Deep with Jay

Pride House Media

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!

  1. 10/22/2025

    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 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 involved. 00:00 Introduction and Welcome 00:43 Season One Recap and Reflections 01:38 Listener Feedback and Future Plans 02:40 Personal Reflections and Gratitude 04:31 Episode Highlights and Behind the Scenes 10:00 Deep Conversations and Vulnerability 16:10 Exploring Mental Health 18:59 Personal Stories and Coming Out 20:23 Body Image and Fitness 23:00 Life Updates and Listener Questions 26:36 Finale and Thank You Connect with Us: Follow Deep on @deepwithjay for updates, exclusive content, and more.Want to share your own hookup story? Submit it anonymously at questions@deeppodcast.studio—you might just hear it on the next episode!  Don’t forget to subscribe to Deep with Jay so you never miss an episode. Leave us a review and let us know your favorite moment!

    31 min

  2. 10/15/2025

    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 reality. But that’s not all! Sherry and host Jay take it a step further by diving into viewer submissions. That’s right—this episode features YOUR juiciest, funniest, and most cringe-worthy hookup confessions. From awkward encounters to steamy surprises, Sherry and Jay read, react, and, of course, add their signature commentary. You’re going to LOVE this episode. Sherry Vine brings her signature wit and charm to the conversation, while Jay adds the perfect dose of cheeky humor. It’s outrageous, it’s enlightening, and it’s guaranteed to make you laugh out loud. So grab your headphones, because this episode is one for the books. Episode Breakdown: 00:00 Welcome and Introduction00:24 Meet the incomparable Sherry Vine01:51 Life, career updates, and what’s next for Sherry02:58 Theater dreams and acting aspirations07:36 Hot hookup stories and wild experiences10:59 The evolution of hookup culture: pre-app vs. app era13:46 Navigating hookup apps like a pro14:12 Unexpected encounters (and a few surprises!)19:10 Safety tips and preferences when it comes to hookups27:30 Fetishes, fantasies, and unique requests33:03 Awkward hookup stories you need to hear to believe33:32 The infamous "No Door Dilemma"33:42 Porn preferences and guilty pleasures34:36 When theft and trust issues ruin the mood39:06 Nudes, blackmail, and keeping things secure40:45 Foot fetishes and unexpected kinks45:00 Viewer Submissions: Sherry and Jay react to your hookup confessions50:23 Craziest hookup locations (spoiler: you’ll never guess!)53:55 Sherry’s Sex and Drag documentary: the story behind the story58:45 Final thoughts, laughs, and farewellConnect with Us: Follow Deep on @deepwithjay for updates, exclusive content, and more.Want to share your own hookup story? Submit it anonymously at questions@deeppodcast.studio—you might just hear it on the next episode!Keep up with Sherry Vine @misssherryvine—she’s a must-follow for all things fun and fabulous.  Don’t forget to subscribe to Deep with Jay so you never miss an episode. If you loved this chat with Sherry Vine (and we know you did), leave us a review and let us know your favorite moment!

    1h 3m

  3. 10/08/2025

    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 relatable episode of Deep!  Highlights:  00:00 Intro & Episode Overview  01:26 Portola Music Festival & Sober Reflections  07:55 TV Binge Recap  12:46 Phone Woes & Social Media Struggles  18:28 Listener Q&A: Sexy Vibes, Preferences, & More  33:51 The Deep End: TikTok Ads Rant

    39 min

  4. 10/01/2025

    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 meaningful goals, and the importance of being your own biggest supporter. From navigating the challenges of launching a new podcast to fostering healthy relationships and finding joy in solitude, Eddie and Jay offer actionable insights that listeners can apply to their own lives. This episode is a reminder that resilience, self-love, and personal growth are within everyone’s reach. Episode Highlights 00:00 – Introduction: Welcome to Deep. 00:36 – Part 2 with Eddie Carrington Begins: Building on a powerful first conversation. 01:02 – Bite-Sized Achievements: How small wins lead to big change. 02:50 – Overcoming Self-Doubt: Breaking free from the inner critic. 04:38 – The Power of Self-Motivation: Fueling your drive from within. 06:29 – Embracing Your Own Strength: Recognizing and celebrating your unique abilities. 16:33 – Finding Joy in Solitude: The beauty of being comfortable with oneself. 20:56 – Healthy Relationships and Self-Worth: How to nurture self-respect while building meaningful connections. 25:50 – Final Thoughts and Deep End Segment: Eddie and Jay share closing reflections and practical takeaways. 30:23 – Closing Remarks and Credits. Write to me at: GoDeep@deeppodcast.studio Follow me at @deepwithjay or @furrypup

