Podcast Summary: "Zach Zimmerman is Not Evil"
So True with Caleb Hearon (Headgum) -- November 13, 2025
Guest: Zach Zimmerman
Episode Overview
In this heartfelt, sharp, and unflinchingly funny episode, beloved host Caleb Hearon sits down with comedian and writer Zach Zimmerman. As they "sort it all out and identify what’s really real," Zach unpacks a transformative—and mostly off-limits—summer, navigates family dynamics, shares harrowing and hilarious stories from online dating, and the pair reflect on the limits and rewards of vulnerability, setting boundaries, and the nature of being "good" or "evil." The conversation is marked by quick-witted banter, moments of real honesty, and musings on religion, sexuality, family, and the art of comedy.
Key Discussion Points & Insights
Boundaries and Sharing in Comedy
- Zach’s approach to boundaries: Zach jokes about coming into the podcast with a list of 10 off-limit topics, highlighting the tension comedians feel between vulnerability and self-protection.
- (02:05) Zach: “Yep. It's called boundaries, baby. I'm learning what they are.”
- (02:39) Zach: “That's what she loves about me. I, like, open up and I share my innards so people can, like, poke around. … But I'm realizing, like, oh, not everyone has—I'm sort of violating my own boundary now.”
- On the dangers of oversharing: They discuss the risks of openness, especially in the comedy world, and the importance of withholding aspects of yourself ("giving them the code to the safe").
- (03:06) Caleb: “Well, you're giving them the code to the safe.”
Identity, Background, and Location
- Zach’s upbringing: Raised evangelical and navigating a religious family, Zach is now exploring healthier boundaries ("the summer I turned broken") and learning to put himself first.
- Regional identity: Funny banter on whether Missouri is Midwest or South, illustrating the duo's knack for small, relatable observations.
- (05:14) Caleb: “Some people talk about Missouri as the south, but … there's really two Missouris and one of them is Southern, One of them is Midwestern. I am squarely from the Midwestern portion.”
Dating App Horror Stories & Modern Romance
- Zach’s catfishing/extortion story: Zach shares a cautionary tale about being scammed on Grindr by someone posing as a trans woman, who tried to blackmail him with fake nudes and personal info.
- (07:27) Zach: “This scammer has sent a report of my name. They have my address, my age, a list of possible family members… and then a picture of a penis, which is not my penis. I never sent this.”
- (08:59) Zach: “I'm just texting my—like, that's not my dick, Mom, that's not my dick. And I think she was most offended by just being reminded that I'm queer in her inbox.”
- Loss of imagination in hookup culture: Both bemoan the "death of ambiguity" with explicit photo sharing, longing for more mystique and playfulness.
- (11:01) Zach: “My big beef with Grindr right now isn't the bots. It's the death of imagination. People … are showing me a dick in your ass. … Write a poem!”
- (12:22) Caleb: “I'm like. The whole fun is that we, like, meet each other, we make out for a little bit … You've removed the whole entire enjoyment of the process.”
Gender, Power Dynamics, and Conflict
- "Tell a man no, get ready for a show": Zach’s catchphrase for the summer. He notes how men often react theatrically or poorly to even small rejections or refusals.
- (13:18) Zach: “Tell a man no, get ready for a show. All you have to do is tell a man a little itty bitty no. They will put on a production … it shows everything about the person.”
- Navigating, naming, and owning boundaries in relationships and dating.
- (15:16) Zach: “Maintain your ‘no’; don’t personalize their reaction. … It's not to hold firm to it. Don’t give in.”
Family, Love, and Conditionality
- Mother-son dynamics: Zach reveals a powerful, painful realization: the love he receives from his evangelical mother may not be unconditional after all.
- (22:54) Zach: “That she loves me unconditionally was a lie.”
- (22:57) Zach shares a moment when his mom said she’d been “praying” he would date a woman, which was "funny and hurtful at the same time."
- Trying to ‘fix’ family members: Zach talks about his book-in-progress, Shipmother, chronicling his attempt to change his mother’s religious/political beliefs via a cruise—realizing along the way that “trying to fix her” has distracted from discovering himself.
- (21:28) Zach: "What I learned, me being obsessed with her... was at the expense of me being obsessed with myself and learning who I am."
- Conditional love and parental wounds: They reflect on how childhood parental support—or lack thereof—has shaped their adult confidence and relationships.
