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

Season 3 Episode 15

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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:

  • Why anxious and avoidant partners are so often drawn to each other
  • The core fears each style brings into the relationship
  • What it actually takes to make this pairing work (and when to walk away)
  • How to shift from triggering each other to co-regulating each other
  • Practical tools for healing your attachment style — whether you’re dating, nesting, or exploring non-monogamy

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.

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