Note: I am testing two versions of my new post on rationality and romance.

Please upvote, downvote, or non-vote the below post as you normally would if you saw it on the front page (not the discussion section), but do not vote on the other version. Also, if your last name begins with l–z, please read and vote on this post first. If your last name begins with a–k, please stop reading and read this version instead.

Rationality Lessons from Romance

Years ago, my first girlfriend (let's call her 'Alice') ran into her ex-boyfriend at a coffee shop. They traded anecdotes, felt connected, a spark of intimacy...

And then she left the coffee shop, quickly.

She told me later: "You have my heart now, Luke."

I felt proud, but even Luke₂₀₀₅ also felt a twinge of "the universe is suboptimal," because she hadn't been able to engage that connection any further. The cultural scripts defining our relationship said that only one man owned her heart. But surely that wasn't optimal for producing utilons?

And thus began my journey toward rational romance — not at that exact moment, but with a series of realizations like that about monogamy, about the assumed progression toward marriage, about the ownership of another person's sexuality, etc. I began to explicitly notice the cultural scripts and see that they might not be optimal for me.

Rationality Skill: Notice when things are suboptimal. Think of ways to optimize them.

Gather data

But I didn't know how to optimize. I needed data. How did relationships work? How did women work? How did attraction work? I decided to become a social psychology nerd. The value of information was high. I began to spend less time with Alice so I could spend more time studying.

Rationality Skill: Respond to the value of information. Don't keep running in what is probably the wrong direction just because you've got momentum. Stop a moment, and invest some energy in figuring out which direction to go.

Sanity-check yourself

Before long, I noticed that Alice was always pushing me to spend more time with her, and I was always pushing to spend more time studying psychology. I was unhappy, and I knew I could one day attract better mates if I had time to acquire the skills that other men had; men who were "good with women."

So I broke up with Alice over a long conversation that included an hour-long primer on evolutionary psychology in which I explained how natural selection had built me to be attracted to certain features that she lacked. I thought she would appreciate this because she had previously expressed admiration for detailed honesty. Later, I realized how hard it is to think of a more damaging way to break up with someone.

She asked that I kindly never speak to her again. I can't blame her.

Rationality Skill: Know your fields of incompetence. Sanity-check yourself by asking others for advice, or by Googling "how to break up with your girlfriend nicely" or "how to not die on a motorcycle" or whatever.

Study

During the next couple years, I spent no time in (what would have been) sub-par relationships, and instead invested that time optimizing for better relationships in the future. Which meant I was celibate. But learning.

Alas, neither Intimate Relationships nor Handbook of Relationship Initiation existed at the time, but I still learned quite a bit from books like The Red Queen and The Moral Animal. I experienced a long series of 'Aha!' moments, like:

"Aha! It's not that women prefer jerks to nice guys, but they prefer confident, ambitious men to pushovers."
"Aha! Body language and fashion matter because they communicate large packets of information about me at light speed, and are harder to fake than words."
"Aha! Women are attracted to men who make them feel certain ways and have positive subjective experiences. That's why they like funny guys, for example!"

Within a few months, I had more dating-relevant head knowledge than any guy I knew.

Rationalist Skill: Scholarship. Especially if you can do it efficiently, scholarship is a quick and cheap way to level up.

Avoid rationalization

Scholarship was comfortable, so I stayed in scholar mode for too long. I hit diminishing returns in what books could teach me. Every book on dating skills told me to go talk to women, but I thought I needed a completed decision tree first: What if she does this? What if she says that? I won't know what to do if I don't have a plan! I should read 10 more books, so I know how to handle every contingency.

The dating books told me I would think that, but I told myself I was unusually analytical, and could actually benefit from completing the decision tree in advance of actually talking to women.

The dating books told me I would think that, too, and that it was just a rationalization. Really, I was just nervous about the blows that newbie mistakes (and subsequent rejections) would lay upon my ego.

Rationalist Skill: Notice rationalizations and defeat them: Consider the cost of time and trust happening as a result of rationalizing. Consider what opportunities you are missing if you don't just realize you're wrong right now.

Use science

The dating books told me to swallow my fear and talk to women. I couldn't swallow my fear, so I tried E&J brandy instead. That worked.

So I went out and talked to women, mostly at coffee shops or on the street. I learned all kinds of interesting details I hadn't learned in the books:

Politics, religion, math, and programming are basically never the right subject matter when flirting.
Keep up the emotional momentum. Don't stay in the same stage of the conversation (rapport, storytelling, self-disclosure, etc.) for very long.
Almost every gesture or line is improved by adding a big smile.
'Hi. I've gotta run, but I think you're cute so we should grab a coffee sometime" totally works when the girl is already attracted because my body language, fashion, and other signals have been optimized.
People rarely notice an abrupt change of subject if you say "Yeah, it's just like when..." and then say something completely unrelated.

After a while, I could talk to girls even without the brandy. And a little after that, I scored my first one-night stand.

I was surprised by how much I didn't enjoy casual flings. I wasn't very engaged when I didn't know and didn't have much in common with the girl in my bed. But I kept having casual flings, mostly for their educational value. As research projects go, I guess they weren't too bad.

Rationalist Skill: Use empiricism and do-it-yourself science. Just try things. No, seriously.

Try harder

By this time my misgivings about the idea of owning another's sexuality had grown into a full-blown endorsement of polyamory. I needed to deprogram my sexual jealousy, which sounded daunting. Sexual jealousy was hard-wired into me by evolution, right?

It turned out to be easier than I had predicted. Tactics that helped me destroy my capacity for sexual jealousy include:

Whenever I noticed sexual jealousy in myself, I brought to mind my moral objections to the idea of owning another's sexuality.
I thought in terms of sexual abundance, not sexual scarcity. When I realized there were thousands of other nearby women I could date, I didn't need to be so needy for any particular girl.
Mentally, I continually associated 'jealousy' with 'immaturity' and 'neediness' and other concepts that have negative affect for me.

This lack of sexual jealousy came in handy when I grew a mutual attraction with a polyamorous girl who was already dating two of my friends.

Rationality Skill: Have a sense that more is possible. Know that we haven't yet reached the limits of self-modification. Try things. Let your map of what is possible be constrained by evidence, not popular opinion.

Finale

I now enjoy higher-quality relationships — sexual and non-sexual — of a kind that wouldn't be possible with the social skills of Luke₂₀₀₅. I went for years without a partner I cared about, but that's okay because the whole journey was planted with frequent rewards: the thrill of figuring something out, the thrill of seeing people respond to me in a new way, the thrill of seeing myself looking better in the mirror each month.

There might have been a learning curve, but by golly, at the end of all that DIY science and rationality training and scholarship I'm actually seeing an awesome poly girl, I'm free to take up other relationships when I want, I know fashion well enough to teach it at rationality camps, I can build rapport with almost anyone, my hair looks great and I'm happy.