Dating Advice for Women: Why Do the Smartest Women Have the Toughest Time Dating?

I confess: I love smart women. I love it when she can write a sonnet, use Euler’s formula, code Perl, play a concerto, speak half a dozen languages, run a company, quote Chaucer, diagnose diabetes, compose a quartet and converse brilliantly. Especially in a big city like Los Angeles or New York, looks alone do not suffice. I need, nay, require the intellectual engagement, and legions of smart, educated men feel similarly.

So it pains me to no end to see my smart, educated, lovely female friends remain single, alone and lonely in spite of their best efforts. These are amazing women! Surely there is something wrong with the world if they remain single for so long. That’s what compelled me to write The Tao of Dating: The Smart Woman’s Guide to Being Absolutely Irresistible.

What compels me to write this article today is a recent trip to the Harvard-Yale Game festivities, reminding me of how smart, educated women routinely sabotage their own chances for romantic fulfillment.

Because, as fabulous as these ladies are, all of their failed relationships have one thing in common: themselves. And frankly, telling them that men are losers or even proving it conclusively doesn’t improve anyone’s plight. Useful advice is about something you can change.

Now I’ve been running and attending young alumni events for Harvard, Princeton, Yale, Stanford, MIT, Columbia, Duke, Swarthmore, Penn, Cornell, Berkeley, Brown, Dartmouth, Oxford, Cambridge and similar well-regarded institutions for a while.

I’ve also been privy to the dating woes of hundreds of men who wrote me subsequent to their reading The Tao of Dating for Men.

From these emerges this brand-new list which builds and elaborates on the earlier article, Why the Smartest People Have the Toughest Time Dating. Here we go:

1. Some smart women put themselves in a no-win bind when it comes to finding an intellectual match.

A smart woman wants to date a smart man, since men less intelligent than her frankly bore her to tears. She wants to be able to hold a stimulating conversation with her partner and to know that he’s at least equal to her (if not better) in this department.

However, once a relationship with Mr Smartypants is under foot, often she unconsciously starts to compare and compete with him. She feels intimidated by his intelligence: “Is he smarter/more educated/more successful than me?” Now she’s feeling silly when she doesn’t know something, or tries to one-up him and have the upper hand. The guy doesn’t quite know what’s happening, except that the very trait that made him attractive in the first place is now causing tension.

So stop competing, Ms Smartypants — love is not a contest. In the immortal words of Boy George, “You’re my lover, not my rival.” Instead, celebrate one another for the qualities you each have to offer. Speaking of Ms Smartypants…

2. Smart women bring their inner CEO to the date.

Let’s say you’re a CEO (or doctor, or lawyer, or some other authority figure). Your job involves managing people and telling them what to do. Occasionally, you have to cut them short and redirect their focus to what’s important, or argue to make your point in a pivotal meeting. All in a day’s work.

Here’s the key point to remember: when you’re on a date with a guy, you’re no longer at work. So if you unconsciously keep on doing those things that make you so effective at the office, you may end up alienating him – especially if he’s also a CEO. Strictly speaking, this does not set a man’s heart aflame (though it may give him heartburn).

In her insightful book on why men don’t call women back after a date, Rachel Greenwald lists this ‘Boss Lady Syndrome’ as the #1 reason men run, based on a survey of thousands of men.

Remember that guys admire and respect a woman who can take charge and kick ass. Guys respect and absolutely adore a woman who can take charge and kick ass but doesn’t feel the need to prove it around him. According to Marianne Williamson’s insight in A Woman’s Worth, “In intimate relations with men, I want to major in feminine and minor in masculine.”

3. Smart women don’t make love a top priority.

If love and meaningful companionship aren’t more important to you than a project, paper, or pet, then you can skip this part entirely.

But if love really matters to you and you don’t aspire to a monastic life, put in as much time and energy into dating and romance as you do into other things you excel at.

Dating is not an afterthought for when you’ve taken care of everything else. As far as anyone can tell, deep, meaningful relationships are the most important part of life.

So let’s not leave it to chance, shall we? If you like a guy, make him feel it. Give him at least as much time and energy as your spreadsheet, term paper, chihuahua or Facebook page. A smart guy knows exactly where he is on your priority list, and if it’s too low, he will move on.

4. Smart women mistake a person for real fulfillment.

Smart women can sometimes get really excited over a guy’s resume, especially when he’s gone to the right schools and held the right jobs. Then they get stuck in a miserable marriage and wonder what went wrong when everything seemed so perfect.

There’s minimal correlation between a guy’s resume and how good he can make you feel. Fulfillment is not a person; it’s a feeling. If his company isn’t fulfilling, you’re probably with the wrong guy.

5. Smart women overthink it.

All women are master overthinkers; smart women just have extra brainpower to burn on it. So they’re experts at twisting themselves into knots of doubt, indecision and self-sabotage. “Does he like me? What does he really think about me? What does he think I think about him? And what do I think he thinks I think about him?”

Stop. Simplify. Did you enjoy his company? Then see him again and see what happens. Otherwise, don’t.

6. Smart women underplay their feminine charms.

Newsflash from the cosmos: masculine things gravitate towards feminine things. So if you want more masculine things (e.g. guys) in your life, then cultivate your feminine energy. Men are suckers for your sensuality, the swing of your hips, the nape of your neck, the curve of your lips. They absolutely love it when you take pleasure in the physical world through touch, food and sex.

Men also love it when you’re open to needing and receiving their help. They like to feel useful and wanted, even though they know full well that you can open doors and run companies on your own. Receptivity is a quintessential feminine quality, so if you want more good men in your life, be receptive to their offerings.

7. Smart women are waiting for love to show up versus showing up as love.

My friends often ask me at parties to summarize all 280 pages of The Tao of Dating for Women in a sentence.

I do their ADD-addled brains one better by boiling it down to just three words: Be the light.

If you’re embodying joy, compassion and sensuality, telling him how great he is, making him feel like a billion bucks and the conqueror of worlds, you have no competition. Anywhere. Good men will come out of the woodwork to find a goddess like you.

So lead with love. You always possess the power to elevate others, so why wait? Dare to use it now. You’ll never say ‘all the good ones are taken’ again.


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Categories: Dating for Women