Podcast Summary: You Made It Weird with Pete Holmes — Guest: Jonathan Scott

Episode Date: October 25, 2023
Podcast Theme: “Everybody has secret weirdness, Pete Holmes gets comedians to share theirs.”
Guest: Jonathan Scott (Property Brothers)

Overview

This episode features a deep, playful, and candid conversation between comedian/podcaster Pete Holmes and TV renovation star Jonathan Scott. The two connect over their shared quirks, relationship perspectives, and philosophies on life, touching on everything from family and fame to emotional vulnerability, wedding planning, and their mutual love of magic. The warm, fast-paced banter is marked by honesty and self-reflection, with both Pete and Jonathan frequently relating stories of personal “secret weirdness.”

Key Discussion Points & Insights

1. Secret Weirdness and Set Mishaps

Time: 06:00–08:18

• Jonathan shares his on-set forgetfulness: leaving his fly down, phone ringing during takes.
  • Quote: "Half of my show has been shot with my fly hanging open." (Jonathan, 06:29)
• Talk turns to cleanliness quirks — washing hands before touching anything post-bathroom and the irrational “rules” they set for themselves.
• Hilarious aside: Jonathan justifies picking his teeth with high-denomination bills, claiming they’re cleaner than ones.
  • Quote: “In my mind, I justify it, that the higher the bill, the fewer people have touched it... Do not put a one anywhere near your mouth.” (Jonathan, 07:22)

2. Twin Life and Social Oddities

Time: 08:18–11:10

• Jonathan discusses being constantly lumped with his twin, Drew, both in media and public perception.
• Common twin misconceptions and awkward questions: “If you get hit, does he feel it?”
• Pete draws parallels to how people interact with any visible difference or rarity, like extreme height or red hair, and the awkward social license people feel.

3. Fame: Boundaries and Social Media

Time: 11:11–12:46

• Jonathan reflects on public encounters and boundaries, explaining the challenges of being interrupted in private moments.
• Stories of rude fans and the double-edged sword of social media trolling.
  • Quote: “You’re human. You’re allowed to be sick, you’re allowed to have a bad mood, you’re allowed to not be invaded.” (Jonathan, 12:40)

4. Anger, Emotional Expression, and Relationship Dynamics

Time: 12:46–30:00

• Pete opens up about his complicated relationship with anger, stemming from his childhood.
• Jonathan relates as the “peacekeeper” in his family, sharing that he never fought in previous relationships—sometimes to the detriment of emotional honesty.
  • Quote: “In my first two relationships—five-year relationships each—never got in a fight.” (Jonathan, 15:11)
• Both discuss learning the value of authentic conflict and emotional safety in relationships.
• Candid stories about handling “tones” and unspoken frustrations with their partners, with both partners (Val and Zooey) framed as expert conflict-resolvers.
• Memorable moment: Pete’s philosophy on marital communication — “You can blurt out a truth. Sometimes I say to Val, ‘This isn’t the entirety of how I feel, I just want to tell you what my pain is.’” (Pete, 17:41)
• Humor interwoven as they compare notes on marriage, dinner parties, “tone” in arguments, and how sensitivity and performance intersect at home.

5. Weddings, Traditions, and Second Chances

Time: 46:09–54:55

• Both men, remarried, celebrate the freedom and intentionality of second weddings.
  • Quote: “Second wedding’s the best... First wedding, no bagpipes. Second engagement, bring in the bagpipes.” (Jonathan, 52:53)
• Jonathan talks about proposing to Zooey Deschanel at Edinburgh Castle, with moving discussions about including personal traditions.
• They stress making weddings (and homes) reflect the actual couple and not external expectations.
  • Quote: “You just want your wedding to look like your love.” (Pete, 48:09)
• Both are adamant about not letting others dictate who gets invited, prioritizing emotional health over obligation.

6. Emotional Healing, Baggage, and the Importance of Letting Go

Time: 30:23–38:12

• Both reflect on how past relationship failures teach self-worth and set new standards.
• Pete recounts therapy, forgiveness, and the challenge of “not carrying the past”; brings up the story of the two monks as a parable for letting things go.
  • Quote: “Are you still carrying her? I put her down an hour ago.” (Pete, 32:44)
• Discussion of the conscious decision to grow and not drag old traumas or obligations forward.

7. Honesty and Compassion in Dating

Time: 39:39–45:53

• Jonathan shares stories of dating post-divorce, enforcing clear boundaries, and the complexities of being honest about intentions.
• Pete and Jonathan relate on the difficulty of not leading people on—even when intentions are clear.
• Further discussion on the feminine “nurturing” intuition and pacing of relationships.

