That's only possible if you are born into money. Even then he avoids giving out concrete advice. If I'm going to spend 20$ on a book I might as well read one by a billionaire.
I haven't read "Art of not..." because it came off as one of those books cashing in on "stoicism for bros". As I understand it, that's the book that made him truly famous.
My original comment refers only to what he wrote in "Models", which was written several years earlier. I would much sooner read a book about dating from a relatively average looking, average seeming guy than somebody who never had problems dating to begin with.