x

75% of people globally want unbiased news (Pew Research) but are concerned they're not getting that.

Get balanced coverage with Symby. See how stories are covered across diverse outlets and spot when one side covers a story the other skips.

PODCAST

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

Kiley ‘Sexyswingerchic’

The Pineapple ExpressOnce 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,

health & fitness sexuality

All Episodes

67:41

114: From ER Nurse to Hotwife with Adult Content...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/10/09

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 worldThe hotwife lifestyle: what it really means, negotiation, consent, ...

en-us

43:23

113: How Parts Work Transforms Polyamory:...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/08/29

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...

en-us

68:17

112: Anxious + Avoidant: Can This Relationship Ever...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/08/22

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...

en-us

77:09

111:The Damage Of Decolonizing Love & The Polyamory...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/08/15

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) 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 'decolonizing love' can inadvertently cause harm, especially for Bla...

en-us

50:10

110: 'Tolyamory' and The Dangers Of Practicing Non...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/07/11

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...

en-us

65:01

109: Hard Truths: Women’s Pleasure, Shame, and the...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/07/04

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...

en-us

70:39

108: How to Throw a Kick-Ass Play Party (and Be a...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/06/27

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...

en-us

78:33

107: Building Real Connection In Swinging and...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/06/22

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...

en-us

61:58

106:Solo Polyamory 101: How to Date Yourself and...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/06/06

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...

en-us

77:52

105: After the High: Breaking Up, Breaking Open —...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/05/23

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...

en-us

72:43

Power, Swinging, & the Diddy Trial: A Trauma-Informed...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/05/16

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...

en-us

66:00

104: Good Luck to You, George Golburn: What it’s like...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/05/09

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, ...

en-us

66:56

Redesign Your Damn Relationship: Non Monogamy,...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/04/18

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...

en-us

61:49

102: The Other Side of Cheating— What Ashley Madison...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/04/12

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 🔓...

en-us

70:11

101: Connective Sex And Non Monogamy With Reid from...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/04/04

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...

en-us

83:11

100: Love, Soulmates & My Journey Back to Monogamy –...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/03/19

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

en-us

68:26

99: Hierarchical Polyamory, Big Feelings, and...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/02/21

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...

en-us

64:11

98:For Better or Even Better: 7 Lessons on Love &...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/02/14

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...

en-us

71:45

97: Men and Emotional Intelligence In Non Monogamous...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/02/07

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...

en-us

77:50

96: Holding Space for Heartache: Grief in the...

The Pineapple Express: A Millennial’s Guide to Love,... ·

2025/01/10

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 intima...

en-us

113 results

Similar Podcasts

Доктор Тройняшкин

Доктор Тройняшкин

The Dry Eye Treatment PODCAST

Dry Eye Treatment

Différent et alors ?

PATRICK SULAY

Kyle Kingsbury Podcast

Kyle Kingsbury

The Real Weight Loss Coach

Matty Lansdown