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PhilGoetz comments on More art, less stink: Taking the PU out of PUA - Less Wrong
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One of the first things you should learn in a Less Awkward class is that the name "Less Awkward" contains 2 words, both of which have negative associations, and thus is a poor choice of name.
(I like it, though.)
"Overcoming bias" has one negative word in conflict with one very strong positive word. "Less Wrong" is two negative words. But this is not a bad thing - Robin would like everyone to read Overcoming Bias, but I don't know if EY wants everyone to read LW. You could use an emotionally-unattractive name as a filter, to keep out less-rational people.
I've had people say they liked the name "Less Wrong". Your heuristic may be too simple.
The simple explanation seems to be that the two negatives cancel out, similar to "Not Meaningless" or "Without Shame". But maybe the explanation just seems simple/apparent to me because those two examples, and "Less Wrong", are emotionally attractive to me.