Would you ever date an AI boyfriend? Before you say absolutely fucking not, consider this: plenty of people who swear they’d never have an “AI relationship” are already turning to chatbots for reassurance, emotional processing, difficult conversations, or the occasional late-night spiral. This week, Amanda is joined by Bridget Todd (@bridgetmarieindc), host of There Are No Girls on the Internet and author of Love at First Prompt: AI and the Future of Intimacy, to overthink what happens when technology starts creeping into our most private emotional spaces. They talk about women using AI for romance because dating men feels increasingly hostile, neurodivergent people using chatbots to rehearse human connection, the appeal of a boyfriend who literally never gets tired of talking about books, and the very real misogyny baked into “girlfriends who never say no.” But in the world of large language models, who gets to own, shape, and profit from the parts of us that feel most intimate. An inquisitive spiral about loneliness, desire, digital intimacy, and who gets access to our inner worlds.
Further Listening: Love at First Prompt by Bridget Todd

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What if you actually get your dream job... and then realize you're not living the dream you thought you would? This week, Amanda is joined by Cherie Brooke (@cherie.brooke) and Jean (@_jeanluo), hosts of the Tiger Sisters podcast (@tigersisterspodcast), who both left impressive corporate careers after discovering that the jobs their younger selves would have killed for no longer fit the lives they wanted. Together, they overthink golden handcuffs, the privilege built into pursuing passion, and why a job doesn’t have to provide purpose, identity, money, joy, and self-actualization all at once. They talk about taking sabbaticals, experimenting before making a giant career leap, letting yourself “fade in and out” of ambition, and why a perfectly good job that pays the bills might actually be part of your dream life.  A thoughtful spiral about ambition, career pivots, and building a dream life instead of obsessing over one perfect job.
Further Listening: Tiger Sisters Podcast

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 We say we want more human connection, so why can texting “want to hang?” feel weirdly like begging? This week, Amanda is joined by ICU nurse, New York Times bestselling author, and Stories from a Stranger host Hunter Prosper (@hunter_prosper), whose work interviewing strangers has taught him that connection often starts with something deceptively simple: actually listening. Together, they overthink why we assume we’re burdening our friends, the case for the humble 20-minute “micro hang,” and how to be vulnerable without accidentally oversharing your way into an intimacy level you never signed up for. They also get into our increasingly unrealistic expectations around constant communication, why one awkward social moment probably isn’t being dissected in the group chat, and how many potential friendships die because everyone is waiting for someone else to make the first move.
A thoughtful spiral about loneliness, vulnerability, and being brave enough to say hi first.

Further Reading: Stories From A Stranger by Hunter Prosper

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Are you ambitious... or just exhausted? This week, Amanda is joined by award winning journalist and author of The Ambition Penalty, Stefanie O'Connell (@stefanieoconnell), to unpack one of the most misunderstood words in our vocabulary, ambition. They explore why ambition isn't a fixed personality trait, how corporate culture rewards some people while penalizing others for the exact same behavior, and why women are so often expected to walk an impossible tightrope between being "too much" and "not enough." They answer listener thought spirals about external validation, comparison, girlboss burnout, trad wives, capitalism, and whether it's possible to want a big life without letting your achievements define your worth. A validating spiral about redefining success and realizing your ambition was never the problem.
Further Reading: The Ambition Penalty by Stafanie O'Connell

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This week, Amanda is joined by entrepreneur, former supreme court attorney and professional poker player, and author of You Can Just Do Things, Cate Hall, to unpack why starting over feels so terrifying and why it might be the very thing that leads us toward a more authentic life. Together, they chat about the fear of quitting, the sunk cost fallacy, why we crave a tidy life story, and how to tell the difference between running away from something and running toward yourself. They also answer listener thought spirals about toxic jobs, divorce, changing careers, moving across the world, getting "too old" to begin again, and whether it's ever really too late to start over.
Further Reading: You Can Just Do Things by Cate Hall with Sasha Chapin

