Podcast Summary: Reclaiming with Monica Lewinsky

Episode: Elizabeth Gilbert
Date: September 9, 2025
Host: Monica Lewinsky
Guest: Elizabeth Gilbert

Episode Overview

In this episode, Monica Lewinsky speaks with renowned author Elizabeth Gilbert (not Wurtzel) about reclaiming one’s self, the complexities of female desire and identity, the meaning of friendship with oneself, and the ongoing journey of healing, grief, and spiritual growth. The conversation weaves between personal stories—especially from Gilbert’s new memoir, All the Way to the River—and broader cultural and spiritual reflections about womanhood, relationships, creativity, and discovering joy despite adversity.

Key Themes & Discussion Points

1. Reclaiming Self: Friendship, Presence, and Solitude

• Starting Point—Living With vs. By Oneself
  Monica opens by quoting Gilbert:

  “I don’t live by myself, I live with myself.” (03:02)
  Touchstone for the episode: what it means to companion yourself rather than merely exist alone.

• Friendship with Self as a Practice
  Gilbert describes her journey from self-critique to “self-friendliness”:

  “Transforming [my harsh inner voice] into a voice of friendliness … has been a game changer.” (07:54)

• Aloneness vs. Loneliness
  Both discuss how solitude can be nourishing and how relationships can paradoxically amplify loneliness:

  “The loneliest I have ever been in my entire life ... sometimes two is far lonelier than one.” – Gilbert (09:16)
  “I've got the best roommate. Like, Liz is my roommate. We like all the same stuff.” – Gilbert (10:18)

• The Joy of Self-Partnership
  Gilbert shares benefits of celibacy and living alone, summarized in the freedom from having to “attune my energy to anybody else’s mood.” (17:57)

2. Celibacy, Female Autonomy, and Changing Narratives

• Journey to Celibacy
  Gilbert reflects on three decades of relationships, then embracing celibacy as unfamiliar territory (“door B”):

  “Few women in history have been able to find out because it hasn’t been permitted.” (12:40)

• Celibacy for Freedom vs. Power
  Gilbert cites A History of Celibacy:

  “Men choose celibacy for power. Women choose celibacy for freedom.” (14:02)

• Energetics of Sex and Self-Protection
  Monica and Gilbert share about becoming more intentional about where they “give their energy,” acknowledging shifting views in themselves and society about sex and singlehood. (15:09 – 16:45)

3. Female Desire, Overgiving, and Social Programming

• Double Standards & Cultural Critique
  Monica references an Elizabeth quote about societal outcomes for men vs. women:

  “Bill Clinton got a presidential library, and Monica Lewinsky got a punchline.” (18:49)
  Discussion follows on reclaiming narrative as a woman, and whether culture is progressing.

• Transforming Culture Individually
  Gilbert:

  “One woman at a time, we can transform this completely … I’m not going to wait for the culture to transform before I transform.” (20:13–21:02)

• The Cost of Overgiving
  Monica brings up Gilbert’s book chapter “A Brief History of Female Overgiving,” which looks at how women’s traditional roles drain their life force:

  “Married women live less long than single women…[there’s a] marriage benefit imbalance.” – Gilbert (30:58)

4. Storytelling, Creation, and Legacy

• Writing as Progeny
  Gilbert likens her books to children, passing on cosmic “information”:

  “The books I write … this is my progeny … I’ve downloaded this information from the cosmos.” (35:49)

• Living with Creativity and Healing
  Both discuss “self-directed art therapy” and using creative processes as personal healing and contribution to the world. (35:54–37:45)

5. Grief, Codependency, and Spiritual Transformation

• Core Narrative of All the Way to the River
  Elizabeth recounts leaving her marriage for her best friend Raya (diagnosed with terminal cancer), cycling through romantic joy, then the devastation of addiction, caregiving, and codependency:

  “For every depraved drug addict, there’s somebody who loves them dearly… I became the vampire’s assistant.” (27:24–27:26)

• Karmic Predicaments & Surrender
  The discussion broadens to universal lessons about facing collective and personal bottoming out:

  “There is nobody who will not at some point find themselves cornered in a karmic predicament.” (28:01)

• Recovery and Mercy
  Gilbert on recovery:

  “There’s nothing on earth that can save me from myself except a higher power.” (29:03)
  And the need to extend “the hand of friendship to somebody who is suffering,” including oneself. (61:24)

6. Acceptance, Joy, and Reclaiming Vitality

• Making Peace with Plans Unraveling
  Monica and Gilbert bond over lives not turning out as intended, moving through disappointments with more wisdom each time:

  “Everyone I know could write a book called Not Exactly What I Planned.” – Gilbert (55:14)

• Finding Intimacy and Compassion in Hardness
  They discuss extending “mercy” to self/others, referencing Brene Brown and the Dalai Lama. (59:29–63:59)

• Current Reclamation Projects
  Gilbert shares about reclaiming physical vitality through rest and sabbatical. Monica reflects on reconnecting with excitement and joy, and the need to seek them proactively in hard times. (66:49–70:03)

Notable Quotes & Moments

• “I’ve given myself permission … to use just absolutely hideous language in my inner voice. And so transforming that into a voice of friendliness has been a game changer.” – Gilbert (07:54)

• “You can not want to do something again and still appreciate that you did it.” – Gilbert (12:34)

• “Women give their lives, literally their life force, to whoever they love.” – Gilbert (32:53)

• “My only job is to replicate myself. But what that means is: what are you leaving behind?” – Gilbert (34:38–35:49)

• “The thing you want the least to happen is going to at some point … and when Rhea was diagnosed … my soul said … ‘make it worse.’ … There’s some treasure in here for me that I have not found.” – Gilbert (56:01–57:54)

• “Universal human compassion isn’t universal if it doesn’t include you.” – Gilbert (63:14)

• “God gives the brightest students the toughest assignments. ... I found God on the bathroom floor. I found God at my rock bottom. ... The fast way is through suffering.” – Gilbert (65:12–66:36)

Timestamps for Key Segments

| Time | Segment | |-------------|------------------------------------------------------| | 03:02 | Beginning: Living with oneself vs. by oneself | | 09:16 | On loneliness and self-partnership | | 12:40–14:30 | Celibacy for freedom vs. power | | 18:49 | Double standards: Desire, culture, and legacy | | 20:13–21:02 | Transforming culture as individual women | | 27:24–28:41 | The dark descent: Addiction, codependency, grief | | 30:58 | The marriage benefit imbalance for women | | 35:49–36:38 | Storytelling as legacy, urge to create | | 55:14 | Accepting unplanned life outcomes | | 59:29 | Mercy and self-acceptance (Brene Brown anecdote) | | 66:49 | Reclaiming vitality & sabbatical plan (Elizabeth) | | 68:41 | Monica: "What are you most excited about?" | | 70:06 | Closing reflections and gratitude |

Tone & Language

The conversation is deeply candid, generous, and intellectually probing, blending humor with spiritual and emotional vulnerability. Monica interjects warmth and self-deprecating honesty; Elizabeth weaves in insight, compassion, and wit. Both provide memorable, sometimes raw, language—balancing the “messy” with the hopeful.

For Listeners New to the Show

This episode embodies the spirit of Reclaiming: openhearted, digressive but focused on the big questions—how to be a friend to yourself, how to survive and transform grief, how art and service redeem pain, and how women can author their own destinies amid persistent cultural forces. It's an essential listen for anyone seeking honest discussion about the personal and collective process of reclaiming what trauma, time, or society may have taken away.