    32 min

  5. 09/24/2025

    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 personal struggles with body image and the journey he undertook to overcome them. This episode is packed with practical tips, heartfelt advice, and motivation to help you redefine your relationship with fitness and yourself. In fact, the conversation was so inspiring that it became a two-part special—stay tuned for the second half coming soon! Don’t miss this powerful, no-nonsense “kick in the ass” you didn’t know you needed! 00:00 Introduction and Guest Welcome 00:58 Eddie's Aerobics Journey 02:15 Training and Commitment 04:29 The Importance of Mental Readiness 04:56 Diving into Fitness and Body Image 05:20 Eddie's Fitness Journey 10:23 Struggles with Self-Image 15:07 The Impact of Social Media 21:19 The Struggles of Early Modeling 21:58 Authenticity and Charisma in the Industry 23:10 The Role of a Tough Coach 26:15 Success Through Small Goals 34:54 The Importance of Movement at Any Age 38:19 Conclusion and Next Episode Teaser Write to me at: GoDeep@deeppodcast.studio Follow me at @deepwithjay or @furrypup

    41 min

  6. 09/17/2025

    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 being outed in high school, the aftermath with his family, and the ultimate acceptance he found. 00:00 Introduction: Welcome to Deep 00:41 Jay's Coming Out Story Begins 01:51 Childhood Struggles and Family Background 09:06 Discovering Sexuality and Early Experiences 14:52 High School Life and Coming Out 25:57 Family Reactions and Acceptance 38:50 Reflections on Trauma and Growth 52:23 The Deep End: Embracing the Messy Middle 55:45 Conclusion and Call to Action Write to us at: GoDeep@deeppodcast.studio LinkedIn Follow me at: @deepwithjay

    57 min

  7. 09/10/2025

    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 the transformative power of connection. They share deeply personal stories, emphasizing the value of supportive friends, stepping out of comfort zones, and fostering meaningful social connections. Whether you're navigating your own mental health journey or looking for ways to strengthen relationships, this episode delivers inspiration, vulnerability, and practical tips for building resilience. 00:00 Welcome and Introduction 01:17 Meet the Guest: Aaron Hall 02:22 A Decade of Friendship and Relationships 15:26 Navigating Mental Health Challenges 24:40 The Sound of Music and Emotional Numbness 24:53 A Dark Night and a Lifeline 25:29 The Weight of Reaching Out 26:38 A Neighbor's Help 27:46 Reaching Out to Friends and Family 28:27 Early Warning Signs and Seeking Support 29:07 The Importance of Showing Up 37:28 COVID's Impact on Friendship 42:05 Saying Yes to Social Invitations 44:46 The Antisocial Epidemic 51:29 The Show 'Big Boys' on Hulu 54:25 Wrapping Up and Final Thoughts You can write to us at Questions@GynoInfo.net And follow us on:  Instagram @gynoinfoYou can follow Aaron @LoganoTron The article referenced in this episode is from The Atlantic and can be accessed here:  https://www.theatlantic.com/magazine/archive/2025/02/american-loneliness-personality-politics/681091/

    54 min

  8. 09/03/2025

    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 you.’  Tune in now for Jay’s unique blend of vulnerability, wisdom, and entertainment - You’re sure to love it! 00:00 Introduction and Welcome 00:39 Life Updates and Personal Stories 02:05 Gym Experiences and Social Tips 06:21 Q&A: Fears, Love, and Future Plans 09:09 Q&A: Fitness and Fun 11:16 Q&A: Relationships and Intimacy 24:49 Final Thoughts and Farewell You can write to us at GoDeep@DeepPodcast.Studio And follow us on:  Instagram @deepwithJay

    28 min
See All (13)

3.5
out of 5
13 Ratings

About

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!

Information

  • Creator
    Pride House Media
  • Years Active
    2K
  • Episodes
    13
  • Rating
    Explicit
  • Copyright
    © 2025 Deep with Jay
  • Show Website
    Deep with Jay

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