Yeah, tumblr's hard to have one on one complicated conversations.

I completely agree. I've found actually that for the people I'm really really engaging with, inevitably the question of 'can we take this to email / skype / gchat' gets brought up, because people just want to get away from the Tumblr communication system to something that's private once more - or if the discussion was already private and happening through fanmail - just something where you can keep your sent mail responses. *g*