Whenever my gf owes me money I keep telling her « i don’t accept EUR ». It was annoying her at first but know she really likes the game and buys BTC regularly so she’s ready!
The above aside, when I orange pill someone, I try to make it real easy on them. Advise they install Relai App (very easy onboarding, relatively low fees & light KYC), explain how a BTC wallet works and stress that « no you don’t have to buy a full bitcoin at once ». At this point, to illustrate, I send them their first sats, (from experience, a tangible transaction tends to stick more). Before they know it, they’ve stacked their first fraction of a BTC through Relai. Once that’s done, I go on explaining all the things they cannot do with a regular bank (fees & delays for sending money to a friend abroad, having to wait for Mon morning to call your banker if you want to send more money than your threshold allows on a saturday evening -and having to explain why etc.) And I usually end with an « inflation » lecture, relatively effective these days. If at this point I see they’re still interested we go on a talk about cold storage.