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A single compliment in a dish pit changed everything. Kitty Pine walked us through the moment a chef called them the “best dishwasher” he’d ever seen—and how that flipped a switch from surviving to building a life in comedy. What followed wasn’t a straight shot to the spotlight, but a messy, hilarious path across Hawaii, Colorado, and Vegas, with brutal early bombs, a sudden first win, and the slow, stubborn craft of shaping ten minutes that work anywhere.
We dig into how “Kitty Pineapple” was born: a radio call-in bit that turned into a persona made of people Kitty loves—their fearlessness, logic, and style—stitched into something authentic. We talk about writing jokes that land with strangers on the mainland, then glide at home in Honolulu; we talk about why some Vegas rooms feel cold and why Hawaii feels like a hug. There’s a tender turn when Kitty recalls parents seeing the show for the first time in years, not fully getting the material but bursting with pride, and a random Uber clip of Dad bragging that still hits like a standing ovation.
The conversation goes deeper: boundaries with clout-chasers, listening to intuition, and moments where Spirit seemed to nudge Kitty away from danger. We unpack bodybuilding years, enhancements, and how hormone shifts unexpectedly clarified identity. The runway heels, the short dresses, the purple hair—it’s not a gimmick, it’s alignment. And there’s momentum beyond stand-up: a new romantic comedy series, Made to Shine, where Kitty plays a transgender comedic influencer, debuting on Amazon and Viva One.
If you’re chasing a reinvention, wrestling with family acceptance, or trying to write material that wins over a room that doesn’t know you yet, this one’s for you. Hit play, then share your turning point and the persona you had to build to become yourself. If you’re new here, follow and subscribe, drop a review to help others find the show, and send this to a friend who needs a nudge toward their next chapter.

• why asking for a yes still matters
• a dish pit compliment as a turning point
• early bombs, first wins, and open mic lessons
• inventing “Kitty Pineapple” from people we love
• social media resets versus keeping memories
• sensing energy, trusting Spirit, and boundaries
• moving from Hawaii to Colorado to Vegas for love and stage time
• writing material that works on the mainland and at home
• handling stares, kid questions, and staying gracious
• family acceptance, tradition, and showing up
• fashion, heels, confidence, and stage presence
• quitting competition cuts while keeping healthy training
• hormone impacts, embracing change, and identity
• new acting role: Made to Shine on Amazon and Viva One