A cute couple flirts on an old wooden boat
Published by  
Wes Myers
October 10, 2023

What Can Money Buy for Rich Single Men?

Some think money can buy the woman of your dreams. Experience says otherwise.
Wes Myers is the co-Founder and CBO of Keeper, an experienced matchmaker, and relationship expert. He is an Iraq veteran and Wharton MBA.

It is common wisdom that older, wealthier men have their pick of young, attractive women. 

After helping all sorts of driven, successful people find their life partner, I’ve concluded it’s not that simple.

For men seeking long-term partnership, here’s the real impact of wealth, what money can’t buy, and the most common money mistake you may be making.

Why Wealth Matters

Among our marriage-minded clientele, very few women are openly searching for a man with a particular sum of money. (True gold-diggers are rare.) Instead, women are attracted to money in large part due to what it represents: intelligence, security, and possibility. 

Wealth implies a man has positive traits that can benefit him, his wife, and their future children. Wealth increases the likelihood that a man is smart, hard-working, and good with people. It can even make a woman feel desired: “He’s wealthy, successful, and able to get what he wants. If he wants me, that feels good.” 

These traits certainly increase a man’s attractiveness. Money, however, isn’t everything.

What Money Can't Buy

There’s a common perception that a wealthy man can attract mates by the power of his wealth alone. In reality, we find that wealth is worth approximately 1 to 1.5 points on a 10-point scale. Wealth will not turn a 5 into a 9. You still have to be a well-rounded person who’s enjoyable to be with. 

When a woman is deciding who to marry, she considers a host of dimensions, including: 

  • Age
  • Physical appearance
  • Lifestyle 
  • Culture
  • Relationship dynamics
  • Sociability
  • Values
  • Personality
  • Wealth
  • etc.

Impressive success in one area can’t always counterbalance failure elsewhere. From my observations:

  1. Wealth can compensate for a few years of undesired age difference, but rarely a massive gap. 
  2. Wealth can excuse a guy being particularly busy, especially during the beginning stages of a relationship, but it can’t overcome a complete lack of availability or social skills. 
  3. Wealth can overcome a small aesthetic differential, but it can’t make a frog a prince.  

I recently saw a mid-twenties woman reject an attractive, late-thirties, six-foot-tall millionaire because she thought he looked too domineering in his photos. While this guy was unquestionably good-looking, one perceived negative prompted her rejection.

The Big Money Mistake

Having paired many couples at Keeper, I’ve come across enough wealthy men in their late-30s to early-40’s wanting to marry a woman in her mid-20s. These men typically have high standards. They’re not merely seeking a young, attractive woman. They’re seeking a young, attractive, intelligent, competent, sociable, fun woman who’s not a gold-digger. 

While these men certainly have a lot to offer, they’re also seeking women in the uppermost percentiles of desirability. And for many of these women, age is a factor. Here might be her thought process: “If I’m 25 now, and I don’t want to have kids for a few more years, dad’s going to be in his 40s by the time I do. That puts him in his 60s when the kids graduate high school. Where will that leave me?” 

Many women therefore prefer a partner closer to their own age (usually just a couple to a few years older). It’s true that younger men are generally less wealthy than older men, but most women aren’t seeking exorbitant sums. Instead, our conversations with women have demonstrated that they judge money in this context on a logarithmic scale, perceiving:

  • $1M to be much more than $100k
  • $10M to be only a bit more than $1M
  • $100M to be nearly the same as $10M 

Women consider themselves adequate judges of a man’s potential. So, while a man closer to her own age doesn’t have the proven track record of an older gentleman, she might prefer to bet on the younger man’s potential and work toward building the life she wants with him. 

Despite this structural difficulty, we’ve had success matching these personas together. These pairs tend to work best when the woman is picky about traits other than age and the man is picky about personality more than appearance. If you are a middle-aged man who wants to be with a younger woman, be sure to view yourself holistically. 

Due to your financial success, you probably have an abundance mindset. When a woman rejects you, you may simply shrug and move on without any change to your approach, confident that someone else will be interested. We often see wealthy, older men rejected by attractive women for reasons other than age. 

In one recent case, a mid-30s woman turned down an early-50s man not for his age, but because he’s out of shape. The man shrugged, saying, “I’m fat; no way to change that.” But there is a proven way to change that! 

Time and time again, rejected men re-commit themselves to working harder, thinking that increased wealth will solve their attractiveness problem. But remember the logarithmic scale.

Nearly all of the wealthy men who join Keeper explicitly say, “I don’t want a gold-digger.” They seek a partner who wants them, not their resources. It follows logically that money can’t be the solution to their dating troubles. Instead of focusing on acquiring more money, start using it to overcome your weaknesses: 

  • If you’re physically unfit, hire a nutritionist and a trainer. 
  • If you’re not particularly social, hire a charisma coach or take an improv class. 
  • If your work is all-consuming so you have no time for partnership, reorganize it to carve out more time for her. 

Improving your approach

At Keeper, we only make 100% matches, meaning every pair is dealbreaker-free. This commitment is part of the reason 1 in 5 Keeper first dates turn into long-term relationships. But success requires overcoming your shortcomings. In some areas of life, you’re rewarded for playing to your strengths. But to succeed in dating, you may have to focus on improving your weaknesses. 

In working toward finding your match, we help you identify where you’re falling short. We’ll help you understand what you need to make the next big step. (Hint: it’s not more swiping.) For a free consultation on the quest to find your life partner, click here.

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