Revenge is one of our oldest fantasies. It's sharp, seductive, but rarely as satisfying as it promises to be. This week, host Amanda Montell (@amanda_montell) is joined by lawyer, author, and Assistant Clinical Professor of Psychiatry at the Yale School of Medicine, James Kimmel Jr. to overthink our obsession with revenge: why it feels so good in theory, why it rarely delivers in practice, and what it reveals about our deepest wounds and longings. Together, they explore how the brain processes revenge almost like an addictive substance - flooding us with momentary relief, then keeping us hooked in a cycle of suffering. From the neuroscience of vengeance to the quiet, radical possibility of letting go, this conversation opens up a gentler path through pain. A soft spiral into anger, control, and the sacred art of breaking the cycle.

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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“Ditz.” It’s a word that sounds harmless, silly, soft-edged, even cute. But underneath it is a long, messy history of gendered judgment. This week, host Amanda Montell (@amanda_montell) is joined by journalist and author Koa Beck (@koabeck) to gently spiral about the cultural construction of ditziness: where the word came from, who it’s been used against, and what it reveals about how we punish femininity for being either too much… or not enough. Together, they unpack how "ditzy" became shorthand for whiteness, blondness, and a very specific kind of Southern California-coded femininity, despite the fact that the so-called “ditz” in pop culture (Elle Woods, Cher Horowitz, Regina George) is often brilliant, strategic, and socially powerful. Is ditziness a stereotype, a defense mechanism, a flirtation tool, or all three? What happens when smart women lean into softness? And how do internalized misogyny and impossible expectations make it feel safer to play dumb than to risk being called bossy, smug, or shrill? A quietly radical spiral into language, performance, and the politics of not being taken seriously on purpose or by accident.

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.

- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.

- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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Can you be trained by a gaslighter to gaslight yourself? This week, Amanda (@amanda_montell) is joined by Harvard historian and sociologist Rebecca Lemov (@rebeccalemov) to overthink gaslighting, a word that’s become part of our everyday vocabulary, but whose origins and implications run deeper than we realize. Together, they trace gaslighting’s roots in psychology, politics, and culture, and explore how this slow erosion of truth can shape our relationships, our self-trust, and our collective understanding of reality.
A quiet spiral about doubt, distortion, and the radical act of believing yourself.  

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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Should I move or stay where I am? Take the job or turn it down? Text back or disappear into the ocean? This week, host Amanda Montell (@amanda_montell) is joined by Vicki Tan (@vickiheart), a digital product designer and author, to gently spiral about indecision: why it’s so hard to choose, what’s actually hiding underneath all that back-and-forth, and how much of it is really fear dressed up as logic.
Together, they unpack the mental clutter, perfectionism, and quiet grief that decision making so often stirs up, and ask what it would feel like to choose without trying to be perfect. A spiral into possibility, analysis paralysis, and the sacred mess of not knowing what comes next.
Further Reading: Ask This Book A Question by Vicki Tan

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

Head to https://Greenchef.com/50MAGICAL and use code 50MAGICAL to get 50% off your first month, then 20% off for two months with free shipping.

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In the digital age, the people we feel closest to sometimes don’t even know we exist. This week, host Amanda Montell (@amanda_montell) is joined by Jessica Zier and Lizzie Li, PhD students at Northwestern University who study parasocial relationships, to spiral about the emotional life of one-sided intimacy. Together, they explore how digital closeness blurs the line between connection and projection, and why it makes perfect sense that we feel so seen by people who’ve never met us. A soft spiral into loneliness, identity, and the very human instinct to reach for connection, even through a screen.

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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The case of Amanda, a writer whose internal monologue won't stop narrating her life, instead of just letting her live it.

Listen to Proxy with Yowei Shaw

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What happens when the future is something you have to build, but others get to inherit? This week, host Amanda Montell (@amanda_montell) is joined by journalists Wailin Wong and Stacey Vanek Smith (@svaneksmith) to overthink the emotional, historical, and spiritual weight of generational wealth: what it gives, what it withholds, and who it was never designed for. Listen as they explore the systems that have kept generational wealth out of reach for so many marginalized communities, the guilt of those who inherit it and do care, and the quiet alienation of watching others take it for granted.
A layered spiral into privilege, precarity, and what it means to want stability in a world that’s never been fair.
Further Listening: The Indicator from Planet Money
Further Reading: Machiavelli For Women by Stacey Vanek Smith 

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

Head to https://Greenchef.com/50MAGICAL and use code 50MAGICAL to get 50% off your first month, then 20% off for two months with free shipping.

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In an age where everyone has to have a hot take, how does this shape our inner voice? This week, host Amanda Montell (@amanda_montell) is joined by journalist Fortesa Latifi (@hifortesa) to unpack the emotional weight of opinion overload: the pressure to react, post, and declare where we stand before we’ve even had a chance to feel what we feel. Together, they explore what it means to live in a world where silence is suspect, nuance is suspicious, and uncertainty is quietly taboo. What do we lose when we’re expected to be explainable at all times? A soft spiral into the exhaustion of constant takes, the grief of unspoken thoughts, and the quiet rebellion of saying “I don’t know yet.” 

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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How much of who you are is really you—and how much is habit, circumstance, or a story you started telling yourself a long time ago? This week, host Amanda Montell (@amanda_montell) is joined by journalist and author Olga Khazan (@olganator) to explore the strange, sticky concept of personality: where it comes from, why it feels so permanent, and whether we can actually change it. We touch on the appeal of personality frameworks like Myers-Briggs and the Enneagram, but zoom out to ask deeper questions: Do people ever really change, or do we just learn how to act differently? What happens when we no longer feel like the person we’re known to be? A quiet spiral about identity, adaptability, and the mysterious choreography of who we become.Further Reading: Me, But Better: The Science and Promise of Personality Change by Olga Khazan 

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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Why do we, against all logic, evidence, and bank account balances, still kind of believe that billionaires earned it? This week on Magical Overthinkers, host Amanda Montell (@amanda_montell) sits down with writer and cultural critic Dasia Sade (@dasiadoesit) to unravel the glittery, gaslight-y spell of billionaire worship in America: how it started, who profits from it, and what it’s doing to our collective sense of possibility (and sanity). From Calvinism to Musk, we trace how a stew of religious guilt, PR manipulation, and celebrity obsession shaped a culture where having a billion dollars feels aspirational instead of deeply dystopian. Plus: why most of us can’t actually comprehend how much a billion is, what billionaires are really doing with all that money, and what it might take to finally break the spell (spoiler: it’s not another Forbes profile).

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.- To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack.- Pick up a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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