The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging
The Pineapple Express
Once a swinger podcast… now a real-time journey through modern love.
Hosted by Kiley — queer, non-monogamous, neurodivergent, ex-sex worker turned sex and relationship coach — The Pineapple Express explores the messy, magical, ever-evolving world of love, sex, intimacy, and emotional growth.
This podcast is for anyone navigating:
- Non-monogamy, polyamory, or swinging
- Monogamy after openness (or vice versa)
- Relationship transitions, breakups, and rediscovering self-worth
- ADHD, neurodivergence, and nervous system repair in love
- Sexual empowerment and authentic connection
Each episode blends real-time storytelling, expert interviews, and unfiltered reflections on:
- Ethical non-monogamy, polyamory, and swinging
- Emotional intelligence and intimacy and of course SEX
- Boundaries, communication, and healing attachment wounds
- Queerness, identity exploration, and sex-positivity
- Neurodivergent love, pleasure, and partnership
You’ll laugh, cry, and maybe even journal after. Kiley’s here to stir the cauldron — and remind you that pleasure, connection, and love are allowed to evolve.
This isn’t your average relationship podcast.
It’s personal. It’s sacred. It’s a little unhinged.
And it’s exactly what you’ve been craving.
Why Listen?
Because you're not looking for perfect love — you’re looking for real love.
Because you’re healing, growing, and rewriting the rules — and want company along the way.
Subscribe now and ride The Pineapple Express, where we talk about sex, love, and everything in between — with zero judgment, just curiosity, courage, and connection.
The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging
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
Subscribe to my Substack for exclusive content: The Pineapple Express Substack.
💡 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
🛍️ Exclusive Deals Just for You
- FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick.
- SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic.
- Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic.
- 💬 Let’s keep the conversation going! Follow me for updates, insights, and inspiration:
- Instagram:@Thepineappleexpresspodca...
