A sunrise at the Arch, a long overnight drive, and a confession most of us dodge: sometimes the tears just don’t stop, and the only thing that steadies you is the road. We head back to St. Louis to face a stack of old memories—prom photos, a busted elbow, a skyline that still knows too much—and use humor to navigate the heaviness. It’s raw without being bleak, funny without being flippant, and honest about how weird and human it is to cry next to someone you love while pretending you’re fine.

We dig into the small mechanics of hiding big feelings—the fake yawn, the damp sunglasses, the careful breath—and the bigger question of when to share and when to protect your own space. Emotions show up like antique store finds: pretty in the aisle, awkward at home, and tough to part with even when they don’t fit your life. We talk about being “on reserve” for other people’s loneliness, setting boundaries without burning bridges, and why the instinct to go numb can feel easier than being open. Along the way, there’s a rant about bench pressing, a case for gentler movement, and a reminder that presence often starts with a walk, a laugh, and a phone on airplane mode.

This story isn’t about perfect healing; it’s about staying with yourself long enough to hear what the feelings are saying and then deciding what to keep. If you’ve ever driven home just to remember why you left, or stared at a city that holds both joy and regret, you’ll recognize the pulse here. Press play, ride shotgun through the nostalgia and the noise, and leave with a lighter grip on what no longer serves you.

If this resonates, subscribe, share with a friend who might need it, and drop a review. Tell me: what place still messes with your heart, and what did it teach you to carry?

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What happens when you combine perfect hoodie weather, exceptionally potent cannabis, and sidewalks that require the vigilance of a bomb squad technician? Welcome to Portland, Oregon – a city that demands you look up at its breathtaking beauty while carefully watching every step.

The contradictions of Portland create the perfect backdrop for reflection. One moment I'm admiring the stunning architecture and fall colors painting the sky in magnificent hues, the next I'm dodging "dog" waste with the agility of an Olympic athlete. This constant shifting between appreciation and avoidance becomes a metaphor for life itself – finding beauty despite obstacles.

My adventures took unexpected turns, from dropping an AirPod on an airport bathroom floor (creating an existential hygiene crisis) to visiting what I can only describe as a "witch coffee shop" complete with tarot readings and crystal-infused beverages. The cannabis scene lived up to its reputation, leading to a sushi experience where I questioned whether decorative flowers were meant for consumption (they weren't, but I ate one anyway to the visible confusion of the chef).

The most profound moment came during an evening walk as dusk settled over the city. As the sky transformed through different shades of blue, I found myself overwhelmed with abstract gratitude – not directed at anything specific, just a general appreciation for being present in that beautiful moment. Sometimes thankfulness doesn't need a target; it can simply exist as recognition of the wonder around us.

From serendipitous encounters with strangers who became temporary companions to observations about the eclectic Sunday crowd, Portland revealed itself as a place that embraces individuality in all its forms. The city doesn't hide its flaws but somehow integrates them into its unique character, creating an authenticity that's increasingly rare in our world.

Ready to join me on more adventures? Check out our new merch at BobbyJcocks.com and catch me on tour with Cactus Tate – dates and locations on my website!

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The open road has a way of pulling profound thoughts from even the most distracted minds. Cruising down highways lined with autumn-kissed trees, this episode captures the stream-of-consciousness reflection that can only happen behind the wheel.

Bobby dives deep into the peculiar hill he's willing to die on – hot coffee versus canned coffee – and why he'll defiantly order a steaming cup even in the sweltering Texas heat. The conversation shifts to life's small revelations, like his first childhood discovery of cruise control and how it terrified him to see his aunt seemingly driving without feet on the pedals.

The meat of the episode tackles a modern philosophical dilemma: how much understanding should we extend to those who seem incapable of reciprocating? When someone cuts you off in traffic, are you obligated to imagine they're rushing to the hospital? Or is there a point where collective consideration breaks down when only some people practice it?

Throughout the journey, Bobby shares moments of connection that punctuate his nomadic lifestyle – attending Nikki Glazer Day at Busch Stadium, bonding with her family, and even getting invited to smoke with her neighbors. He reflects on the liberation that comes with emptying his storage unit, letting go of VHS tapes and memorabilia that once seemed essential to preserving his memories.

Whether you're a fellow road warrior or simply enjoy listening to unfiltered thoughts, this episode offers a window into the comedian's mind as he navigates both highways and life itself. Check out Bobby's website for new tour dates – he's booking shows and ready to bring his unique perspective to a venue near you.