Cool Girl, Get Real… at 55

Getting Real (And Why It’s Harder Than It Looks)

I’m 55 years old and I love it. Midlife has stripped away most of the pretending. I know what matters to me now, and what doesn’t.

That’s how I became the cool girl I always wanted to be.

It’s not a performance. When you meet me, you’re getting the real deal. That part is easy, showing up as I am.

The harder part is that sometimes the past shows up anyway. In unexpected places. Like a hotel room in Mexico. I went there to chill. And it was chill… until it wasn’t.

From Cool Girl to Hot Mess

I’m in a relationship that matters to me. One where both of us are trying. We care, share goodwill, and have a real desire to get it right. Which, it turns out, is exactly the kind of relationship that asks you to stop relying on your old strengths and develop new ones.

The thing I’m learning isn’t how to communicate better.
It’s how to ask for what I need while I still need it.

That sounds small. It’s not.

In Mexico, we had a moment, nothing dramatic, no raised voices, no villainy. I was talking about something from my childhood. One of those memories that still carries weight, even though I’ve mulled it over many times. He listened. He was kind. And then he said something like, “I can’t imagine what that must have been like.”

Which was true.
And empathetic.
And somehow… not enough.

I answered him and explained a little more. And then the conversation just sort of stopped there, hovering politely above us. No follow-up. No curiosity. No sense that he wanted to step closer to it with me.

What surprised me wasn’t his response.

It was my own.

I didn’t say anything about what I was feeling or what I needed in that moment. I didn’t ask him to get curious or imaginative. I translated myself, wrapped it up neatly, and carried on.

That’s an old skill of mine.
It’s also what cool girls do. We smooth over the rough patches.

I learned that competence early. My childhood trained me to be self-sufficient, emotionally fluent, and very good at handling things on my own. I don’t melt down easily. I don’t demand. I don’t reach out mid-fall.

That skill has served me well in life.

It’s just not intimacy.

And it got in the way here. Not because I fell apart, but because my old competence stopped working.

What I’m learning now, slowly and imperfectly, is that partnership requires a different muscle. One that activates before I retreat into my own head.

The moment I feel that familiar tightening, the sense that I’m alone when I want connection, that’s the moment I need to speak. Not later, once I’ve processed it. Not once I’ve made it reasonable.

Right then.

The sentence I’m practicing is almost embarrassingly simple:

“Can you ask me a couple questions about this?”

That’s it.

No indictment. No backstory. No emotional PowerPoint presentation. Just an invitation.

This has been harder than I expected. Not because he’s unwilling, but because it goes against a lifetime of cool girl conditioning. When you’re used to being the strong one, asking for engagement can feel like asking for too much. When you’ve learned to handle things alone, requesting curiosity feels strangely vulnerable.

I can see now that instead of asking for curiosity, I often tried to manufacture it, asking a barrage of questions, hoping the other person would feel how good it is to be interesting.

Turns out not everybody experiences that as connection.

My modeling of curiosity wasn’t landing with my romantic partners. They ran for the foxholes rather than face my well-intentioned bombardment.

Meanwhile, I thought I was modeling empathy. What’s more empathetic than wanting to understand deeply?

Cool Girls Get Engaged

I’m coming to understand a crucial distinction: empathy is not the same as engagement.

Someone can care deeply and still not know how to step into terrain they’ve never walked. Someone can be well-intentioned and still stop short of curiosity. That doesn’t make them cruel. It makes them human.

And it makes the relationship a place where skills, not just feelings, matter. Namely, my ability to recognize what I need and ask for it in the moment.

What gives me hope is that this isn’t a story about someone refusing to meet me. It’s a story about me learning how to name what I need in order to be met where I am.

I’m working on naming the moment instead of managing it away. On choosing partnership over personal strength and endurance.

I’m not finished learning this. I’ll still miss the moment sometimes. I’ll still default to translating myself when I could simply ask.

But I’m practicing.

And if you’re someone who grew up being capable, who learned to hold complexity alone, who prides yourself on not needing much, this might sound familiar.

Sometimes growth doesn’t look like becoming stronger.
It looks like interrupting competence long enough to say:

Stay with me here.

Scroll to Top