Rule #49 - Always work into the conversation: "Yeah, I have tons of money. But how does one buy happiness?"

This one is very interesting. Note how the line talks about wealth indirectly. The focus on the line is on happiness, which allows the guy to talk about his wealth without being showy. This is the best way to reveal someone about yourself. Also note the philosophical question. Once you have built basic rapport with a woman, asking such philosophical questions can often help you deepen the rapport.
Smart Dating Rule: Show, not tell.
Smart Dating Rule: Ask philosophical questions when building rapport.