
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
105: After the High: Breaking Up, Breaking Open — with Jack from @polarityunscripted
In this raw, vulnerable follow-up to Episode 100, I share the painful, unexpected breakup with my partner after four blissful months of connection, intimacy, and what felt like “the one.” This episode is my real-time unraveling — the moment where fantasy meets grief, and I’m left to begin again.
Joining me is my dear friend and guest, Jack from Polarity Unscripted (listen to his podcast here), who gently and powerfully holds space for the ache, the anger, the longing, and the deep truth that not all love stories are meant to last.
We talk about:
- The grief of sudden endings in relationships
- The courage it takes to let go when your nervous system still wants to hold on
- What it means to begin the journey into solo polyamory not from empowerment — but from devastation
- How friendship, tenderness, and presence can carry you through heartbreak
This episode is for anyone who’s loved hard, lost deeply, and is learning to rebuild not just their love life — but their relationship to themselves.
🎙️ 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 |
🎙️ 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...