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How To Woo A Woman: Stop Thinking And Be The Ball


“You want me to tell my version of the…” “Yeah, you tell your version.”

Thus begins a tale of tragedy. Of cluelessness. Of obliviousness. Of an all-too-familiar trait of men worldwide: painful, horrible naiveté. It starts with that time Nicole Kidman found her way to your apartment with the sole intention of being wooed, and you did not woo. You instead stumbled, bumbled, and fumbled such that she began to doubt your interest in women in general.

Okay, maybe this exact scenario never happened to you. Nicole Kidman never showed up at your apartment. She did, however, show up at Jimmy Fallon’s apartment under a rather thin premise. If only Fallon had heeded the sage advice Ty Webb imparted to Danny Noonan in “Caddyshack” he might have avoided tragedy. But Fallon was not in touch with the unseen force that guides the universe; he was not being the ball. As such, this happened.

While most young men aren’t Jimmy Fallon—which is generally a positive because the world would be a dismal and cacophonous space if the default personality were defined by laughing at one’s jokes before getting to the punchline—many do suffer from his cluelessness. Many in the past suffered from similar cluelessness. Many more will suffer in the future. If only there were simple clues for young men to pick up on, such suffering could be avoided.

Except the clues do tend to be rather simple and obvious. This truth doesn’t matter, because men are generally blind to even the most glaring of invitations. If women were men, they’d hire those dudes who guide airplanes into the gate to guide men into the…you get what I’m saying. But they don’t hire those dudes, so the young men are left with little choice but to stare down the young women—young women who really want nothing more than to be lead in the oldest of dances—and instead awkwardly offer up cold brie and saltines.

Start By Shutting Up

As a former young man whose specialty way, way, way back in the day was talking his way out of bedrooms, I am wholly sympathetic to this predilection. To my credit, I was less oblivious to opportunity. I was deft at recognizing opportunity. My stumbling block was with accepting that with great opportunity comes great responsibility—the responsibility to sweep her off her feet and carry her away. Or at least make a move without first asking permission.

But we were taught to politely ask permission; to ensure that the young woman we happened to find ourselves with was cool with us gingerly leaning in for a kiss. (Pro tip: If you’re in a situation in which petting of the light to heavy variety seems natural, she’s cool with light to heavy petting. If you don’t believe me, bust out the love contract so she can call an audible, magically produce a previously unmentioned boyfriend, and ask you to leave.)

To be fair, it’s not totally our fault. Roger Scruton elaborates:

Beauty can be consoling, disturbing, sacred, profane; it can be exhilarating, appealing, inspiring, chilling. It can affect us in an unlimited variety of ways. Yet it is never viewed with indifference: beauty demands to be noticed; it speaks to us directly like the voice of an intimate friend. If there are people who are indifferent to beauty, then it is surely because they do not perceive it.

Ahh yes, beauty. We cannot help but notice it, even if we get exhilarated to the point of being chilled. So excited that the only choice is to hide it. Too frightened to make a move lest we give the girl an opportunity to say, “Hey, I like that.” It’s much safer to continue not being romantically involved with one another. For if there is one thing we know for sure, it is that that young woman is not interested in us. No matter how she leans in, twirls her hair, puts up with brie and saltines.

Wooing Isn’t About Knocking Boots

This isn’t about sex. Well, it is, but not just about sex and it’s not about having sex with your crush tonight. Probably. You may currently be on the cusp, so I’m not going to feign clairvoyance and take any option off the table. But that’s not the thrust of the argument. (Phrasing.) We’re here to discuss extra time and her kiss. Sex will come later. The whole process could take years, depending on the styles and preferences of you and the woman you’re wooing. So it could also come sooner. (Again.)

Don’t be too polite. Be a little wry.

