23. Raising Boys In Today’s World: Reimagining Boyhood, Masculinity & Raising Emotionally Strong & Connected Boys
Podcast: More than MilestonesPublished On: Tue Jan 27 2026
Description: 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, 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.Loneliness in motherhood and why we were never meant to parent alone.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.Follow Ruth on Instagram: https://www.instagram.com/ruthwhippman/Subscribe to Ruth’s Substack: https://substack.com/@ruthwhippmanVisit Ruth’s Website: https://www.ruthwhippman.com/Get Your Copy of BOY MOM: Reimagining Boyhood in the Age of Impossible Masculinity: https://links.milestonesandmotherhood.com/amzn/boy-mom-reimagining-boyhoodGet Your Copy of America the Anxious - Why Our Search for Happiness Is Driving Us Crazy and How to Find It for Real: https://links.milestonesandmotherhood.com/amzn/america-the-anxious-bookLinks & Resources💻 Website & Blog: https://www.milestonesandmotherhood.com/📱Follow KC for daily motor milestone tips & parenting support: https://www.instagram.com/milestones.and.motherhood/🎧 Follow podcast updates & new episode drops: https://www.instagram.com/more.than.milestones/🆓 Get my free tummy time training: Mastering Milestones with Confidencehttps://www.milestonesandmotherhood.com/freetraining📬 Join the email list for milestone tips + podcast updateshttps://idyllic-hat-942.myflodesk.com/fwefz61097🛒 Shop KC’s favorite mom & baby finds: https://links.milestonesandmotherhood.com/amazon/amazonstorefrontmm🤝 Sponsor or guest inquiries?Contact us at podcast@milestonesandmotherhood.com
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