Description

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 Introduction
• 00:24 Meet the incomparable Sherry Vine
• 01:51 Life, career updates, and what’s next for Sherry
• 02:58 Theater dreams and acting aspirations
• 07:36 Hot hookup stories and wild experiences
• 10:59 The evolution of hookup culture: pre-app vs. app era
• 13:46 Navigating hookup apps like a pro
• 14:12 Unexpected encounters (and a few surprises!)
• 19:10 Safety tips and preferences when it comes to hookups
• 27:30 Fetishes, fantasies, and unique requests
• 33:03 Awkward hookup stories you need to hear to believe
• 33:32 The infamous "No Door Dilemma"
• 33:42 Porn preferences and guilty pleasures
• 34:36 When theft and trust issues ruin the mood
• 39:06 Nudes, blackmail, and keeping things secure
• 40:45 Foot fetishes and unexpected kinks
• 45:00 Viewer Submissions: Sherry and Jay react to your hookup confessions
• 50:23 Craziest hookup locations (spoiler: you’ll never guess!)
• 53:55 Sherry’s Sex and Drag documentary: the story behind the story
• 58:45 Final thoughts, laughs, and farewell

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!
• 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!