The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging - podcast cover

The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging

Kiley ‘Sexyswingerchic’ thepineappleexpresspodcast.buzzsprout.com

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.














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Episodes

114: From ER Nurse to Hotwife with Adult Content Creator Serenity Cox

Send us a text In this episode of The Pineapple Express , I sit down with Serenity Cox — former ER nurse turned erotic content creator and hotwife lifestyle influencer — to explore her dramatic transformation, boundary-pushing relationship models, and how she’s rewriting the rules of desire and consent. We discuss: Her journey: from nursing in emergency care to filming and sharing intimate moments with her partner and the world The hotwife lifestyle: what it really means, negotiation, consent, a...

Oct 09, 20251 hr 8 minSeason 3Ep. 13

113: How Parts Work Transforms Polyamory: Transforming Jealousy, Fear, and Attachment Wounds

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 , showi...

Aug 29, 202543 minSeason 3Ep. 14

112: Anxious + Avoidant: Can This Relationship Ever Work? — with Jack from Polarity Unscripted

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 bre...

Aug 22, 20251 hr 8 minSeason 3Ep. 15

111:The Damage Of Decolonizing Love & The Polyamory Community,Race, and the Swinger's Lifestyle— with Tiffany @RealPolyLife

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 of 'decolonizin...

Aug 15, 20251 hr 17 minSeason 3Ep. 8

110: 'Tolyamory' and The Dangers Of Practicing Non Monogamy To Keep Your Partner

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 fel...

Jul 11, 202550 minSeason 3Ep. 7

109: Hard Truths: Women’s Pleasure, Shame, and the Silent Impact of ED With Dr. Elliot Justin

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...

Jul 04, 20251 hr 5 minSeason 3Ep. 6

108: How to Throw a Kick-Ass Play Party (and Be a Kick-Ass Guest) with Ally Isman

Send us a text Ever wondered what makes a play party unforgettable (for all the right reasons)? In this sizzling episode of The Pineapple Express , I’m joined by Ally Isman , founder of Passport2Pleasure and mastermind behind the KAVANOS: Lisbon Wedding Night experience—an invite-only, immersive destination play party held in a historic Portuguese palace. Together, we break down everything you need to know to host or attend a play party like a pro , from curating energy and consent culture to cr...

Jun 27, 20251 hr 11 min

107: Building Real Connection In Swinging and Polyamory with The Non-Monogamy Card Game

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, vulnera...

Jun 22, 20251 hr 19 minSeason 3Ep. 5

106:Solo Polyamory 101: How to Date Yourself and Others with Confidence

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 dating yoursel...

Jun 06, 20251 hr 2 minSeason 3Ep. 4

105: After the High: Breaking Up, Breaking Open — with Jack from @polarityunscripted

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 de...

May 23, 20251 hr 18 minSeason 3Ep. 3

Power, Swinging, & the Diddy Trial: A Trauma-Informed Breakdown with Dr. Emma Smith, PhD

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 relat...

May 16, 20251 hr 13 minSeason 3Ep. 3

104: Good Luck to You, George Golburn: What it’s like to be a male escort—

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, th...

May 09, 20251 hr 6 minSeason 3Ep. 2

103: Redesign Your Damn Relationship: Non Monogamy, Conscious Monogamy & Breaking the Rules with Dr. Joli Hamilton

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 . Wheth...

Apr 18, 20251 hr 7 minSeason 3Ep. 1

102: The Other Side of Cheating— What Ashley Madison Can Teach Us About Modern Relationships with Paul Keable

Send us a text 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 ...

Apr 12, 20251 hr 2 min

101: Connective Sex And Non Monogamy With Reid from ReidAboutSex

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...

Apr 04, 20251 hr 10 minSeason 3Ep. 1

100: Love, Soulmates & My Journey Back to Monogamy – Special Guest Tyler

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 hap...

Mar 19, 20251 hr 23 minSeason 2Ep. 30

99: Hierarchical Polyamory, Big Feelings, and Demisexuality:An Open Conversation with Laura Boyle

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 partne...

Feb 21, 20251 hr 8 minSeason 2Ep. 29

98:For Better or Even Better: 7 Lessons on Love & Life with Lauren Hayes SwingingLifestyleCoach

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 relat...

Feb 14, 20251 hr 4 minSeason 2Ep. 27

97: Men and Emotional Intelligence In Non Monogamous Relationships With Justin Nault

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 thrivi...

Feb 07, 20251 hr 12 minSeason 2Ep. 29

96: Holding Space for Heartache: Grief in the Swingers Lifestyle

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 intim...

