> ## Content Index
> Fetch the complete content index at: https://www.datingdoneright.net/llms.txt
> Use this file to discover other available public pages before exploring further.

# Hillary: She never gave up. But I gave up trying to make her laugh
- URL: https://www.datingdoneright.net/hillary-she-never-gave-up-but-i-gave-up-trying-to-make-her-laugh/
- Published: 2026-09-21T00:51:34.000Z
- Updated: 2026-10-07T03:14:13.000Z
- Author: Alan Jacobson
- Tags: #Import 2026-10-10 01:12

She: *I’m confused. Are you being silly?*  
He: *Of course!*  
She: *Well, it’s annoying.*  
He: *But I was trying to be funny!*  
She: *Then try harder.*

That was Hillary in a nutshell. No wasted words, no sugarcoating. An ESTJ through and through — decisive, structured, and completely unimpressed by fluff. For her, humor had to earn its keep. If the joke didn’t land, it wasn’t “almost funny” — it was a distraction from the task at hand.

With Hillary, there was never ambiguity. You always knew where you stood, because she would tell you. Some people found her blunt. I found her refreshing. She wasn’t going to coddle me, and she wasn’t going to fake-laugh just to keep the peace. If I wanted her respect, I had to bring clarity, precision and substance.

ESTJs are often called “The Generals” of the Myers-Briggs world. They like order, systems, plans that work. Hillary embodied that. She could walk into a room, size up the mess and start issuing directions before anyone else had finished asking, “What should we do?”

But there was a misalignment between us. Humor — for me — isn’t just entertainment. It’s essential. It’s how I connect, how I share joy, how I make sense of the world. I don’t just love to laugh. I love to make *other* people laugh.

Hillary didn’t need that. For her, efficiency mattered more than amusement. If a joke fell flat, she wouldn’t cushion it with a polite chuckle. She would simply tell me it wasn’t funny and move on. Direct, decisive, no wasted energy.

That’s the ESTJ way. And for a while, it was bracing, even refreshing. But in the long run, it left me feeling unseen in a part of myself that matters most — the part that finds joy in making others smile.