The Pineapple Express: A Millennial’s Guide to Love, Evolution, Relationships & Sex Positivity
The Pineapple Express: A Millennial’s Guide to Love, Evolution, Relationships & Sex Positivity
🎙️ New Episode Every Week!
Yes, this used to be a swinger podcast… but things evolve. Just like we do.
Meet Kiley—queer menace, local witchy woman, non monogamous misfit-turned-monogamous, ADHD daydreamer, astrology nerd, ex-sex worker, and your favorite TikTok swinger-turned-relationship coach.
She’s here to stir the cauldron.
This space isn’t just about swinging anymore (though we’ll always have love for a well-planned orgy). It’s about modern relationships, real transformation, nervous system repair, intimacy after heartbreak, and letting your pleasure evolve with you.
Let’s talk about the messy, magical middle.
Let’s talk about sex, sexuality, and soul-level connection.
Let’s talk about what happens when the swinger girl becomes the soft, sacred version of herself—and still loves to fuck.
This is not your average relationship space.
This is Kiley’s world. You’re invited.
The Pineapple Express is a podcast for people navigating the messy, magical, and ever-evolving world of modern relationships.
Every week, we explore what it means to grow in love—whether you're monogamous, non-monogamous, polyamorous, curious, or completely redefining what partnership looks like for you.
This isn’t just another relationship podcast. It’s a real-time audio journal, a resource hub, and a safe space for conversations that go beyond the surface—rooted in sex positivity, emotional wellness, and authentic self-discovery.
🎙️ We dive into topics like:
- Monogamy & Non-Monogamy
- Ethical Slutdom, Polyamory & Conscious Relationships
- Relationship Transitions & Emotional Growth
- Queerness, Bisexuality & Identity Exploration
- ADHD & Neurodivergence in Love
- Communication, Boundaries & Intimacy
Whether you’re opening your relationship, closing it, rethinking how you love, or trying to love yourself better—The Pineapple Express is here to ride with you.
🛎️ New episodes drop weekly. Subscribe now and grow with us.
Why Listen?
Because you're tired of relationship advice that doesn’t reflect your reality. Whether you’re in a traditional relationship, ethically non-monogamous, figuring out your sexuality, or somewhere in between—this podcast is for you.
Hosted by Kiley, a certified sex and intimacy coach with lived experience in swinging, non-monogamy, and evolving into monogamous love, this show offers real, vulnerable, and often funny conversations about what it means to grow in partnership.
You’ll hear personal stories, expert interviews, and unfiltered reflections on love, identity, neurodivergence, boundaries, and becoming your most authentic self.
If you’ve ever asked, “Is it normal to change in love?”—this podcast says YES. And we talk about how.
Subscribe now and ride The Pineapple Express, where we talk about love, sex, and everything in between—without judgment, just curiosity and connection.
The Pineapple Express: A Millennial’s Guide to Love, Evolution, Relationships & Sex Positivity
102: The Other Side of Cheating— What Ashley Madison Can Teach Us About Modern Relationships with Paul Keable
In this episode of The Pineapple Express: A Guide to Millennial Love, Evolution, and Relationships, I sit down with Paul Keable, Chief Strategy Officer at Ashley Madison, to explore the real reasons people seek connection outside of traditional monogamy.
We talk about:
💬 Why infidelity happens in long-term relationships
🌱 The emotional complexity behind secrecy and unmet needs
❤️🔥 The future of non-traditional relationships in a rapidly evolving world
🔓 How platforms like Ashley Madison are creating space for conversations around autonomy, desire, and honest exploration
This is not an episode about shame or judgment. It’s a conversation about what it means to be human in relationships, especially when the expectations of monogamy don’t match someone’s lived experience.
Whether you're monogamous, non-monogamous, or questioning the rules you've been taught, this episode will leave you thinking deeply about communication, choice, and connection.
📎 Learn more about Paul Keable and his work at Ashley Madison:
https://www.ashleymadison.com
Paul Keable's Authority Magazine Interview
🎧 Subscribe to The Pineapple Express for weekly episodes on love, growth, and relationships that reflect real life—not just romance novels.
🎙️ The Pineapple Express Podcast
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💡 Events & Coaching
- Coaching sessions: Book time with me.
💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom.
OPEN's Free Peer Support Group
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- 💬 Let’s keep the conversation going! Follow me for updates, insights, and inspiration:
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