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IN THIS EDITION: We all know you're not supposed to look needy and clingy. That doesn't work. So how can some guys succeed at being persistent with women who aren't initially so into them?
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HERE ARE THE TWO BIGGEST QUESTIONS I'M ASKED NOWADAYS
"What is THE best, most original and PROVEN way to approach women in the real world right here, and right now in 2026?"
How To Approach And Meet Women In 2026
"What do I need to know (or else) about how AI is affecting all things related to women and dating?"
Get Up To Speed With AI...In One Easy Audio
Obviously, there are tons of other questions I can answer as well, As always, you can hit "reply" and ask away.
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QUESTION FROM A READER
Hey Scot,
I have been getting your newsletters for a while, and I had the pleasure and benefit of a couple of phone coaching sessions. You talk a lot about being a chooser as opposed to being a chaser. That makes perfect sense to me.
But there is another concept that also makes a lot of sense to me, and this is the concept of being PERSISTENT.
Example: Woman goes on date with Man. Woman thinks Man is "nice" but well, she isn't too excited about him.
Man is persistent though, and then thanks to his persistence, they end up going on a second date, a third date, and so on, until Woman develops real feelings for Man.
Then Man proposes to Woman for marriage and Woman giddily accepts.
Didn't the guy "chase" her though?
So my dilemma is that the concept of being a chooser seems to go against, as I am understanding it, the concept of being persistent when we meet that woman who is really special.
And even when it comes to being persistent--how does one be persistent without coming across as a stalker or being a pest?
One could say that it's all about making a strong impression in the beginning, but what if for whatever reason that doesn't happen?
I am wondering all this because I've met a lot of women this past year. There were maybe two women in particular who each seemed like she could be really special, but I wasn't really able to spark attraction in the 90 minutes we met for drinks (as I was in other women I wasn't as excited about).
I came across as a good guy but that was it. And in this day of short attention spans and women insisting on "instant chemistry", it does seem that doing that usually won't cut it when it comes to getting a second date.
And needless to say, I never ended up getting together again with these women.
So yeah, I do find myself thinking about these "near-misses" and "what-could-have-beens".
What if I was more persistent? And would have there been a way for me to have been more persistent without being a pest/coming across as a stalker?
Anyway, thanks for reading.
Mike (Paradise Valley, AZ)
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Hello Mike. It's good to hear from you.
This is a great topic. And it's a tricky one, isn't it?
After all, isn't it a solid example of chasing vs. choosing when we continue to pursue a woman who doesn't seem all that interested at first?
Maybe or maybe not, as I see it.
Amazingly, the truth of the matter, essentially, is that you really CAN still be "selecting" even as you assert your will for a woman to be in your life.
How so? Well, whereas "chasing" is rooted in desperation and fear of loss, "choosing" in this instance is more a matter of knowing what you want and going after it, failure not being an option.
Since women do tend to follow a man's lead, the strategy CAN actually prove successful.
The case of Michael Jordan's courtship with his first wife is a famous example, as she was famously reticent to date an NBA player at first.
The marriage ultimately ended in failure in the form of divorce years later, so "success" here is indeed a relative concept, as it so often is.
Nevertheless, when it does indeed work to be persistent with a woman who isn't initially so into you, it's almost always because you as a man finally started to demonstrate masculine qualities of leadership and having a clear plan of action.
This definitely involves replacing any "soft", tentative demeanor you may have had at first with a bolder, more directed presence.
It involves stepping up and showing up where you may have only been along for the ride on the first date, maybe in the hopes of "playing it safe" and not offending her.
Certainly, you'll have to go for broke a little more the next time you see her if you want to turn things around.
Obviously there also has to be some sort of real-world chance for that next meeting to happen, which you might be able to finagle via follow-up conversation on the phone, etc.
It's important to understand that the woman has to have at least LIKED you and felt reasonably safe and secure in your presence in order for there to be ANY chance of success...ever.
Pushy, creepy and/or weird guys don't get "do-overs" with women in this life.
Similarly, if you've really managed to get yourself fully banished to the dreaded "just be friends zone" it's highly improbable that you'll ever get the return ticket back into her world.
Truly, she'll have to be the on the fence about you to some degree.
Assuming that's the case, like any true champion you should play to win instead of running "Prevent Defense" as I've written about before.
Bold moves are called for here, although I cannot underscore enough that we're talking about assertiveness rather than aggression.
There's a HUGE difference, and the yardstick by which to measure it is how much her perception of safety and security is taken into consideration.
One important caveat is that executing the strategy I'm talking about here to perfection rather than ruin requires literally more confidence in oneself than the woman has even in herself.
If that sounds a bit esoteric, think about it for a minute and it'll make sense.
That leads to a second, and arguably more significant caveat. If the woman isn't initially attracted to you, your leadership could potentially result in her feeling as if she's settled for you.
You never, ever want a woman to be with you because of personal inability to say "no", which is a costly character flaw.
You certainly also don't want or need a woman in your life who's only there out of a sense of guilt, obligation or even flat-out coercion. Manipulation is ultimately worthless to you in the long run.
I think you can see the fine line there.
If a woman is repulsed by you despite your unrelenting pledges of undying love and associated temper tantrums, that's one thing.
But if she's "undecided" or talks about "taking it slow", then be proactive and bold. Go for what you want.
Similarly, if what's keeping the two of you apart is purely a matter of, say, social politics (e.g. what others might say, her "having been hurt in the past", an unwanted ex who won't go away, etc.) then feel free to lead in that persuasive manner if you innately sense that the two of you should be together.
Be Good,
Scot McKay
X & Y Communications
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