Blackmail is one we went over extensively in law school.
You can’t say “I’m going to besmirch your good name (release the pictures I have, etc) unless you pay me $”. That’s blackmail.
You can say “”I’m going to besmirch your good name (release the pictures I have, etc)”.....then the person offers to pay you money to go away.
Blackmail is putting the other person to what is legally an impermissible choice. You just have to leave off the “unless you pay me” part and let them fill that in themselves. Then its not considered blackmail.
"Hey, remember those great nude photos we took of each other, back when we were an 'item?' Well, the National Enquirer has offered to buy them from me and publish a big expose! Isn't that wonderful? Aren't you happy for me? You know, I could really use the $$$ that the Nat'l Enquirer is offering. What do you think?"
Even if there weren't any photos, the tabloids would pay big bucks for a lengthy, in-depth interview.
Yep, that's how one does it without being guilty of extortion!
Regards,