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Dealing with Sharp, Quick-Witted Women

wit2One of the coolest parts about being in the business I’m in is that I’ve made lifelong friends with other dating and relationship guru types who I collaborate with.

Even though we all live in different parts of the world, we talk all the time over phone and Skype and we all get together a few times a year to share ideas, etc. Not too long ago I was in Vegas for just such a “mastermind” meeting. And as it turned out, the ideas started flowing even as I was still in the check-in line for the Luxor.

Ahead of me were four guys who, as MTV would say, “appeared to be in their early twenties”. They were pretty fired up, and clearly there for the party. Imagine Hawaiian shirts, flip-flops and beer logos and you’re on the right track. And ahead of THEM in line was a somewhat attractive woman in decidedly more “business casual” attire, carrying a computer bag. One of the four dudes was particularly taken by her, and his other three buddies started encouraging him to strike up a conversation.

There was no wimping out of this one, so sure enough…he tapped her on the shoulder, introduced himself and asked her what she was doing in Vegas.

Not a bad start, by any measure.

Sure enough, the woman wheeled around with a smile, introduced herself and answered the question. As it turned out, she was a badass sales manager from New York City there for her company’s national sales conference. She exuded raw confidence and carried herself with a sense of personal strength that was nothing short of impressive. And above all, she was super-quick with exactly the right words at the right time—and they were almost always wry and witty.

She lived up to the mid-town Manhattan persona in every way. She had made it there, and therefore she could likely make it anywhere. Our hero had bitten off more than he could chew. From the opening salvo onward he grew more and more intimidated and had less and less to say to her. I seriously had to take a step backward in line myself because the guy was literally BACKING OFF from her as the conversation continued. He would have bumped into me had I not given him that extra space.

In his mind, it was clearly as if she was a jaguar in the wild…beautiful to behold, but you’d better be ready to run for your life at any moment. It was at that precise moment that I felt the slightest smile cross my face. She was a dead-ringer for someone I knew in college. Someone I had fond memories of.

Now, it’s not really my style to step in and give unsolicited advice to guys in situations like these…and I didn’t. But I couldn’t help but think how POWERFUL it would be to tell a woman like her something like that.

“You know, you remind me of someone I know”, said with a warm, confident smile. And let’s face it, it’s likely we ALL indeed have known someone like that. And we we’re probably digging her, even if she was a real handful to deal with at times, right? So what’s the magic in saying something like that?

Simply put, it switches the power dynamics of the conversation over to your favor immediately. Suddenly YOU’RE in control of what’s being talked about. Amazingly, no matter how “alpha” the chick is, she’ll probably allow that to happen seamlessly, too. Never mind the honest truth that she probably prefers it that way and was waiting all the while for you to show some social leadership. The more pragmatic factor is that you will have created irresistible intrigue in her, and she’ll be compelled to follow down that trail.

She’ll likely say, “Oh REALLY? What’s she like?”

That’s when you can say something to the effect of, “Well, I don’t REALLY know you yet, so I can’t REALLY tell if you’re like her. But she’s…” Then you’d list the honest positives about the woman you’ve got in your mind’s eye. Just in case I need to spell it out, the elegant beauty of this interaction lies in the fact that you are not paying compliments directly to the sharp-witted woman you’re talking to. You’re talking about SOMEONE ELSE.

This gives the woman the desire to tell you more about herself…probably validating that she is, in fact, like what you guessed she’d be like. After all, you just rattled off a list of POSITIVE traits. At that point she’s selling herself to you, even if in a subtle, conversational way.


Importantly, note that your initial announcement that she reminds you of someone should be UNQUALIFIED. You’re not saying, “Oh…you remind me of someone I’m CRAZY ABOUT”, or “I know someone who’s just like you…awesome and sexy.” That sort of thing would be both needy AND a bit creepy if you ask me. Remember, you DON’T actually know much about her yet. You’d simply let your warm, knowing smile subtly communicate that your thoughts are positive ones. An added bonus there is that your positive vibes make her first impression of you all the better. Negativity and/or stand-offish behavior never work in one’s favor in situations like that…ever.

Anyway…back in line at the Luxor our hero ended up “bonking” at the finish line. He was eventually too tongue-tied in awe of this woman to even ask her for her phone number, let alone suggest that they go gallivanting around Vegas together after hours. That’s really a shame, because in case you didn’t notice he DID approach her pretty effectively and yes…she DID respond in a positive manner. The woman was actually very friendly—just devastatingly sharp as well, that’s all.

Eventually we all got to the head of the line and were directed to one of probably two dozen different check-in counters. As fortune would have it, I ended up right next to the woman who the guys in front of me had been talking to. As we both got our room keys, our eyes met. She smiled.

I said, “That guy between us in line…I think you overwhelmed him a bit, huh?”

“Yeah”, she responded, a bit whimsically. “What’s up with that? I’m just a girl, right? He was kind of cute, too. Oh well…”

All I could say was, “Hey…he’s pretty young. He’ll learn.”

She smiled and nodded, before heading off to her hotel room. Meanwhile, out of the corner of my eye I saw the four guys headed the other way.

Hopefully, what happened in Vegas will stay in Vegas. After all, I’m sure that guy who was in front of me in line doesn’t want it to happen again somewhere else.

==> Check out my latest program here

Be Good,
Scot McKay

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About scott mckay Scot McKay burst onto the men's dating advice scene in 2005 and was selected as a guest for both Doc Love's radio show and David DeAngelo's Interviews With Dating Gurus series within a year. Through a combination of "deserving what you want" and decoding the opposite sex's thought process, Scot talks about how a masculine, confident man of true character and leadership skill is an authentic representation of the man the most desirable women want, obviating the need for tricks and mind games. Check out his website here.

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