Chapter 25: Every Relationship is an Exchange

Steve Jobs once spotted a woman in a parking lot, walked up, and asked her to dinner that Saturday. She said yes. Walking back to his car, on his way to meet with important clients, he stopped himself: if this were his last day alive, would he rather sit through a business dinner or take her out tonight? He turned around, caught her before she drove off, and asked her to dinner that same evening. She said yes again. Eighteen months later, they were married. Winning in dating starts here: with the willingness to act immediately on what you want.

Relationships aren't optional extras to a well-run career or a well-lived life. They are the substance of both. In the end, what you remember is rarely the balance sheet. It's the people, the places, the ordinary moments the work never gave back.

How to Win in Dating

Boldness alone doesn't work if you have nothing to offer. Every relationship, however romantic it feels, is built on exchange. Ayn Rand argued that nobody loves another person selflessly; we love others for what they provide. Love, in this sense, is a business deal, and you improve your position by improving your offer. This is why people work so hard on their looks, their careers, their charm: not vanity, but leverage.

The Hook

Attraction begins with a hook, the same way marketing does. You need something that draws attention before anyone can appreciate your depth. Money is an exceptional hook for attracting women. Beauty is a phenomenal hook for attracting men. Neither promises substance, but both reliably get you noticed. As Marilyn Monroe said, "Don't you know that a man being rich is like a girl being pretty? You wouldn't marry a girl just because she's pretty, but my goodness, doesn't it help?"

Kindness, by contrast, is not a hook. Nobody falls for kindness first; it only registers once someone is already attracted. Barbara Walters admitted she was drawn to men who were smart and powerful, unsure why, then supplied the answer herself: she'd always hoped a strong, successful man would take care of her so she wouldn't have to take care of herself. That's the function of a hook: it promises to solve a need before a word is exchanged.

Appeal to the Fish

The fisherman baits his hook with worms because fish like worms, not because he does. Money itself isn't the real hook. The real hook is what money buys: the spontaneous flight to Hawaii, the restaurant that doesn't take reservations, the experiences that make life feel expansive. Nobody falls for a number in an account. They fall for what the number makes possible, and if you cannot show them that, the number does nothing for you.

Beauty isn't the real hook either. What beauty delivers is. Looks open the door and do very little afterward, which is why sexual skill will carry a relationship further than beauty alone ever will. Beauty is an introduction. Skill is the reason anyone stays.

The sex coach Ruth Ramsay tells her clients to stop treating sex as an act and start treating it as a discipline: something you study the way you would study tennis, with patience, attention, and a willingness to be bad at it before you are good. Almost no one does this. That is exactly why it works. It is the one skill everyone assumes they already have and no one practices.

Money, looks, and sexual skill are all worth building, whether you are a man or a woman. But they are not weighted equally by everyone. On average, heterosexual women put more weight on resources and status than men do, and heterosexual men put more weight on physical attractiveness than women do. Know which hook you are fishing with, and sharpen that one first.

Then remember that averages describe crowds, not the person sitting across from you. Broad hooks pull volume, and volume is the wrong goal once you know who you want. Everyone carries an image of the partner they are looking for. Most have never said it out loud and some would deny it, but it is there, and it is specific. People broadcast it constantly in what they admire, what they complain about, and who they have loved before. The closer you resemble that image, the more they will want you.

This is also the basis of real compatibility. As Esther Perel observed, people tend to give others what they themselves would want to receive, which usually isn't what the other person actually wants. True compatibility isn't sameness; it's the ability to give each other exactly what each of you needs.

The Sufficiency Principle

There is such a thing as being too impressive. The psychologist Dean Simonton found that people gain the most social influence and following at an IQ around 119, the 90th percentile, notably above that of the average college graduate but below that of the average graduate of an elite university. The same holds in dating: people report the strongest attraction to partners around the 90th percentile of intelligence. Smart, but not intimidatingly so.

The broader lesson is to aim for sufficiency, not excess, in health, knowledge, relationships, and wealth. Push any one of these to the 99.9th percentile and the others tend to suffer. Sit instead at the 80th to 90th percentile across all of them, and the combination itself becomes rare, without making you someone too extreme for others to comfortably want.

Going on Dates

Bad relationships almost always come down to bad selection. Who you choose determines everything that follows, and it is not your job to fix someone who is not built for a stable, loving partnership. Choosing someone naive or easily manipulated is a mistake in any domain, whether you're hiring, befriending, or dating: work with, and love, only people you admire.

Compatibility matters more than chemistry. You need to agree on money—whether to save, spend, or splurge—since financial friction sinks more relationships than almost anything else. You need matching "generative drives," the psychiatrist Paul Conti's term for the urge to build and create something in the world. You need similar comfort levels: pairing a partner who wants to watch Netflix with one who wants to run ultramarathons is a mismatch waiting to surface. And you need to laugh at the same things, and be able to make each other laugh.

Above all, you need mutual investment. The dating coach Matthew Hussey's rule: don't invest in someone based on how much you like them; invest based on how much they invest in you. But interest alone isn't enough either. Clementine Churchill's advice to her daughter Mary cuts the other way: don't marry someone because they want to marry you, but because you want to marry them. Both conditions have to hold.

Attractiveness matters too, just not as much as people think. A useful test: if you want to sleep with them and would be comfortable introducing them to your parents, they're attractive enough.

Money Matters

Jane Austen never let a suitor's income go unmentioned, not because money is everything, but because pretending it's nothing is naive. Even wealthy families feel the strain. The week before Barbara Bush's wedding, her father, then earning the equivalent of $417,000 a year, pulled her aside and warned her that money breaks up more marriages than anything else. When she pointed out that her own mother kept a drawer full of unpaid bills, he explained his solution: he told his wife half his income was the whole of it, then quietly used the other half to bail her out at Christmas and their anniversary, "and she thinks I'm a great hero."

The better standard is a partner who fuels your ambition rather than competing with it or resenting it. Eleanor Roosevelt gave Franklin the belief that "he would amount to something someday."

That said, extreme ambition has its own price. Highly successful people remarry often. Samuel Johnson called second marriages "the triumph of hope over experience." Deion Sanders, the only athlete to play in both a World Series and a Super Bowl, is on his third marriage and has said, "I'm married to football; baseball is my girlfriend," meaning ambitious people are often already spoken for by their careers. The balance to strike: too little ambition and they'll never build anything; too much and they'll never have time for you.

The Trip Test

Around three months in, take a long trip together. It's the clearest test of whether the relationship can survive daily life. Oprah Winfrey's version: if you can survive eleven days in cramped quarters with someone and still come out laughing, the bond is real.

Managing the Downside

Only date people who make their interest obvious through consistency, predictability, and quick replies. Anyone who can't manage that isn't worth your time, regardless of how you feel about them.

Beyond that, treat dating like any other risk: set a stop-loss. For men, that means not spending heavily on the first few dates, and if a woman hasn't slept with you after three dates, moving on rather than continuing to invest. For women, the equivalent is the "what are we" conversation around three months in: if he won't commit to exclusivity by then, walk away. These shift by culture, but as a baseline for reducing wasted time, they work.