Raising Boys
In Today’s World
EPISODE 23:
Reimagining Boyhood, Masculinity &
Raising Emotionally Strong & Connected Boys
In This Episode:
Ruth Whippman, author and journalist, joins us today to unpack America’s obsession with happiness, the loneliness baked into modern motherhood, and what it really looks like to raise boys in today’s complicated cultural landscape. Drawing from her books BOY MOM and America the Anxious, Ruth shares why the way we pursue happiness often backfires, how isolation impacts parents (especially moms), and the contradictory messages boys receive about masculinity, emotion, and identity. This conversation is honest, nuanced, and deeply relevant for anyone raising sons or simply trying to parent with more clarity and compassion.
Topics we cover:
America’s happiness obsession and why it often leads to more anxiety.
The surprising common factor that actually contributes to long-term happiness.
Loneliness in motherhood and why we were never meant to parent alone.
Social media, comparison, and the pressure to be the “perfect” parent.
Contemporary boyhood and the conflicting messages boys receive about masculinity.
Anxiety, gender roles, and the psychological impact of labeling boys as “toxic”.
How early messaging shapes boys’ emotional development.
Roughhousing, nurturing, and the unique role of fathers.
Nature vs. nurture when raising emotionally intelligent boys.
Screen time, sports overload, and the importance of unstructured play.
Ruth Whippman
MORE ABOUT THIS EPISODES’S GUEST
Ruth Whippman is an author, essayist, and cultural critic from London, now based in the United States. Her writing has appeared in The New York Times, Time, and The Guardian, and her widely shared essays—including Enough Leaning In, Now It’s Time for Men to Lean Out and What We Are Not Teaching Boys About Being Human—have reached hundreds of thousands of readers. She also writes the Substack I Blame Society.
She is the author of Boymom: Reimagining Boyhood in the Age of Impossible Masculinity (Harmony/Penguin, 2024) and America the Anxious (St. Martin’s Press/Macmillan), a New York Times Editors’ Choice and one of Newsweek’s “Nine Books to Change the Way You Think.” Named by Fortune as one of the “sharpest minds” of the decade, Ruth is a frequent podcast and radio contributor and a sought-after speaker, with appearances at Google, TEDx, UC Berkeley, and Somerset House. She lives in California with her husband and three sons.
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