Women Who Give Men Money: What a Sugar Momma Is Really Buying (and the One You Probably Already Know)

In the first letter I told you how to find a sugar momma. Men wrote back with the same question in different words: but what is it actually like? What does a woman with money want from a man, when she plainly doesn't want his money?

So here's part two. Four women, four very different deals, and the one lesson I didn't fully understand until I was old enough to look back.

Advanced dating

Think of it this way. Young women, when you're young, are mostly in the same spot you are. Not much money. They want you to pay. Underneath it, most of them want the same thing: to be your girlfriend, and eventually to be married. There's nothing wrong with any of that. But after enough of it, it's the same conversation at the same table.

A sugar momma is in a completely different position. She doesn't want your money. So whatever she wants, it's something else. That's why I call it advanced dating. You can't run the usual play, because the usual play is built on her needing something you can buy.

What she wants is the interesting part. Four stories.

The businesswoman who said "I think you're smart"

I was teaching at a school in Tokyo during the bubble. One of the students was an older woman, around forty, not pretty, thin, and more fun to talk to than anyone I'd met in the country. She owned a string of businesses. After class she'd say, let's have dinner, and take me somewhere fancy, and talk about things the young girls never talked about. Business. Life. How things actually work.

She never pushed for anything. She just made sure we had the best of whatever we did. If I wanted steak, we had steak. If I wanted the club, we took the car, not the train.

Then one day she said: I think you're smart, and I think you need to learn Japanese. And she signed me up for the best Japanese school in the country, an old one run by Catholic brothers who spoke it like natives, and paid the whole thing. I thought I could just pick the language up on the street. She knew better.

A while later she said: I've got a business in China, we're opening bowling alleys, do you want to go? She was buying up old bowling alleys from Japan and America when the boom died, ripping out the lanes and the machines, and rebuilding them in Pudong. We flew over and opened one. She offered to make me the manager and leave me there.

I didn't take it. I was happy in Japan. But the offer did something to me that no gift ever did. It wasn't money. It was a smart woman who had built real things looking at me and saying: you can do more than you think. She saw things in me I couldn't see in myself. For a year she was a mentor as much as anything.

When my parents visited, she bought my mother a three-thousand-dollar teapot. When we walked past a hotel boutique she'd say, you'd look good in that, and I'd walk out measured for a suit I'd never have bought. I didn't care much about any of that. It was funny, and it was nice.

After about a year she started to fall for me, got jealous, and turned into a regular girlfriend. The thing that made it special was gone, and I moved on. I've never stopped being grateful to her.

The horse carriage in Singapore

The second one was married, with a wealthy husband and a little daughter. She knew exactly how many girls I was seeing, because she'd been a student at my school, and she made a decision: I'm older, I have a kid, so I'm going to make sure this one keeps me around. She did it by being cool, and by never making it a problem.

She took me to California. She took me to Singapore. Downtown there used to be a white horse and carriage, the whole prince-and-princess thing, and you could pay to ride it. The first thing she wanted to do was ride it.

I was raised in a trailer park. My reflex was: no, that's a rip-off. She laughed and said, I want to do it. So we did it, and because she was so happy, I had a wonderful time.

That ride taught me something about my own mind. If I had been paying, I'd have sat there sour, thinking about the price. With her paying, I could just be in it. I found out that I enjoyed things I'd trained myself to sneer at because I couldn't afford them. The spontaneity, the "let's just do it," turned out to be one of the great pleasures of my life. Some of the things that look like rip-offs are only rip-offs at your price.

The two heiresses

The third was very young, with a body from a magazine and a plain face, and more money than any of them. First date, she gave me an eighteen-karat gold chain so heavy I couldn't run in it. Second date, a gold watch that turned out to be made by Rolex under another name. I didn't know what either was worth. I didn't know anything about gold.

She wanted to fund any business I believed in. The cash is there, the people are there, the computers are there, and I want to marry you, and my father's company is behind it. It moved too fast, and I lost interest. But it was the same deal underneath: anything you want, done, now.

The fourth was the best of them, and I lost her by my own mistake. Her father founded one of the big drug companies in Japan, and a founder in Japan is something close to a god. She had grown up with that money and still worked hard, sold software, had her own life on top of her father's fortune, played golf, never dyed her hair. Smart, presentable, could talk to anyone. I called her the first lady, because if I'd ever become president, she was the one.

We fell out over something I did. My fault, start to finish. She loved me to the end. I don't know what my life would have been if I'd gone that way, and I don't spend my time on it, but I'll tell you plainly: it was my mistake, and I regret it.

What she's actually buying

Put the four together and you can see it.

A man who says yes. The thing that made me a sugar momma's man wasn't my face. It was that I was game. Wake up in Bangkok with no plan, she says there's something happening in the Maldives this weekend, how long do you need to get ready? And I say: what do I need to wear? We buy a jacket on the way, we buy the tickets on the way to the airport, and by dinner we're somewhere else. I can't think of one reason not to go. Most men think of six. She picks the one who thinks of none.

A man who isn't lazy. This is the part I got wrong for years, and the reason I avoided this topic. I don't want men to hear "women who give men money" and get soft. The women who gave me money gave it to a man who was teaching all day, studying at night, and building things. The businesswoman paid for school and offered me a company to run. The heiress wanted to fund a business. They were investing, not feeding. A lazy man gets a fur coat and a short shelf life.

Her own fun, her way. A woman with real money is often bored. She can't spend it all and she's tired of everyone around her wanting a piece. What she wants is to do something fun with someone cool, right now, the way she wants to do it. That means she'll sometimes have opinions you don't share. So does any friend. Her ideas were usually better than mine anyway, because at that age I didn't know what I didn't know.

Gifts are what she wants to give. The chain, the watch, the fur coat: those were things they wanted to buy, not things I wanted. That's how you tell a regular sugar momma from a good one. The regular one wants to dress you and show you off. The good one asks what you need and wants you to be happy. The great one wants to build something with you.

A man who understands he's not for sale. The best of them knew they were paying, and knew I was in demand, and never once made the money a leash. They were less jealous than the young girls, not more. That only works if you keep your own life, your own work, and the ability to walk away any day. The day you need her money, it's over.

The one you probably already know

Here's the thing I didn't say in the first letter.

A woman with money doesn't go off with a stranger. She's careful. She knows what she likes. So the most likely sugar momma in your life is a woman you already know: the older woman with money who's been quietly supportive, who gives you the attaboy, who seems to want you to do well. That's the signal. She already gives a damn about you. The relationship you have with her now could become something else.

How you bring that up is its own letter, and I'll write it. The short version is that you don't ask. You become the kind of man she wants to say yes to, and you let her.

A man asked me on the recording: I'm 28, is that too old? No. It's on the high side, but no. It's never really about age. It's about whether you're game, whether you're going somewhere, and whether being around you is fun.

Know what you'd actually want

One more thing. The sugar mommas that found me matched me: spontaneous, travel, steak, the water, golf. Another man might want a woman who takes him to the symphony and the lectures, and that's a different woman. So before you go looking, know what you like. And be honest that you probably don't know yet. Asia taught me I love fish, after thirty years of calling myself a steak man. You find out by trying things. That's what she's offering you, more than the money: a wider life than the one you can afford.

Get yourself right first. Don't get lazy. Keep your own life. Say yes.

If you want to do this kind of honest talk in person with men who've lived a little, that's a summit. And if you'd rather start with the man in the mirror, start here.

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