Jacob’s Authentic Wanting

Dogfooding my own exercise: figuring out my dating desires and how I'm going to fulfill them.

Second Person isn’t about me. I’m not trying to be mysterious: my personal life is quite visible online, and I’ll talk more about my dating past and my marriage with Terese in later chapters. But most of my insights come from combining hundreds of theories about human nature I’ve read with hundreds of dating stories I’ve heard from friends and strangers, not from my biography.

The Second Person is the one you should be seeking. The one that last week’s exercise was designed to help you see with a bit more clarity. It’s not me. Probably.

But, as it happens, I am also seeking a romantic relationship.

It is said you shouldn’t take dating advice from married people since they’ve been out of the game for too long. And you obviously shouldn’t take dating advice from single people. Well - Terese and I are both married and looking to date other people because we love other people too.

Note: this isn’t a polyamory blog. I’m neither an activist nor a theorist of polyamory specifically. I happen to practice ethical non-monogamy, a fact that’s contingent on who Terese is as much as on my own disposition. And in any case, this blog isn’t about me.

Except for this post. This post is all about me.

Over the last several years I have delighted in a few extramarital relationships. They have all transitioned to platonic friendships for various reasons:

• She wanted to focus on finding a husband first.

• She moved to the Bay Area, took Ozempic, and became asexual.

• She was looking for work while I had a newborn baby, and we lost momentum.

• She was young and not looking for anything permanent.

• I convinced her that marriage is good and she decided to date for marriage again.

• She decided she only likes me in small doses.

Of course, I cherish these friendships as well. But I am also looking for a lover. And this means that I should introspect on what I’m looking for, identify who out there might be looking for me, and plan a strategy to bring the two of us together.

Below is my honest attempt at last week’s exercise and the feedback I would give myself based on it. Over the next several months, I’ll provide updates on what I’ve been doing and the results.

It’s time to practice my own dog food.

What Jacob Wants

The obvious thing to know about dating me is that I am happily married with two young daughters in New York City. This obviously disqualifying for any woman looking for a husband or live-in partner. But it’s a draw for any woman who wants to be around a family man: a woman in an open marriage, a single mom who wants to know I can be trusted around kids, or anyone who loves spending time with toddlers.

Toddlers are more fun to hang with than you think

I’m looking for a relationship to last indefinitely but without escalating anywhere, a relationship that isn’t instrumental but an end in itself. Perhaps the closest analogue is dating in high school — you know you won’t move in together, but you’re excited just to be with each other when you can. But also we have money now and can fly to the Bahamas for a weekend, so it should be more fun than high school. I think this would work best with a woman who already has the family/primary situation that she wants, but I’m willing to be surprised by a skilled solo-poly practitioner.

I’m horny on main, but I want sex that builds a deeper connection, not for it to be the sole focus of the relationship. I love women who match this vibe. If you’ve slept with everyone in your friend group because they’re wonderful people and you just like them, I think you’re a wonderful person and I already like you.

Not very important: I’m 37, 5’9” barefoot, slightly overweight but functionally fit, drink lightly and drug rarely, in good health, not so handsome that you’d date me for my looks nor so ugly that you’d reject me for them. None of this was very important to anyone who has dated me. Physical appearance isn’t very important to me either. My bar for attractiveness is easily cleared by 90%+ of my female friends and beyond that I mostly care about your soul. With that said, if you’re a dark-haired MILF who looks like you could be a former athlete then you’ve already got my pulse going.

Important:

• I find competence and ambition extremely attractive in a woman. It’s the hottest thing. It’s also the inspiration I need, having reached a point in my life where I’m fighting the temptation to coast. I want to date someone I admire.

• I spend a lot of my day reading, writing, or socializing in very cerebral communities. I crave more physical engagement, less System 2.

My dream partner is passionate about something that does not involve screens or text. Dancer, potter, energy healer, psychoanalyst, jungle explorer. I want you to be excited to take me with you to a world that’s new to me. I met an acro yogi last year who taught me in one session how to hold her flying with my arms stretched overhead. That wasn’t just a fun activity for me, but also a powerful demonstration of her physical skill — it was incredibly hot.

I once had a crush on a girl because she was incredibly astute at reading the emotional undercurrents of conversations. It seemed like magic to me. I am bad at many, many things, and if you are incredibly good at any of them I will find you magical.

One of my core skills is that I’m very entertaining. If you find yourself often bored by conversation, I’m your man. I can easily switch between riffing comedy bits to deep brainstorming to telling stories. You can just prompt me with “tell me something” and you’ll be at least mildly amused.

