A friend of mine once downloaded something malicious to his Linux machine and wasn’t worried about it. Then some time later, while browsing his files from a Windows machine, saw it and was like, “hey, what’s this?” Oops.
He’s a tech savvy guy, so I’m guessing the fact he had downloaded it himself really let his guard down.
Something similar happened with NHL player Jaromir Jagr. An 18 year old woman threatened to publish photos of herself in bed with him if he didn’t pay. His response was that he doesn’t care.
https://thehockeynews.com/news/jaromir-jagr-blackmailed-with-photo-could-not-care-less-about-it