Why I Hate & Love Pickleball

Three generations discuss the world we live in from their own perspectives: icks, red-flags and attractions.  

Three generations discuss the world we live in from their own perspectives. We ended up having quite a bit of controversy.

We apologize for not releasing any new episodes over the past few weeks. Between Presley's law school finals and Bill's AI startup, we just couldn't find the time. In this episode, we recap our last conversation and dive into a discussion about relationships.

Picking up where our Valentine's episode left off, this is the first of three chaos‑filled installments where Austin—our fearless 20‑something—spills his 'icks,' red flags, and absolute deal‑breakers.

"Revenge is a dish best served cold." After the Valentine's episode—our chaotic detour into Gen Z "icks" and red flags, where Bill practically dry‑heaved at the mere idea of dating—he came back swinging. This time, Bill didn't just serve Presley one dish… he rolled out an entire tasting menu of payback.

It was our boss Verne's birthday, and Presley's good‑natured determination dragged Bill—despite his fatigue and total lack of interest—on a late‑night shopping trip.

The suffering continues. Bill's boomer brain short‑circuits as Presley unleashes yet another round of her infamous 'icks.' Her heart is absolutely in the right place—unfortunately, her advice only pushes Bill further toward the Dark Side.

What is an "ick?" Presley, the sweet and ever‑supportive cohost, valiantly tries to steer Bill's love life with advice and encouragement. Predictably, it goes off the rails almost immediately — and she absolutely refuses to give up.

At long last, the episode that refused to die finally meets its dramatic end. The mall adventure wraps with Bill getting hopelessly overstimulated in a game room while Presley, ever the responsible one, hauls him home like a frazzled babysitter.

The Mall saga continues—this time with window‑shopping detours and a Korean hot dog taste‑test you can practically hear. Every bite, every crunch, all captured. Along the way, Presley drops a revelation about her future earnings… and why she's totally at peace with it.

On today's remote episode Presley tells Bill he dresses like a "geriatric fart," and that it's time for a wardrobe upgrade. To bring Bill out of his Great Depression fashion era and into the modern age, Presley bribes Bill by using milk tea and Korean corn dogs.

Last episode went off the rails—so much so that we're officially renaming it 'Recapping.' This time, we're back on track as Presley dives into the hidden corners of Bill's mind with her signature game, '200 Questions.' Expect revelations, chaos, and yes… Toxic Waste candy and potato chips make an appearance.

What do you want to know about Bill? To Presley, he's an enigma—so she dives straight into his quirks, instincts, and thought patterns by asking the questions she really wants answered. And yes, it gets weird fast. What's under your pillow? Who's on your grudge list? Was Jesus a marathoner? Tune in and see how far this conversation runs.  

Do dreams have meanings? Who knows. We're not experts, and we're not exactly losing sleep over it. Presley dreams about her teeth falling out and brains in glass cases. It doesn't mean anything about her… or does it?

Presley shares her experiences from her first semester in law school, including preparing for finals and the story of how she met her husband.

We had our first guest, Rachel Crandall, an engaged medical student at the University of Houston with extensive clinical, leadership, and humanitarian experience across five continents. This is part two of our first "three-way" interview. 

We had our first guest, Rachel Crandall, an engaged medical student at the University of Houston with extensive clinical, leadership, and humanitarian experience across five continents. This is part one of our first "three-way" interview. 

In this special holiday episode, we explore the deeper meaning behind the season—beyond the lights, the meals, and the gifts. Together, we reflect on traditions of giving and the ways holidays remind us of our shared humanity. Even in times when differences feel sharper than ever, the holidays offer a chance to pause, connect, and celebrate what unites us. From stories of generosity to reflections...

Presley and Bill dive into a candid, cross-generational conversation—sharing what they love and loathe about their own generation and each other's. It's honest, funny, and full of surprising insights.

Presley and Bill dive into a candid, cross-generational conversation—sharing what they love and loathe about their own generation and each other's. It's honest, funny, and full of surprising insights.

We talked more about nothing. It better than great.  

We talked about absolutely nothing. It was great!

Two generations. One absurd reality. Infinite hot takes. Welcome to Boomer vs Zoomer Chat , where a wisecracking Boomer and a chronically online Zoomer collide in the most unhinged group chat you never asked to join. From AI panic to avocado toast inflation, we roast the chaos of modern life—one brutally honest convo at a time. It's hilarious. It's heartbreaking. It's real. We don't always agree,...

Two generations. One absurd reality. Infinite hot takes. Welcome to Boomer vs Zoomer Chat , where a wisecracking Boomer and a chronically online Zoomer collide in the most unhinged group chat you never asked to join. From AI panic to avocado toast inflation, we roast the chaos of modern life—one brutally honest convo at a time. It's hilarious. It's heartbreaking. It's real. We don't always agree,...

The Future of Pickleball and AI