Claim OwnershipThe Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging
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© 2025 The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging
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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.
112 Episodes
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Send us a text In this episode, Kiley explores how Parts Work, most commonly associated with Dr. Richard C. Schwartz’s Internal Family Systems (IFS) model, can transform your experience of polyamory and consensual non-monogamy. You’ll learn how to identify your inner Managers, Firefighters, and Exiles, and how to lead from your calm, compassionate Self — even in the middle of jealousy, fear of abandonment, or metamour conflict. We’ll also connect these tools to Jessica Fern’s Polysecure, show...
Send us a text In this episode, Kiley sits down with Jack Bohannan from Polarity Unscripted to explore one of the most talked-about — and often misunderstood — relationship dynamics: the anxious–avoidant attachment pairing. Drawing from her own past relationship (where the answer to “can it work?” felt like a definite no), Kiley brings a candid, real-world perspective to the conversation, while Jack offers his deep expertise on polarity, emotional intimacy, and secure relating. Together, we b...
Send us a text The Damage of Decolonizing Love & Black Polyamory: Tiffany @RealPolyLife on Race, Community & Swinging Join us for a powerful conversation with Tiffany (@RealPolyLife) https://www.instagram.com/realpolylife?igsh=MTRhYWg4Yngwd3h5Zg== a Black polyamorous educator and influencer, as she unpacks the complex intersections of race, and intimate relationship structures within the polyamory and swinger communities. We dive into how the not so well-meaning efforts...
Send us a text Let’s talk about the thing no one wants to admit: sometimes we say yes to non-monogamy not because we want to—but because we’re afraid to lose someone we love. In this episode, we dive deep into the term “tolyamory” (coined by Dan Savage), the danger of choosing open relationships out of fear instead of desire, and how to tell if you’re actually aligned with non-monogamy… or just tolerating it. We’ll unpack: The red flags of “tolyamory”Why consent isn’t just a checkbox—it’s a f...
Send us a text In this powerful episode of The Pineapple Express, sex and relationship coach Kiley George sits down with Dr. Elliot Justin, founder of FirmTech and a leading voice in sexual wellness innovation, to explore the often-overlooked emotional and physical impacts of erectile dysfunction (ED) on women. We talk about how ED affects women's sexual confidence, why so many partners feel shame, guilt, or self-blame, and how sex tech tools like FirmTech’s Ring are helping couples reconnect...
Send us a text Want to deepen your relationships without another awkward check-in? In this episode of The Pineapple Express, we explore how The Non-Monogamy Card Game is changing the way we connect—with ourselves, our partners, and our playmates. Whether you're polyamorous, exploring ethical non-monogamy, or just want better conversations in your situationships, this tool is pure gold. Join me and Ayala & Kristen the creators of The Non Monogamy Card Game as we share how connection, vulne...
Send us a text Are you curious about solo polyamory? Wondering how to build fulfilling relationships while prioritizing your own growth and independence? In this solo episode of The Pineapple Express Podcast, host Kiley breaks down everything you need to know about solo polyamory: why people choose it, how to navigate the challenges, and how to embrace your authentic self along the way. Learn why solo polyamory is a rising trend in ethical non-monogamy Discover practical tips for datin...
Send us a text 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 d...
Send us a text What’s the difference between kink and coercion? How do trauma bonds form—and why do people stay in abusive relationships? In this powerful episode, sex and relationship coach Kiley George sits down with trauma-informed therapist Dr. Emma Smith, PhD, to unpack the ongoing Sean “Diddy” Combs trial and what it reveals about consent, power dynamics, and survival responses. From celebrity influence to “freak-off” parties and nervous system shutdowns, we explore how trauma shapes re...
Send us a text In this episode of The Pineapple Express, I’m joined by George — a straight male escort based in Australia who helps women feel confident, desired, and deeply connected to their bodies. George shares his journey as a full-service male companion, what it means to offer women a safe space for sensual exploration, and how his work often mirrors the emotional intimacy and healing portrayed in Good Luck to You, Leo Grande. We talk about the legal realities of sex work in Australia, ...
