Hillary: She never gave up. But I gave up trying to make her laugh

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.