July 3, 2020

I work with a lot of amazing, successful women. A lot. And I am constantly impressed by these women’s tenacity, drive, and achievements in life. Most have made their financial wealth on their own and are very proud of that, as they should be. But with this success sometimes comes difficulty in finding a partner. Why is this?

As a recent example, I asked a client—late 50s, from New York, partner at a consulting firm—how her last date went:

“He was nice and well mannered, and we had a common interest in helping local youth. Also a common divorce experience. I’m unclear on his career history/track… therefore don’t know his leadership, achievement capability or financial security status. Questionable interest/experience/passion for international experiences, which is essential for me!”

My response:

“As for this – ‘Unclear career history/track…therefore don’t know his leadership, achievement capability or financial security status’ — you are not hiring him… you’re looking to date him. So, while, of course, this is important, so is how someone makes you feel when you’re together. It’s important to pay attention to those softer things too because you don’t want to date a resume. You want to date a real person who is also interested in learning about you and who treats you well. No need to size him, or anyone, up in one meeting. (I wouldn’t be doing my job well if I didn’t say these things. Please do keep them in mind.) Let me know if/when you plan to see him again.”

The important thing to note here is that my client is treating the dating experience like an interview process with the question in mind of, “Is he good enough for me?” This is not the way I recommend dating. First, everyone is “good enough” in their own way. Some people are more compatible, of course, but to so overtly judge someone based on his or her status is shortsighted. Rarely do you hear a happy couple talk about the merits of his or her partner’s “leadership ability.” A boss would, and should, be looking for this quality. But “leadership ability” doesn’t keep you warm at night.

Now, I am the first person to recognize that very often, someone successful—especially if this person built that success (and I mean financially) through hard work and motivation—wants to find someone equally successful. Not everyone’s drive is for the same thing, though.

The problem, especially for highly successful women, is that they often want the same caliber of man. I don’t begrudge anyone for that. But let’s say there are a small handful of men in that category. Now that we’ve narrowed it down to them, we have to assume that they are looking for the same caliber of woman. Some are, of course, but some aren’t. So now the pool has dwindled down immensely.

While a woman might look for her professional peer, often, while a man may certainly appreciate the drive, intellect, and success of a woman, he is also looking for qualities in a partner that he won’t find in his likely-intense work environment. These qualities are kindness, warmth, and affection. Let’s hope he’s not getting those from his fellow law partner!

What does this all mean? There’s a mismatch. Should successful women lower their standards? Never! But rather, it’s important to remember that men and women are different and that there is more to a partner than the on-paper resume details. As I told my client, to size someone up based on the dollar signs on his W-2 is shortsighted. You don’t know a person on a first date. Or even a third or fourth. And on those later dates, you might find that this is someone who treats you better, has more time for you, and makes you feel secure. Because the flip side of every quality is the opposite quality… financial success could also mean workaholic, constant traveler could also mean discontent with (or absence from) home life, lots of “stuff” could also mean lots of debt. What I’m saying is that we never know the full picture, so it’s important to evaluate someone on who he or she is today—not a past divorce, not a bank account, and not perceived leadership status. Might that all be part of the equation? Sure. But it’s only part. Take each person as a whole, not as a list of stats and numbers that may or may not make you happy in the long run.

“Why Can’t I Find a Man of My Caliber?”

18 thoughts on ““Why Can’t I Find a Man of My Caliber?”

  • July 3, 2020 at 3:35 pm
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    Why can’t any woman find a man of her caliber? Not rocket science. Once women began to come out of their closets (being silent among men), they began to learn that men are NOT their equals. Medical School, more women. Law School, more women. College, more women. Men are good for lifting heavy objects and fighting. Even H L Mencken understood women’s natural superiority nearly 100 years ago. Sorry. You want an equal? Find a woman friend.

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    • July 3, 2020 at 7:08 pm
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      This attitude does not sound healthy to me. (I’m assuming you are a man based on your name being David.) I also find women to be incredible. I find that more of my friends are women than men. That said, I would never suppose that one sex is better than another. There are amazing qualities in both. And all genders have their own amazing benefits that they add to society that are often lacking in other genders. Diversity is beautiful – we mostly speak about diversity of ethnicity and culture, but the diversity of emotions, diversity of understanding, diversity of intuition, etc, also add so much to our civilization and to the potential for progress. I daresay that belittling your own sex (again, sorry for assuming you are a man based on your name), does not benefit you or help anyone. You are as amazing as any other man or woman in your own unique way.

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  • July 3, 2020 at 3:45 pm
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    Excellent feedback frpm you, Erika! How are you? Sharon Kaplan. xo

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    • July 3, 2020 at 3:49 pm
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      So glad you enjoyed. Always wonderful hearing from you! xoxo

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  • July 3, 2020 at 5:47 pm
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    Very good article
    In Fl I really struggle to find successful educated woman so I have the same problem as your client . Perhaps I need to change how I think about it.

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    • July 3, 2020 at 5:50 pm
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      I find that they are in abundance! But I agree — you have to decide the hierarchy of what’s important to you. Are you searching proactively? On any site, I recommend choosing your search criteria and then being very active on the site.

