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Re:5 Reasons Why I Want Digg for Girls by cabalamat on Tuesday November 18, 2008 @02:02PM (#368565)
There's a web app (forget what it's called) that analyses the writing on a web page and decides whether a man or woman wrote it.

So something like this could be largely automated, start off with a collection of links then categorise them according to the text on the page and/or the writing of the person linking to them.

Re:5 Reasons Why I Want Digg for Girls by Alex3917 on Tuesday November 18, 2008 @02:53PM (#368625)
http://bookblog.net/gender/genie.php

It doesn't work well enough for what you're proposing though. The accuracy (according to their blog) is roughly 50%, which is no better than chance.