The Nature of Good, Evil, and Morality
- Do we all have the capacity for great evil? Spirited back-and-forth on the classic 'button' dilemma and whether power corrupts, with both hosts poking holes in each other’s definitions and hypotheticals.
- (44:45) Zach: “One button kills a man, but you get a billion dollars.”
- (47:40) Caleb: “I really don't think I would take that button. ... I wouldn't.”
- God, Jesus, Religion, and Power: Zach shares a 'hot take' about the narratives around God and Jesus—posing God as the "original narcissist" and arguing people prefer identifying with God’s power rather than Jesus’ sacrifice.
- (53:05) Zach: “God, to me, is the original narcissist. ... God is evil. Jesus was good.”
- (53:25) Zach: “Nobody wants to be Jesus … because Jesus is harder.”
Therapy & Self-knowledge
- Different kinds of therapy: Zach and Caleb swap stories about therapists, the struggle to find a good fit, and whether therapy is always helpful.
- (19:48) Zach: "Therapist beats dad. ... Therapist is dad. ... Or sort of the non judgmental, shameless, kind, loving and supportive father figure."
- Personal growth: Zach describes being in the midst of learning who he is after years of prioritizing others’ needs, catalyzed by recent personal upheaval.
- (20:53) Zach: "I'm starting a process of learning who I am. Post putting other people's needs before mine."
Comedy, Vulnerability, and 'When Is It Ready?'
- When to take personal material to the stage: Both discuss striking the right balance between authenticity and exploitation of pain, with a nod to Tig Notaro’s legendary cancer set as a masterclass in this tightrope walk.
- (59:57) Caleb: “It is simply not any audience's responsibility to, like, caretake for you through whatever shit you're going through. You better be making them laugh.”
Notable Quotes & Memorable Moments
- On boundaries in comedy:
Caleb (03:06): “Well, you're giving them the code to the safe.” - On family and conditional love:
Zach (22:54): “That she loves me unconditionally was a lie.” - On apps and nudes:
Caleb (12:22): “The whole fun is that we, like, meet each other, we make out for a little bit... You've removed the whole entire enjoyment of the process.” - On power, morality, and evil:
Zach (47:30): “One button kills a man, but you get a billion dollars.” Caleb (47:42): “I really don't think I would take that button.” - On God and Jesus:
Zach (53:05): “God, to me, is the original narcissist. ... God is evil. Jesus was good.” - On vulnerability and healing:
Zach (56:45): “I didn't mean it as a bit. But you're right, it is quite a funny bit.” - On giving and receiving love:
Zach (64:03): “Love is listening. Love is noticing. Love is... commitment to one’s spiritual growth, the willingness to extend oneself.”
Timestamps for Key Segments
- Boundaries and sharing as comics: 02:05–04:32
- Catfishing/Grindr scam story: 06:32–09:59
- Loss of mystery in dating apps, nudes & LPSG: 10:53–12:39
- ‘Tell a man no, get ready for a show’/reactions to boundaries: 13:18–15:19
- Family love/conditionality/‘Shipmother’ book: 21:01–23:39
- Therapists as dads; learning selfhood: 19:00–21:01
- Morality, evil, and the philosophical ‘button’ dilemma: 43:09–47:42
- God vs. Jesus—hot takes on religion: 53:05–54:11
- When is something ready for stage? 57:52–61:24
- Rapid-fire True/False segment: 66:34–69:16
- Closing segment: “What is so true to you?”/acts of love: 62:06–65:20
Tone & Highlighted Moments
- Jokes about not being able to discuss Zach’s transformative summer become both an intentional running gag (“That was rude. One of the funniest things you’ve done...”) and an honest reflection on the need for processing before public sharing.
- Heartfelt moments land side-by-side with playful ribbing about podcasts, masculinity, and sexuality.
- Candid, affirming exchanges about queer love, family wounds, therapy, and the little acts of care that define community.
Takeaways
- The episode is a smart, unsparing, but loving look at the navigation of personal boundaries, especially for comedians who make life into material.
- Themes of conditional vs. unconditional love (especially parental), self-knowledge, queer dating, and the playful yet serious dance between being "good" or "evil" run throughout.
- Both Caleb and Zach bring a blend of insight, wit, and warmth, making the episode a rewarding listen for anyone wrestling with vulnerability, family, and the quest to be “so true.”