Ep 03 - “I’m Doing the Song!” Ash Diggs on Cat’s in the Cradle, Comedy, and Family episode artwork

EPISODE · Jan 22, 2026 · 57 MIN

Ep 03 - “I’m Doing the Song!” Ash Diggs on Cat’s in the Cradle, Comedy, and Family

from I Hate You. What's For Dinner? · host Gillian Boudreau & Rob Galligan

Most parents set out with the best of intentions to prepare their children for the world. Of course, our actions and behaviors don’t always have the intended effect. Parenting is hard, and sometimes we screw up in ways that damage our kids and our relationships with them.So what do we do with our parenting regrets?Today, comedian Ash Diggs joins us to talk about the regret and repair in parent-child relationships, using the classic Harry Chapin tear-jerker “Cat’s in the Cradle” as our jumping-off point. We dig into why that song hits some of us so hard, how class and race impact parental survival brain, and the evolution of parent-child relationships when everyone is willing to look at themselves and try something new.Listen to the full episode to hear:How parents’ focus on achievement and stability can affect mental health and relationshipsWhy turning real-life pain into comedy can be a double-edged swordHow his parents’ willingness to engage in hard conversations has allowed their relationship to positively evolveThe not-so-simple relationship between material safety and psychological safetyLearn more about Ash Diggs:Instagram: @ashdiggs_Learn more about I Hate You. What’s For Dinner?Connect with Gillian Boudreau, PhD.:WebsiteInstagram @clearconnectionpsychologyConnect with Rob Galligan, PhD.:Instagram @dr.robert.galliganResources:Harry Chapin - Cat's In The CradleThe Autobiography of Malcolm X

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Ep 03 - “I’m Doing the Song!” Ash Diggs on Cat’s in the Cradle, Comedy, and Family

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