So I have the typical of introvert/nerd problem of being shy about meeting people one-on-one, because I'm afraid of not being able to come up with anything to say and lots of awkwardness resulting. (Might have something to do with why I've typically tended to date talkative people...)
Now I'm pretty sure that there must exist some excellent book or guide or blog post series or whatever that's aimed at teaching people how to actually be a good conversationalist. I just haven't found it. Recommendations?
Offline practice: make a habit of writing down good questions you could have asked in a conversation you recently had. Reward yourself for thinking of questions, regardless of how slow you are at generating them. (H/T Dan of Charisma Tips, which has other good tips scattered around that blog).
If it's worth saying, but not worth its own post (even in Discussion), then it goes here.