More than Milestones
More than Milestones
Kaitlin Rickerd
23. Raising Boys In Today’s World: Reimagining Boyhood, Masculinity & Raising Emotionally Strong & Connected Boys
46 minutes Posted Jan 27, 2026 at 9:00 am.
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Ruth Whippman, author and journalist, joins us today to unpack America’s obsession with happiness, the loneliness baked into modern motherhood, and what it 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, and the contradictory messages boys receive about masculinity, emotion, and identity. This conversation is honest, nuan...