I consider myself like a Johnny Appleseed of these ideas. My blog is where I’m most open about my views, but with friends/co-workers/family, I just spread little seeds. Sometimes with people the ground isn’t fertile or properly tilled, and the seeds won’t take. Think about Hurricane Katrina’s aftermath (as reported): that did more to “till the soil” for pro-self-defense gun ownership arguments than you’d think. The seeds planted during that time for me with some of my friends yielded tangible results.

Rather than saying “I have 25000 rounds for my main battle rifle and my house has razor wire, a minefield, and snarling hounds around it” after Katrina, “boy it’s nice to have a shotgun or 45 sitting around” should suffice.

Then that person gets home and has to think: man, if that (again, as reported) happened in my area, what would I do?

I usually avoid saying “the end is neigh” in these types of conversations as well.

For the first type, I’d also strongly suggest keeping them away from the hysterical pro-gunners (i.e., that crazy talk about revolution you mentioned in the next paragraph). It’s going to make a very big difference to the on-the-fence person if their first experience is someone like Sebastian-PGP or someone like straightarrow. First impressions matter, and PR matters!

For the second type, your analysis is essentially spot on. Going all apeshit (like many commenters have done to, say, KTK on our blog) is exactly counterproductive. I’d also recommend that, while sticking to calmly citing facts, you try to avoid getting into Kevin Baker-esque verbosity. (Sorry, KB…)