01/12/2012 07:23 pm ET Updated Mar 13, 2012

Women And Money: Dating Tips From Kate Middleton, Britney Spears And Angelina Jolie

Women earn more than their husbands in 1/3 of two-income households.With this newfound financial freedom comes an age-old dilemma. Who picks up the check?

Fortunately, thanks to the hard work of the women who have come before us, women are free, free, free to get an education and pretty much any job we desire, so, these days, many of us can afford to pick up our own check anytime we wish to.

But should we?

If you were transported back in time a century, the waiter would hand the bill directly to the man you were dining with, and the woman would be expected to "be a lady and let him pay." Those old mores are more than a little responsible for keeping women barefoot, pregnant and without a vote for nearly a century and a half after America was founded.

But old mores die hard. The current version of "be a lady and let him pay" is based upon the assumption that letting him pay the bill makes him feel more manly and is simply more romantic. Plus, it's a gauge of just how into you he really is. But is this true?

I looked at three very high profile women and a few throughout history, and what I discovered was that the real question isn't who picks up the check.The real question is: What kind of relationship are you interested in? Picking up the check (or not) sends a subtle relationship signal to your date early on about the kind of relationship that you are interested in. Not who wears the pants, but, rather, who pays the bills. And rest assured, there is a good man available for any arrangement you choose.

So, would you rather be Princess Kate, Britney Spears or Angelina Jolie?

Girls Who Pick Up.

Do you own your own castle?

Are you so wealthy that the only guy who can pick up your check is Prince Harry?

Let's face it. Britney Spears could have dated a prince or perhaps even an Internet billionaire, if she wanted to play the damsel in the relationship. However, she picked a dancer to be the father of her two children -- someone she would have to support. In December, she got engaged to Jason Trawick, her former agent (i.e. another man she supported).

Now, Britney divorced her first (and second) husbands, but picking up doesn't necessarily doom the relationship. Queen Elizabeth II and Prince Philip have been married for centuries (okay, since 1947). Who knows what goes on behind the castle walls, but the adoring public wants to see and touch their Queen, and you will never see the Prince Consort upstaging her.

If you have more money than the Queen of England (like J.K. Rowling does), or have a dream job that you want to place as a priority in the relationship, or are looking for someone to play a supportive role to you, then, by all means, reach for the check (with all of the femininity that you desire to summon) on ALL of your first dates. Be aware, however, that if you do reach for that check on the first date, and he lets you pay it, he's also sending a tacit signal to you -- that he's fine letting you support him!

The challenge of being a woman who rules the roost in a relationship is finding a great guy and not just a gigolo who is fawning all over you because he likes your lifestyle! This is certainly possible. Cindy Lou Hensley, daughter of a wealthy Phoenix, Arizona beer distributor, seems quite pleased with her choice for a husband, Senator John McCain. Let's hope Jennifer Aniston's romance turns out so well.

Girls Who Are Provided For.

American girls have been doing pretty well when it comes to finding their Prince Charming. Grace Kelly, the former Queen of Monaco and Princess Caroline's mother, was an American actress when Prince Rainier came calling. Her Majesty Queen Noor of Jordan was originally just a California girl. But the most famous commoner to marry a royal today is Catherine, Duchess of Cambridge.

Princess Kate went from Waitey Katie party girl to royal philanthropist and People headliner overnight. Queen Noor is now one of the most important voices for peace in the world, and, even more importantly, a symbol for women's equality in the Middle East.

Smart, motivated women can carve a niche for themselves, even if their husbands are the rich, famous ones -- provided he respects, loves and believes in her and lives in a land where women are valued. Princess Kate and Queen Noor's lives are certainly very different from that of Dr. Zenat Karzai, the First Lady of Afghanistan, who is rarely seen in public or heard from. Dr. Karzai may be living the life of her dreams behind closed doors, but she is certainly not setting an example of empowerment for the women in her country.

Girls Who Want an Equal Partnership (and Pick Up the Check Sometimes)

They won't even admit when the first date actually occurred, and if it occurred on the set of Mr. and Mrs. Smith, then the catering crew probably picked up the tab. What we do know about the Jolie-Pitt family is that both Angelina Jolie and Brad Pitt command beaucoup bucks for their films and are rich enough, on their own, to buy homes, planes and nannies for the kids.

Do they support and applaud one another's dreams? It is widely reported (and documented) that when Jolie is working, Brad entertains the kids and vice versa.

So is it possible that Angelina picked up the tab on the first date, or on some of their well-publicized date nights away from the kids? Who knows? However, it is evident that Angelina has established a very equal partnership with her very hot baby daddy and life companion, Brad Pitt.

Are you a Queen, a Damsel or a Democrat?
Now ... Some psychiatrists insist that women should be wary of men who don't reach for the check. Pop authors will say that if the dude doesn't reach for the bill, he's just not that into you. However, the truth is that romance is a dance and there are dances today where men take the lead and others where partners kick up their heels pretty much on their own, but in close proximity to one another. Picking a great dance partner is far more important than insisting on the minuet or some other time-worn tradition while the tango is pulsing in the background.

The most important decision you'll ever make isn't who pays, but whether if this guy a really great person who will delight you, empower you, respect you and love you. With lovers and husband candidates: It pays to pick a good one, regardless of who buys lunch.

About Natalie Pace:
Natalie Pace is the author of You Vs. Wall Street and Put Your Money Where Your Heart Is, and the founder and CEO of the Women's Investment Network, LLC. She is a blogger on and a repeat guest on national television and radio shows such as Good Morning America, Fox News, CNBC, ABC-TV,, NPR and more. As a philanthropist, she has helped to raise more than two million for Los Angeles public schools and financial literacy. Follow her on For more information please visit