Hi guys. : )

Those of you who are single or divorced…have you ever looked back at your dating history and thought, “Wait… how did I end up with the same person again?”—just with a different haircut and a different job—you’re not crazy.

You’re probably dealing with attachment patterns. Oh the joy.

On a recent episode of Free & Failing, I sat down with renowned relationship therapist and SAFE author Jessica Baum to talk about why so many of us repeat the same relationship dynamics over and over again… especially after divorce.

And if you’re thinking, “Oh great, another conversation telling me I’m the problem,” don’t worry. This one is actually hopeful.

Also slightly therapy-adjacent in the best possible way.

Why This Book Made Me Cry (In a Good Way)

Before we even got into the interview, I had a bit of a fangirl moment.

A few months after my divorce, I didn’t just read Jessica’s book. I “did” Anxiously Attached, and allllll its prompts. Breathing exercises. Completing “homework” like collecting pictures from childhood and feeling all the feelings that come to mind, etc.  I’m not sure a single page went unstained from tears.

Like a lot of people, I had taken the online quizzes and knew I probably leaned toward the anxiously attached side of the spectrum. But knowing a label and actually understanding your patterns are two very different things.

Jessica’s work helped put words to all the toxic, unhealthy, frankly traumatic experiences I’ve had in relationships but couldn’t quite articulate.

Why certain people feel intoxicatingly magnetic.
Why rejection can feel like emotional freefall.
Why dating after heartbreak sometimes reopens wounds you thought were healed.

Spoiler: it’s not random.

Your Attachment Style Is Running the Show

One of the biggest takeaways from our conversation is that our earliest emotional experiences shape how we show up in love as adults.

That doesn’t mean your childhood determines your destiny forever. But it does mean our nervous systems learn certain patterns early on.

For example:

• Some people chase closeness and reassurance.

• Some people instinctively pull away when things get too intimate.

• Some people swing between both.

These patterns aren’t character flaws. They’re adaptations.

Your brain essentially learned, “This is how relationships work.”

The problem is that the patterns that helped us survive emotionally when we were younger don’t always create healthy adult relationships.

Why Dating Can Trigger Old Wounds

If you’ve ever gone on a date and thought you were doing great emotionally… until suddenly you weren’t… attachment theory might explain why.

Dating can activate implicit memory—which is just a fancy way of saying your body remembers emotional experiences even when your conscious mind doesn’t.

So when someone pulls away, takes longer to text back, or seems uncertain, it can unconsciously tap into deeper fears of abandonment or rejection.

Your brain isn’t just reacting to the person in front of you.

It’s reacting to an entire emotional history.

Fun, right?

But here’s the hopeful part: awareness changes everything.

You Can Change Your Relationship Patterns

One of the most encouraging parts of Jessica’s work is her belief that attachment styles are not life sentences.

They’re patterns that can shift.

Healing often starts with recognizing your attachment style and the emotional triggers that come with it. From there, you can begin building what Jessica calls secure relationships—connections where trust, emotional safety, and communication replace anxiety and chaos.

This doesn’t happen overnight. (Wouldn’t that be nice?)

But small shifts matter:

• Slowing down emotionally in early dating

• Choosing partners who have the capacity for emotional presence

• Building trust gradually instead of diving headfirst into intensity

Basically: fewer fireworks, more foundation.

Which may sound less exciting at first—but tends to lead to relationships that don’t implode six months later.

Finding “Secure Anchors”

Another concept Jessica talked about that I love is the idea of secure anchors.

These are people in your life—friends, mentors, partners—who have the emotional capacity to be steady and supportive without trying to fix you.

Secure anchors help regulate your nervous system. They model healthy emotional dynamics. And they create a sense of safety that allows real healing to happen.

Translation: you don’t have to do this work alone.

In fact, we usually can’t.

Dating After Divorce (But Smarter This Time)

A lot of listeners of Free & Failing are navigating dating after divorce. Which can feel like being dropped back into the jungle with no map and questionable Wi-Fi.

Attachment work doesn’t magically eliminate heartbreak or awkward first dates.

But it does help you approach relationships differently.

More self-aware.
More intentional.
And a lot less likely to ignore red flags because someone is charming and emotionally unavailable.

(We’ve all been there.)

The Goal Isn’t Perfect Love

If there’s one thing I took away from this conversation, it’s this:

The goal isn’t to become a perfectly secure human who never gets triggered and always chooses flawlessly healthy partners.

That person does not exist.

The goal is to understand yourself well enough that you can interrupt old patterns and choose differently.

And maybe—just maybe—stop dating the same person in a different outfit.

If you want to dive deeper into this conversation, you can listen to my full interview with Jessica Baum on the Free & Failing podcast.

Trust me—it might just change the way you see your entire dating history. xo