What happens when you become a dad again in your 50s, but this time with three grown kids already out in the world? Diapers for Two tells true stories about family, aging, identity, and the emotional math of fatherhood. Hosted by Dan Shimmerman, a dad raising a toddler while navigating life with three adult children, the show blends humor, heart, and quiet reflection. It’s about second chances, small rituals, and finding meaning in moments most people overlook.At its core, it’s about what it means to keep showing up for the people you love, across decades, mistakes, and second chances.
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In this episode, Dan explores the unexpected negotiation lessons that come from raising a toddler. After days spent reviewing executive contracts and equity terms, he finds himself bargaining over snacks, bedtime routines and the importance of putting on pants. Through humor and reflection, Dan looks at how the tiniest negotiations can reshape our understanding of influence, patience and what winning really means.
E25: Rejected! (00:12:44)
When his two-year-old daughter tells him to go back to work, Dan unpacks the emotional sting of parental rejection, both in the toddler years and beyond. From silent walks with his teenage daughter to a career decision that quietly distanced him from his father, this episode explores what it means to be pushed away by the people we love most, and how staying close, even from the hallway, can be an act of love.
E24: The Calm Inside The Chaos - A Fireside Chat With Kirk Martin (01:11:09)
Dan sites down with parenting expert, Kirk Martin for a wide-ranging fireside chat about the parenting journey. They explore self-reflection, information overload and how to support both strong-willed and quieter kinds without losing connection along the way.
E23: Schooling Dad (00:11:48)
In this episode, Dan reflects on what it's like to parent four kids who are all in wildly different relationships with school. From a toddler just learning what a triangle is to a daughter presenting academic research and teaching undergrads, it's a look at learning across generations, and how fatherhood keeps teaching him, too.
E22: Toddlerland (00:10:19)
What would happen if adults started acting like toddlers? In this episode, Dan explores three classic toddler behaviors - shouting everything, changing your mind every ten seconds, and crying over nothing and everything - and imagines what it would look like if those same habits showed up in grown-up life. It's funny, reflective and surprisingly honest. Because as absurd as toddler behavior can be, some of it might just be what we need more of.
E21: Still Learning (00:14:27)
In this episode, Dan shares three life lessons he's learned while parenting in his fifties. These aren't grand revelations or polished insights, just honest reflections on what he missed the first time and what he's trying to do differently now.
E20: Judging The Judgers (00:14:28)
In this episode, Dan takes a funny and honest look at the quiet world of parental judgment, from snack opinions to sleep sack debates. It's a sharp, self-aware ride through the chaos of trying to do your best while everyone's watching.
E19: Some Messier Truths (00:15:26)
In this episode, Dan reflects on three quietly complicated parts of his life right now. From navigating fatherhood in his fifties, to wondering if he's showing up enough for his older kids, to the shifting shape of his relationship, it's a look at the moments that don't always get talked about. Honest, thoughtful and deeply human.
E18: Wooden Blocks And Robot Dogs (00:15:58)
In this episode, Dan reflects on the toys that shaped his life as a dad across four kids and five decades. From Fisher-Price barns and Bakugan battles to robot dogs and wooden blocks, it's a funny and heartfelt look at how play has changed, what it reveals about parenting, and why the simplest toys might still be the most powerful.
E17: What Should I Name This Episode? (00:12:29)
In this episode, Dan dives into the surprisingly high-stakes world of baby naming, from family traditions and personal stories to the rise of unusual trends. With humor and heart, he reflects on how a name can be an act of heritage, creativity or simply love.
E16: The DEFCON Guide to Toddler Tantrums (00:17:01)
In this episode, Dan shares his go-to strategies for navigating toddler meltdowns using humor, calm presence, and a surprising DEFCON-inspired scale. From imaginary bees to quiet tea parties with stuffed animals, he explores how redirection, peripheral engagement, and giving kids control can turn chaos into connection.
E15: The Soundtrack of Us (00:14:10)
In this heartfelt episode, Dan reflects on how music has shaped his life as a father, from cassette loops in his childhood home to bedtime playlists with his toddler, Ruby. A chance encounter with a Stephen Sanchez song sparks memories across generations, connecting him to his kids in ways only music can. Equal parts nostalgic and tender, this episode explores how songs become family heirlooms, and the soundtrack to our lives.
E14: The Leopard And The Lorax (00:12:44)
In this lighthearted episode, Dan trades deep reflection for pure fashion comedy. From his three-outfit wardrobe to Lori's wild Lorax vest and Ruby's toddler runway looks, he explores how his family's style choices couldn't be more different.
E13: According To Plan (00:13:30)
When Dan's son Jacob was born, there were no doctors, just a shoelace and adrenaline. Twenty years later, his daughter Ruby arrived in calm, quiet order. Against the backdrop of these two births, this episode explores the plans we make, the ones that fall apart, and the surprising beauty that sometimes shows up anyway.
E12: Beautiful Lives Here (00:13:07)
What makes a home beautiful? In this episode, Dan opens the door to every house that has held his family. From the noisy magic of young children to the quiet rhythms of growing independence, he reflects on how time, change and love can reshape our sense of beauty.
E11: My Emotional Support Monkey (00:12:19)
Everyone has something they hold onto. Sometimes it's a teddy bear. Sometimes it's a blanket. Sometimes it's a stuffed monkey named Junior. In this episode, Dan explores the comfort objects that stick with us longer than most friendships. From childhood sidekicks to the parenting moments that make you realize you never really outgrow them, it's a look at the soft, strange and sentimental things we carry. Because some attachments aren't meant to disappear.
E10: Is She Talking Yet? (00:12:41)
At the playground, another dad asks, “Is she talking yet?” It’s a simple question, but for parents, it’s never just about talking. In this episode, Dan reflects on milestone anxiety, raising four kids across 25 years, and why he no longer keeps score. Because the real parenting wins? They’re not on the checklist.
E9: Snackcidentally In Love (00:15:00)
Snacks aren’t just snacks. They’re bribes, comfort, and emotional life preservers. In this episode of Diapers for Two, Dan dives into the toddler snack economy, the generational snack gap, and the secret world of late-night adult snacking. Because sometimes, a graham cracker is the only thing holding the day together.
E8: Carry-On Luggage and Emotional Baggage (00:15:26)
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.
E7: Daddy's Little Girl, Meet Daddy's Little Girl (00:14:04)
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.
E6: Motorboat Legs and Other Victories (00:12:29)
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.
E5: Four Kids, Four Menus (00:16:01)
Mealtime can feel like navigation for 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.
E4: Accidental Rituals (00:17:57)
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.
E3: Is This Gentle Enough For You? (00:17:55)
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.
E2: Daddy's Popsicle (00:15:44)
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.
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