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Why are we so afraid of getting older? Is it really about wrinkles... or are we actually afraid of losing our purpose, our identity, and the people we love? This week, Amanda is joined by oncologist, bioethicist, and Eat Your Ice Creamauthor Dr. Ezekiel "Zeke" Emanuel (@drezekielemanuel) to unpack our culture's obsession with staying young. Together, they explore why the wellness industry's promises of longevity miss the point, why curiosity matters more than looking 25 forever, and why some of the happiest, most meaningful years of life may still be ahead of us. They answer listener thought spirals about Botox, becoming "invisible," feeling behind in adulthood, retirement, and whether getting older has to mean becoming less yourself. A hopeful spiral about learning to fear aging a little less... and living a little more.

Further Reading: Eat Your Ice Cream by Ezekiel J. Emanuel, MD

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Why does failure feel so much bigger than it actually is? This week, Amanda is joined by entrepreneur, author, and leadership coach Jane Marie Chen (@janemarie.chen) to spiral about failure: why we're so terrified of it, why we avoid it at all costs, and why it often hurts so much more than the thing that actually happened. Together, they explore perfectionism, rejection, burnout, imposter syndrome, and the childhood experiences that shape our relationship to failure long before we ever encounter it. And what if failure isn't evidence that we're unworthy? What if it's simply the price of catching bigger waves? A reflective spiral about risk, resilience, and learning to love yourself even when things don't go according to plan.

Further Reading: Like a Wave We Break by Jane Marie Chen

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No matter how old we get, there’s a decent chance a small part of us is still trying to impress, understand, forgive, rebel against, or be comforted by our mothers. This week, Amanda is joined by writer and editor Ashley Oerman (@ashleyoerman), author of Motherf*cked, to spiral about one of the most loaded relationships in the human experience: the one between mothers and their children. Together, they unpack the impossible expectations placed on mothers, the ways our earliest relationships shape our adult identities, and why "mommy issues" have become both a punchline and a profound psychological reality. A tender spiral about the stories we spend a lifetime trying to rewrite.

Further Reading: Motherf*cked: How to Stop Your Mothers Toxic Drama from Ruining Your Life by Ashley Oerman

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When we first aired this episode in 2024, burnout felt like the defining emotional state of modern life. Two years later… honestly, not much has improved. If anything, burnout has shape-shifted. The girlboss hustle era may be less aspirational than it once was, but it’s been replaced by new flavors of exhaustion: constant digital overwhelm, economic anxiety, doomscrolling, and the strange pressure to be “healing” productively at all times. So this week, we’re revisiting Amanda’s conversation with the brilliant Amelia Nagoski (@burnoutbookgroup), co-author of Burnout: The Secret to Unlocking the Stress Cycle, for a much-needed refresher on what burnout actually is. Together, they unpack what happens when our bodies get stuck in an incomplete stress response cycle, why modern life keeps us there, and what it actually takes to start feeling better. If you’re emotionally fried, physically depleted, or somehow both overstimulated and numb, this one’s for you. We’ll be back in two weeks with a brand new episode.
Further Reading: Burnout: The Secret to Unlocking the Stress Cycle by Emily Nagoski, PhD, and Amelia Nagoski, DMA

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What does “thinking critically” actually mean and why is everyone so convinced they’re already good at it? This week, Amanda is joined by psychologist and author of Radical Thinking, Peter Lamont to explore how all of our beliefs are shaped by a limited slice of what we notice and how we interpret it, which means disagreement is inevitable. Peter reframes critical thinking as something quieter and more uncomfortable: recognizing the limits of your own perspective and being willing to engage with people who see the world differently. From the role of the internet and social media to why curiosity might matter more than certainty, this episode is a grounded spiral about attention, interpretation, and learning to question your own thinking before anyone else’s.

Further Reading: Radical Thinking: How to See the Bigger Picture by Peter Lamont

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