So we told you how to pick up an artist chick and a sporty girl. That was child’s play compared to the roller coaster ride of emotions that is dating a rich girl. It can be done… but proceed with caution, friend.

The older, the easier

The stereotype of a "snobby little rich girl" is probably one of the most apt stereotypes out there — everyone under the age of 25 is already too cocky for their own good and add a stack of hundreds and a lifetime of pampering to the pile and you’ve got one super entitled, very bitchy girl. 

But as rich girls age, that edge of entitlement is replaced with a softening boredom with their lives in general. And thanks to easy living and some light (to major) plastic surgery, this cougar with cash to burn is a tight, tight package waiting for you to be her dangerous hobo (anyone who pulls in fewer than 6 figures a year is a hobo to a rich girl). 

That’s not to say you can’t crack the nut that is a young rich girl. But the amount of effort it takes to pull that move off isn’t going to repaid by the fruit of your labor. Because young rich girls don’t give head. So aim OLDER.

Talk the talk

You don’t have to drop a wad of cash on a rich girl and you don’t have to be dressed in the finest of Italian leathers (in fact, skip the finest of Italian leathers, dude). But if you don’t TALK like you’re a rich guy (and like you’ve been a rich guy all your life), you’re going to go down in flames.

Rich people don’t take vacations. They "holiday." They don’t have couches. They have "sofas." They don’t talk about doing the dishes or cleaning up after themselves because they all have "a girl" who does that stuff for them. The 1993 Will Smith film "Six Degrees of Separation" has a great primer on how to expertly fake it like a rich guy. 

The goal here isn’t to memorize canned dialogue and try to impress the rich girl in question. You just need to confidently converse as if you’ve had money in the bank your whole life and make sure to not raise any red flags with phrases like like, "Man, SPAM is tasty!" or "I have to get home early to see if my food stamps were delivered." 

Spend big…once

Rich girls are, first and foremost, girls. And like with any girls, a little chivalry goes a long, long way. So be prepared to plunk down some bucks for a swanky meal, some drinks and bottle service at a lounge your rich girl likes to frequent on weeknights. 

But don’t start gritting your teeth just yet. Once you’ve proven that you can hang, paying the check just becomes a matter who’s quickest to the draw. And since you’re not a rich guy, don’t be a credit card cowboy. Let her pay. Trust us, she won’t notice. When there are that many zeroes in your account (with a number at the left side rather than the right of said zeroes), a $1500 bottle of vodka is nothing. 

Letting her pay after your initial encounter isn’t being dishonest… you never said you were rich. You were just telegraphing that you know about the finer things in life and spending lots of money on said things (no matter who gets the tab) doesn’t cause you to flinch. 

Be frivolous and mean

Rich people have few real, everyday problems. Yes, they have relatives who get sick and yes they have their mini crises (just look at the Lohans… yick). But do rich people ever have to worry about losing their jobs? No. Do rich people ever have to wonder if they’ll have enough money to cover their mortgage? Of course not… they probably don’t even have mortgages. They own the banks, after all. 

And a life without those little worries causes rich people to lose what us poor folk call "perspective." And no "perspective" means you’re in for an easy, boring life. So what do the rich do when they get bored? They do frivolous shit and then they’re mean to each other. 

If you want a primer in rich girl frivolity, just rent "The Talented Mr. Ripley." Or look at Paris Hilton’s life story — it’s all tanning, boats, wasting cash, doing drugs and having lots and lots of sex. The fun part is, you don’t have to partake in all the frivolous activity… just be there when it goes down and jump on board when it comes to the sex part. 

After bouts of frivolous fun, rich people turn on each other and get catty and mean. Who can blame them… they’re bored out of their mind. If you were set for 10 lifetimes, you’d probably start some bizarre PR feud with your best friend too. When the mood turns sour with your rich girl, don’t take it personally. Just diss her harder than she disses you and wait a week. Then call her up, feign some tears and apologize. She’ll be back in your arms, asking you which Italian Count you’re a descendant of in no time. 

Have fun…then flee

Rich people can slum it and poor people can live it up. But no one jumps their social class ever, really. Just ask the parents of your rich girl… they had to earn their cash the hard way and they still think like you and your ilk, which is why they loathe their daughters hard partying, fast spending ways.

Unless the rich girl is a gem in the rough, she’s going to be little more than a fun lost weekend or two. Don’t get attached. Even if she falls for you and, against her parents better wishes, the two of you get hitched, you’re going to be in for a miserable life… you’ll never be able to provide for her in the manner she’s used to. And if she’s cool slumming it for the rest of her life, well then buddy, she was never a rich girl at all… she was a phony, just like you. Which means you’re perfect for each other!

Happy hunting! Or should we say, digging?