I have two sisters aged 17 and 14, and mom and dad aged 40-something. I'm 22, male. We're all white and Latvian. I translated the articles as I read them.
I read Never Leave Your Room to the oldest sister and she expressed great interest in it.
I read Cached Selves to them all. When I got to the part about Greenskyers the older sister asserted "the sky is green" for fun. Later in the conversation I asked her, "Is the sky blue?", and her answer was "No. I mean, yes! Gah!" They all found real life examples of this quickly - it turns out this is how the older sister schmoozes money and stuff out of dad ("Can I have this discount cereal?" followed by "Can I have this expensive yogurt to go with my cereal?").
I started reading The Apologist and the Revolutionary to them but halfway through the article they asked "what's the practical application for us?", and I realized that I couldn't answer that question - it's just a piece of trivia. So I moved on.
I tried reading about near-far thing to them, but couldn't find a single good article that describes it concisely. Thus I stumbled around, and failed to convey the idea properly.
In the end I asked whether they'd like to hear similar stuff in the future, and the reply was an unanimous yes. I asked them why, in their opinion, haven't they found this stuff by themselves and the reason seems to be that they have have no paths that lead to rationality stuff in their lives. Indeed, I found OB through Dresden Codak, which I found through Minus, which I found through some other webcomic forum. Nobody in my family reads webcomics not to mention frequenting their forums.
The takeaway, I think, is this: We must establish non-geeky paths to rationality. Go and tell people how to not be suckers. Start with people who would listen to you. You don't have to advertise LW - just be +5 informative. Rationality stuff must enter the mass media: radio, TV, newspapers. If you are in a position to make that happen, act!
I would also like to see more articles like this one on LW - go, do something, report back.