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The Daily Whatever Show, Sept 25: Parenting Teens in Trump Times with Melissa Corrigan & Ally Hamilton

Three brilliant women on launching teens into the world when the world’s on fire

Note: Please join us for The Daily Whatever Show tomorrow as we welcome the incredible

to the show to talk about citizen journalism.


Today’s The Daily Whatever Show was a love letter to fierce, thoughtful women navigating the wild ride of parenting teens in late-stage America.

kicked things off with her matchmaking skills—because why stop at introducing one smart, fiery woman to the conversation when you can have three? So in came and , and I gracefully bowed out so they could take center stage. (Okay, fine—Substack Live forced me out because apparently three is the magic number. Substack, if you’re listening: fix it. We want more chairs at the table.)

What followed was an hour of honesty, humor, and real talk about launching kids into adulthood while the world feels like it’s on fire. Ally opened up about sending her son off to his first apartment and helping him buy his first car, while her daughter is already planning college tours. On paper, these are milestones worth celebrating—but she was candid about the anxiety humming underneath: what kind of country are our kids stepping into? Will there even be a free press when her daughter, who dreams of being a journalist, graduates?

Melissa’s story added both depth and fire. With six kids ranging from grade school to early twenties, she’s juggling every stage of launch at once. Her older kids are asking big, unsettling questions about the future: What do you major in if AI eats all the jobs? How do you plan your life when the ground feels like quicksand? Melissa spoke powerfully about the importance of creating a safety net—offering kids a place to come home to without shame when the world trips them up. She also shared the harrowing reality of raising politically engaged kids while dealing with an abusive ex who’s drifted far to the right, and how weaponized custody battles could become the next front in America’s culture wars. Heavy? Yes. But the way Melissa told it—raw, unflinching, and razor-sharp—was galvanizing.

Dana, for her part, held space like a pro. She brought her own perspective as a mom of two teen girls, asking the questions that keep so many parents up at night: Is it safe to send your daughter to a red-state college? How do parents of boys raise sons to resist radicalization when the algorithm is hunting them daily? What does responsible parenting even look like in an era of relentless online toxicity? The answers—communication, connection, vigilance, trust—were a reminder that there’s no app, no shortcut, no parental control stronger than actually talking to your kids.

What made this conversation so special was its balance. It was heavy but never hopeless, personal but always political, urgent yet still filled with laughter. Ally, Melissa, and Dana shared stories that were funny, heartbreaking, and deeply inspiring—all without sugarcoating the real dangers of this moment.

By the end, the three of them had built something more than a feminist rant: it was a survival guide for raising kids into adults who care, question, and refuse to be swallowed by the madness. And honestly? That’s exactly the kind of conversation that makes me proud to give up my seat.

Because three smart women holding court about the future is a show worth watching every time.

~LW



Thank you

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