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PODCAST

Zoomer vs Boomer

William Wong & Presley Gregory

Zoomer versus Boomer Chat is a candid conversation between two generations trying to understand each other. One"s lived it, one"s Googled it. Together, they unpack life"s joys, struggles, and absurdities with humor and heart. It"s funny. It"s sad. It"s real. And somehow, it brings us closer. 🧡 New episodes weekly. Join us for the journey

society & culture comedy interviews

All Episodes

01:01

Trailer: Self-Esteem

Zoomer vs Boomer ·

2026/10/04

As usual, Presley takes a serious topic and corrupts it enough to make Bill lose his footing. He needs a moment to understand and compose himself — and honestly, that's why we love her. The full episode will drop on October 5th.

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0:26

Zoomer vs Boomer Trailer

Zoomer vs Boomer ·

2026/10/03

Zoomer vs Boomer is a cross‑generational showdown between Presley and Bill — two voices, two eras, and one weekly argument neither of them can resist. In this trailer, they introduce the heart of the show: real conversations, real disagreements, and the hilarious, honest moments that happen when Gen Z and a Boomer try to understand each other. It's fast, funny, and sets the tone for the debates, stories, and surprises that define the podcast.

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01:15:34

Kicked in your DUPR

Zoomer vs Boomer ·

2026/09/15

Zach, Presley's husband and closest friend, sits down to share his wrestling trauma and the story of how their relationship began. Together, they open up about the real‑life challenges of staying fit as a couple — including a running joke in their marriage known as "defensive driving." DUPR is the standard rating system used in pickleball, ranging from 1.0 to 7.0. Higher DUPR ratings generally indicate stronger players, based on match outcomes and performance trends.

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01:04:15

A Paige Out of Presley's Life Book

Zoomer vs Boomer ·

2026/09/01

Paige — Presley's lifelong bestie and childhood partner‑in‑crime — joins the pod for a deep dive into the secrets, stories, and chaos they never told anyone growing up. From middle‑school mischief to navigating dating in their 20s, this episode is all about friendship, glow‑ups, and the hilarious reality of figuring life out together.

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39:51

Brunch at 99 Ranch Market

Zoomer vs Boomer ·

2026/08/24

Presley and Bill are both stressed and swamped, so to shake off the pressure, they brunched at a 99 Ranch Market. In a rare twist of character, Bill tries to play the gracious host — a surprising move given it's Presley's first time navigating a Chinese market. Between dumplings, laughter, and cultural firsts, the two find a moment of calm amid the chaos.

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56:03

The Grievance Episode

Zoomer vs Boomer ·

2026/08/17

Presley and Bill finally sit down to catch up, swapping stories from a week that somehow involved both HMart lunch and Costco dinner. Bill tries to stir the pot with a ridiculous made‑up story just to see how Presley would react… but the plan crashes and burns spectacularly. Then, in a moment that shifts the whole tone of the conversation, Presley drops a bombshell: she's resigning from her job.

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48:18

Bombshell has Entered the Villa - Part 2

Zoomer vs Boomer ·

2026/07/20

The second part of our discussion with Lindsay, a 40‑year‑old woman, dives into marriage, divorce, and stepping back into modern dating — revealing the lessons, surprises, and second‑chapter courage that come with starting over.

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38:33

A Bombshell has Entered the Villa - Part 1

Zoomer vs Boomer ·

2026/07/13

Lindsay, a 40‑year‑old woman, opens up about marriage, divorce, and stepping back into modern dating — sharing the lessons, surprises, and second‑chapter courage that come with starting over.

en

38:18

30-Something Guest - Part 2

Zoomer vs Boomer ·

2026/07/02

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

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41:36

30-Something Guest - Part 1

Zoomer vs Boomer ·

2026/06/22

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

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01:00:20

We are SO back!

Zoomer vs Boomer ·

2026/06/15

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.

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48:35

Our 20-something Guest

Zoomer vs Boomer ·

2026/04/13

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.

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49:28

A dish best served cold

Zoomer vs Boomer ·

2026/04/06

"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.

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33:20

Shopping for a B-Day gift

Zoomer vs Boomer ·

2026/03/30

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.

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38:31

Valentine's Day - Part 2

Zoomer vs Boomer ·

2026/03/16

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.

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33:54

Valentine's Day - Part 1

Zoomer vs Boomer ·

2026/03/09

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.

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44:05

Convicts of Interest - Part 3

Zoomer vs Boomer ·

2026/03/02

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.

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28:43

Convicts of Interest - Part 2

Zoomer vs Boomer ·

2026/02/23

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.

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34:40

Convicts of Interest - Part 1

Zoomer vs Boomer ·

2026/02/16

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.

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01:03:10

All About Bill - Part 2

Zoomer vs Boomer ·

2026/02/09

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.

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83 results

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