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 crossed

• The Hanukkah menorah debate: do you start with eight candles or one, and why each side is right

• The gentile who asked to learn the whole Torah on one foot, and the very different answers Hillel and Shammai gave

• Why 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 law

• Why we almost always rule like Hillel, and the surprising reason it comes down to humility

  
  

  Pull up a chair, pick a side, and remember: the rest is commentary.

Resources:

• Hillel and Shammai, sayings and character

• Machloket l’shem shamayim (a dispute for the sake of heaven)

• Korach’s rebellion against Moses and Aaron

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 Isaiah

• Nahum 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 faith

• Zephaniah 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 other

Grab 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:

• Micah

• Nahum

• Habakkuk

• Zephaniah

• Haggai

• Malachi

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 do

• What a prophet (and a leader) is supposed to be: tough on the people, defender to Gd, never a politician

• Joel and the locusts, the seven-year famine, and when punishment came measure-for-measure

• Famous Amos (great cookies, great prophet) and why prosperity might be the harder spiritual test

• Obadiah the convert who saved 100 prophets from Jezebel, the rabbinic tradition that Rome is Edom, and the famous widow with the miraculous oil

• Micah and the morality prophets: how “idolatry” in our day reads as money, power, and the corruption that comes with success

We 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.

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 satisfaction

• Shavuos 101: the forgotten major Jewish holiday, why your boss has never heard of it, and why it matters

• How 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 lever

• The Book of Ruth, the ultimate story of loyalty, conversion, and the origins of King David

Whether 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 References

• Pirkei Avot 4:19

• Proverbs 24:17

• The Ten Commandments

• Book of Ruth

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 regrets

• Jay’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 prayer

• ChayaLeah’s pitch for Cultural Amnesia by Clive James and why Remains of the Day is still on her mind

• Why understanding Jewish prayer word by word is a total game changer

• Life and Fate by Vasily Grossman, a book they both call the best they’ve ever read

Hopefully 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." — Jay

All the books we mention:

• Arab Nationalism in the Twentieth Century by Adeed Dawisha

• God in Search of Man by Abraham Joshua Heschel

• Souls on Fire by Elie Wiesel

• Sages and Dreamers by Elie Wiesel

• Night by Elie Wiesel

• The Last Consolation Vanished by Zalmen Gradowski

• Hostage by Eli Sharabi

• On Killing by Dave Grossman

• Elusive Prophet: Ahad Ha’am and the Origins of Zionism by Steven Zipperstein

• As a Driven Leaf by Milton Steinberg

• Anonymous Soldiers by Bruce Hoffman

• To Pray as a Jew by Hayim Halevy Donin

• The Hour of Our Death by Philippe Ariès

• Arrows of the Dark (two volumes) by Tuvia Friling

• Life and Fate by Vasily Grossman

• The Road by Vasily Grossman

• Cultural Amnesia by Clive James

• Remains of the Day by Kazuo Ishiguro

• The Facemaker by Lindsey Fitzharris

• My Prayer (two volumes, Chabad teachings on prayer) — could not confirm Amazon listing, may need manual search

• Rebel and Statesman-The Early Years: The Life and Times of Vladimir Jabotinsky: Volume One by Joesph Schechtman

• Fighter and Prophet; The Jabotinsky Story; The Last Years by Joesph Schechtman

• The Bronze Horseman by Paullina Simons - this is ChayaLeah’s book. Jay dissavows

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 Moonies

Get ready to learn everything you ever wanted to know about prophecy but were afraid to ask.

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 Bible

• What Adam and Eve tell us about whether opposites actually attract

• Why 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 back

• Trust vs. love: which one is actually the foundation of a lasting relationship

• The Baal Shem Tov’s classic “you can, you just don’t want to” and why it applies to your marriage right now

• Why 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." — Rabbi

Whether 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 Solomon

• Mishlei (Proverbs) by King Solomon

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 nurse

• Why your parents just want to feel significant — and no, a text does NOT count

• The generational divide around phones, Uber apps, and why nobody remembers their Kaiser password

• What to do when your relationship with your parents is, well, complicated

• The Rabbi’s reflection on his Holocaust-survivor father and putting yourself in your parents’ shoes

• Jay on caring for his mom while raising a young daughter and feeling guilty about feeling guilty

• ChayaLeah 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.

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.

On this chag episode, we tackle a section of the Haggadah that almost everyone breezes past: Jacob's fateful decision to "temporarily" settle in Egypt, only to buy land, put down roots, and stay for 17 years.

From that ancient real estate deal, the conversation spirals into the big questions Jewish families are wrestling with right now:

• What does Israel really mean to diaspora Jews?

• Is "dual loyalty" just an antisemitic trope, or something worth actually thinking about?

• Why did 80% of Jews choose to stay in Egypt even after centuries of slavery?

We don't talk about rising antisemitism, the war with Iran, and what it means to say "Next year in Jerusalem" from your living room in Long Beach. ChayaLeah shares her family's Passover prep rituals (poster boards, car detailing, kids moving the fridge), and we a passionate case that any level of observance counts.

Don't let the perfect be the enemy of the good. 🍷\

Resources Mentioned-

• Genesis 46:27 - Jacob’s family settling in Egypt

• Exodus 13:18 - Circuitous route out of Egypt

• The Four Questions explained - Chabad.org

• The Rebbe’s seder table - Chabad.org