I had the pleasure recently of doing a coaching call with a woman.
Now, before we go into what we discussed — no, this is not something I expect I will be doing on the regular. I’m more open to it than before, and this woman presented a compelling exception. But I still have much work to do with men, and limited time to do even that. Branching out into women is a whole different marketing strategy and even to some extent way of coaching. And I’m not sure I’m interested in going that direction; certainly not now.
That said, it was very interesting to be on the other side of the fence. We were doing one of my classic 3 hour deep dives that I do with every new client. Much was the same. But some things were very different.
You face the same kind of core issues with men and women: self-sabotage, and fear about rejection from the opposite sex. But how this self-sabotage and fear manifests is very different.
So let me tell you about this woman, and the main problems she had.
First, the good. She’s thin and attractive, intelligent, kind, anti-woke, mentally stable, and has great personality and sense of humor. She’s healthy — very much into yoga and clean foods. And she wants to get married and have children.
Now, the bad. She’s in her mid-late 30s. And although she’s been celibate the last couple of years as part of her healing journey, she’s had a very promiscuous past.
Yep, the bad are pretty bad. I know that a lot of guys here wrote her off almost immediately when they read that. The age was bad enough. The promiscuity is the nail in the coffin.
Interesting, isn’t it, the differences between men and women here? Equal issues with fear of rejection from the opposite sex. But while a man would worry about how successful or tall he was, the woman worries about her age and sexual history. Different crosses to bear.
Anyway, I of course don’t blame guys for rejecting her. I even told her as much — a lot of guys will reject you for this. There is nothing you can do about it.
But what I want to explore is: is it impossible for such a girl to find a guy? Or at least, a guy she actually in turn respects and desires?
Because let’s be honest. We know that this woman will have no problem finding *a* guy. Even unattractive women find buyers; attractive ones get them easily, even when they are miserable human beings. The issue when it comes to marriage though is that whatever a woman has been through, she almost always remains picky. In fact, the more a woman’s gone through, often the more picky she becomes (it protects her ego). If she settles, it’s out of desperation. And she hates herself and the man for it.
It’s this variable that I zeroed in on with her. She told me at first that what she wanted was a man who was open and accepting, non-judgmental, not opinionated. I pushed back on this because I didn’t buy it. She also wanted her man to be strong and confident. But how can a man be strong and confident without any conviction in his beliefs or boundaries?
As I suspected, a lot of these superficial checkmarks she had for men were based on her own insecurity around being judged. You see this a lot in feminine circles. Wounded women have a profound fear of being condemned by the masculine. And it’s understandable, because a lot of time these women in fact became wounded because they were condemned in the first place by men unfairly. This mistreatment by men created a rebellion cycle. These women engaged in reckless behavior in response, thinking their libertinism was “freedom.” They emerged from it damaged; a self-fulfilling prophecy.
But the difficulty with this kind of sexual past — which is to me the main issue, because although late in the game, she can still have kids, and there are plenty of eligible men older than her who would be interested — is that she judges herself for it. So is it really accurate to say she wants a non-judgmental, accepting man?
Here’s what I think would happen if she met a guy who really shrugged off her past. Because there are only three types that would fit into this category.
The first is a saintly type of man. A man who has done so much inner work, is so spiritually advanced, that he isn’t triggered, threatened, or disgusted by who she was. He accepts she has evolved outright, and let’s her past go instantly as irrelevant compared to who she is now.
Obviously any woman would love to be with such a man. This guy is basically Jesus! But in practice, few men are here — and more importantly, few men here are single, and would be interested in committing to a woman who was not at that same level of development.
So we can rule this guy out as an improbability.
The second type of guy who shrugged off her past is a predator. I don’t mean that in the criminal sense. But what I mean is this is a guy who doesn’t care about her past because he doesn’t care about her, and has no intentions of actually being with her. He sees her as a slut, and whatever her recent transformation, deep-down sexually open. He wants to get his, even if it means bringing her backwards. There’s no future with this type of guy, because his goals are different than hers. He’ll give her the acceptance she’s looking for, simply to seduce her into spreading it.
And then there is the third type of guy, who is simply weak and unconfident. He “doesn’t care” — because he views the girl as out of his league, and he wants her no matter the baggage she has. On the surface this might seem like a reasonable compromise for the girl to make, but this “acceptance” comes with all sorts of hidden costs. Because whatever he says, such a man really does care about her past — and she can sense it. He’s resentful, insecure, jealous, and also sexually needy. He accepts her sexual past, because he wants her sexual acceptance. The pressure and demands are endless, along with guilt and manipulation. For her, this relationship is just another way of being sexually used by a man — except this time without the freedom.
