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 • 4 episodes
Deep with Jay
Latest Episodes
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 ...
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Season 1
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Episode 104
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46:48
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...
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38:47
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, ...
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Season 1
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Episode 103
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32:22