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

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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and Relationships, we're diving headfirst into the world of relationship design, jealousy, and letting go of the outdated love scripts that no longer serve us.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 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 default

This 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.

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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
 🔓 How platforms like Ashley Madison are creating space for conversations around autonomy, desire, and honest exploration

This 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.

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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 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 casual

Whether 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!

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💡 Events & Coaching

• Coaching sessions: Book time with me.

💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom.
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🛍️ 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

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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 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. 💛

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Support the show

🎙️ The Pineapple Express Podcast
Subscribe 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.
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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 partner. This episode is full of laughs, heartfelt moments, and insights you won’t want to miss.

🎧 Tune in now and join the conversation!

🔗 Listen to Laura’s podcast and explore her work here.

Support the show

🎙️ The Pineapple Express Podcast
Subscribe 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.
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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 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.com

Get The Book Here https://www.swinginglifestylecoach.com/evenbetter

Follow Lauren On Social Media 

Instagram 

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Support the show

🎙️ The Pineapple Express Podcast
Subscribe 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.
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🛍️ 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.
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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 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 relationships

Justin 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 Media

Tiktok

Instagram 

Youtube 

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Support the show

🎙️ The Pineapple Express Podcast
Subscribe 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.
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🛍️ 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.
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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 intimate story of love, loss, and the transformative power of connection. https://queerloveproject.substack.com

This 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 in e

Support the show

🎙️ The Pineapple Express Podcast
Subscribe to my Substack for exclusive content: The Pineapple Express Substack.

💡 Events & Coaching

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💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom.
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🛍️ 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.
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In 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:
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• Explore Non-Monogamy Through Astrology | Learn more & register.
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Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off

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What 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 allyship
• How 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 Podcast
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• Explore Non-Monogamy Through Astrology |

Support the show

🎙️ The Pineapple Express Podcast
Subscribe 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.
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