
Some episodes start light. This one starts with a candle. We begin with Jay’s yahrzeit for his mom, twelve years gone and still deeply missed, and the Rabbi walks us through what the anniversary of a death really means in Jewish tradition. From there we widen out to a fast day heavy with history and a piece of tech that might change how any of us learns Torah.In this episode, we get into:What yahrzeit means and why we say Kaddish for eleven months, then every year afterThe Rabbi’s own story of counting down the days, and the strange sadness when Kaddish endsThe five tragedies of the 17th of Tammuz and the start of the Three WeeksWhy you can get engaged during the Three Weeks but not married (and what that says about free will)Yochai, the new AI tool that turns anyone into a Torah study partner
Jul 8
49 min

What makes two rabbis who disagreed about almost everything the most celebrated pair in Jewish history? This week we sit down with Hillel and Shammai, the original dynamic duo, and the answer turns out to be the way they argued, not what they argued about.In this episode, we get into:The lost art of disagreeing with someone you actually like and respect, and why Judaism treats a good argument as something close to sacred.Machloket l’shem shamayim: what makes an argument “for the sake of heaven,” and where the line gets crossedThe Hanukkah menorah debate: do you start with eight candles or one, and why each side is rightThe gentile who asked to learn the whole Torah on one foot, and the very different answers Hillel and Shammai gaveWhy Hillel’s golden rule (”what you don’t want done to you, don’t do to others”) is not the same as “love your neighbor as yourself”Lenient versus strict: how two yeshivas, two personalities, and one open door shaped Jewish lawWhy we almost always rule like Hillel, and the surprising reason it comes down to humilityPull up a chair, pick a side, and remember: the rest is commentary.Resources:Hillel and Shammai, sayings and characterMachloket l’shem shamayim (a dispute for the sake of heaven)Korach’s rebellion against Moses and Aaron
Jun 17
1 hr 5 min

We made it to the finish line. After two earlier episodes, we wrap up the Twelve Prophets and tie a bow on them all. Along the way we get into why these texts barely show up in yeshiva, a much-debated Midrash about Adam and the animals, and whether religion or just plain ideology has driven the worst of human history. Then we go prophet by prophet, all the way to the very last words of prophecy.In this episode, we get into:Micah, and the “swords into plowshares” verse that 99 percent of the world wrongly credits to IsaiahNahum and the fall of Nineveh, plus a thorny question: if God wanted the exile, why blame Assyria for carrying it out?Habakkuk, who opens by arguing with God and reduces all 613 commandments to one: the righteous shall live by his faithZephaniah on fear, fight-or-flight, and the command “do not fear”Haggai, Zechariah’s colored-horse visions, and Malachi closing the prophets with the hearts of parents and children turning back to each otherGrab a book of the prophets and read along with us. It only takes a few minutes a day, and as we say in here, it’s no great honor to be ignorant. Resources:MicahNahumHabakkukZephaniahHaggaiMalachi
Jun 10
57 min

We picked up where we left off with the Twelve Prophets (Trei Asar), and Hosea throws us straight into one of the strangest stories in all of the Tanakh. Gd is furious that the Jewish people are chasing idols, so He gives Hosea an unusual assignment: go marry a woman of ill repute, have kids with her, and name them “Not My People” and “No Mercy.” It’s harsh, it’s strange, and the Rabbi calls it the most dramatic living metaphor any prophet was ever asked to act out.In this episode, we get into:Hosea, the harlot metaphor, and the Kabbalistic question of whether Gd can actually be affected by what we doWhat a prophet (and a leader) is supposed to be: tough on the people, defender to Gd, never a politicianJoel and the locusts, the seven-year famine, and when punishment came measure-for-measureFamous Amos (great cookies, great prophet) and why prosperity might be the harder spiritual testObadiah the convert who saved 100 prophets from Jezebel, the rabbinic tradition that Rome is Edom, and the famous widow with the miraculous oilMicah and the morality prophets: how “idolatry” in our day reads as money, power, and the corruption that comes with successWe also kept circling back to something: most American Jews don’t think about Gd as Someone with expectations. That’s exactly the tension Hosea was preaching into 3,000 years ago. Same story, different costumes. Hit play, and stay with us for Part 3, where we close out the Twelve.
Jun 3
57 min

