Reading all these comments to glean the knowledge within is not adverse to my goals, I'd just prefer to read a guide or the results of a formal discussion group if it exists. I couldn't find one. So, @XFrequentist: Is there a discussion group? If not, can we please start one?

If anyone else knows of relevant articles on LW, or another website or in a book, please link me stuff like this: http://lesswrong.com/lw/818/how_to_understand_people_better

My Goal: To start building one of these: http://lesswrong.com/lw/4ul/less_wrong_nyc_case_study_of_a_successful in Vanocuver, Canada.

That is to say, whether formal or informal, a community of rationalists and like-minded folk that is dynamic, diverse, proactive, and sex-balanced (the last quality is desired, but not as vital as the others).

Or, at least, getting to be friends with people who win at life and with whom I share values.

A friend and I realized that through networks like OKCupid (http://lesswrong.com/lw/2tw/love_and_rationality_less_wrongers_on_okcupid) or the Freethinkers Club at my university, we had access to more preferable samples of the population. The abilities to a) pick out these individuals and b) build effective social connections fuel my confidence and optimism that my plan might work.

However, I lack the skills. I can hold up a conversation, but I want to get better at making new friends quicker. I have never practiced PUA, NLP, social engineering, whatever. I don't believe this plan will involve much invoking of the Dark Arts. This letter is directed at those who wish to guide or learn along with me, or those who otherwise care. Feel free to leave any suggestions.