Dating for Nerds

In the spirit of sharing strong opinions, I figured I’d write a post about relationships. A note to self kinda thing.

I’ll try and keep it short. This is mostly for nerds in their 30s and 40s.

“Hell yeah!, or no.” — Derek Sivers

“Smart, interesting, not-cooked. Pick two.” — Paul.

Step 1: Get comfortable being single. Dating is a huge waste of time and energy.
Step 2: If you find somebody really cool (smart and interesting), jump in and love them like crazy. Do this a few times. Understand the mechanics of infatuation.
Step 3: Understand optimal stopping theory.

Here are the key things that you need to look for…

  • Culture, ideas about the world, background, language etc.
  • Career, is this person happy in what they are doing, building, learning.
  • Locality, live and work in the same area and plan to stay in the same city/town for a while.
  • Mental health, tricky one, but get a feel for it.
  • Religion, kinda boring, but could be a show stopper.
  • Kids, yes/no/maybe.
  • Dog/cat person. I suspect it’s a very useful personality indicator.
  • Burner, yes/no, I’ve found this to be an interesting aggregate for a number of metrics.
  • Health and fitness, not too much, not too little.
  • How busy they are.
  • Can’t hurt to know their MBTI personality type.

Have a chat about the above in the first three weeks of finding somebody that passes the optimal stopping filter (step 3). Be honest.

Good first date question, ask person to complete the following: “If you really knew me, you would know…?” and “What would your friends say is your superpower?”

“Work ethic, taste, integrity, curiosity. The rest you can learn.” —

Generally a good spec: Smart, calm, healthy, interesting, resourceful. In that order. Calm is a superpower.

Remember: “Needing nothing, attracts everything.” Bonus points, read/listen to the book Models by Mark Manson.


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