This is the rare story of a family who became more Jewish not through tradition, but through reinvention.

In this conversation, Jacob Gersen opens up about his family history, upbringing, marriage, his childrens journeys and what it meant to support Jeannie Suk Gersen through an Orthodox conversion. He speaks honestly about feeling like an outsider, the vulnerability of joining an Orthodox community later in life, the shift toward public Jewish identity after October 7 and how Jeannie’s boldness reshaped his own relationship to Judaism. A rich, thoughtful and moving portrait of modern American Jewish life.

Key Takeaways

1. Identity and belonging are rarely linear.
2. Conversion can transform more than one person.
3. In a post–October 7 world, choosing to be visibly Jewish carries new meaning.

Timestamps:

[00:00:00] Learning to live publicly as a Jew

[00:05:00] Deep cultural Judaism and inherited ambivalence

[00:09:00] Turning to Eastern religions at Brown instead of Judaism

[00:11:00] Early interfaith marriage and unexpected rejection

[00:14:00] Raising children with two religious identities

[00:17:00] Feeling inadequate next to a non-Jew who practiced more Judaism

[00:19:00] Finding Rabbi Minz and beginning Jeannie’s Orthodox conversion

[00:23:00] Outsider feelings in Orthodox spaces

[00:33:00] Building belonging: the need for support systems in shul

[00:45:00] Rejecting the instinct to “keep your head down” after October 7

Links

• ⁠Jacob Gersen - Harvard Law School⁠
• ⁠Project Ruth Website⁠
• ⁠Rabbi Adam Mintz⁠
• ⁠Meredith Berkman’s LinkedIn⁠

I thought religion might divide us. Instead, it shaped everything we became.This episode dives deep into love, faith, and identity — following a couple who built a Jewish family that didn’t fit the mold. It’s a story about the tension between devotion and tradition, how community can both challenge and embrace, and what it really takes to belong. You’ll hear how one family redefined what “Jewish continuity” looks like in today’s world — and what we can all learn about courage, compassion, and connection from their journey.Key Takeaways

1. Real inclusion in faith communities requires courage, conversation, and empathy — not conformity.
2. Love and shared values can be stronger than cultural or religious barriers when grounded in honesty.
3. The journey to belonging isn’t about labels — it’s about creating space where everyone feels at home.

Timestamps

[00:00] Creating a Vibrant Jewish Community

Peter opens with the idea of building a diverse and welcoming Jewish community.

[01:11] Episode Intro: Orthodox Conversion and Context

Adam introduces the topic and Project Ruth, framing the conversation in a post–October 7th world.

[02:15] Introducing Peter Bregman and His Family Story

Peter shares his Sephardic background, his mother’s Holocaust experience, and his spiritual roots.

[07:47] Meeting Eleanor: Love Across Faiths

Peter describes meeting Eleanor at Princeton and their early conversations about religion.

[12:09] Family Pressure and Cultural Expectations

The moment when Peter discusses family disapproval, his mother’s Holocaust-driven convictions, and the tension it caused.

[18:46] Marriage Despite Resistance

Peter explains how they decided to marry, moved the wedding up, and faced family backlash.

[24:58] Conversion Challenges and Community Pushback

Peter recounts struggles convincing Orthodox rabbis to convert their children and the theological reasoning behind resistance.

[33:45] Practicing Judaism Together

A discussion about raising Jewish children, community response, and finding belonging through schools and Chabad.

[46:41] Eleanor’s Conversion After October 7th

Peter reflects on how the war, identity, and community shaped Eleanor’s decision to convert and his emotional response.

[55:58] Final Reflections on Inclusion and Belonging

Peter closes with gratitude and hope for a more open, supportive Jewish community

Links

• Peter Bregman LinkedIn
• Bregman Partners
• Project Ruth Website
• Rabbi Adam Mintz
• Meredith Berkman’s LinkedIn

What happens when your conversion is accepted in one community but rejected in another?

This episode dives into the remarkable journey of Danielle Tomson, a scholar of political communication and Jewish convert, who shares how her path to Judaism reshaped her life, identity, and spirituality. From her early encounters with Jewish friends in Pittsburgh to deep involvement at Yale and New York’s Orthodox communities, Danielle reflects on how she found her place within Jewish tradition—even navigating the complexities of undergoing two conversions.

She also explores the meaning of Yom Kippur, describing how the High Holidays evolved from feelings of guilt to a season of joy, healing, and spiritual repair. With insights ranging from sea glass metaphors to the politics of conversion recognition worldwide, Danielle offers a refreshing and deeply personal perspective that resonates with seekers, lifelong Jews, and anyone exploring faith, identity, and belonging.

Key Takeaways

• Conversion isn’t a one-time act—it’s a journey of belonging, identity, and sometimes painful politics.
• Yom Kippur shifts from guilt to joy when seen as an invitation to repair, not punishment.
• Jewish community is found at the crossroads of tradition, spirituality, and personal truth.

Timestamps:

[00:00] First Yom Kippur as a new Jew – Danielle’s emotional experience in Central Park

[02:10] Danielle introduces herself: background, studies, and first conversion story

[04:00] High school in Squirrel Hill and first Jewish friendships

[06:00] Discovering Orthodoxy, Yale experiences, and struggle to find a conversion path

[10:25] Family ancestry, Jewish connections, and stories of possible Jewish lineage

[13:09] Why Danielle converted twice and the politics of recognition

[19:40] Deep dive into halacha, learning shochet skills, and continued Jewish study

[28:01] Rethinking Yom Kippur: from guilt to joy through teshuva

[37:34] Fasting for the first time – challenges and how she prepared

[43:00] Experiences with ultra-Orthodox communities and finding beauty in diversity

Links

• Danielle Tomson
• Project Ruth Website
• Rabbi Adam Mintz
• Meredith Berkman’s LinkedIn