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

Send us a textAre 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 yourself—and others—without losing your independence Explore the emotional, social, and logistical challenges of solo poly lifeTune in and empower yourself with the tools to thrive in your own solo polyamory journey—on your terms, at your pace, and with no apologies.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 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...

Send us a textIn 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 relationshipsThe courage it takes to let go when your nervous system still wants to hold onWhat it means to begin the journey into solo polyamory not from empowerment — but from devastationHow friendship, tenderness, and presence can carry you through heartbreakThis 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. Support the show🎙️ 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 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...

Send us a textWhat’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 relationships—especially in non-monogamy—and how to reclaim agency, safety, and self-awareness in the bedroom and beyond.Topics include:The psychology behind trauma bondsWhat real consent looks likePublic gaslighting, kink myths, and the Diddy trialWhy your body might be saying “no” even when your mouth says “yes”Whether you’re healing from toxic love or rethinking everything you thought you knew about desire and safety—this one’s for you.🛑 Trigger Warning: Discussion of sexual abuse, trauma, and coercive control.Dr. Emma Smith is a licensed professional counselor, AASECT-certified sex therapist, and trauma specialist based in Nashville. She works with individuals and couples across Tennessee, Texas, Virginia, Maryland, and DC. A longtime advocate for sexual assault survivors, the LGBTQIA+ community, and military families, her work blends existential philosophy with integrative sex therapy to help people reclaim embodiment and desire after trauma.Website: https://soliloquie.coInsta: @emmasmithphdHer Substack has a guide for people looking to find a good therapist and questions to ask: https://open.substack.com/pub/emmasmithphd/p/swipe-left-on-bad-therapy-a-no-bs?r=1u9ku3&utm_medium=iosDisclaimer: Emma mentions RAINN but we feel this is important to mention https://www.huffpost.com/entry/sexual-assault-hotline-bans-resources-marginalized-trump-rainn_n_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 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...

Send us a textIn 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, the importance of decriminalization, and how ethical sex work can be a powerful tool for empowerment, especially for women navigating shame, touch, and pleasure.Whether you're curious about sex work, intimacy beyond the binary, or what it looks like when men serve women’s desire with integrity — this is a must-listen.✨ Topics covered: • Male sex work & companionship for women • Sex work decriminalization in Australia • Embodied confidence, pleasure, and healing • Erotic care work and ethical intimacy • George Golburn’s  path to becoming a companionhttps://www.instagram.com/george_goulburnhttps://bio.site/georgegoulburnSupport the show🎙️ 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 | 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 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...

Send us a textIn 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 you’re monogamous, polyamorous, non-monogamous, or somewhere in between, this episode is packed with juicy insights about: 💥 What it means to consciously design your relationship 💋 Why jealousy isn’t the villain—it’s a signal 🧠 The intersection of desire, autonomy, and emotional safety ⚡ How to reclaim your power in love by ditching the defaultThis is for anyone who’s tired of feeling trapped in traditional relationship roles, craving more freedom and intention, or ready to explore alternative relationship structures with clarity and confidence.🔗 Learn more about Dr. Joli Hamilton: 👉 https://www.jolihamilton.com🎧 Tune in now to start breaking the rules, not your heart—and discover how to design a love life that’s as bold, brilliant, and badass as you are.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 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...

Send us a textIn 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 Ashley Madison are creating space for conversations around autonomy, desire, and honest explorationThis is not an episode about shame or judgment. It’s a conversation about what it means to be human in relationships, especially when the expectations of monogamy don’t match someone’s lived experience.Whether you're monogamous, non-monogamous, or questioning the rules you've been taught, this episode will leave you thinking deeply about communication, choice, and connection.📎 Learn more about Paul Keable and his work at Ashley Madison: https://www.ashleymadison.com Paul Keable's Authority Magazine Interview🎧 Subscribe to The Pineapple Express for weekly episodes on love, growth, and relationships that reflect real life—not just romance novels.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 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...

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 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...

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 DancewearSupport 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 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...

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.

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 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...