"You Made It Weird with Pete Holmes"

Episode: Father Greg Boyle Returns

Date: September 10, 2025
Guest: Father Greg Boyle

Episode Overview

In this rich and heartfelt conversation, Pete Holmes welcomes Father Greg Boyle—Jesuit priest, founder of Homeboy Industries, and author of several lauded books, including his latest, Cherished Belonging. The episode is a profound exploration of spirituality, compassion, community, and the deep human longing for belonging, tenderness, and transformation. Through playful banter, vulnerable storytelling, and honest questions, Pete and Father Greg delve into the paradoxes of faith, the pain of othering, the practice of mercy, and the daily work of keeping the heart “wet” and open. Their dialogue is filled with insights from personal experience, theological musings, and memorable stories from Homeboy Industries and beyond.

Key Discussion Points & Insights

1. The Wounds of Being Seen and Misunderstood ([02:14]–[05:35])

• Pete opens up about being wounded by years of feeling misunderstood as a comedian in Christian circles—torn between his vocation and spiritual life.
• Father Greg and Pete discuss balance between touring/professional obligations and family, acknowledging the intentionality behind their choices and the privilege of choosing space.
• Quote:
  Pete: “I go out once a month…one weekend I’m gone, but most people just go like, ‘I could never do that.’” ([04:29])
  Father Greg: “Except you and I know that it kind of has more intentionality than not…you hear ‘one a month,’ you go, ‘Good for you.’” ([04:46])

2. The Practice and Effects of Softening & Openness ([06:51]–[09:44])

• Greg describes his morning practice (prayer, reading, reflection) and how it fosters gentleness and “spaciousness” in the midst of chaos.
• The power of intentional spiritual practices: reading and reflecting softens the heart, helps maintain compassion in daily encounters.
• Quote:
  Father Greg: “Reading somebody who you like…and then you put it down, you go, wow, I feel open, softened, ready.” ([07:38])
  Pete: “How close we were to love…we’re so close. But when we’re tight, I feel so far.” ([07:53])

3. Anchoring Ourselves in Tenderness & The Mystical Filter ([12:01]–[16:20])

• Anchoring daily life in cherishing and tenderness through spiritual rituals, breathing, reading, and community.
• The ‘mystical filter’: Interpreting scripture through a lens of love and intuition, filtering out images of a wrathful God that don’t resonate with experience.
• Quote:
  Father Greg: “Once you know the God of love, you fire all the other gods. That’s part of the filtering—to say no, I don’t believe in that God ever.” ([16:09])
  Pete: “A shepherd in a field would know: ‘This doesn’t sound like God to me.’” ([16:48])

4. Accessible Spirituality vs. Religious Elitism ([18:35]–[21:44])

• Faith as lived experience, not expertise—confidence in “the gift of the lens” to everyone, not just scholars.
• Story: Socorro, an uneducated parishioner, confidently rejects wrathful images of God—“God is not like that”—highlighting the accessible nature of divine intuition.

5. Mercy vs. Forgiveness & The Parable of the Prodigal Son ([23:56]–[25:53])

• Mercy as fundamental: Mercy exceeds forgiveness—unconditional, abundant, initiates relationship without prerequisites.
• Reframing atonement: Challenging tradition that sees Jesus as a sacrifice to appease an angry God. Emphasizing a “change of mind” about God, not God changing about us.
• Quote:
  Father Greg: “Mercy is the father running to the kid and saying, I don’t want to hear your fake-ass apology. I love you too much. You’re home.” ([24:24])
  Pete: “There’s no atonement. The Prodigal Son remembers that he’s his father’s child. That’s it.” ([25:15])

6. Othering, Inclusion, and the Temptation to Divide ([29:05]–[32:57])

• The “hard sell” of inclusion and belonging: The Gospel is subversive because it dissolves boundaries, making belonging unconditional.
• Human tendency to create “us and them”—roots in marketing, tribalism, fear; how religious institutions profit from indictment rather than invitation.
• Quote:
  Father Greg: “The church had a choice: indictment or invitation. Indictment filled the pews…but we didn’t trust love.” ([30:18])
  Pete: “There’s this unbearably delicious temptation to other people.” ([29:47])

7. The Power of Cherishing and Community “Dosing” ([42:36]–[47:18])

• No one can do this work alone: At Homeboy Industries, transformation comes from collective “dosing” of affirmation, tenderness, and attention.
• Small gestures matter: A simple text, a smile, a word of recognition can be the nudge that keeps someone moving forward.
• Quote:
  Father Greg: “Everybody’s giving a dose…If enough people do that, then I think people feel held.” ([43:30])
  Father Greg: “It has a cumulative tenderizing effect on people.” ([47:18])

8. Keeping the Heart “Wet”—Joy, Tenderness, and Relational Practice ([49:45]–[52:52])

• “Wet” and “juicy” as metaphors for aliveness: The difference between brittle/dry and flourishing/joyful is openness to compassion.
• Generosity as a clue to identity: When generous or loving, we feel most truly ourselves (cf. Rupert Spira).
• Quote:
  Pete: “When you’re generous…don’t you feel like your real self? And aren’t you compelled to give it away?” ([52:13])
  Father Greg: “Juicy is not a fleeting happiness. It’s joy.” ([50:45])

