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BlackHumor comments on Transsexuals and otherkin - Less Wrong
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Take 1000 typical males, 1000 typical females, 1000 transexual males, 1000 transexual females, 1000 typical males tasked to pretend they are female and 1000 typical females tasked to pretend they are male. Then you let each of these talk anonymously over text chat with 100 randomly chosen of the others and assign probabilities of them being in each of these categories. Then you run statistics to determine the general ability to distinguish each of the categories from each of the others.
I'd expect that {typical!male, trans!male, and troll!male} would be almost complexity distinguishable from {typical!female, trans!female, and troll!female}, that it often would be possible to distinguish typical!X from trans!X, but that trans!X are very rarely mistaken for troll!X... this matrix of possibilities is kinda huge so I wont bother filling it out more unless you specifically request it since you probably get my point by now.
I suspect that you're vastly underestimating how similar people are.
My guess is that people's guesses will be essentially random, except possibly for the trolls (because they're trying, and so will be portraying caricatures of the opposite sex instead of actual people).
I know that I personally have never so far been able to tell men from women over a purely text channel without having been told explicitly, which I assume would be off limits. Though now I think of it that's not entirely true; I would guess from lesswrong demographics that you, Armok, are male. ('course, if you happened to be female that would prove my point nicely.)
I have. There are text analyzers which give statistical likelihoods on the gender of the author of a given piece of writing. They generally give fairly wide confidence margins, but their algorithms are pretty simple and they don't apply a lot of heuristics that humans can use. Even the best gender analyzer can only guess with limited confidence, but a person's writing style offers considerably more than zero information about their gender.
It wouldn't be off limits, and you're supposed to specifically be fishing for their gender and they're supposed to be cooperative except for the trolls.