You’ve gotta play it like Basquiat or Leo in Titanic; wear fingerless gloves, squint a lot, and say things like “Mister, I meet 
a lotta people with money, but whadda they got to show for it?
Rich girls are hot because their moms are hot. But they’re also insane because their dads are inbred sociopaths with Nazi fetishes. All of this makes dating one for a short period of time an excitingly weird mixture of prescription pills, naps, crazy arguments, depressing music, room service, therapists, tattoos that cost more than cars, jet lag, and guestlists. It’s gonna be fun! They won’t stick around forever, however, as they’re genetically pre-disposed to breed among their own kind. But as long as you understand you’ll never be anything more than just a stopgap to them, you’re in with a shout.
THE HELP Unless you’re a horrible, horrible human being, dating a girl with a maid is gonna make you feel like the worst person on Earth; like the conscientious son of a plantation owner
MEETING THEM This is all about timing. There’s a point in every rich girl’s life where they stop accepting daddy’s handouts and start nicking it from his wallet instead. This is when you strike. This is your brief window of opportunity.
The first step is identifying the bars/clubs that these girls frequent. One of a rich girl’s favorite activities is to go and look at other rich-people-who-are-pretending-to-be-poor playing in bands. A good way to find these is to check your local listings for who’s playing in your area, cross-reference band names with the internet, and look out for names like Charlie or Rupert or Frederick. That’s where you’ll find gold.