Let’s be honest: when someone you’re not a fan of gets bad news, there’s a tiny, guilty dopamine hit. We open this episode by confessing that impulse out loud and digging into what Pirkei Avot (and King Solomon) have to say about rejoicing at your enemy’s fall. Spoiler: it’s a whole thing.In this episode, we get into:The ethics of Schadenfreude and what Pirkei Avot teaches about resisting that guilty satisfactionShavuos 101: the forgotten major Jewish holiday, why your boss has never heard of it, and why it mattersHow the giving of the Torah turned a tribe into a nation (and why shared ancestry alone isn’t enough)The Sam Harris morality debate: can you have ethics without God?The trolley problem, Jewish style: why the Torah says you can’t pull the leverThe Book of Ruth, the ultimate story of loyalty, conversion, and the origins of King DavidWhether you’re prepping for Shavuot or just want to know if you’re a bad person for enjoying celebrity gossip, grab some cheesecake and press play. 🧀Episode ReferencesPirkei Avot 4:19Proverbs 24:17 The Ten CommandmentsBook of Ruth
May 20
1 hr 2 min

The rabbi’s out this week, so we’re are doing what any self-respecting book nerds would do: geeking out about reading. In this episode, we get into:Jay breaks down his “30 pages a day” habit (spoiler: it adds up to 10,000 pages a year)ChayaLeah confesses her Shakespeare regretsJay’s system for building a daily reading habit (and why you should keep three books going at once)The “Chan-book-ah” book haul: Arab nationalism, Elie Wiesel, Holocaust memoirs, and Jewish prayerChayaLeah’s pitch for Cultural Amnesia by Clive James and why Remains of the Day is still on her mindWhy understanding Jewish prayer word by word is a total game changerLife and Fate by Vasily Grossman, a book they both call the best they’ve ever readHopefully you’ll get some ideas for your next book from this episode.Quote of the episode:"I realized I was never going to be the smartest person in a room, but I could be the most well read." — JayAll the books we mention:Arab Nationalism in the Twentieth Century by Adeed DawishaGod in Search of Man by Abraham Joshua HeschelSouls on Fire by Elie WieselSages and Dreamers by Elie WieselNight by Elie WieselThe Last Consolation Vanished by Zalmen GradowskiHostage by Eli SharabiOn Killing by Dave GrossmanElusive Prophet: Ahad Ha’am and the Origins of Zionism by Steven ZippersteinAs a Driven Leaf by Milton SteinbergAnonymous Soldiers by Bruce HoffmanTo Pray as a Jew by Hayim Halevy DoninThe Hour of Our Death by Philippe ArièsArrows of the Dark (two volumes) by Tuvia FrilingLife and Fate by Vasily GrossmanThe Road by Vasily GrossmanCultural Amnesia by Clive JamesRemains of the Day by Kazuo IshiguroThe Facemaker by Lindsey FitzharrisMy Prayer (two volumes, Chabad teachings on prayer) — could not confirm Amazon listing, may need manual searchRebel and Statesman-The Early Years: The Life and Times of Vladimir Jabotinsky: Volume One by Joesph SchechtmanFighter and Prophet; The Jabotinsky Story; The Last Years by Joesph SchechtmanThe Bronze Horseman by Paullina Simons - this is ChayaLeah’s book. Jay dissavows
May 14
58 min

What does it actually take to be a prophet? Spoiler: it’s not just hearing voices and shouting in the marketplace (though there’s some of that). In this kickoff to our new series on the Trei Asar, the Twelve Prophets of the Tanakh, we set the stage before diving into the individual books. Think of this as Prophecy 101 with a side of cult talk, because honestly, the line between “biblical prophet” and “guy with millions of YouTube followers” is thinner than we’d like to admit.In this episode, we get into:📜 What prophecy actually is in Judaism, according to Maimonides, and why Moses was working on a totally different frequency from everyone else👑 The three pillars of Jewish leadership (king, high priest, Sanhedrin), and where the prophet fit🎤 Who got tapped to be a prophet, why some were reluctant 🚫 Why prophecy ended after Haggai, Zechariah, and Malachi, and what replaced it🤔 What we’d actually do if a prophet rolled up today (hint: probably an institution)😬 False prophets and cults like, Sabbatai Zvi, Jim Jones, the MooniesGet ready to learn everything you ever wanted to know about prophecy but were afraid to ask.
May 7
59 min