But: this means plenty of hot takes and forceful arguments. Going hard is simply more fun than soft platitudes. A girl once broke up with me because I argued against a room full of her medical school friends that we should have a market for kidneys. She found my assertiveness terrifying; I lost respect because she couldn’t summon one solid argument against selling kidneys. The most attractive thing a girl can do is beat me in a fair debate — you have to trust that I’m rooting for you to do so.

Orbital Velocity

There’s a key to deep compatibility with me that I would call sanely decoupling from social reality. It’s probably best explained with examples.

My wife has decided to stay home with the kids for several years instead of working even though we didn’t have a single stay-at-home mom among our friends (and we both think the “trad” movement is laughable). We simply figured this is what’s best for our family.

A lot of women say that the main reason they don’t do this is the lack of respect SAHMs get — from society at large and, as a consequence, from their husbands. But I spent years encouraging my wife to ignore social judgment when something important is at stake, and being very proud of her whenever she did. From small things like choosing a different drink when all her colleagues get an afternoon coffee to switching advisors halfway through grad school. I want people who can answer “what is good” instead of substituting the question “what is normal”.

My close friend told me once that an ex might leak nude photos of her online, which was only a problem because they were ugly and she didn’t want future boyfriends to see her like that. I immediately suggested that she do a boudoir photoshoot to have tasteful nudes to publish in case the unflattering ones leak. She found this suggestion delightful, in large part because I was the only person who didn’t react to this story with what were you thinking?!

My superpower is that What Would People Think has very little hold over me. Not because I’m an insane schizophrenic, but the opposite. I can be as normal as anyone at your mom’s Thanksgiving: clean shirt, wife, kids, corporate job. But I can choose to ignore what everyone else is doing when it suits me. This doesn’t require unusual bravery, it’s just natural to me. And it’s what I look for in others.

I admire anyone who holds their own frame. If you trust me with it, I will join you with no reservation. My best friends often get into what were you thinking?! trouble. I respect them for thinking, even if it’s troublesome, and they respect that I’m always there to help and not to judge.

I have a model of mainstream culture, or normiedom, as a planet with a powerful gravitational field. Anyone close to the surface falls inward under the pressure to be normal, and the only stable orbits are a good distance away from normality. Subcultures in orbit that appear completely incompatible when projected on the surface in fact get along surprisingly well: rationalists, hippies, political dissidents, sex workers, artists, hackers, etc.

From the surface, everyone in orbit looks like they’re in a cult. In truth, only some of us are.

I’m a rationalist online micro-celebrity with a dating blog. Realistically, anyone who dates me is at least in orbit. But what I really want is someone who flies freely between the orbital tribes and down to the surface, not beholden to any of them. Tell me a substantial critique of rationalism and you have my heart.

Free fliers are rare. Almost everyone thinks of themselves as a free thinker, even as they’re busy conforming and policing the norms of their own slightly-esoteric tribe. Of course, I am worried that the same is becoming true of me as well, especially as I spend more time in the comfort of the many my-type-of-esoteric friends I’ve made through the years. Only a beautiful woman fully committed to her own bit could send me flying freely again.

Agency

Where would I meet such a woman?

My best source of dates has been simply putting up a Google form on my old blog. It gets one or two submissions each year, but every single girl I’ve met through this was strongly compatible and we had a great time. Many are still close friends.

Back in 2021, four women in a row filled out my form and then found a (different) boyfriend within a month. This was probably mostly selection effect for openness to dating, but I would like to think that the questions on my form helped sharpen their focus. This was an inspiration for the “wanting” exercise I offered to subscribers.

But: the writer of a blog about lack of agency in dating can’t rely solely on passive inbound.

Dating apps suck, don’t showcase my strengths, give me no filtering power, and select for the opposite of the traits I’m looking for.

I mostly meet new people through online-first communities like LessWrong and my part of Twitter. Pros: smart weirdos are a given, there’s good variety, and many people already like me for my online writing. Cons: 80-20 gender ratio, Twitter has anti-polyamory vibes, and the in-person events skew much younger. I probably won’t meet my magic woman from an alien tribe at a Twitter meetup, but I could perhaps meet the person who will introduce us. I need to follow up with friends who have large networks and esoteric interests.

Let’s flip this: where is my excellent future lover meeting new people other than through her friends? Probably the gym or the studio or the jungle. Pros: I get to expand my comfort zone and just do those things. Cons: I’m no good at those things, have no social proof in these spaces, and no way to tell who may be non-monogamous and interested. Contra-cons: these sound like excuses to be a coward. Nothing bad will happen to me if I sign up for a dance class or pottery workshop and chat up anyone who seems alive and not on social-script autopilot.

Worst case: I get locally canceled and have to find a new gym; it wouldn’t be my first time.

Alright, wish me luck.