Originally published on November 19, 2019:

I’m a straight, single, cisgender woman who has been dating in New York for 5 years.

Send help.

But because I believe in the importance of turning my experiences into something useful for others, here’s an insight for single men looking to meet someone special, even if you define “special” as “for the next 3 hours.”

Guys I’ve dated have fallen into 1 of 2 categories:

Men Who Want More Money

Guys who’d love a major windfall—or at least a 15% raise, where 95% of people live. They want nicer things, a safety net, a bigger place, and the ability to go to fancier places. They want, perhaps, to feel more valued at work. At the root is self-consciousness about how much they make—and how can you blame them? We’ve sadly drilled into the collective consciousness that income is roughly equal to a male’s worth as a human being, just as we’ve come to the way that women have been conditioned to prioritize their appearance.

Men Who Know That They Have Lots of Money

If they don’t live in Obviously Expensive Buildings, they’re in Amazing Places inside more modest buildings. Maybe they’ve come to this level of comfort another way—by birth, upbringing, schooling, surname, associations.

Socioeconomic class is revealed in the obvious cues: job/title, their relationship to work, their level of autonomy at work, what they tend to notice, and what they get stressed out about. Other cues are more subtle—think of body language, posture, speaking ability, physique, clothes/shoes (brand, coordination, upkeep, how well they’re tailored), accessories (think of watches and belts and cuff links), and even their haircut.

When guys who know that they’re rich are dating, deep down, they tend to be paranoid that women only want them for their money or connections.

Imagine yourself as a billionaire, for a second: 99% of the people around you on a daily basis are explicitly around you for your money. They’re the employees, people you’ve hired, subjects of business deals, clerks and servers and drivers. People you contract out and hire will charge as much as humanly possible. Family members whose ability to pay their mortgage or maintain a vacation home requires staying on your good side. How can you not get paranoid after a while?

It reminds me of rule #6, in If Life is a Game, These Are the Rules:

“‘There’ is no better than ‘here.’ When your there has become your here, you will simply obtain another there that will again look better than here.”

So here’s what I wish that ALL guys—especially those dating and peacocking in the ever salary-conscious city of New York—knew. What’s more important/attractive than you what you have is your relationship to what you have.

The worst and most uncomfortable outings are with the overly self-conscious, the apologetic, the people who are constantly comparing themselves to the ghost in the room, needlessly stressing themselves out.

People are less interested in what you have, and more interested in how comfortable you are with yourself.

It’s not how much you have. It’s the difference between what you have and what you spend. If you have more than you spend, you’re rich. If you spend more than you have, you’re not. If you live cheaply, it’s easy to be free.
–Derek Sivers