elect of New York City. He points to a small number of Jewish supporters as evidence, while promoting a worldview in which Israel is framed as a genocidal, apartheid project.

New York is home to the largest Jewish community in the diaspora. When that city elects a proudly anti-Zionist mayor, it sends a message far beyond one municipality. It raises hard questions: What does it mean for Jewish security, for public discourse about Israel, and for the way younger Jews understand the connection between antisemitism and anti-Zionism? Does this moment push more Jews to consider aliyah, or does it demand that they stay and push back? And what does kiruv look like in an atmosphere saturated with hostility, confusion, and ideological pressure?

My guest confronts these questions every day. Rabbi Mark Wildes is the founder of Manhattan Jewish Experience, which has spent decades helping unaffiliated Jews in their 20s and 30s build a deeper relationship with Torah, Shabbat, and the Jewish people. In our conversation, we talk about what he fears will tangibly change on the ground as a result of Mamdani's election, why the supposed split between anti-Zionism and antisemitism is so dangerous, and how Rabbi Wildes speaks to students who are center-left, skeptical about Israel, or openly anti-Zionist.

We also discuss his new book, The Jewish Experience: why he chose to organize basic Judaism around the concepts of God, Torah, prayer, Shabbat, chesed, and tikkun olam; why Shabbat and Jewish wisdom are the best first steps for Jews who feel worn down by the headlines; and how to reclaim tikkun olam from its political distortions without abandoning the real Torah value behind it.

We also look at "spreadsheet kiruv," which emphasizes metrics in determining how successful an outreach program is; how outreach can avoid treating people as projects, and why one small act — a Shabbat meal, a class, even a moment of being pulled into a dance circle — can change a Jewish life in ways none of us may even recognize.

This is a wide-ranging conversation that touches on so many aspects of kiruv, including ma'amarei Chazal, politics, Pet Sounds, and Sgt. Pepper.

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

In recent weeks we have watched something many of us hoped we would not see in the United States: openly anti-Zionist and even openly antisemitic voices moving from the margins into the mainstream. Zohran Mamdani's victory in New York raises the chilling possibility that hostility to Israel is now an electoral asset. At the same time, parts of the American right are flirting with figures like Nick Fuentes, a Holocaust denier who says Jews do not belong in Western civilization.

To make sense of this moment, I spoke with Jonathan Greenblatt, CEO and National Director of the Anti Defamation League. We discussed why anti-Zionism is, in most cases, antisemitism; what Mamdani's rise should signal to American Jews; why some university leaders defend the indefensible; where the Jewish community itself has made mistakes in fighting antisemitism; how to confront hatred coming from both sides of the political spectrum without turning it into a partisan game; and more.

This is a blunt, timely, and deeply important conversation for anyone who cares about Jewish security and moral clarity in public life.

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

Is Jewish unity even possible?

In this urgent episode Rav Yosef Zvi Rimon faces the hardest questions raised by the draft crisis and by the widening gaps between Charedi, Dati Leumi, Modern Orthodox, Traditional, and Secular Jews. He explains why unity is not a slogan but a practical necessity and religious obligation with real consequences for security, community, and our shared future. With clarity and empathy he maps a path for principled disagreement, mutual responsibility, and practical steps that families, shuls, and schools can take right now.

If you are tired of talking points and want a serious plan for healing rifts while staying true to conviction, this conversation is for you.

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

What does the morning after really look like... when the dawn reveals not only light, but rubble and work?

In this deeply personal conversation, Scott and Dr. Erica Brown ask how we craft a vision of where we're going when optimism feels naïve, unity is fragile, and joy and grief insist on sharing the same space. Drawing on Rabbi Sacks's distinction between optimism and hope, they explore how to build active hope through autonomy, giving, and purpose. They define Jewish unity as purposefulness rather than groupthink, wrestle with isolation and rising antisemitism in the diaspora, and consider Rav Kook's "songs" of soul, people, humanity, and world in a time when many Jews feel pushed out of humanity's choir.

Along the way, Scott reflects on grandparenting amid loss; Erica introduces the idea of "prophetic social justice" and the power of a "destination postcard"—a concrete picture of a better future; and together they share practical ways families can bind their children's wounds through volunteering and virtue.

This is the morning after—honest, unsentimental, and stubbornly hopeful.

Subscribe to Dr. Erica Brown's wonderful new Substack, Sacred Stamina, by clicking here.

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

This episode is dedicated to the complete recovery of יהונתן איתן בן בת שבע ברכה.

How do we move from private anguish to collective strength? In this deeply personal and wide-ranging conversation, Rabbi Leo Dee shares the story of the day his wife and two daughters were murdered, and the seven-facet framework he built to keep living with faith and purpose. We walk through Family, Friends, Fitness, Frumkeit (spiritual life), Function (purpose), Finances (trust and control), and Fun (simcha/growth)... first as practices for an individual in pain, and then as a national toolkit for a people living through ongoing trauma.

