What Dating Securely Has Taught Me

What Dating Securely Has Taught Me

In this personal episode, I take you behind the scenes of a recent dating experience that stirred up both growth and grief — and revealed just how far I’ve come on my attachment healing journey.

As someone who used to operate from a fearful avoidant (leaning anxious) attachment style, I now move through dating with much more self-trust, clarity, and compassion. But that doesn’t mean the old patterns don’t still surface — especially when connection, chemistry, and unmet needs collide.

I’ll walk you through how I navigated this dynamic from a secure place, the conversations I had, and ultimately, how I honored myself enough to walk away when alignment wasn’t there — even when it felt good in the moment.

If you’ve ever struggled to balance attraction with long-term compatibility, or felt pulled between your heart and your values, this episode is for you.

Takeaways include:

  • The difference between chemistry and compatibility

  • How to identify your unmet needs in real time

  • Why even "kind and available" people might not be the right fit

  • What it looks like to actually date from your secure self

  • How to exit with integrity when your paths don’t align

🎧 Plus: Only 2 more days to join the My Secure Self Membership for just $1 your first month! Get access to group coaching, monthly workshops, and tools to help you build secure, aligned relationships HERE.


Looking for 1:1 support, learn more about attachment coaching here.

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Episoder(153)

What God Taught Me About Secure Attachment

What God Taught Me About Secure Attachment

In this episode, I share what God taught me about secure attachment, why people will inevitably let us down, and how finding security in something greater than ourselves can transform the way we exper...

14 Jun 8min

Lessons From Dating an Avoidant and an Anxious Partner

Lessons From Dating an Avoidant and an Anxious Partner

In this episode, I share the lessons I've learned from dating both avoidant and anxious partners, how each relationship highlighted different areas for growth, and why the goal isn't hyper-independenc...

10 Jun 13min

Why Anxious + Avoidant Relationships Can Work

Why Anxious + Avoidant Relationships Can Work

Are anxious and avoidant relationships really doomed, or have we oversimplified the conversation?In this episode, Jessica explores why attachment styles alone don't determine relationship success, the...

5 Jun 17min

The Paradox of Avoidant Healing: Learning to Lean Into Intimacy Despite the Fear

The Paradox of Avoidant Healing: Learning to Lean Into Intimacy Despite the Fear

In this episode, we explore the paradox of avoidant healing and why intimacy can feel both deeply comforting and deeply threatening at the same time.We talk about:why avoidant attachers often push awa...

12 Mai 12min

Building Connection From Stability, Not Emotional Need

Building Connection From Stability, Not Emotional Need

Why do we crave connection so deeply… yet feel so unstable in relationships?In this episode, I dive into the difference between seeking love from emotional need versus a grounded, secure place within ...

21 Apr 15min

The Avoidant Experience: Love, Numbness & Inner Conflict With Bilnita Armstead

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In this episode, I sit down with Bilnita Armstead, a listener of the podcast, who shares her experience navigating a dismissive/fearful avoidant attachment style. We talk about how early relationship ...

29 Mar 36min

The Attachment Rollercoaster: How to Feel Without Losing Control

The Attachment Rollercoaster: How to Feel Without Losing Control

In this episode, we explore why love can feel like an emotional rollercoaster—full of intense highs and painful lows. You’ll learn how different attachment styles shape your reactions in relationships...

20 Mar 15min

Feeling Like You’re the Problem in an Anxious–Avoidant Relationship

Feeling Like You’re the Problem in an Anxious–Avoidant Relationship

In this episode, we unpack why anxious attachers often feel like they’re “too much” in relationships — especially when paired with avoidants. I break down how this dynamic creates a distorted sense of...

24 Feb 12min

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