How do you introduce your friends to LessWrong?

Sometimes I'll start a new relationship or friendship, and as this person becomes close to me I'll want to talk about things like rationality and transhumanism and the Singularity. This hasn't ever gone badly, as these subjects are interesting to smart people. But I think I could introduce these ideas more effectively, with a better structure, to maximize the chance that those close to me might be as interested in these topics as I am (e.g. to the point of reading or participating in OB/LW, or donating to SIAI, or attending/founding rationalist groups). It might help to present the futurist ideas in increasing order of outrageousness as described in Yudkowsky1999's future shock levels. Has anyone else had experience with introducing new people to these strange ideas, who has any thoughts or tips on that?

Edit: for futurist topics, I've sometimes begun (in new relationships) by reading and discussing science fiction short stories, particularly those relating to alien minds or the Singularity.

For rationalist topics, I have no real plan. One girl really appreciated a discussion of the effect of social status on the persuasiveness of arguments; she later mentioned that she'd even told her mother about it. She also appreciated the concept of confirmation bias. She's started reading LessWrong, but she's not a native English speaker so it's going to be even more difficult than LessWrong already is.