Instead of drilling into tactics, we explore the principles that make the Seven Facets portable, from the home to the community to the nation: how language and presence matter, how practice can carry belief, how purposeful action restores dignity, how trusting what we can't control quiets anxiety, and how measured joy can coexist with memory.

This episode is for anyone who refuses to let grief have the last word—and wants concrete, Torah-true ways to help themselves, their family, and Am Yisrael heal.

Click here to order Rabbi Dee's wonderful new book, The Seven Facets of Healing.

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

Charlie Kirk's assassination is a shocking, tragic act of violence. Murder is a desecration of the image of God, full stop. We condemn it unequivocally, and we pray for comfort for his family and for all who were harmed.

At the same time, Charlie Kirk was a complicated public figure. He was outspokenly pro-Israel and often advocated for Jewish safety; he also voiced criticisms of Israel's current government. He advanced positions that many in the Orthodox world consider essential, and others consider deeply problematic. He defended Israel vigorously, and he also gave a platform to voices widely regarded as openly antisemitic. All of that can be true at once, and ignoring any part of that picture does our community no favors.

In the days since his death, we've seen Orthodox individuals and organizations release statements ranging from restrained condolences to sweeping praise that some would call over-the-top. Today we're going to step back and ask, dispassionately and honestly: what should Charlie Kirk's legacy be for Orthodox Jews?

This is neither a eulogy nor an indictment. Our aim is to slow the rush to hot takes and consider how a mature community remembers someone who meant very different things to different people.

I have three guests on today's episode: Rabbi Yitzchok Adlerstein, Rabbi Benjamin Kelsen, and Rabbi Pesach Wolicki. Together we'll explore where they agree, where they diverge, and what that means for real life: how institutions and leaders speak publicly, and how we keep our disagreements from corroding relationships. Above all, we'll try to conduct this conversation in a way that is truthful, proportionate, and humane.

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

Is it possible—maybe even Jewish—to be angry at God? From Abraham's challenge at Sodom to Job's cries of despair, Tanach is filled with voices that confront the Divine. But what does that mean for us today, when we struggle with personal tragedy, global antisemitism, and the ongoing pain of the seemingly endless war against Hamas?

In this wide-ranging conversation on the Orthodox Conundrum, Scott Kahn speaks with Rabbi Dr. Raphael Zarum, Dean of the London School of Jewish Studies, about whether anger at God is heresy or a profound act of faith. Along the way, they discuss biblical protest, repentance, the Shoah, the morality of Israel's current war, the themes of Rosh Hashanah, contemporary crises, and whether confronting God can actually bring us closer to Him.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

This episode is partially a detective story, partially an analysis of daring ideas, and partially an invitation to discover new methodolgies of confronting challenges to Orthodox Judaism.

Rav Kook drafted L'Nevuchei HaDor over a century ago—then the manuscript largely disappeared from view, resurfaced piecemeal, and sparked debates about redaction and "censorship." In this follow-up to our popular episode with Professor Marc Shapiro, I speak with Rabbi Aryeh Sklar, translator of the new English edition, to unpack both the history of the text (why it was sidelined, what changed between versions, and who may have been protecting whom) and the ideas that make it urgent now: how Rav Kook navigates tensions between moral intuition and Torah; his approach to challenges from writings of the ancient Near East; why heresy can refine faith; his respectful stance toward other religions; and much more. As we approach Rosh Hashanah and Yom Kippur, we ask what this early, daring Rav Kook can offer a polarized 2025 about creative teshuva, intellectual honesty, and religious confidence without fear.

Check out the wonderful new podcast, Women Talking Mitzvot, co-produced by Deracheha.org and Beit Midrash Migdal Oz, with Rabbanit Shayna Goldberg and Rabbanit Dr. Yosefa Fogel Wruble. To listen, click here (Apple) or here (Spotify).

Exclusive deal for Orthodox Conundrum listeners: code perplexed20 will give 20% off if they pre-order L'Nevuchei HaDor through kodeshpress.com.

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com

As one 929 cycle ends and the next begins, Scott talks with Rabbi Benny Lau—founder of 929—about why the project started, what it hopes to change in Jewish life, and what a shared, chapter-a-day cadence can build across communities. They also tackle the harder questions: the risks of using Tanach as a direct guidebook without the mediating lens of the Oral Tradition, how to engage ethically with challenging passages, and where pluralism meets red lines. Practical takeaways included: how beginners can start this week, and what to do when you fall behind. Whether you're all-in on 929 or cautious about it, this episode is about reading Tanach deeply—and responsibly.

Check out the wonderful new podcast, Women Talking Mitzvot, co-produced by Deracheha.org and Beit Midrash Migdal Oz, with Rabbanit Shayna Goldberg and Rabbanit Dr. Yosefa Fogel Wruble. To listen, click here (Apple) or here (Spotify).

We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.

To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com