High Holidays Study Group

By AI TorahAugust 31, 20260 sources cited
High Holidays Study Group

High Holidays Study Group: 45-Minute Session

"Who Shall Live and Who Shall Die? — Taking the High Holidays Personally"


A Note on This Session

This session is designed for a traditional but non-observant family — people who feel a connection to the High Holidays but may not engage deeply with the liturgy or texts year-round. The goal is emotional resonance + practical takeaway, not halachic detail. Everything here can be shared at the Rosh Hashana or Yom Kippur table.


PART 1: OPENING HOOK (5 minutes)

Open with this question — no wrong answers:

"Think of one moment in the past year where you genuinely surprised yourself — either by doing something better than you expected, or worse. What made the difference?"

Let a few people share. Then say:

"That moment — that gap between who you were and who you could be — is exactly what the High Holidays are about."


PART 2: THE CORE TEXT (15 minutes)

The Text: Unetaneh Tokef

One of the most powerful liturgical poems of the High Holiday season, recited on both Rosh Hashana and Yom Kippur

Read this aloud together — even if people don't know it, the words are striking:

"On Rosh Hashana it is written, and on Yom Kippur it is sealed — how many shall pass away and how many shall be born, who shall live and who shall die, who shall reach the end of his days and who shall not... who shall be at peace and who shall be tormented, who shall be poor and who shall be rich, who shall be humbled and who shall be exalted."

"But Teshuvah, Tefillah, and Tzedakah avert the evil decree."

[Unetaneh Tokef, High Holiday Machzor]


Discussion Questions for the Text (pick 2):

  1. "Who shall be at peace and who shall be tormented" — do you think this refers to external circumstances, or internal states of mind? Can you be tormented even when life looks good from the outside?

  2. The prayer says the decree can be averted — not erased. What's the difference? What does it mean that we still have agency even after something is "written"?

  3. The three words: Teshuvah (return/repentance), Tefillah (prayer), Tzedakah (charity/justice). Why these three specifically? What do they have in common?


The Leader's Teaching on the Three Words:

Share this insight — it usually lands powerfully:

Teshuvah is about your relationship with yourself — looking honestly at who you've been.

Tefillah is about your relationship with something larger than yourself — pausing to acknowledge you're not in complete control.

Tzedakah is about your relationship with others — turning inward awareness into outward action.

The High Holidays ask us to repair all three relationships — with self, with the universe, and with other people — within ten days.


PART 3: THE STORY (10 minutes)

A Story Worth Telling at the Table

This story is drawn from Chassidic tradition and is perfect for a family setting:


A student came to his rabbi before Yom Kippur, distressed.

"Rabbi," he said, "I have made a list of everything wrong I did this year. It is a long list. I am ashamed."

The rabbi said, "Good. Now make another list."

"What list?" asked the student.

"Everything God did wrong to you this year," said the rabbi. "Every disappointment. Every loss. Every time life was unfair."

The student was shocked. "Rabbi, we can't do that—"

"Write the list," said the rabbi quietly.

The student, reluctantly, wrote it. It was also a long list.

The rabbi looked at both lists and said:

"Now. On Yom Kippur — you forgive God for His list. And ask God to forgive you for yours."


Why this story works:

  • It meets people where they are — including those who are angry at God, who feel life has been unfair
  • It reframes Yom Kippur not as groveling, but as a two-way relationship
  • It gives everyone in the room — believers and skeptics — an entry point

Follow-up question: "Is there something from this past year that you need to 'forgive' — release your grip on — before you can really move forward?"


PART 4: THE PRACTICAL TAKEAWAY (10 minutes)

The "One Thing" Exercise

The Talmud teaches:

"A person is obligated to say: The world was created for my sake." [Sanhedrin 37a]

This isn't arrogance — it means: your choices matter. Your change matters. The world is different because of what you do.

Give everyone 2 minutes of quiet to write down (on paper or their phone):

"One relationship I want to repair before the year ends." "One thing I want to do differently this coming year." "One person I need to say sorry to — or thank."

They don't share it. It's private. But they keep it.


The Halacha with a Human Face

Share this quietly — it usually moves people:

Jewish law requires that before Yom Kippur, we seek forgiveness directly from the people we have hurt — not just from God. God cannot forgive us for wrongs done to other human beings. Only the person we hurt can do that.

[Based on Mishnah Yoma 8:9 and Rambam, Hilchot Teshuva 2:9]

"Yom Kippur does not atone for sins between a person and their fellow until they have appeased their fellow." [Mishnah Yoma 8:9]

Discussion: "Is there someone in your life you've been waiting for the right moment to apologize to — or to reach out to? What's stopped you?"


PART 5: CLOSING — THE GIFT TO TAKE HOME (5 minutes)

End with this thought — memorizable and repeatable:

The Baal Shem Tov, founder of Chassidic Judaism, taught that the word Teshuvah doesn't really mean "repentance." It means return — coming back to who you truly are.

The High Holidays are not saying you are broken and need to be fixed. They are saying: You lost your way a little. Come home.

Leave the group with this final question for the table:

"What does 'coming home to yourself' mean to you? Who were you at your best this year — and how do you find your way back to that person?"


📋 LEADER'S CHEAT SHEET

| Section | Time | Key Point | |---|---|---| | Opening question | 5 min | The gap between who we are and who we could be | | Unetaneh Tokef text | 15 min | Teshuvah/Tefillah/Tzedakah = 3 relationships | | Chassidic story | 10 min | Yom Kippur as a two-way relationship | | Practical exercise | 10 min | One thing, one person, one change | | Closing thought | 5 min | Teshuvah = return, not punishment |


🕯️ BONUS: TABLE TALK CARDS

Print these and leave one at each place setting

Card 1: "What's one thing you're proud of from this past year that you don't talk about enough?"

Card 2: "Who in your life has forgiven you for something — and did you ever really thank them for it?"

Card 3: "If this year could have a title — like a book or a movie — what would you call it?"

Card 4: "What would the best version of you do differently next year?"


Shanah Tovah — may your study group inspire a sweet and meaningful new year 🍎🍯

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