#59: The optimization question.

Why the optimization over optionality distinction matters in dating.

I wrote this after having a rather frank conversation with a close friend. He encouraged me to share our conversation here, and I said, what the hell—why not?

There’s an idiom I keep seeing in different manifestations on Twitter. It’s always something like this: “We worship at the altar of choice.”

I’ve questioned this in the past because I don’t think it’s actually true. I don’t think “keeping your options open” has ever really been about options, so much as maxing out your true potential and not having a good sense of where that boundary is. At some point, there are diminishing returns, and a lot of people don’t realize that.

For the upwardly mobile dice rollers, the upper middle class, and those who lie just a little bit beyond that, there’s this never-ending quest to find the best of anything. The best apartment, the best city, the best social circle, it goes without saying the best romantic partner.

One counter-argument I’ve seen is that you see people just racking up experiences, with no longterm understanding of how those experiences are going to impact them. This is sometimes true. I’m certainly guilty of it myself!

But that said, “Doing something for the story,” is more often than not a post hoc rationalization for why an uncomfortable situation is okay. You didn’t think XYZ would break your heart/pressure you into sex/coerce you into doing whatever thing you’re retrospectively not O.K. with, but here you are. You did it for the story.

Optionality suggests people are seeking these experiences out specifically and determinedly, experience for experience’s sake. I might want chocolate cake. I might want vanilla cake. Again, sure, some people are, but most aren’t. It’s not about not knowing if you want X or Y. It’s about wanting whichever between X or Y is the best, and not knowing the answer to that question.

An example I like to give is cities. Nobody is choosing between Miami, Austin, San Francisco, and some farm in Maui. It’s not like people aren’t sure if they want to live on a farm as bohemians, or as high six figure earners in a trendy city. The reason they’ve narrowed down the list to Miami, Austin, and San Francisco is because those are the three places they’re most likely to find the best of whatever it is they’re looking for.

Keeping your options open is about not accepting your personal limitations, not an inability to pick a lane. There is still time become Jeff Bezos, even at thirty-five.

A long way of saying: “I want to taste every fruit,” and “I want to taste the most delicious fruit there is, even if it means I forego any fruit at all” are two very different states of being.

You see this quite a bit with women who are dating in San Francisco.

Here is something everyone knows, but nobody wants to say out loud:

San Francisco is one of the easiest places to date in the country, if you’re an even okay looking woman under the age of 30, who wants a standard-issue, heterosexual monogamous relationship. I literally cannot think of another place in the country with this many nice, employed, and crucially, single-and-ready-for-a-girlfriend men.

There are a lot of gold/status diggers in the Bay Area, they just don’t look like the ones you might find in Miami or New York. They don’t have any of the signals of a gold digger.

They’re often very likable. They’re not flashy. They’re single.

They are single because they’re holding out for a high net worth or otherwise high status man.

It’s not that these women are struggling to find someone. They’re struggling to find a man who’s sufficiently high status or high net worth or both. Maybe they dated a guy like this in their early twenties and it didn’t work out. But a lot of women’s M.O. is to lock down status, especially in a city with such a high capita of multi-millionaires and billionaires.

The women who’ve tasted this fruit once a sense of entitlement that that’s the lifestyle they deserve and they won’t settle for anything less. They carry the same airs as people who won’t deign to work at FAANG because it’s beneath them, yet may spend months or years unemployed. And look, I get it, but let’s not kid ourselves that this isn’t what’s going on here.

That’s why there are a lot of nice girls who are “mysteriously” single.

There are plenty of edge cases, and I’m not exactly suggesting every single woman here is holding out for her very own Patrick Collison.

I have tons of friends who just haven’t clicked with someone or struggle for other reasons, and that’s real.

But this is a type, and you know it when you see it.