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

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

Kiley ‘Sexyswingerchic’

113 episodes

3 weeks ago

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, ...

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Health & Fitness

All content for The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging is the property of Kiley ‘Sexyswingerchic’ and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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, ...

Show more...

Health & Fitness

Episodes (20/113)

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

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

3 weeks ago

1 hour 7 minutes

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

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, show...

2 months ago

43 minutes

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

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 b...

2 months ago

1 hour 8 minutes

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

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...

2 months ago

1 hour 17 minutes

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

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 f...

3 months ago

50 minutes

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

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...

4 months ago

1 hour 5 minutes

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

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...

4 months ago

1 hour 10 minutes

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

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, vulne...

4 months ago

1 hour 18 minutes

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

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 datin...

5 months ago

1 hour 1 minute

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

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 d...

5 months ago

1 hour 17 minutes

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

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 re...

5 months ago

1 hour 12 minutes

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

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, ...

5 months ago

1 hour 6 minutes

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

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. Whether...

6 months ago

1 hour 6 minutes

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

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 🔓...

6 months ago

1 hour 1 minute

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

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...

7 months ago

1 hour 10 minutes

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

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 happ...

7 months ago

1 hour 23 minutes

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

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 partn...

8 months ago

1 hour 8 minutes

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

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 rela...

8 months ago

1 hour 4 minutes

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

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 thriving...

8 months ago

1 hour 11 minutes

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

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 inti...

9 months ago

1 hour 17 minutes