Which means that if she is to find real love and acceptance in practice, she must first go through the crucible of being judged by a man she cares about. She is going to have to face her own shame — and his. Because of course, when men reject a woman because of her sexual past, it’s not just for objective reasons about her judgment. It’s because a woman’s sexual past triggers his own shame. Shame about measuring up to her past partners; social shame about committing to such a woman, about what it says about himself.
So she is going to have to not only forgive herself, but forgive him. She’ll have to hold space for his negative reaction, and be gracious about it — while also holding fast to her own knowledge and esteem about the changes she’s made, and what she deserves going forward.
This is a tall order for a woman! To fully acknowledge her mistakes, and fully accept the difficulties a guy might have with them. But to also still fully accept herself, and to be willing to let him walk away.
But if she can do this, I don’t think she will have a terribly difficult time getting the kind of relationship she wants from a man. Because she’ll have shown not only in words but in actions, that she really has changed from the kind of woman she was before. And it will be hard for a man not only to feel this and respect it, but to be attracted to her for it.
The problem with most women in this situation is that whatever they say, they haven’t really come to terms with their past. They are afraid of male judgment, and then when it inevitably comes from mistakes they have made, they hypocritically judge the men in turn. This rejection only feeds their long-standing dissociation from intimacy and avoidance of tension with the masculine that got them into the position of being promiscuous to begin with. There is nothing that conveys weakness for a woman more than sleeping around. You don’t have to enforce boundaries when you’re promiscuous. You can tell yourself you’re “doing it for yourself.” But really you’re just giving men — men who don’t deserve it — everything they want from you. Saying no not only to them, but to yourself, is a lot harder to do. But it’s necessary to have self-respect.
Understand, whether a woman is sleeping around or seeking acceptance from men for her failings, it’s the same thing emotionally: she is looking for validation from the opposite sex. A man will rightly discern a woman ashamed of previously being a slut could very easily return to being one. She needs to be OK with herself first. But to truly be OK with herself, she needs to test it by facing the rejection of others. She has to go through it and survive to come to terms with it and really move on. The irony is once she’s done this, she can understand what the man who likes her is going through, and can almost comfort him about it. I’m not saying to go overboard. But to be able to understand his position, and to expect and give him space. This maturity is so rare, it’s enough to make many guys question their knee-jerk reaction of ending things. They’ll probably have more emotions to work through. But they can do it.
So this is coaching for a woman. But what are guys meant to take away from all of this?
Well, it’s not that you should feel shamed or guilt-tripped into accepting women who’ve had a bad sexual past. Not only does guilt not work in creating healthy relationships (you’ll just turn into a liar, aka one of those weak or predatory guys), but you are entitled to a woman without baggage. I don’t blame any man for having a different set of standards, and sticking to them.
But at the same time, there are some hard truths here we need to start talking about.
And that is that, the woman I spoke to is not an anomaly.
There are a lot of women out there today who bought the “casual sex is consequence free” moniker when they were younger, who have been changing with the times, and are otherwise solid women. They want a different life than the one they had before. They want to build a supportive and initiate relationship with a man now, not a superficial and transactional one.
I understand a lot of guys will say, “that’s all well and good — too little too late.”
But I also think it’s worth considering on a case-by-case basis, whether the sum of what is offered by such a woman is really worth passing up. And I say this for two reasons.
First, nobody is perfect. Many guys have their own skeletons; things they are ashamed of about themselves or their past that they can’t change, and that they feel make them less desirable to the opposite sex. The point of this is not to encourage settling, but rather humility and grace. If we want forgiveness and acceptance, we need to be able to offer it in turn. The second we fall into extractive dynamics with the women, the second we fall into power dynamics. And in power dynamics there is never real love. Only leverage.
But second, because if a woman has really processed her past and faced her fear of rejection over it, then in many ways she is closer to being a better girlfriend than a girl with less of a history. She has been tested and overcome; she is more self-aware and more mature. And thus can support and give you more of what you need in a relationship, rather than simply take from you to compensate for her self-loathing.
Unfortunately, most women with a checkered pasts aren’t like this. The damage to their self-worth is too great, and they cocoon up in self-rationalizations. They pretend their actions didn’t have consequences, and that the problem is others focusing on these flaws. They are simply too afraid to grow. This is the most common trajectory: lack of responsibility, and avoiding the kind of interactions with men that will make them face it. Eventually they don’t simply have more challenging odds to get the relationship they want. They have impossible ones.
