I watched Millionaire Matchmaker earlier today. Man alive, you can certainly get away with a lot if you are a millionaire.
Test her palate by asking her to eat duck embryos?
Go to a spa for your first date so you can see her in a bikini?
Ask her about her sex life in your second conversation?
Tell a girl you will try X, and you will like it?
Sure, I've made mistakes before like taking a girl to a greek restaurant only to discover she's a vegetarian, but that was in the 90's before it was a fad, but nothing like some mistakes these guys make and are still able to get away with it.