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  • July 3, 2020 at 5:52 pm
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    Greetings Sharon: Well written overview of the challenges faced by successful professional women. Here’s one man’s perspective. I dated a successful female attorney. I myself was financially secure and enjoyed success in my own profession. We both shared a desire to remarry – she was divorced, I widowed. It soon became apparent however. that she needed to exert control. It manifested in little things, like a waiter mixing up a dinner order. It would upset her. I suggested whenever she felt the need to assert herself to take three deep breaths and ask “Is this worth agonizing over?” She felt I was being overly critical. She was a remarkable woman whom I still miss. However, her inability to release her masculine energy and let me be the male in the relationship doomed us.

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    • July 3, 2020 at 6:06 pm
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      Carl, I appreciate your sharing that. Whether her inability to let go was tied to her success or was just her personality, we don’t know. In the end, successful or not, it sounds like there was an incompatibility there. There’s a way to exert control without being pushy or stepping on someone else’s toes, but it’s a fine line.

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      • July 4, 2020 at 6:13 am
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        Great advice thank you for sharing this perspective!

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  • July 4, 2020 at 2:12 pm
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    Funny, Erika wrote an online dating profile that bragged about a woman client’s M.B.A. and education career. Have you changed your approach?

    Your late 50’s woman client wants a “financially secure” man to pay for “international experiences”. Affluent men in their 50’s will choose younger women. Older men will be retired. Pick your poison – older sugar daddies, 50’s men struggling to pay child support, or cats.

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    • July 4, 2020 at 3:27 pm
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      Sounds like we have a cynic on our hands.

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    • July 7, 2020 at 1:45 pm
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      Women need to have more than just anger, damage, and arrogance to bring to the party even if they are HOT! That is true at any age.

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      • July 7, 2020 at 8:40 pm
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        Same goes for men, regardless of looks or anything else. Leave the past in the past.

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  • July 6, 2020 at 5:04 am
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    Interesting discussion here. I can sympathize with the women wanting someone who is at their level. I have had a hard time finding partners who “have it all” too. The reality is that noone is perfect. In fact, a perfect partner would probably end up being rather boring. However, the men that this 50 year old successful woman is looking for are dating younger women. It is a simple fact that men like me: successful, attractive, and with options usually date younger women. Just as this woman isn’t attracted to men who don’t meet her standards I’m not attracted to women who are too “dominant”. Younger women are usually more flexible, more willing to build a life together, and give me the room to be myself. Younger women are also more furtile: things get harder and harder with respect to fertility above 30. Men like me have options: I’m 43 and dating a 27 year old now. We love each other very very much and our relationship works because of the dynamics between us. It seems to me that SINGLE women who are my age or older lack the femininity and loving characteristics that younger women possess. I do have female friends that possess the warmth, fun, and youthful energy I find so attractive… but none of them are single. I would guess that they aren’t single in large part because they “know how to treat a man”. Unfair as it may be the truth is this: a man of value will not drop his standards to date an older more difficult women any more than an older women will drop her standards to date a man she finds “beneath” her. This is a natural consequence of our modern society: career women have fewer and fewer dating options and are competing with younger more attractive women for the same small pool of men. I do empathize with the women my age and older, but this is a natural consequence of the decisions that they made. When I was a younger man building my life, I was not as attractive as I am now. Women who rejected me then would love to have a shot now. That is a simple spiritual consequence of dating and mating. We are attracted to who we are attracted to. I would encourage the women in this passage to work on herself to improve her attractiveness and femininity. A masculine man like me would find her attitude simply a turn off. Men aren’t ONLY attracted to age, but when you combine her age and her attitude… it’s a no go.

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    • July 6, 2020 at 2:57 pm
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      While I respect what you’re saying, I cannot agree that “SINGLE women who are my age or older lack the femininity and loving characteristics that younger women possess.” This is simply not true. Also not true: Fertility diminishes significantly at age 30. This article wasn’t at all about age. It was about looking at a person as a well-rounded being and not a resume.

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  • July 7, 2020 at 10:34 am
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    First, Dr. Ben’s comments read like a bunch of excuses made by somebody trying to give merit to their poor dating choices. And even if what Ben said is true, what happens when the young woman ages? Trade her in for a new one like you would an old car?

    Anyway, I have to agree with what Erika and Carl said. I dated a bunch before meeting the woman I’m with now and what I found was that there are a ton of women that turn dating in to more of a shopping experience. They would even have numbered lists of requirements right in their profiles. Now, I can understand things like religion and stuff but some of these lists were absurd. The point is that many of the woman dating these days are flooded with a ton of men and start sifting through them like they would clothing on a rack, and as such start applying filtering criteria to help them sort. Not entirely a bad thing but they soon forget that relationships are about compatibility and forming connections, not what color his eyes are or if he is 6′ tall vs 5’9″. Successful woman have more problems as well in that they often forget about the things that men are attracted to, such as softness, femininity and simply letting the man be the man. The biggest issue I found though was that many women in my age group of mid 30s to early 40s simply never learned how to form connections or be in a long term relationship. Divorced women seemed to be the exception.

    I feel I’d be remiss if I didn’t mention the biggest complaint I heard from women during my dating, and that was that a lot of men weren’t looking for a relationship, but instead something more casual. Many expressed frustration and disgust with encountering and trying to filter out such men.

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  • July 7, 2020 at 1:41 pm
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    You’re advice is spot on Erika!
    Too many Karens and feminists – they are often unhappy and seriously damaged. They should be SEEKING and not just “looking for”. Seeking implies purpose and having realistic goals. They want a highly successful, Alpha Male? Then they need to stop trying to be an alpha female – it will NEVER work.

    Reply

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