Jan 10, 20251 hr 18 minSeason 2Ep. 28

95: Power, Domination, and Power Dynamics: Part 3 Lions, Tigers and Systems of Harm In Non Monogamy and Swinging OH MY!

Send us a text In Part 3 of this series, we take a journey down the yellow brick road to explore how The Wizard of Oz serves as a metaphor for the systemic issues that persist in our world today. From the glittering Emerald City we talk about how to step into allyship in a real impactful way! In this episode, we’ll explore: How The Wizard of Oz illustrates systemic oppression and power dynamics. Practical tools for having skillful, empathetic conversations about privilege and bias. Steps you can...

Jan 03, 20251 hr 38 min

94: Power, Domination, and Power Dynamics: Part 2 Some Wicked Lessons About Swinger Spaces

Send us a text What can a glittering "Good Witch" and a misunderstood green-skinned rebel teach us about allyship? A lot more than you might think. In this episode of The Pineapple Express , Kiley George and Professor Playtime break down power dynamics and the unlearning and relearning phase of allyship. We’ll connect these lessons to real-world dynamics of privilege, power, and justice—unpacking systems like whiteness, patriarchy, and monogamy, and how they shape our relationships and communiti...

Dec 28, 20241 hr 11 min

93:Power, Domination, and Power Dynamics: Part 1 Unpacking Privilege and Systems of Harm In Swinger Spaces

Send us a text In this powerful episode of The Pineapple Express , host Kiley George (swinger expert and non-monogamy advocate) and guest Bridget, aka "Professor Playtime" (integrity coach and educator on intersectionality and allyship) we talk about power dynamics, privilege, and systems of harm that shape our relationships and communities. We also discuss the risks and rewards of stepping into allyship, especially in light of recent political changes, and share insights into how challenging sy...

Dec 20, 20241 hr 16 min

92: Swinging and Sex Without Shame With Dr. Tina Schermer Sellers

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 ca...

Dec 13, 20241 hr 3 minSeason 2Ep. 25

91:Non-Monogamy, Sex Work, and Challenging Societal Norms with Author Zara Shah

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 o...

Dec 06, 20241 hr 19 minSeason 2Ep. 24

90:Non-Monogamy, Mental Health, and Sexual Liberation with Ann Russo

Send us a text Welcome to The Pineapple Express Podcast ! In this episode, we talk about the transformative intersection of non-monogamy, mental health, and sexual empowerment with the inspiring Ann Russo. Ann is a radical educator, writer, and activist committed to building liberatory practices rooted in care, accountability, and collective well-being. Together, we explore how embracing non-monogamy can be a path to personal growth and emotional resilience. Ann shares their insights into disman...

Nov 22, 20241 hr 19 min

89:Protecting Lifestyle Clubs And The Fight for Consensual Adult Spaces in Acadia Parish and Beyond

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 Cha...

Nov 15, 202448 minSeason 2Ep. 27

88: Layers of Liberation: Exploring Feminism And Non Monogamy with Mel Cassidy

Send us a text In this powerful episode of The Pineapple Express , Kiley sits down with Mel Cassidy to dive deep into the intersectionality of feminism. Together, they unpack how feminist values overlap with diverse identities, exploring the unique challenges and triumphs of navigating gender, race, sexuality, and non-monogamy. They’ll discuss the evolution of intersectional feminism, its impact on modern relationships, and how inclusivity in feminist spaces can create a stronger, more resilient...

Nov 08, 20241 hr 33 minSeason 2Ep. 26

87: Male Bisexuality And It's Evolution In Non Monogamy with "Boyslut" Zachary Zane

Send us a text Get ready for an eye-opening and no-holds-barred conversation on this episode of The Pineapple Express Podcast ! We’re joined by Zachary Zane—an acclaimed writer, and the brilliant mind behind Boyslut: A Memoir and Manifesto . We talk all things evolutionary, including the evolution of male bisexuality in the world of swinging and non-monogamy. Zachary shares personal stories and insights on what it’s like to navigate bisexual identity as a man, breaking down outdated stigmas and ...

Nov 01, 20241 hr 11 minSeason 2Ep. 25

86:Swinger Horror Stories: Avoiding Newbie Nightmares – Vetting Clubs, Dodging Scams, and Protecting Your Privacy

Send us a text In this episode of The Pineapple Express Podcast , I reveal the secrets to avoiding newbie swinger horror stories and protecting your privacy in the lifestyle. Whether you’re just starting out or looking to refine your experiences, I'll give you the tools you need to vet swinger clubs , avoid scams , and stay safe on social media . Don't let your fantasy turn into a nightmare—swing smarter with our essential tips. I also highlight venues like The Body Shop , https://bodyshopclubs....

Oct 25, 202459 minSeason 2Ep. 24
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