

The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging
Kiley ‘Sexyswingerchic’
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 swingingMonogamy after openness (or vice versa)Relationship transitions, breakups, and rediscovering self-worthADHD, neurodivergence, and nervous system repair in loveSexual empowerment and authentic connectionEach episode blends real-time storytelling, expert interviews, and unfiltered reflections on:Ethical non-monogamy, polyamory, and swingingEmotional intelligence and intimacy and of course SEX Boundaries, communication, and healing attachment woundsQueerness, identity exploration, and sex-positivityNeurodivergent love, pleasure, and partnershipYou’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.
Episodes
Mentioned books

Apr 4, 2025 • 1h 10min
101: Connective Sex And Non Monogamy With Reid from ReidAboutSex
Send us a textThe Pineapple Express: A Guide to Millennial Love, Evolution, and RelationshipsIn 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 unpack the deeper stuff:✨ What does it really mean to stay emotionally connected during casual or multiple sexual connections? How do you create sex that feels nourishing—not just exciting? Can casual sex be intimate? (Spoiler: Yes. And Reid tells us how.)We talk about: – The difference between “porn sex” and “connected sex” – How to bring heart, intention, and intimacy into non-monogamous dynamics – Tools for checking in with partners before and after play – Why emotional presence during sex matters—even when it’s casualWhether you’re new to ethical non-monogamy or years into your journey, this episode is packed with wisdom, warmth, and permission to slow down and get real about what turns you on—emotionally.About Reid Mihalko: Reid is a world-renowned sex and relationship coach who blends humor, heart, and skill-building to help people create more intimacy and connection in their sex lives. You can learn more about him at reidaboutsex.com.🛎️ Don’t forget to rate, review, and share this episode with your non-monogamous community!Support the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Mar 19, 2025 • 1h 23min
100: Love, Soulmates & My Journey Back to Monogamy – Special Guest Tyler
Send us a textLeaving 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 happens when you choose a different path than the one you thought you’d always be on. If you’ve ever wondered what it’s like to transition out of non-monogamy—or if you’re just a sucker for a good love story—this episode is for you.Plus, you’ll notice the audio and editing are next level. We’re stepping up our game for this new chapter! And since this is Tyler’s first time on the podcast, let’s show him some love—who knows, you might hear him on other shows soon!🔗 Listen now and join us for this intimate conversation about love, change, and finding what truly fits. 💛🎙️ The Pineapple Express PodcastSubscribe to my Substack for exclusive content: The Pineapple Express Substack.💡 Events & CoachingCoaching 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 YouFirmTech 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 | ExSupport the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Feb 21, 2025 • 1h 8min
99: Hierarchical Polyamory, Big Feelings, and Demisexuality:An Open Conversation with Laura Boyle
In this conversation with Laura Boyle, an expert in polyamory and relationship coaching, listeners dive into the intriguing concept that "hierarchical polyamory is just demisexual swinging." They unpack the emotional landscape of non-monogamy and how labels shape connections. Laura shares insights about the evolution of relationships, the importance of emotional bonds, and the societal perceptions surrounding these dynamics. With plenty of humor and heartfelt moments, the discussion offers a refreshing perspective on navigating love in all its forms.

