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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 break down:
This episode blends attachment theory, , and Jack’s signature polarity framework to give you actionable steps you can use in your own relationships — no matter your style.
📌 Find Jack Online:
If you’ve ever wondered whether anxious and avoidant partners can build something lasting — or if you’ve lived the highs and lows of this dance yourself — this is the episode you don’t want to miss.
Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off
https://www.thenonmonogamycardgame.com/products/the-game
Support the show
🎙️ The Pineapple Express Podcast
Subscribe to my Substack for exclusive content: The Pineapple Express Substack.
💡 Events & Coaching
💜 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
By Kiley ‘Sexyswingerchic’4.3
5353 ratings
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 break down:
This episode blends attachment theory, , and Jack’s signature polarity framework to give you actionable steps you can use in your own relationships — no matter your style.
📌 Find Jack Online:
If you’ve ever wondered whether anxious and avoidant partners can build something lasting — or if you’ve lived the highs and lows of this dance yourself — this is the episode you don’t want to miss.
Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off
https://www.thenonmonogamycardgame.com/products/the-game
Support the show
🎙️ The Pineapple Express Podcast
Subscribe to my Substack for exclusive content: The Pineapple Express Substack.
💡 Events & Coaching
💜 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

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