8. Home Life, Family, and Holiday Traditions

Time: 73:09–84:45

• Sentimental discussion about building meaningful family rituals, particularly around the holidays.
• Jonathan and Pete both identify as “bad gift-givers” as a result of family patterns, but embrace intentionality as a way to rewrite the script.
  • Quote: “You just write it down. That’s all a great gift giver is.” (Pete, 74:43)
• Jonathan describes how he and Zooey design their home and family life specifically to nurture happiness, ease, and connection—including solarium dinner parties and custom home improvements.
• Pete: “A space can say, I see you.” (Pete, 83:51)

9. Celebrity IOU, Fame, and Authentic Generosity

Time: 84:45–91:23

• Inside scoop on working with celebrities on Celebrity IOU, highlighting stories with Brad Pitt, Michael Bublé, and others.
• Most celebrities are genuine and kind; the show enforces a “no douchebag” rule—if they sense it’s a publicity grab, they pass.
  • Quote: “It has to be genuine. And heartfelt, which is why we haven’t had you on the show.” (Jonathan, 88:42)

10. Jonathan’s Secret Life as a Magician and Clown

Time: 92:04–104:51

• Jonathan’s childhood as a professional clown and magician—learned from a Parks & Rec ad and self-taught through books.
• They nerd out on magic, favorite tricks, nerves, and the subtleties of mentalism and sleight-of-hand.
  • Quote: “I intentionally designed illusions to fool other magicians. And it pisses them off.” (Jonathan, 98:21)
• A deeply felt admiration for wonder, play, and the lessons magic offers about focus, calm, and humility.

11. Hypnotism and Picking the Right Audience

Time: 104:51–106:51

• Hypnotism as an art akin to magic—success depends on the subject’s willingness to go along.
• Learning to “read” people and take cues from their openness.

12. Philosophy, Faith, and the Meaning of Life

Time: 108:21–110:34

• Both give open, accepting answers about faith, drawing lines between spirituality and institutional religion.
• Jonathan critiques organized religion being co-opted for agendas, shares his belief in “something bigger,” and prioritizes living in the present.
  • Quote: “The meaning of life is to live it.” (Jonathan, 108:21)

Notable Quotes & Memorable Moments

• “When I orgasm, he feels it.” (Jonathan on the classic twin experience, 09:08)
• “Lurch looks like your after photo.” (Pete, 16:23)
• “Baby love, I just sat down… Would you mind getting them? That’s all I need… But if you cloak it, then I go like, why are you cloaking it?” (Pete, 19:55)
• “Nine out of ten times, if you say something that's bothering you, the response is better than you thought it would be.” (Jonathan, 16:36)
• “Second wedding’s the best... That’s like losing your virginity. Second wedding is like, all right, I know a couple moves.” (Pete, 47:54)
• “A space can say, I see you.” (Pete, 83:51)
• “We’ve implemented a no douchebag rule… it can’t be to promote the movie.” (Jonathan, 87:01)
• “I intentionally designed illusions to fool other magicians—and it pisses them off.” (Jonathan, 98:21)

Standout Segments with Timestamps

• Secret Twin Jokes & Social Awkwardness: 08:18–10:13
• Emotional Expression & Relationships: 13:26–20:28
• Wedding Philosophy: 47:46–50:52
• Making Holiday Traditions & Reclaiming Past Pain: 73:09–77:29
• Celebrity IOU Stories (Brad Pitt, Michael Buble): 84:45–90:56
• Jonathan’s Magician Backstory & Magic Geek-Out: 92:04–104:51
• Deep Dive: Meaning of Life and Spirituality: 108:21–110:34

Episode Tone

The conversation is warm, honest, and playful, alternating between self-deprecating humor, deep personal insight, and imaginative riffing. Pete and Jonathan trade wisdom and jokes in equal measure, creating the feel of newfound best friends sharing secrets late into the night.

For Listeners New to the Show

This episode is a rich sampler of the You Made It Weird ethos: curiosity, vulnerability, laughter, and the joy of celebrating the weird in all of us. Whether you’re into relationships, interior design, holiday memory-making, magic, or just love authentic connection, this one delivers in spades.

Listen for:

• Great marriage advice, emotional intelligence, and insights on personal growth.
• Hilarious stories about fame, twins, and home renovation gone weird.
• The hidden lives of magicians, clowns, and the power of letting go.
• Philosophy, healing, “second chance” living, and plenty of laughs.