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!
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 relationships, mental health, body image, and more. Featuring heartfelt gratitude for listeners, the episode underscores the podcast's mission of diving into sexy, messy, and unwell conversations. Jay also teases future content and invites fans to stay connected and...
15 Oct 2025
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 (and self-proclaimed “wh&re”), joins Jay for a no-holds-barred chat where they explore the wild world of hookups—think straight-identifying men who are into drag queens, fetishes you didn’t know existed, and the evolution of hookup culture from pre-app cruising to today’s swipe-right reali...
8 Oct 2025
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 experience on mushrooms, it’s an episode packed with real talk. It is Jay at his most authentic. Plus, Jay answers listener questions in a candid Q&A segment—including some super sexy questions that almost make him blush. Don’t miss this fun, raw, and relatab...
1 Oct 2025
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 about their personal experiences, sharing powerful anecdotes and practical wisdom that encourage listeners to embrace their individuality and cultivate resilience. Their intimate discussion touches on overcoming negative self-talk, setting small but meani...
24 Sept 2025
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 body image. Together, they unpack the often skewed perceptions we have of our own bodies in pursuit of the unattainable. Jay and Eddie dive deep into issues like how we see ourselves, our self-esteem, and the critical role of mental health in fitness. Jay also opens up about his p...
17 Sept 2025
Get to Know the REAL Me: Coming Out and My Unexpected Childhood
In this deeply personal and moving episode of 'Deep,' host Jay shares his candid and heartfelt coming out story. From his challenging childhood in a small town in Georgia, dealing with parents struggling with addiction, to his experiences with bullying and self-discovery, Jay opens up about his journey to understanding his sexuality. Amidst struggles and family issues, he recounts finding solace in school and theater, which provided an escape and community. Jay discusses the challenges of bei...
10 Sept 2025
Breaking the Stigma: Gay Men’s Guide to Better Mental Health
In this episode of Deep, host Jay sits down with long-time friend and special guest Aaron Hall for a heartfelt conversation about their decade-long friendship, past relationship, and the critical topic of mental health. Together, they open up about their personal struggles, offering an honest look at the challenges they’ve faced and the importance of seeking professional help. Jay and Aaron reflect on the emotional toll of the COVID-19 pandemic—tackling themes of isolation, depression, and th...
3 Sept 2025
Jay Goes DEEP: Answering Your Juicy Questions
In this episode of DEEP, Jay takes listeners on a journey through an open and honest "Ask Me Anything" session. He shares personal insights, tackling questions about his biggest fears, future aspirations, fitness strategies, and even some lighthearted and intimate secrets. Packed with humor, heartfelt advice, and genuine moments, this episode is a must-listen for fans of real, unfiltered conversations. Plus, don’t miss Jay’s inspiring perspective on the transformative power of saying ‘thank y...
27 Aug 2025
Dancing on the Edge: The Truth About Gay Nightlife
In this episode of Deep, host Jay sits down with Brian Kent, a celebrated DJ, music producer, and former nightclub owner, for a raw and revealing conversation about the darker side of gay nightlife. They reflect on their decade-long friendship while diving into Kent's journey from sneaking into clubs as a teenager to becoming a central figure in San Francisco's nightlife scene. Kent opens up about the unspoken challenges of owning a gay nightclub, from navigating the relentless pressures of t...
20 Aug 2025
Breaking the Rules: Redefining Gay Relationships and Monogamy
In this very personal episode of Deep, I reflect on my recent struggles with grief, recounting the significant losses of close family members over the past decade. I also discuss how grief has impacted his routine and mental health, and the importance of therapy and processing emotions. But most importantly, I dive deep into the complexities of gay relationships, sharing my experiences with monogamy, open relationships, and the evolution of relationships post-breakup. I answer questions...
13 Aug 2025
Cruising Etiquette- Inside Gay Cruising Culture
In this super sexy and wild episode of DEEP, Jay heats things up with legendary LA party host Rob Aquino for a sizzling deep dive into the world of cruising. From mastering the subtle art of public flirting to embracing the thrill of hooking up, this episode is packed with juicy insights. Rob and Jay also tackle how to gracefully handle awkward moments, celebrate the importance of casual sex, and delve into the lost art of generational cruising wisdom. Whether you’re curious, experienced, or ...
13 Aug 2025
Navigating Masculinity: Finding Your True Self Beyond Gender Norms
In this episode of DEEP, host Jay dives headfirst into the complexities of masculinity and the power of embracing one’s true self beyond societal gender norms. He shares personal stories about growing up in the South, exploring his masculine and feminine sides, and how life-changing moments in theater helped shape his identity. ✨ What’s in this episode? Personal insights from Jay on navigating masculinityTips on embracing authenticity and breaking free from gender stereotypesListener Q&A ...
5 Aug 2025
Diving In: The Start of Something Deep
Welcome to the very first episode of the DEEP podcast, where host Jay sets the stage for what’s to come—an exciting exploration of gay men’s lifestyle, covering everything from fitness and relationships to mental health and sex. Jay gets personal, sharing his journey, what inspired him to launch DEEP, and why authenticity and vulnerability are at the heart of every episode. Listeners can look forward to engaging conversations, guest appearances, and audience Q&A moments designed to connec...
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Apple Podcasts (US)
3.5 / 5
13 ratings
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