Send us a text In this episode of The Pineapple Express: A Guide to Millennial Love, Evolution, and Relationships, we're diving headfirst into the world of relationship design, jealousy, and letting go of the outdated love scripts that no longer serve us. My guest is the incredible Dr. Joli Hamilton—psychologist, TEDx speaker, and founder of The Institute for Creative Relating—who’s on a mission to help people create intentional, empowering relationships that actually fit their lives. Whether...
Send us a text The Pineapple Express: A Guide to Millennial Love, Evolution, and Relationships In this episode, I sit down with the legendary Reid Mihalko—sex and relationship educator, creator of Sex Geek Summer Camp, and the brain behind reidaboutsex.com—to talk about something that often gets overlooked in non-monogamy: connective sex. Whether you’re navigating swinging, polyamory, or open relationships, it can be easy to get swept up in novelty, scheduling, and logistics… but Reid and I u...
Send us a text Leaving Swinging & Embracing Monogamy – A Love Story with Tyler 💛🎙️ For our 100th episode, we’re diving deep into love, soulmates, and my journey from non-monogamy back to monogamy. In this milestone episode, I’m joined by my partner, Tyler, as we have an open and honest conversation about how our relationship evolved, what led me to step away from swinging, and how we navigated this huge shift together. We’re talking love beyond labels, redefining commitment, and what happ...
Send us a text In this episode of The Pineapple Express, I sit down with my friend and non-monogamy expert Laura Boyle, creator of Ready for Polyamory. We dive into the provocative idea that “hierarchical polyamory is just demisexual swinging,” unpacking big feelings about different forms of polyamory and non-monogamy. We explore how labels and dynamics shape relationships, challenge stereotypes, and share our personal journeys—mine includes a surprising move toward monogamy with my new partn...
Send us a text In this episode of The Pineapple Express, I sit down with Lauren Hayes, author of For Better or Even Better: 7 Lessons on Love & Life from a Non-Monogamist. Lauren shares her journey into non-monogamy and the transformative lessons she’s learned along the way. We explore the key themes of her book, including navigating jealousy, fostering deeper communication, and redefining love and commitment through the lens of ethical non-monogamy. Whether you’re curious about open rela...
Send us a text What does it mean to embrace true masculine power while navigating non-monogamy? In this episode of The Pineapple Express Podcast, we sit down with Justin Nault, creator of King vs. Prince, a transformative program guiding men from ego-driven behaviors to grounded, confident leadership. With a background in entrepreneurship, music, and holistic health, Justin helps men develop emotional mastery, radical self-acceptance, and authentic leadership—all essential skills for thriving...
Send us a text 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 inti...
Send us a text Ready to break free from sexual shame and embrace a more fulfilling, authentic life? In this episode of Pineapple Express, host Kiley George sits down with renowned sex therapist and author, Dr. Tina Schermer Sellers, to explore the transformative power of sex-positive thinking and how to overcome societal and religious stigmas around swinging, non-monogamy, and intimacy. Dr. Sellers brings her expertise in dismantling shame-based beliefs to discuss how individuals and couples ...
Send us a text In this episode of The Pineapple Express Podcast, we sit down with Zara Shah, author of Non-Monogamy and Sex Work, published by Thornapple Press. Together, we explore the intersections of sex work and non-monogamy, unpacking topics like intimacy, economics, social rejection, sexual health, and the impact of societal norms on mental health. Zara shares powerful insights into the challenges and triumphs within non-monogamous and sex work communities, offering a fresh perspective ...
Send us a text In this impactful episode of The Pineapple Express Podcast, host Kiley George explores the proposed Acadia Parish ordinance targeting sexually oriented businesses and its potential consequences for lifestyle clubs and consensual adult spaces. Discover why these spaces are essential for people practicing non-monogamy, swinging, and ethical open relationships, and how misconceptions about them drive unfair laws under the guise of "public safety." Kiley shares parallels from The C...
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love this I have to show this to the wife