Raising Boys When Masculinity Feels Broken
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In this episode, Henry sits down with Ruth Whippman, author of BoyMom, for a conversation about boys, masculinity, motherhood, and the emotional lives of young men. Ruth is a British author, journalist, and cultural critic living in the United States. A former BBC documentary director and producer, her writing has appeared in The New York Times, Time, New York Magazine, The Guardian, HuffPost, and elsewhere. She is also the author of America the Anxious, which was named a New York Post Best Book of the Year, a New York Times Editors’ Choice, and a Paperback Row pick. Fortune described her as one of the “25 sharpest minds” of the decade.Henry and Ruth discuss the pressures boys face from an early age, the influence of online spaces, the appeal of figures like Andrew Tate, and the difficulty of holding boys accountable while also taking their suffering seriously.This conversation looks at boyhood with both compassion and clarity. What are boys being taught about manhood? What are they learning to hide? And how might parents, educators, and communities help boys grow into men with emotional honesty, accountability, and a deeper sense of connection?