Episode Summary: You Made It Weird with Pete Holmes – "We Made It Weird #229"

Date: October 3, 2025
Host: Pete Holmes
Co-Host: Valerie

Overview

In this "We Made It Weird" installment, Pete Holmes and his wife/co-host Valerie embark on their signature blend of reflective humor and vulnerability, exploring themes around embarrassment, creativity, authenticity, emotional coping, "coolness" across generations, sobriety, addiction, and the psychological quirks of show business. The conversation weaves between personal stories, philosophical musings, and lighthearted asides, creating a portrait of two people continually seeking meaning (and laughs) in the weirdness of everyday life.

Key Discussion Points & Insights

1. Embarrassing Creative Misadventures

[02:11–11:40] Valerie’s Failed Proof-of-Concept Video

• Valerie recounts an embarrassing attempt to film proof-of-concept FaceTime snippets with her friend Lisa as a "sizzle reel" for a pilot about their friendship.
• The effort, meant to capture their natural rapport, was a technological flop: “We had like, 11 minutes of FaceTiming and screen recording... and there was no audio, because of course there wasn’t.” ([06:47])
• Pete compares this vulnerability to show business in general: “At the end of the day, I’m saying, wait till you get a load of this. And when they say pass, it’s like turning the lights on at an orgy… you just feel so exposed.” ([10:23])

Memorable Quote:

“The story of you two failing at this humiliating endeavor is the cleanest, purest... I’m gonna buy all of it because you guys are dorks. You’re hardcore fucking dorks. That’s what the show is about.”
— Pete ([14:10])

2. Millennial Cringe, Earnestness, and the ‘Coolness’ Wall

[15:15–20:56] Generational Reflections

• Valerie observes how Gen Z perceives millennial vulnerability as "cringe," but argues that being earnest and honest is more rewarding than being "cool."
• Pete draws a metaphor comparing being cool to the "coming soon" partition walls at the mall: “Being cool is... the veiling of your desperate attempts to get it together.” ([18:14])
• Discussion on how trying to be authentic often collides with the teenage/young adult urge to shield one’s awkwardness from scrutiny.

Memorable Quote:

“I still haven’t even met that bitch.”
— Valerie on forming identity while young ([19:35])

3. The Need to Be Seen, ‘Dorkiness,’ and Parental Influence

[21:19–24:43] Vulnerability vs. Self-Protection

• Both hosts acknowledge a deep need to be “seen and known, like, truly known,” even in their strangest or “nastiest” parts. ([22:28])
• Valerie considers her mother’s excessive talking—symbolic of overbearing adults who crowd out kids’ ability to develop autonomy and “coolness.”
• Pete notes, “Kids want to be cool, but they want you to be cool,” emphasizing the importance of giving children space. ([27:47])

4. Parenting, Emotional Space, and Leela’s Profound Observation

[28:11–30:37] The Power (and Pain) of Love

• Valerie shares an interaction with their daughter, Leela, whose insight reveals her sensitivity: “Too much love can hurt you... If somebody comes with too much love for you, you’ll have to dodge it.” ([29:09])
• The hosts recognize the intensity of children’s emotions and value giving them quiet space to process.

Memorable Quote:

“She feels everything 10 out of 10. So she feels love 10 out of 10, too.”
— Valerie ([30:18])

5. Addiction, Avoidance, and Sober Curiosity

[31:22–40:33] Sex & Love Addiction, Emotional Numbing

• Pete references a Louis CK interview about experiencing emotion without addictive outlets: “When I stop and allow the feeling... it’s a sensation. It passes through your body, and it just wants to be honored.” ([32:21])
• Valerie echoes similar themes from Elizabeth Gilbert’s memoir about sex and love addiction, noting: “Addiction is addiction. Her sex and love addiction is the same as... heroin addiction.” ([37:13])
• They discuss how all forms of compulsion (food, fantasy, love, sex) serve as avoidance of uncomfortable feelings.

