In general I approach the problem of orange pilling someone as explaining fiat money, not bitcoin. I mean the barrier to understanding bitcoin is understanding money in general first. Since almost everybody has some issue with money that they cannot express correctly, I tend to help them do just that. So I don't use bitcoin as a conversation starter, I use money.
As for books, I have high hopes that Lyn Alden's new book, Broken Money, could be just the ticket, as it doesn't have bitcoin on the cover. (I haven't read it yet). :)