modern love

If you want to prompt someone to be authentic and playful and generative, you usually just need to ask them something where they have a rich experience to pull from but have never pulled an answer from that experience before . If you ask two or three increasingly detailed questions about something they tell you, you get there.

The type of person I’m assuming we’re looking for here is 1) someone that you will find fascinating to talk to after you’ve talked for 20,000 hours, 2) you feel comfortable with them talking through the hardest and most painful decisions you will face in your life, and 3) the conversation is wildly generative for both of you, in that it brings you ... See more

There is a trope in romance that when you meet the person you are supposed to be with, you can talk about anything. You can apparently inverse that too: if you talk about anything that pops into your mind, you can tell if you're supposed to be with the person by judging their reaction.

That is perhaps the most solid dating advice I have, by the way—show the inside of your head in public, so people can see if they would like to live in there.

I deduced that Johanna was probably an Alice. You can learn a lot by observing how people hang out with their friends. She laughed like a hyena, and they were obsessing over some obscure book, and they were so raw and cute. I’d never been as intrigued by a human being before.

And now I could sort of gesture at what I liked—kind people who are intellectually voracious and think it is cute that I obsess so hard about ideas that I fail all status games.

A relationship, like a movie or book, doesn’t fail when it comes to an end.