Do you want people to like you?
After two hours of monologue at lunch, I was reminded why the Harvard research is so simple: ask follow-up questions, and watch people light up.
Do you want people to like you?
The answer is very simple: ask questions.
I was recently on the East Coast for business and I had lunch with someone who, no joke, over the course of an almost two hour meal, went on a monologue about himself and asked me exactly zero questions.
At the end of the meal, as we were walking out of the restaurant, he remarked, "man, that was fun!"
It was. For him.
People feel good when you ask them questions, and I had done nothing but.
I'm partly to blame for this. I'm an inveterate question asker, and it can sometimes cause people to ramble. But this was next level.
The sad truth is that this isn't uncommon—not in my experience, and apparently not in others' either. I regularly hear from women whose dates launch into similar monologues. And that's on a first date, when you'd expect people to be at their most self-aware.
Harvard researchers quantified this effect: across multiple studies involving hundreds of conversations, people who asked more questions were consistently rated as more likable by their conversation partners. The effect was particularly strong for follow-up questions—those that build on what someone just shared.
So, my friends, here are a few of my favorite questions to ask people:
When someone shares something as a quick aside (that they got divorced, their business failed, they had their first kid—whatever), ask:
"What was that like for you?"
"How did that change things?"
"What led you to that decision?"
These always lead somewhere interesting.
Conversations should be a game of tennis, rallying back and forth. It's no fun to hit the ball against the wall by yourself.
Want better conversations? Follow the golden rule: in your next conversation, aim for a 50/50 split between sharing and asking. Notice how different it feels, and how much more your conversation partner lights up.
David Brooks wrote a book I loved that deep dives on this exact topic last year. It's called How To Know a Person and it's required reading for anyone who aspires to be an exceptional conversationalist.
Originally published in the I want you to hate me issue of Never Enough.

Andrew · Victoria · September 4, 2025
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