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mattnewport comments on Generalizing From One Example - Less Wrong
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This reminds me of some of the literature on fallibility of introspection. (If you have time only for one essay, read "The Unreliability of Naïve Introspection" and try the experiment with the playing card.)
As far as generalizing about an entire gender: It's extremely likely that I know a wildly unrepresentative sample of women, but why would you assume that the pickup artists don't? I imagine they meet vast numbers of women, but if they find them all at parties and clubs and bars, they're going to meet the kinds of women who go to parties and clubs and bars, not the ones who spend their time gardening at home or who go to all-women gyms to avoid being hit on or the ones who play D&D with their brothers in the basement. Even if their statements are accurate about that sort of woman (which I am not yet prepared to believe), that doesn't make them applicable to the entire gender, and the stereotype remains wildly inappropriate and offensive. If you're hearing things about men as a group that don't apply to you or any men you know, then chances are you're not hearing from someone who has a really ideal sample. If a female friend of mine complains about her sixth boyfriend in a row being a jerk, I don't conclude that men are jerks, I conclude that she has terrible taste.
They don't find them all at parties and clubs and bars. There's a whole raft of material on 'day game' - approaches in non-obvious places like bookshops, grocery stores, museums, the high street, etc. which are designed in part to reach women who are unlikely to be encountered in clubs and bars.
Thank you for the correction; that still won't reach women who don't get out much in places where they can be easily approached (my gardening/D&D in the basement/all-women gym examples still hold, for instance).
One of the reasons the seduction community has been a topic on less wrong is the application of rationality to success in everyday life. If there is any significant subset of desirable women who are not easily approached then someone in the seduction community will have tried to figure out a way to engineer an approach opportunity. If there are a lot of attractive single gardeners in the world then there is probably a blog somewhere that extols the virtues of garden centres as potentially fruitful pickup venues.
You can argue that the consensus judgement of the community as to what constitutes an attractive/desirable woman is flawed but to the extent that the 'hard to reach' women you describe are considered desirable, the likelihood is that someone will have tried to figure out how to reach them effectively.