Sleeping with Money: Lessons Not Learned from Sex and the City

The most popular description of the HBO show Sex and the City that’s given on Urbandictionary.com is the most accurate in my opinion:

“A now retired HBO series in syndication that chronicles the life of four single heterosexual women living in New York City who behave like stereotypical single gay men living in New York City.”

Back in my crazy single days, I had a friend who would call me Carrie Bradshaw. Carrie and I had the aspiring writer thing in common, but it was mostly that I had expensive taste in clothes, and a penchant for dating successful men. I was even entangled with someone who resembled a younger Mr. Big, but that’s something I’d rather forget.

I began to feel uneasy about consistently ending up with engineers and doctors. I often didn’t have to pay my full share on dates. The times I did spend money, I was spending way too much. After a while I started to feel judged by peers because I wasn’t meeting guys my own age or income bracket. It’s not like I was dating out of my income bracket on purpose. Or was I?

It seems taboo to talk about men who date wealthier men, and I don’t believe it should be. Perhaps this dating pattern is a bad, or there may be a reasonable explanation. I now have some considerable distance from the days when I was like Carrie Bradshaw. Here are some lessons learned from dating beyond my income bracket. I’m not sure if my experience extends to women dating women, but perhaps women readers would like to share their experiences.

Understand Your Attraction

Understanding your attraction to Mr. Moneypants does more than just defend yourself against the barrage of criticism you may or may not receive from your friends or acquaintances. If you’re dating a rich guy, it’s good to know why. Here are few questions I wish someone asked me:

1) What’s the first thing you liked about him? Was it his looks? Charm? Humor? His apparent wealth? Or did you like the whole package, as in, all the above?

2) If you met this guy without knowing what he does for a living, would you still go on a date with him?

3) After a few dates, the guy you like loses his high-paying job. Assuming nothing else about him changes, would you still date him?

4) How do you gauge your own financial security?

5) What’s the one thing you wish you could change about him?

With the exception of going on one date with a rich guy just to know what it would be like, I personally have never dated anyone because I had knowledge that they make a lot of money. However, for all the other occasions, I seriously had to ask myself what was going on with all the guppies on my dating resume.

Zac is the man I’m going to spend my life with, and he is a scientist. Apparently I’ve always had a thing for guys with a mathematical mind, which makes sense because I’m the complete opposite. I wouldn’t feel challenged or entertained by a dreamer like me. Perhaps it is fair to say that science guys tend to make more money, and that’s why I kept ending up with wealthier men.

Let’s dig deeper. I would have never stopped dating a guy because he was no longer rich. If there were other reasons to like the guy, my opinion would likely not change about him.

However, it would be fair to say that one thing I found appealing about wealthier men was that they didn’t have the same worries I had about living paycheck to paycheck. It was refreshing to be with someone who can enjoy life in more ways than I could. At times it felt like an escape from my broke and stressful life.

If there were anything I wish I could have changed about the past guys I dated, I did wish they were closer to my age. I had a hard time relating to guys under 30, but I realize now that it had a lot to do with my defenses. Twenty-somethings range so much in terms of income and success, that many times the idea of dating a twenty-something raised many insecurities about my career and my sense of financial responsibility. Looking back, it would have been dumb to try to compare myself to the slightly older and wealthier men I was dating. They were in essence, unfair competition, and I was perfectly free to be young, searching and striving to find the right career for me.

Expectations

It’s a good idea to evaluate your expectations. Do you think settling down with Mr. Moneypants will solve all your financial problems? Or are you giving him a try like you would anyone else? What are the expectations on you?

Be really honest about your expectations. I think if we all had the chance to be taken care of financially by someone else, many of us would take that opportunity.

Then again, just because you perceive that a guy makes a lot of money, doesn’t mean that he actually has all that money, as Nina points out. You too may have to hold down a job to maintain a lifestyle you both wish to share.

I have always had career goals in mind. So for me, I have never had the expectation that a rich guy is going to take care of me.

Ground Rules

More than anything, I wish I laid out some ground rules in the beginning. Basically: who pays for what, how much, and how often?

A nice dinner here and there is a wonderful thing. A nice dinner all the time gets incredibly expensive for the guy who makes less money, even when he chips in just occasionally. Two men of very different incomes need to work out this issue early. It’s been my experience that not being able to talk freely about money concerns can cause resentment, and that’s a shame if you’re dating someone who is a good match. I believe if you both talk about what you can and can’t afford, you’ve cleared the air and created an environment to get to know each other better.

Those are just a few of the lessons I learned about dating beyond my income bracket. Some people may judge, but the bottom line is that if you’re happy with the one you’ve chosen to date, what anyone else has to say shouldn’t matter.