Podcast Summary: Totally Booked with Zibby Owens

Guest: Penn Badgley
Book Discussed: CRUSHMORE: Essays on Love, Loss, and Coming-of-Age
Date: November 17, 2025

Episode Overview

In this engaging episode, Zibby Owens sits down with actor, writer, and podcaster Penn Badgley to discuss his new book, CRUSHMORE: Essays on Love, Loss, and Coming-of-Age, co-written with his Podcrushed podcast collaborators. The conversation weaves through Penn’s creative journey, the book’s candid approach to adolescence and fame, personal revelations about family and loss, and the universal experiences of growing up. Both Zibby and Penn reflect openly and warmly, making the episode a resonant listen for anyone interested in vulnerability, celebrity, and coming-of-age.

Main Discussion Points & Key Insights

1. Origins of the Book and Podcast — The Middle School Focus

• The Genesis of Podcrushed
  • Penn shares that the original idea for the Podcrushed podcast and eventually for the book came from his co-host, Nava Kavalan, during the COVID-19 pandemic.
  • They wanted to capture the unique, often mortifying period of being around age 12:

    "We explored this unique period of adolescence...we thought this period of life is so unique, so incredible and kind of mortifying." (03:23)

• Letting Others Speak
  • Penn notes the difference between guiding a conversation and letting stories unfold through interviews, especially with celebrities.

    "When you're interviewing other people, you're interviewing celebrities...you need to let those celebrities talk." (04:30)

• Returning to the Seed
  • The book is Penn’s way of “returning to the seed of the idea” to tell his and his co-writers' own stories in essay form.

2. The Universal Experience of Coming-of-Age

• Why Middle School?
  • Zibby relates as a parent of middle schoolers, highlighting the universal pain, change, and insecurity that marks those years.
  • She references Penn's episode with Matthew McConaughey to illustrate how everyone has their awkward phases.
• On Hair, Insecurity, and Representation (06:35)
  • Zibby reads aloud Penn's passage about his struggles with curly hair in adolescence, making her own child feel seen.

    "[Curly hair] is such a process. And your words made my fifth grader feel better, just so you know." (06:44)

  • Penn reflects on questioning whether to include such personal anecdotes:

    "I really thought about cutting that...that's really the extent of it—and how this one kid responded to it. That's just how we remember that time, you know. So many feelings." (07:39)

3. Fame, Identity, and the Camera

• Confronting Celebrity
  • Penn dives candidly into his experience of fame and why so few celebrities honestly address it.

    "Our culture is just inextricably, undeniably entangled and obsessed with celebrity…it's so impacted by not just celebrities, but celebrity." (10:19)

  • He wanted to write more explicitly about fame, calling it a fundamental part of his identity akin to fatherhood or religious faith:

    “…the degree of fame I do have…I'm not measuring it, but it's there…It has impacted my life no less than any other thing." (11:28)

• The Invention of the Selfie
  • Penn observes how cameras—and especially selfies—have shaped self-perception and culture:

    "The invention of the selfie, advent of the selfie, that's a huge moment in culture, in terms of the way we view ourselves." (12:46)

• The Trauma of Celebrity
  • He doesn’t shy from the darker side, likening the objectification of celebrities to a form of oppression:

    "Objectification is objectification, and a person who is rendered an object is a person who is rendered an object. You know, and that's the strangeness, I think, of celebrity, is that it really, really does feel to the person experiencing it like a form of oppression." (17:45)

• Giving Back and Humility
  • On responsibility and giving back through celebrity:

    "I think it's everybody's duty to give back, no matter who they are, and that's a unifying principle. I think what's unfortunate about celebrity is how it divides us." (14:21)

4. Family, Loss, and the Realities of Parenting

• Personal Struggles Shared
  • Zibby congratulates Penn on his twins and thanks him for his openness about pregnancy loss:

    "Thank you for sharing your, you know, your lost pregnancy because so many people have gone through that and the loss and the effect on a marriage and all that..." (22:59)

  • Penn talks about the essay “Lineage,” admitting it barely scratched the surface of the complexities around identity, race, and grief.
• Miscarriage and Cultural Silence
  • He argues for more open, honest conversation:

    “We at least need to start by talking about it more...miscarriages...can be really, really painful. I think I would say they universally are painful." (24:06)

  • Zibby quotes the book on the isolating effect of loss and the painful impact on their marriage:

    “My wife and I neared separation, as many do after losses like that, largely because we felt separate, so isolated in a culture that doesn’t talk much about these things or know how to support those going through it." (24:28)

  • Penn reflects on how having children since then changed his sense of loss:

    "It's harder to get in touch with that feeling of loss because my cup truly runneth over." (24:56)

  • He describes the immense care required to raise children and his awe at humanity's capacity for nurturing:

    "It takes so much care for one human being to make it to maturity...It's the most immeasurable thing in existence to me." (27:12)

5. The Limits of Preparation for Life’s Big Moments

• On Readiness and the Human Condition
  • Both discuss how it’s impossible to ever be prepared for the big things—birth, death, or profound loss. The unpredictability is, as Penn puts it:

    "If you could be ready for, let's say, birth or death…everything else would be boring, would be rendered boring." (29:16)

  • Zibby echoes that emotional moments always catch us off guard, regardless of supposed preparedness.

Notable Quotes & Memorable Moments

• On adolescence and insecurity:

  "It is nearly impossible to get through to a fifth through 10th grader...Actually that thing you’re freaking out about on your body…nobody is thinking about it."
  — Penn Badgley (09:13)

• On what fame really feels like:

  "…for people who are like the Britney Spears, you know, the Brad Pitt, the whomever, they cannot escape it. They are living Justin Bieber…they cannot escape it. They are living in this state of, like, the love object."
  — Penn Badgley (16:38)

• On raising children and human resilience:

  "It takes so much care for one human being to make it to maturity. I mean, an insane amount of care. More care than you can. It's immeasurable. It's the most immeasurable thing in existence to me."
  — Penn Badgley (27:12)

Timestamps for Important Segments

• 03:20 — Penn on the origins of the podcast and book; why age 12 matters
• 06:44 — Discussion on adolescent insecurities and Penn’s curly hair essay
• 10:04 — Writing about fame and its complexities
• 12:45 — The consequences of camera technology and the selfie
• 14:21 — Celebrity, humility, and giving back to society
• 22:59 — Zibby thanks Penn for sharing about pregnancy loss
• 24:28 — Penn discusses essay "Lineage" and the challenge of articulating grief & identity
• 27:12 — The immeasurable care and hope embedded in parenting
• 29:16 — Reflections on never being fully prepared for life’s milestones

Overall Tone & Takeaway

The conversation is warm, unguarded, and deeply human, balancing wit with profundity, and vulnerability with insight. Both Zibby and Penn invite listeners into their private worries, joys, and philosophies, making this a standout episode for anyone drawn to stories of growing up, grappling with self-image, parenthood, and the strangeness of modern fame. Penn’s reflections will resonate with teenagers, parents, and anyone who’s ever felt awkward—or found unexpected strength in the process of reflection.

If you’re seeking honest book talk with a side of soul-searching, this episode delivers—reminding us that behind every public persona lies a complicated, evolving, and very real human story.