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5/14/2026 0 Comments

Hurts, Hopes, And Healings

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I had dinner with my friend Solomon last night. I found myself talking about a relationship from my past that still haunts me - a topic we’d touched on before during one of our Olive Garden chats. He already knew the circumstances; he knew the lingering regrets and the unrelenting sharp edges of the pain.

In the middle of the conversation, without a hint of hesitation, he asked: "Have you ever apologized to her?"

Two things struck me about that question. First, I’d been wrestling with that exact thought lately, and it felt as if he could see into the center of my internal struggle. Second, as I drove home, I thought about the ease with which he asked it.

"Have you ever apologized?" can easily sound like an attack. This didn't. It sounded like care.

Solomon and I mused last night that we’ve been meeting for these dinners for six years. At our first meal, we would have been hesitant to even mention our hurts, hopes, or healings. These days, those topics are the main course. In fact, I think we keep showing up for the possibility of those conversations (and for him to pressure - I mean, encourage - me to return to ultra-running).

Driving home, I wondered if this is the true measure of a meaningful relationship: the capacity to ask, without hesitation, "What are your hurts, your hopes, and your healings?"

I’m not talking about superficial hurts, like a back that aches in the morning, but the deep wounds that feel like they are on a mission to haunt a life forever. Not the superficial hopes, like wanting clear skies for a birthday party, but starting your own business hopes that terrify you. And not the superficial healings of visible injuries, but the quiet, internal restoration required to become the whole person you've longed to become.

If you want to measure the depth of a connection, ask yourself: How comfortable am I asking these questions? What are your deepest hopes, hurts, and healings? And just as importantly: How safe do I feel answering them?

I look back at my failed marriage and realize that at its heart was an inability - perhaps even a lack of interest - to ask these questions of one another. That is no small void. The "insides" of us are largely constructed of these three things; our minds and bodies are almost always occupied by at least one of them.

When Solomon and I started out, we talked about the world around us. We still do, but more and more, we talk a lot about the worlds inside us.

We all need "Inside World" people. Without them, we only have connections built on "Outside Worlds" that serve to hide who we really are. That isn't a connection at all. It's a barrier - it does a much better job of keeping two people apart than bringing them together.

Part of my own journey has been learning to share my inside world. These Olive Garden chats have played no small part in that. Our hurts, hopes, and healings are vital parts of who we are, but they were never meant to be carried alone.

They are meant to be the magnets that draw us toward one another - and ultimately the glue that keeps us there.
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    Robert "Keith" Cartwright

    I am a friend of God, a dad, a runner who never wins, but is always searching for beauty in the race.

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