Deep with Jay
DEEP is a weekly show hosted by Jay Wilkerson. Here nothing is off limits!
Each episode we dive DEEP into the fun, the sexy and the downright provocative exploration of the stories, ideas and conversations that make us think, laugh and maybe even blush a little bit.
So, get comfortable, open your mind and get ready to go DEEP!
Podcasting since 2025 • 13 episodes
Deep with Jay
Latest Episodes
That's a Wrap: DEEP Season 1 Finale
In the season one finale of 'Deep,' host Jay aka Furry Pup reflects on the podcast journey so far, recapping key moments, guests, and episodes. Jay discusses the evolution of the show, personal growth, and memorable topics such as relationsh...
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Season 1
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Episode 113
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31:17
Hookup Confession with Sherry Vine
Hold onto your wigs and prepare for an unfiltered, jaw-dropping ride, because this week on Deep, Jay gets into the nitty-gritty of hookups with the one and only Sherry Vine!Sherry, legendary drag queen (a...
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Season 1
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Episode 112
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1:02:44
Jay Gets Real Answering Your Steamiest Questions
In this episode Jay gets super personal with listeners—no interviews, no filters, just Jay catching up. From attending the Portola Music Festival in San Francisco while navigating a more sober lifestyle to an unexpected introspective experie...
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Season 1
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Episode 111
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39:08
How to Overcome Self-Doubt, Find Inner Strength and Build the Confidence You Deserve
In this second part of Jay’s conversation with Eddie Carrington, he leads an inspiring and heartfelt talk where, together, they explore the profound topics of self-worth, self-motivation, and the journey to inner happiness. They both open up...
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Season 1
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Episode 110
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31:38
Gay Men & Body Image: The Pressure to Be Perfect in Fitness Culture
In this week’s episode of Deep, Jay sits down with the multi-hyphenate Eddie Carrington—national aerobics champion, Equinox fitness instructor, model, and coach—to explore how gay men approach exercise, fitness, and bo...
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Season 1
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Episode 109
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40:53