The Unfogged Reading Group
MontaigneSomehow, my suggestion for The Prince--backed rather enthusiastically by some, I'll note!--got left off that list.
I think it's quite possible that, as Armsmasher suggested, Montaigne might not present as much intellectual meat as some people might expect from an Unfogged reading group. I don't actually see that as a downside, not if we read his essays as, to be crass, very smart personal blog posts from the past.
Paradise Lost could be a good option. It's fucking beautiful, presents all kinds of aesthetic and theological problems, and is handily divided into manageable segments. Personally, I can't really advocate this choice because Milton is too fraught in both my academic and personal life; I won't come to a reading group on PL without longstanding stakes, that much is for sure.
Burke. Well. I'd be very interested to see the Mineshaft debate Burke, but I'd want them to weigh the Reflections against the Enquiry and then to take the Hastings trial into account... Seriously, though, Burke is a fascinating and problematic character, much richer than the caricature that the third-generation NRO readers and writers make him out to be, but I might be humorless and emotionally involved in an Unfogged discussion of him.
Kirkegaard, I should read more of. Repetition in the abstract I'm not against--as long as it doesn't involve sacrificing Isaac over and over again. My fifteen year-old doubting believer self is still shuddering at the memory of reading Fear and Trembling, but maybe my adult self could approach a different text with a more open mind.
A reading project is worth trying--and it will work better if someone with mainpage authority feels able to crack ye olde whippe.