Memorable Quote:

“The treasure you seek is in the cave that you don’t want to go into. … I can really use the reminder.”
— Valerie ([57:29])

6. The Desire for Approval and the Inability to Please Everyone

[44:46–55:28] People-Pleasing and Existential Security

• Pete relates watching a YouTube video about “bad comedians” and dreaming of convincing the creator to like him. The exchange explores the wound of needing universal approval.
• Valerie notes: “It doesn’t matter if every other person on the planet loved me. I have to convince that one person. Otherwise the whole thing is in the trash.” ([52:15])
• Pete, relating Rupert Spira and Byron Katie, encourages exploring the self that remains when approval is denied: “Even your loneliness is made out of beautiful fireworks.” ([56:03])

7. Resilience Through Discomfort & The Art of "Just Being"

[58:40–67:58] Sobriety, Boredom, and Emotional Practice

• Valerie describes hard-earned resilience in living through uncomfortable alone time—gradually learning from repeating those feelings: “There’s just no other way out than through.” ([61:45])
• Pete reframes this: “If we allow the emotion with a secret intent to get rid of it, it doesn’t work... You have to just go in with flowers.” ([62:00])
• Filming on location, Pete discusses using time alone to practice being present, rather than falling into old escapes (e.g., weed, video games): “Why not explore the true nature of your boredom?” ([65:27])

8. Living Simpler, Sober, and Letting Go

[68:07–71:56] Surrendering Control

• Both reflect on embracing “sober October” energy—doing less, embracing silence, reading instead of endless scrolling, and allowing the present moment to be enough.
• Valerie sums up recent lessons: “I did the best I could. It went how it went, and I’m just gonna lay low for a minute… surrender it over to life.” ([71:56])

9. Slasher Movies, Acting Real Fear, and Set Life

[72:01–76:13] Pete’s On-Set Experience

• Pete shares what it’s like shooting a horror movie, acting out being chased and killed in a physically challenging scene: “My legs are so fucked up. I’m, like, walking downstairs gingerly.” ([74:22])
• Both joke about whether acting out scary or sexy scenes would actually stir real emotion or arousal—they agree awkwardness is frequently more prevalent than intensity on set.

10. Quirky Final Musings

[81:18–84:22] Second-Screening and the ‘Coolest Mouth Accessories’

• The hosts discuss the quirks of solo TV watching (always “second-screening”), the rebel coolness of dental picks, and how even daily habits get tangled up with seeking stimulation.

Notable Quotes & Timestamps

• Pete: “At the end of the day, I’m saying, wait till you get a load of this. And when they say pass, it’s like turning the lights on at an orgy.” ([10:23])
• Valerie: “I still haven’t even met that bitch.” (on identity formation, [19:35])
• Pete: “Kids want to be cool, but they want you to be cool. Because I remember being like, can everybody just like, I still feel this way a lot of the time. That’s why I hate planning.” ([27:47])
• Valerie: “Too much love can hurt you. Like, if somebody comes with too much love for you, you’ll have to dodge it.” ([29:09])
• Pete: “If we allow the emotion with a secret intent to get rid of it, it doesn’t work. It knows. It’s like going on a date and you’re holding flowers, but there’s a knife behind your back.” ([62:06])
• Valerie: “There’s just no other way out than through... actually I’ve been here before. I know how this goes. Just let it.” ([61:45])
• Pete: “Why not explore the true nature of your boredom?” ([65:27])

Episode Flow & Tone

• The episode matches the show’s signature mix of honest exploration and comedic storytelling.
• Pete and Valerie maintain a playful, self-aware banter—even on serious subjects—making philosophical musings feel approachable.
• The language oscillates between casual, earnest, and whimsically explicit, with frequent asides and cultural references.

For New Listeners

• This episode is a stellar example of Pete & Valerie’s core themes: embracing weirdness, understanding psychological wounds, finding humor in vulnerability, and learning to sit with discomfort rather than escape it.
• Their dynamic is both supportive and self-deprecating, making deep dives into embarrassing or emotional territory feel both insightful and entertaining.

Key Takeaway:
You can only find real connection—both with others and yourself—by being open to embarrassment, discomfort, and the awkward chaos of real feelings. The weirdness is the point.