9. Non-Duality and No Otherness ([53:10]–[55:45], [106:21])

• Widening the circle: Living as if there are no outsiders, emphasizing non-dual belonging rather than dualistic separation.
• Boundaries and timeouts exist, but always with the intention of eventual return, not rejection.
• Quote:
  Father Greg: “Once you walk with them, you’re by definition saying, no, they belong to us. They’re not outside this circle.” ([54:03])

10. The Trap of Retribution and Healthy Responses to Harm ([62:17]–[65:57])

• Cultural myth of retribution: American stories center on avenging, punishing, and violence as “strength.”
• Retribution is unhealthy: While human, it isn’t the hallmark of adult wholeness—“mean and cruel is just mean and cruel.”
• Quote:
  Father Greg: “Wanting payback is human. But you couldn’t make the case that it was healthy. Retribution is not the endeavor of a healthy adult.” ([64:06])

11. Transforming Wounds, Not Rescuing ([66:26]–[68:39])

• We don’t have enemies, we have injuries. The key is noticing wounds and being tender to ourselves and others—transformation is communal, not individual rescue.
• Transformation “happens,” it’s not imposed—Homeboy Industries creates irresistible, cherishing spaces.
• Quote:
  Pete: “We don’t have hate, we have wounds…That heals me.” ([65:57])
  Father Greg: “Once people enter it and everybody’s dosing, it’s a system…irresistible, where people go, I was cherished there.” ([68:39])

12. The Longing for Belonging & Welcoming Home ([69:14]–[70:41])

• Religion addresses longing, not just belief or duty. People long for home, welcome, and safety—a “welcome home” at Disneyland or Homeboy touches something universal.
• Quote:
  Father Greg: “People long for that. People long to be at home. People long to be welcomed, included, seen, safe.” ([69:35])

13. Practices of Attention, Effort, and the Humanity of Jesus ([76:21]–[114:31])

• Intentionality in relationship: Attention, even in short bursts, can be transformative—dropping everything for 45 seconds with a loved one is everything.
• Jesus as fully human: Not always at his best, practiced at love, made effortful choices—felt annoyance, asked “Who touched me?” out of real yearning, not omniscience.
• Quote:
  Father Greg: “It has to be fast. State your business. Yes. Check the box. Try to be as attentive and loving and kind and beholding and affirming and prizing and high regard. But this is not going to last long because I have too many people…” ([77:18])
  Father Greg: “I think there are a lot more examples in the gospel where he’s not at his best. He didn’t catch himself. For me, it’s always about relational wholeness.” ([112:40])

Notable Quotes & Memorable Moments

• On Mercy and Love:
  “God became one of us so that the love could become more tender.”
  —Father Greg Boyle ([25:58])

• On ‘Mystical Filter’:
  “Once you know the God of love, you fire all the other gods.”
  —Father Greg Boyle ([16:09])

• On Belonging:
  “Inclusion is what are you including them in? Belonging—if you’re not including them into a belonging space, then I don’t even know what it means.”
  —Father Greg Boyle ([29:05])

• On Transformation:
  “Transformation happens there. That once people kind of enter it and everybody’s dosing, it’s a system—so compelling, irresistible.”
  —Father Greg Boyle ([68:39])

• On Practice and Realness:
  “You want to be practiced…you want to work at it. Otherwise you fall into the places where we all fall into.”
  —Father Greg Boyle ([110:48])

Important Timestamps

• 00:15 – Pete introduces Father Greg Boyle and his newest book Cherished Belonging.
• 02:14 – Pete shares his wound around “balancing” spiritual and comedic life.
• 06:51 – Discussion of “softening,” openness, and spiritual practice.
• 12:01 – Anchoring in tenderness; cherishing others like family.
• 15:38 – The “mystical filter” for engaging scripture.
• 23:56 – Mercy vs. forgiveness and the Parable of the Prodigal Son.
• 29:05 – Belonging, nonviolence, and the hard sell of unconditional love.
• 42:36 – Parasitic friendships, boundaries, and communal “dosing” at Homeboy.
• 49:45 – Keeping the heart “wet” and juicy: joy, compassion, and Ram Dass.
• 53:10 – Non-duality in Greg’s work: no outsiders, no otherness.
• 62:17 – The “water” of cultural retribution, violence, and systemic myths.
• 66:26 – We don’t have enemies, we have injuries; healing through inclusion.
• 69:14 – The longing to be home, welcomed, and loved.
• 77:18 – Balancing attentiveness with practical constraints at Homeboy.
• 110:48 – The importance of effortful, practiced kindness—even for spiritual teachers.
• 112:40 – The real humanity of Jesus: effort, annoyance, yearning for connection.

Tone & Originality

The episode is warm, funny, and deeply honest, rooted in Pete’s curiosity and Father Greg’s gentle wisdom. Both lean into their vulnerabilities, modeling a kind of “tender dialogue” where doubt, laughter, and tears are welcome. The tone is at once playful and profound, balancing big spiritual questions with concrete examples of community, justice, and day-to-day struggles. Father Greg’s language is humble, approachable, and often sprinkled with self-deprecating humor; Pete’s is earnest, animated, and sometimes irreverent—together, their rapport makes potentially dense topics accessible and resonant.

Closing

Pete expresses deep gratitude for Father Greg’s work and wisdom, noting how much more they could have covered together. Father Greg reiterates (jokingly) that he’s really done writing books—though Pete and history suggest otherwise.

Father Greg signs off:

"Keep it crispy." ([115:41])

This episode is a poignant primer on mercy, mysticism, and making space for others (and ourselves!)—reminding us that even one small act of cherishing can change a life.