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
96: Holding Space for Heartache: Grief in the Swingers Lifestyle
In this heartfelt episode of The Pineapple Express, I explore grief in the swinger lifestyle — the losses that aren’t always acknowledged, from friendships and play partners to deep emotional bonds. This episode holds space for heartache, reflection, and healing within non-monogamous communities.
Stay with us until the end, where I share my personal essay, “Silver Springs, Tulip Fields, and Upside Down Pineapples”, featured on The Queer Love Project Substack. It’s a deeply intimate story of love, loss, and the transformative power of connection. https://queerloveproject.substack.com
This episode is dedicated to my dear friend Brad Weiner, who left us too soon, until we meet again teddy bear.
What You’ll Get from This Episode:
🔸 Understanding Grief in Non-Monogamy:
Learn how grief shows up in unique ways in the swinger lifestyle — from the loss of play partners to the emotional impact of community breakups.
🔸 Personal Stories of Grief in the Lifestyle:
Hear real stories about losing close connections, being ghosted, and navigating the unexpected emotional challenges of swinging.
🔸 A Breakdown of the Stages of Grief:
We’ll walk through how Denial, Anger, Bargaining, Depression, and Acceptance show up in non-monogamous relationships and what they teach us about healing.
🔸 An Exclusive Essay Reading:
Listen until the end for a reading of “Silver Springs, Tulip Fields, and Upside Down Pineapples”, my deeply personal essay featured on The Queer Love Project Substack. It's a moving story of love, loss, and finding beauty in unexpected places.
Why Listen?
❤️ If you’ve ever felt the pain of losing a connection in the lifestyle, this episode is for you.
🤝 It’s a reminder that grief is valid, even in non-traditional relationships.
🧡 You'll gain tools to navigate emotional challenges and embrace healing.
📖 Plus, you’ll hear a heartfelt essay that celebrates love, loss, and growth.
This episode will leave you feeling seen, understood, and supported — because grief deserves a
🎙️ 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
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- 💬 Let’s keep the conversation going! Follow me for updates, insights, and inspiration:
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