For any future biographers eagerly following this thread to learn of Alicorn's relationship history, we got back together on July 30th at 9:30 PM PDT, when her plane landed.
For any present day folk (especially those in/around Berkeley) eagerly following this thread in order to learn when/whether it is appropriate to hit on Alicorn: go for it =)
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For the record, I am not myself a member of the seduction community, and in fact got the first draft of this post badly wrong as a result.
My feelings on the question of goals are best stated here.
All that being said: let us say that I am single, and that all I do is sit in my room and write posts on Less Wrong. And let us say that I have a term in my utility function for being in a happy relationship (which I emphatically do). The one would give me excellent advice by telling me to walk outside my bedroom from time to time, rather than writing for an audience which is a) mostly male, and b) geographically far-flung.
So, in this extreme case, we see that there definitely exists non-manipulative romantic optimization. The only question left to ask is how much more optimization we can get before we run into the scuzzy manipulative stuff. I think you and I would agree that that border should be drawn fairly conservatively. Nonetheless, behind that border there probably exists an art well worth learning for those of us who are alone, and wishing we weren't.
...amusingly enough, "sit in my room and write posts on Less Wrong" turned out to be a pretty good move, in retrospect.