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

Send us a textLet’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 felt senseHow to check in with your nervous system before saying yesWhat to do if your partner wants non-monogamy and you don’tHow to reclaim your voice, your boundaries, and your truth—even when it’s hardWhether you’re the one asking or being asked to open up, this episode is for you. Let’s stop calling it love when it’s really fear. 💔➡️💖DAY OF VISIBILITY EVENTS https://www.eventbrite.com/e/3rd-annual-day-of-visibility-for-non-monogamy-picnic-in-the-park-tickets-1398059807519https://www.weekofvisibility.com/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...

Send us a textIn 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 with pleasure, intimacy, and honest communication.This episode blends scientific insights, real talk about libido, and relationship tips for navigating intimacy when things aren’t going “as planned.” If you’ve ever wondered how to support a partner with ED—or how to reclaim your own arousal in the process—this one’s for you.Why ED isn’t just “a man’s issue”How shame and silence affect female arousalWomen’s hidden grief around unspoken rejectionReframing ED with science, compassion, and toolsHow to have the conversation with your partnerThe role of FirmTech's Ring in enhancing erection strength and pleasure for both partnersAvailable on Apple Podcasts, Spotify, and everywhere you stream your favorite shows.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...

Send us a textEver 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 creating sacred sensual spaces that feel both sexy and safe.If you're curious about throwing your own event, leveling up your guest etiquette, or just want a peek behind the velvet curtain of elite erotic events—this episode is your golden ticket.🔍 Keywords: how to host a play party, KAVANOS Lisbon, sex-positive events, Ally Isman, Passport2Pleasure, consent at play parties, how to attend a sex party, non-monogamy events, luxury swinger events, erotic event planning✨ We talk about:What makes a play party actually workCommon mistakes and how to avoid awkward energyHow to design an intentional, inclusive guest listErotic aesthetics, rituals, and ambianceConsent communication and comfort cultureWhy KAVANOS is one of the most exclusive sensual events in the world—and how to apply before it disappears forever Apply now for KAVANOS: Lisbon Wedding Night (August 2) via Passport2Pleasure.com and use “PINEAPPLE” for expedited review.This is not your average play party. This is art, eros, and elevation.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...

Send us a textWant 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, vulnerability, and communication games can ignite intimacy and help non-monogamous folks cut through small talk and get to the juicy stuff. We talk about: – How to use the card game on dates or at play parties – Why asking better questions leads to better connections  – Connection rituals for polycules and swingers – How to avoid surface-level relating in non-monogamyGrab your cards, press play, and let’s get real.Use my exclusive code PINEAPPLE10 for 10% off when you purchase The Non Monogamy Card Game https://www.thenonmonogamycardgame.com/products/the-gameSupport 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...

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 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...

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 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...

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_68263545Support 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...

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 | SSupport 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...

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 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...

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 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...