Inspired by this comment by Michael Vassar:

http://lesswrong.com/lw/1lw/fictional_evidence_vs_fictional_insight/1hls?context=1#comments

Is there any interest in an experimental Less Wrong literary fiction book club, specifically for the purpose of gaining insight? Or more specifically, so that together we can hash out exactly what insights are or are not available in particular works of fiction.

Michael Vassar suggests The Great Gatsby (I think, it was kind of written confusingly parallel with the names of authors but I don't think there was ever an author Gatsby) and I remember actually enjoying The Great Gatsby in high school. It's also a short novel so we could comfortably read it in a week or leisurely reread over the course of a month.

If it works, we can do one of Joyce's earlier works next, or whatever the club suggests. If we get good at this, a year from now we can do Ulysses.