Setting aside religious beliefs and how we apply them, men of the modern world are most simply divided into two types: The natural born Cyranos and the De Guiches. This divide went out for a road trip back when the cool thing to be outraged over was street harassment. Perhaps you remember it. A modern-day Helen of Troy, to switch allusions, took to the streets of Manhattan to raise awareness about the issue. While she failed to launch 1,000 ships, she did launch roughly 102 attempts at conversation, five minutes of creeping, and countless discussions.

It was an offensive, racist good time that mostly proved that men are simply horrible at offering compliments. At least the men in the video tried. Of course, trying and doing a craptastic job isn’t the same as avoiding the naiveté we’ve been discussing. It’s Jay playing forceful wing for Silent Bob-level naiveté, which is possibly worse, full of sound and fury, signifying nothing. No, you have to actually offer something, show a modicum of class, and be a tad polite.

But don’t be too polite. Be a little wry. Make her smile, but never tell her to smile. Remember Webb’s advice. Remember Edmund Burke and “The Character of a Fine Gentleman.”

It is almost impossible for any man to be a fine Gentleman, who has not courage. But as such a Character is not ostentatious or affected, it is equally Essential to it to conceal this Quality. It is only to appear in a composure, formed by a confidence a man finds in himself, that he is able to prevent being disturbed in his own Course by the insolence or brutality of others. The whole Circle of Taste must be open to him; but the affected parts, the Cant of a dealer in pictures, or the Chimeras of a Virtuoso never make their appearance. Such a Character goes through Life with great Smoothness. He is praised by everybody; respected, esteemed, courted, and everything but really Loved. I am not sure as to this last point; for he receives all the marks of Love, except the disagreeable one[s] that arise in Close intimacies, when men are undisguised and unrestrained, and give their Tempers a loose in all humours.

Be composed and confident. Be open to a variety of tastes, if perhaps not brie and saltines. Be respectable and courted. Do not give your tempers a loose. Do this and you too can avoid the pitfalls of naiveté and find love. But don’t forget to listen to Saint Augustine standing on your shoulder, whispering in your ear. As Burke continued:

To be libertine in his practices and opinions is another part of his Character; but he is not a debauchee; ‘tis only so much as it may make him entirely a man of the world. In point of Gallantry he is no way scrupulous. The greatest liberty in his actions, and the greatest decency in his discourse are his Character in that point.

Ahhh, yes. Lord, let us be libertine, but only in moderation. Let us not be scrupulous in our gallantry, but let us be gallant. And, for the love of Pete, allow me to again remind you to never tell a girl to smile.

Give Her a Reason to Smile

Recently, I was walking to my car in a thunderstorm of biblical proportion. Although I was carrying a giant umbrella, it was useless against the winds whipping the waters beneath its edges. It was even more useless against the small lake through which I was trudging. While trudging, I encountered a young woman, one not hard on the eyes, heading in the same direction.

The only recourse is for men to always be open to the possibilities, always risk being a little bit libertine if not licentious.

We arrived at our cars, which turned out to be parked alongside one another. Except we were parked in opposite directions; our driver’s side doors aligned. I paused in a moment of scrupulous gallantry so she could get into her car, and out of the rain, first. While paused, I noticed she was wearing wedges, thus keeping her somewhat elevated above the puddles.

“I should have worn my wedges today. My feet would be much dryer right now.”

She smiled.

In the grand scheme of things, we men are always going to be naïve. Our strength is not in discerning the subtlest of subtle clues. Even if girls were to adopt my idea and hire ramp agents to guide men in, a not-insignificant number would miss the message. The girls could go so far as to hire skywriters to lead men to them and the ramp agents—and a not insignificant number would still miss the message.

The only recourse is for men to always be open to the possibilities, always risk being a little bit libertine if not licentious. And when Nicole Kidman arrives at our front door, we must greet her with more than brie and saltines, with more than awkwardness and video games. We must take the lead. Well, not me. I’m married. Me winning isn’t. You do. And the first step for you is to stop thinking, let things happen, and be the ball.

(So are we not doing phrasing anymore?)