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


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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 deep truth that not all love stories are meant to last.

We talk about:

  • The grief of sudden endings in relationships
  • The courage it takes to let go when your nervous system still wants to hold on
  • What it means to begin the journey into solo polyamory not from empowerment — but from devastation
  • How friendship, tenderness, and presence can carry you through heartbreak

This 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

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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.
  • 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.
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The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & SwingingBy Kiley ‘Sexyswingerchic’

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