Ever found yourself digging metaphorical (or literal) holes you can't escape from? This episode dives deep into the beautifully chaotic reality of living with ADHD, territorial beach behavior, and those moments when we become the unexpected villains in our own stories.

Fresh from Naples, Florida (affectionately dubbed "Nipples, Florida"), I share my passionate dedication to beach hole digging that sparked an unexpected feud with a family over borrowed shovels. There's something primal about defending your sandy territory from strangers who don't respect the craft of hole construction! My frustration with these "shovel thieves" reveals a larger theme – those moments when we feel justified in our reactions, only to question them later.

The sunscreen saga with fellow comic Tatum highlights our stubborn resistance to learning from experience. Despite clear evidence that "I don't burn" was categorically false after day one, she questioned needing protection again on day two! It's the perfect metaphor for how we sometimes refuse to accept reality despite painful consequences.

My Easter adventures back home take an awkward turn when I confront children I believe are stealing eggs we'd hidden for Tatum's daughter, only to discover they were part of a neighborhood scavenger hunt. These moments of misplaced righteous indignation – followed by the awkward realization of my mistake – capture the essence of being imperfectly human.

From making "booger bets" at airports to navigating lost luggage situations, this episode celebrates finding humor in life's frustrations. I'm learning to embrace my "diva bitch era" while acknowledging when my reactions might need tempering with understanding. After all, aren't we all just digging holes and trying to protect what matters to us?

Come see me on tour this spring! Dates in Salt Lake City, California, Cleveland, and Austin are all on sale now. Your support means everything – because yelling at beach families and misunderstanding Easter egg hunts doesn't actually pay the bills.

Bobby Rackleff chronicles his wild adventures as a touring comedian in this honest, hilarious episode that perfectly captures the beautiful chaos of life on the road. From accidentally being marked as needing special assistance at the airport (despite having never requested it) to the nightmarish experience of staying in a Travel Lodge smoking room that felt haunted by the souls of previous occupants, Bobby's travel misadventures will have you laughing and cringing in equal measure.

The episode shines brightest when Bobby recounts his time in New York City, his favorite place in the world, where he spent quality time with friends Carly Aquilino and others. Despite getting only an hour of sleep after talking until 5 AM, the joy of these connections fuels his comedy. With refreshing candor, Bobby discusses the financial realities of being a working comic—how the constant need to save money leads to questionable hotel choices, and how sometimes splurging an extra $50 for comfort is worth it for your mental health and performance quality.

Whether describing his broken three-wheeled luggage, getting bitten by a "nice but also mean" cat, or his momentary existential crisis upon meeting identical twins (one of whom was a former pastor), Bobby's storytelling perfectly balances vulnerability with laugh-out-loud observations. His experiences wandering through malls and discovering that Spencer Gifts somehow still exists taps into a delightful nostalgia that many listeners will relate to.

Ready for more Bobby? Catch him on tour with Cactus Tate in Florida, Salt Lake City, and various California venues through May. Support the show on Patreon for exclusive bonus content starting at just $1 monthly and experience the beautiful, chaotic life of a comedian on the rise!

Ever wonder what really happens when comedians hit the road together? Bobby takes us behind the curtain of comedy touring life, revealing both the hilarious disasters and tender moments that unfold when performers spend too much time in close quarters.

The adventure begins with a midnight dog hunt at Cactus Tatum's house before a painfully early flight. The panicked search through rainy streets ends with relief when the runaway pup is found at a neighbor's home—but it's just the first challenge of many. Bobby perfectly captures that stomach-dropping feeling of potential disaster, comparing it to "when the teacher hands you your paper face down."

Things escalate dramatically at the airport when Tatum suddenly falls ill, leading to an emergency cleanup operation and the purchase of a bright yellow Pittsburgh Pirates hoodie. The incident sparks a friendly rivalry as Bobby defends his response to the crisis: "You want me also to go vomit?" Their friendship endures through these messy moments, revealing how road partners take turns supporting each other through the chaos.

The tour takes them through Soul Joel's Comedy Club in Pottstown (where they're treated exceptionally well) and the Pittsburgh Improv (where audiences react in their own unique way). Bobby shares insights about the unwritten rules of touring relationships—like quietly cleaning hotel rooms without acknowledgment until the one time you forget and someone notices. These small gestures reveal the delicate balance between headliners and feature acts.

Between stories of farting on the road and accidentally calling venue managers by the wrong name, Bobby captures the beautiful absurdity of comedy life. Join him for upcoming shows with Emma Willman, Cactus Tatum, and solo dates across the country—just check the links to find tickets and witness the aftermath of these road stories firsthand.