Feb 14, 2025 • 1h 4min
98:For Better or Even Better: 7 Lessons on Love & Life with Lauren Hayes SwingingLifestyleCoach
Send us a textIn 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 relationships, a seasoned non-monogamist, or just seeking insights to enrich your own partnerships, this conversation is packed with practical wisdom and heartfelt stories. Tune in to hear how Lauren’s experiences can help you embrace love and life on your own terms.🎧 Listen now and discover how to make your relationships not just good, but even better!Learn More About Lauren Here https://www.swinginglifestylecoach.comGet The Book Here https://www.swinginglifestylecoach.com/evenbetterFollow Lauren On Social Media Instagram 🎙️ The Pineapple Express PodcastSubscribe to my Substack for exclusive content: The Pineapple Express Substack.💡 Events & CoachingCoaching 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 YouFirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick.SENSE Shop | Condoms & Lube | Support the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Feb 7, 2025 • 1h 12min
97: Men and Emotional Intelligence In Non Monogamous Relationships With Justin Nault
Send us a textWhat 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 in open relationships. With over 650,000 followers and a thriving 12,000-member Clovis community, he’s leading a revolution in modern masculinity, holistic health, and relationship freedom.🔹 How to transition from Prince Energy to King Energy🔹 The role of emotional intelligence in non-monogamy🔹 Rejecting toxic masculinity & embracing authentic leadership🔹 How holistic health impacts confidence & connection in relationshipsJustin holds a Bachelor’s Degree in Songwriting from Berklee College of Music and is a Certified Nutritional Therapist, Specialist in Sports Nutrition, and Fitness Nutrition Expert. His insights on non-monogamy, modern masculinity, and self-leadership will change the way you approach relationships and personal growth.🎧 Listen now and step into your King Energy!Find Justin On Social MediaTiktokInstagram Youtube 🎙️ The Pineapple Express PodcastSubscribe to my Substack for exclusive content: The Pineapple Express Substack.💡 Events & CoachingCoaching 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 JusSupport the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Jan 10, 2025 • 1h 18min
96: Holding Space for Heartache: Grief in the Swingers Lifestyle
Send us a textIn 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.comThis 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 place iSupport the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Jan 3, 2025 • 1h 38min
95: Power, Domination, and Power Dynamics: Part 3 Lions, Tigers and Systems of Harm In Non Monogamy and Swinging OH MY!
Send us a textIn 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 take today to educate yourself, redistribute resources, and decenter privilege.How to Recognize and address systemic oppression in your communities, including swinger and non-monogamous spaces.Why Listen:If you’ve ever struggled to navigate conversations about equity and privilege or felt uncertain about how to show up as an ally, this episode will leave you with clear, actionable steps to make a meaningful impact.Want to Learn More?Check out Bridget’s work at Professor Playtime for resources on allyship, equity, and non-monogamy..Resource Guide For This Episode:🌟 Stay Connected and Explore More! 🌟Looking for more insights, resources, and exclusive deals? Follow me and my amazing sponsors to stay in the loop on all things non-monogamy, swinging, and relationship empowerment:Clip from themercurialmillennial🎙️ The Pineapple Express PodcastSubscribe to my Substack for exclusive content: The Pineapple Express Substack.💡 Events & CoachingExplore Non-Monogamy Through Astrology | Learn more & register.Boundaries Are Sexy: Building Trust in the Swinger Lifestyle | Support the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Dec 28, 2024 • 1h 11min
94: Power, Domination, and Power Dynamics: Part 2 Some Wicked Lessons About Swinger Spaces
Send us a textWhat 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 communities. In this episode, we’ll discuss:The difference between performative and authentic allyshipHow societal systems like whiteness, patriarchy, and monogamy influence power dynamics and relationships.Why symbolic gestures aren’t enough and how to shift from awareness to meaningful action.Content Warning: This episode includes discussions about race, privilege, gender, and societal power structures.Why You Should Listen:If you’ve ever felt called to do better as an ally but struggled with where to start or how to handle the discomfort, this episode is for you. It’s time to embrace authentic allyship, challenge systems of harm, and build healthier, more equitable relationships in every area of life.Want to Learn More?Check out Bridget’s work at Professor Playtime for resources on allyship, equity, and non-monogamy..Resource Guide For This Episode:🌟 Stay Connected and Explore More! 🌟Looking for more insights, resources, and exclusive deals? Follow me and my amazing sponsors to stay in the loop on all things non-monogamy, swinging, and relationship empowerment:🎙️ The Pineapple Express PodcastSubscribe to my Substack for exclusive content: The Pineapple Express Substack.💡 Events & CoachingExplore Non-Monogamy Through Astrology | Support the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Dec 20, 2024 • 1h 16min
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 systems of power starts with looking inward. This is a conversation for those ready to step up, do the work, and build systems of equity in their communities.What You’ll Hear in This Episode:The impact of whiteness, patriarchy, and monogamy on relationships and social structuresHow these systems condition us to reinforce hierarchies of privilege and controlThe importance of self-reflection in allyship and dismantling internalized biasesPractical tips for creating safer, more equitable spacesResources for those ready to take actionWant to Learn More?Check out Bridget’s work at Professor Playtime for resources on allyship, equity, and non-monogamy..Resource Guide For This Episode 🌟 Stay Connected and Explore More! 🌟Looking for more insights, resources, and exclusive deals? Follow me and my amazing sponsors to stay in the loop on all things non-monogamy, swinging, and relationship empowerment:🎙️ The Pineapple Express PodcastListen now on Apple Podcasts.Subscribe to my Substack for exclusive content: The Pineapple Express Substack.💡 Events & CoachingExplore Non-Monogamy Through Astrology | Support the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...

Dec 13, 2024 • 1h 3min
92: Swinging and Sex Without Shame With Dr. Tina Schermer Sellers
Send us a textReady 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 can cultivate confidence, enhance communication, and deepen intimacy in their relationships. Whether you're navigating the swinger lifestyle, curious about non-monogamy, or seeking a healthier relationship with your sexuality, this episode offers practical advice and powerful insights to help you live a more liberated and pleasure-filled life.Tune in to discover:✅ How to overcome shame and embrace your sexual identity.✅ Tips for creating trust and consent in swinging and non-monogamous relationships.✅ The impact of societal norms on sexual freedom and how to rewrite your narrative.Don’t miss this transformative conversation with Dr. Tina Schermer Sellers, a leading voice in sex positivity and healthy intimacy.🎧 Listen now and start your journey toward sex without shame!🌟 Learn more about Dr. Tina Schermer Sellers at tinaschermersellers.com.Inanna Rising - Your Partner in Health and Healing🍍🍍My Turn🍍🍍Here’s all the info you’ll ever need to have at any point in time about meLiterally everything is right here…Every single link ever mentioned as a Sponsor and info all about me🚂All My Links To Learn More About MeMy WebsiteOnlyfansLinktreeSex CoachingFind me on social mediaISupport the show🎙️ The Pineapple Express PodcastSubscribe 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 Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game 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 up...