An Old Guy With A Lot Of Time To Think; A Reflection On Regret, Youth, And The Words We Did Not Understand When We Said Them

There was a time…

Back when I was 17 or 18, I was dating a girl I really liked.

We had a lot of fun together. We spent time at a cabin in Warrenton, Virginia, and one really memorable night at a wild house in Arlington, Virginia.

When we walked in, there was a shopping cart hanging upside down from a tree near the front door. Next to it was a sign that said:

“What is art?”

Garbage was scattered all over the ground underneath it — the empty remnants of whatever had been in the cart before someone turned the cart itself into the sculpture.

I literally just realized tonight, 40 years later, that the “artist” had dumped out the contents and hung the cart as the statement. The cart was empty. The contents were scattered. Consumption had happened, and what was left was lying there underneath it.

It still makes me laugh.

What do you think the statement was?

That same night in Arlington, we snuggled up together in a sleeping bag like we had done in Warrenton. We were on the floor, wrapped up together, kissing, talking, and giggling before drifting off to sleep.

The ceiling was covered in glowing stars and moons.

It was just one of those special moments in my memory. It still is, and always will be. We laughed and giggled and fell asleep like that. I really thought we would spend years doing things like that.

One quiet evening later, we were at a bar in Old Town Alexandria, Virginia, just drinking a beer and relaxing. Things felt easy and comfortable, so I looked at her and said, completely sincerely:

“I love hanging out with you so much… you’re just like one of the guys.”

She looked at me and said, “We’re leaving.”

She wanted to go home right then. I dropped her off, and we never dated again.

I meant it as the highest possible compliment. To me, “one of the guys” meant comfortable, fun, zero drama — someone I could completely relax and be myself with.

I think I also assumed the time we had already spent together said what I felt. We had kissed. We had laughed. We had held each other. We had shared those quiet little moments that feel enormous when you are young. I thought she knew how much I cared.

But I was a dumb 18-year-old boy, and I had no idea how that sentence would land on a beautiful young woman who thought I cared about her as a young woman.

Looking back now, I can finally understand that what I meant as closeness may have sounded like distance. What I meant as comfort may have sounded like I was moving her out of the romantic place and into the buddy place. What I meant as trust may have sounded like rejection.

I knew what I meant.

I did not understand what she heard.

Honestly, I’ve thought about that moment a lot over the last 40 years.

Some things stick with you because you do not understand them when they happen. You only know the result. You know the silence. You know the look. You know the door closing. You know something broke, but you do not yet understand what you broke.

In a strange way, it feels a little like that shopping cart. I saw it all those years ago and laughed at how absurd it was, but I did not really understand the statement until much later. I saw the object, but I missed the meaning underneath it.

I think I did the same thing with that sentence.

I saw my intention.

I missed the meaning underneath it.

I did not understand then what I understand now. She did not want to hear that I had friend-zoned her or thought of her as just someone cool to hang out with.

She wanted to know that I cared a lot for her exactly for the young woman she was.

And I did.

I really did.

That is the lesson I wish I had understood sooner: words do not land inside our intentions. They land inside another person’s hopes, fears, tenderness, and need to be seen clearly.

When we are young, we often think sincerity is enough. But sincerity still has to learn how to speak.

And sometimes the moments where we feel safest with someone are the moments where we have to be most careful. Comfort can make us careless. Ease can make us assume the other person already knows what we mean. But the heart still listens closely, especially when it is young.

I’m sorry that what I said hurt you. I thought it would bring us closer together, and nothing could have been further from the truth.

I cared about you a lot. I cared about the time we spent together. I cared about those glowing stars on the ceiling, and the laughing, and the quiet, and the feeling that it was good just to be near you.

I am sorry I did not say it the right way.

I’m sorry.

— An old guy who’s had a lot of time to think about dumb things he said when he was young.

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