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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 every kind of relationship.

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

💡 Events & Coaching

• Explore Non-Monogamy Through Astrology | Learn more & register.
• Boundaries Are Sexy: Building Trust in the Swinger Lifestyle | Join the event here.
• 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 | Sh

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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:
🌟 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:

Clip from
themercurialmillennial

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

💡 Events & Coaching

• Explore Non-Monogamy Through Astrology | Learn more & register.
• Boundaries Are Sexy: Building Trust in the Swinger Lifestyle | Join the event here.
• 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:@Thepineappleexpresspodcast
• TikTok: @Sexyswingerchicpineapple
• Facebook: Kiley Ann

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

💡 Events & Coaching

• Explore Non-Monogamy Through Astrology | Learn more & register.
• Boundaries Are Sexy: Building Trust in the Swinger Lifestyle | Join the event here.
• Coaching sessions: Book time with me.

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

🛍️ 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:@Thepineappleexpresspodcast
• TikTok: @Sexyswingerchicpineapple
• Facebook:

Support the show