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Do Successful Women Have A Hard Time Dating?


Is it true that guys avoid powerful gals because their egos can’t handle it? Relationship experts and real men weigh in.

By Amanda May

Roundtable participants
  • Diane Mapes, author, How to Date in a Post-Dating World
  • Steve Nakamoto, author, Men Are Like Fish: What Every Woman Needs to Know about Catching a Man
  • Andy, 30, entrepreneur
  • Craig, 33, recruiter
  • Alex, 25, lawyer
Q: There’s been a lot of talk lately that successful, career-oriented women have trouble creating lasting relationships because men feel intimidated. Do you think that is true?

Steve Nakamoto: The traditional male role is to be the provider and protector. If a guy loses that, he may feel like he’s losing his pride. Many men feel like their identity is wrapped up in what they do and how much
“Many men feel like their identity is wrapped up in how much they earn. A woman who’s more successful than they are may threaten how they view themselves.”
they earn. It’s an external validation of their success, and a woman who is more successful than they are may threaten how they view themselves.

Craig: Many men do get intimidated by a woman who earns more or is more successful. They’re told that they’re supposed to be the breadwinners. I think it’s going to take awhile for society to get used to the fact that with more women working, traditional gender roles don’t necessarily apply.

Andy: Of course it depends on the man, but to feel financially superfluous is emasculating. No one wants to be reminded that he’s a failure, and I can definitely see that putting additional pressure on a relationship.

Q: Do you tend to date women who are more or less successful than you?

Andy: I generally date women who make less money than me. I think the reason is I take my career very seriously. I know that sounds arrogant, but I'm a pretty driven guy, more driven than most men and women. That said, the girl I'm dating now makes more money than I do—a lot more! However, that’s mainly because I’m starting my own company. We both know that over the long-term, I have the potential to make much more than she does.

Craig: I was engaged once when very young to a woman who was not career-minded and wanted to live off me. It was a godsend we didn’t get married! Since then I’ve dated women who’ve made more and less than me, but it didn’t affect the relationship. If you’re with someone you have fun with, why should it matter? I don’t want a wallflower, I want someone who can look after herself.

Alex: As it has turned out, the woman I date are not as successful as I am, but that is purely coincidental. I don't discriminate based on career.

Q: What kind of problems can arise when a woman is more successful than her date?

Andy: The worst thing she can do is emasculate the guy she's dating in public with respect to money. Comments like “Oh, I wish we could come
“Men are sensitive to a woman’s financial clout, so her being sensitive to it as well is a big first step.”
with you, but Bob here doesn't make enough money” said in front of a group of people will make Bob start looking for another woman.

Steve Nakamoto: Successful women tend to work really long hours. Some men may feel like the woman is too busy and doesn’t have time for them. A man who wants to be taken care of by a woman won’t do well in this kind of relationship.

Diane Mapes: I think some women inadvertently send the message that “I’m too busy or too important for you,” and no one likes to sit down at a table with someone who goes on and on about their accomplishments or how busy they are. With online dating, the whole process is accelerated: There’s a tendency for women to dump their resume in a guy’s lap, and it can be overwhelming.

Q: Should a woman try to play down her achievements when meeting a guy for the first time?

Diane Mapes: Absolutely not. That’s the old message that a woman needs to trick a man into marrying her. Who wants someone you need to win with deceit?

Andy: I wouldn't say a woman should "dumb down" her achievements when meeting a guy for the first time, but she doesn't need to emphasize them either. Let a first meeting be what is should be: a chance for two people to get to know each other, not get to know where they went to school, how much money they make and how powerful they are.

Q: What advice would you give to a woman who feels that her financial success is intimidating to men and is getting in the way of her forming a lasting relationship?

Diane Mapes: Women who are very accomplished tend to have very high expectations—perhaps unrealistically so. It’s tough to find someone who seems just right for you, and successful women may have a smaller dating pool because they won’t necessarily “date down” financially like many men are willing to do. I’d advise women to be open-minded. There are a lot of really smart, substantial guys who are attractive in non-traditional ways.

Steve Nakamoto: Women need to do certain things to make sure money is not an issue. For example, let him romance you, spend money on you, even if he doesn’t make much. She should also understand that she shouldn’t buy him expensive gifts—he’ll feel like he can’t reciprocate. Once a man is in love, it’s not as big a deal. At that point even an intimidated guy will let down his guard.

Andy: The vast majority of guys will be sensitive to the woman’s w clout, so her being sensitive to it as well is a big first step. Women can say “It's not my fault that I make more” or “That’s his issue, not mine,” but the problem there is, the connection between two people is being seen only in financial terms. So my advice would be, stop thinking so much about money! Focus elsewhere, and see what develops between the two people involved without a price tag hanging over each of your heads.


Amanda May is a freelance writer living in Brooklyn, NY who’s written for Redbook and other publications.
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