Dan reflects on decades of family travel—from chaotic solo trips with three young kids to navigating airports with a toddler and a suitcase full of white noise machines. It’s messy, hilarious, and unexpectedly tender. Because the best trips aren’t perfect—they’re personal.

What happens when “Daddy’s little girl” meets… Daddy’s other little girl? In this heartfelt episode, Dan reflects on becoming a girl dad again—more than two decades after his first daughter, Abby, changed his life. With Ruby now in the mix, he explores the surprising emotions, generational echoes, and quiet, powerful moments that reveal how love doesn’t divide—it expands.

Dan returns to the toddler swim class—this time as a much older, slightly soggier dad. From laminated emotion cards to “mindful kicks,” the world of early childhood sports has changed. But somewhere between the foam balls and bubble songs, he finds something deeper: a second act of parenting where joy matters more than form. With sharp wit and heartfelt reflection, this episode explores how sports, silliness, and showing up can turn even the smallest splash into something that lasts.

Mealtime can feel like navigation four very different worlds - from a hostage-style broccoli negotiation to a kale-eating celebration. Dan explores what each of his children's eating habits reveal about their personalities - and what family dinners mean when your kids span generations.

The smallest rituals often become the most meaningful - especially when you're not parenting full-time. Dan reflects on bedtime stories, quirky traditions, and the absurd "Life Lessons" he told his kids at night, which somehow still echo years later.

Gentle parenting sounds great - until you're three hours into a toddler negotiation that ends with, "But I don't want to brush my teeth forever." Dan gets honest about the tension between being patient, being present, and not losing your mind.

When Ruby walks in on Dan peeing and proudly announces, "I see Daddy's popsicle," things spiral fast. This is a story about panic, hilarity, and how one moment of comic horror turned into the exact kind of emotional support every new dad needs.

Raising Ruby in 2025 feels like parenting in another universe compared to the early 2000s. In this episode, Dan explores how baby monitors, food and parenting information have changed dramatically - and what it's like to raise a toddler with one foot in the diaper aisle and the other in a pharmacy's joint support section.