King Solomon had a thousand wives, wrote a book of proverbs, and still felt the need to write a whole passionate love poem about a shepherd boy and a maiden. Coincidence? We think not. In this follow-up to our Valentine’s Day episode, we go deeper into what Judaism actually teaches about love, including what Song of Songs reveals about God’s relationship with the Jewish people, and we bring it all the way down to earth with real talk about marriages stuck in a rut, whether people can truly change, and why “I can’t” usually means “I don’t want to.”In this episode, we get into:Shir HaShirim (Song of Songs): literal love poem or divine allegory?Why love is the only personality trait with its own dedicated book in the entire Hebrew BibleWhat Adam and Eve tell us about whether opposites actually attractWhy real love has nothing to do with infatuation, Hollywood, or Taylor Swift (though we do have opinions about her and Travis)Practical advice for married couples who have drifted apart and want to find their way backTrust vs. love: which one is actually the foundation of a lasting relationshipThe Baal Shem Tov’s classic “you can, you just don’t want to” and why it applies to your marriage right nowWhy the Rebbe and Rebbetzin’s relationship might be the greatest love story you’ve never heard"Love goes deeper than what you can do for me. You love the person for who they are and what they are, not what they do for you." — RabbiWhether you're happily married, newly in love, or just trying to remember what you liked about the person across the breakfast table, this episode has something real for you. Come learn, laugh, and maybe text your spouse something nice when it's over. 🕯️❤️Referenced Material-Shir HaShirim (Song of Songs)Kohelet (Ecclesiastes) by King SolomonMishlei (Proverbs) by King Solomon
Apr 29
1 hr 4 min

We’re kicking off a brand new segment called “Dear Rabbi,” where we bring real-life issues to the Rabbi and actually get into it with honest, often hilarious, sometimes painful conversations about the stuff people are quietly struggling with. First up: how to care for elderly parents without losing your mind, your marriage, or your lunch break.In this episode, we get into:Setting boundaries with elderly parents (and why that’s easier said than done)The difference between being a caregiver and being a nurseWhy your parents just want to feel significant — and no, a text does NOT countThe generational divide around phones, Uber apps, and why nobody remembers their Kaiser passwordWhat to do when your relationship with your parents is, well, complicatedThe Rabbi’s reflection on his Holocaust-survivor father and putting yourself in your parents’ shoesJay on caring for his mom while raising a young daughter and feeling guilty about feeling guiltyChayaLeah admitting which of her four sons she’d trust with her medications (spoiler: it’s not all of them)Plus a hot take on Matzo manufacturers who dare to sell non-Kosher-for-Passover matzo. The audacity.Whether you’re navigating aging parents yourself, trying to figure out how much you’re really capable of giving, or just looking for permission to laugh about the hard stuff, this one’s for you. Grab a coffee, settle in, and remember: your parents just want you to call.Got a question for Dear Rabbi? Email us at [email protected] or message us on Substack.
Apr 23
58 min

We kicked off this month's Zoom talking about the Rebbe's birthday and why his legacy still hits so hard, from growing Chabad's global mission to his no-nonsense philosophy on turning obstacles into opportunities. Then we got into full Passover mode: ChayaLeah is prepping a community Seder for 120 people and her game plan is SPEED. We broke down the Ten Plagues (why those plagues, why that order, and how long they actually lasted), talked about why you don't need a minimum number of people for a Seder (but the more the merrier), and heard from Moshe Perelmuter live in Israel about what Passover looks like during wartime, with packed grocery stores but empty Jerusalem streets. We also explored studying the Tanya, which the Rabbi describes as essentially a self-help book for the Jewish soul. And Goldie dropped some hilarious childhood stories about sharing a bedroom with ChayaLeah. It's Passover prep meets life advice meets family chaos.
Apr 9
57 min
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