But we are not talking about those women. We are talking about the ones who genuinely, truly want to heal. Women who have faced their mistakes, or at least are in the process of facing them. These women aren’t stuck in their egos, and they aren’t weak and broken. They’ve confronted themselves, which is extremely difficult to do. It takes great courage and humility to see your dark side, yet move forward with self-acceptance and forgiveness.
The question, however, isn’t what the woman has done. We’re assuming she’s done at least some work. The question is, after she’s forgiven herself, can you forgive her too?
Can you forgive the slut?
I am not telling you to do anything. I am simply posing the question for your consideration.
We are on the brink of a Golden Age. But economic and political reforms are only a small part of what is required to make this happen. The West has been in a psycho-spiritual war the past 60+ years, and our culture has rotted because of it. We have been deceived and manipulated into self-destruction, and are collectively broken and degraded. And the consequences have been that many women who probably would have been normal and healthy in an age with better guardrails, were instead sucked into a different “normal” behavior that was in fact pathological.
In other words, there are a lot of sluts in the west today. A good number of them already want to change. They are, or want to be reformed. And as the culture and consciousness changes, this trickle will become a flood.
Will you be open to one of them, if they were otherwise great relationship material? If — outside of their past, which they had rebuked — they gave you what you wanted in a woman?
This is going to be a dilemma facing guys in the coming years: whether there can be reconciliation between the sexes for all the damage we have done to each other these past decades.
I don’t think everybody will benefit entirely from this reconciliation. There are always casualties of war, and the war of the sexes is no exception. Some will have done too much, gone too far, and they won’t find many willing to take them in afterwords.
But there will have to be some grace given if we are going to make it. There will have to be some acceptance; some letting go of the past. I don’t just say that collectively, but individually. There just aren’t that many virgins out there. There aren’t that many pure girls. Guys get that of course — it’s the foundation of the grievance industry of men on the internet, that “you can’t find a good girl.”
Yet the real point is, are these “stats” what really makes a good girl in this day and age? And when a guy chooses a girl solely on her past versus her maturity, is he making his decision from wisdom, or from ego?
There are always a lot of variables that come into assessing a woman. But the essence of discernment is determining whether the woman in question is looking up or looking down. Whether she has taken that critical first step of self-analysis, self-improvement, and made the decision to change and heal. Or whether she is still in her justifications, her excuses, and her projections.
I can tell you that having worked with over 300+ clients — and heard the stories of thousands of others — I have never seen a relationship fail because of a woman’s past. I have seen relationships fail because the woman couldn’t outgrow her past, or the man couldn’t get over it. But if the woman had firmly moved on, and the man accepted that about her — after the initial processing period of emotional turmoil, it wasn’t only a non-issue. It became a source of strength for them rather than a source of weakness.
Because that’s how it goes with everything in relationships. The more shame you can both transcend, the more free and easy your bond gets. As you both take accountability for your emotions and triggers, you blame each other less. And you love each other more.
Which is why to get to this elevated state, I suggest the following:
Take a woman’s past seriously. But prioritize less the content, than the level of ownership she’s applied to her life. Does she take responsibility for choices? Is she compassionate towards herself and others? And most importantly: is she honest?
Everything flows from this. A woman looking up towards awareness, growth and healing, even if she is starting from a damaged place, has an upward trajectory — and one that is hard to stop. But a woman who is unconscious, or worse yet, self-serving and indifferent about her own actions is a poor investment — even if she hasn’t been through as much or made as many bad decisions yet. She is going downhill. And there are no guarantees she’ll ever change direction.
I’ve been able to predict with startling accuracy for clients which girls would pan out and which ones wouldn’t precisely because I can see which direction a woman’s facing.
But it isn’t always so easy for the layman to tell. They dismiss women with baggage who have turned the corner, while taking too seriously the promises of “good girls” (or not so bad ones) who are claiming this or that noble sentiment or transformation.
I can sniff out this bullshit pretty easily.
But more important than this, is I will teach you to do it too. Anybody can sort through the wheat and the chaff of women. There are teachable signs. But they have to be felt, as much as seen.
Yet as always, the choice is up to you. Maybe you aren’t ready to learn at this level yet. Maybe you need some more pain in your life, some more mistakes and betrayals like so many of those damaged women we like to judge, before you turn the corner, and seek out healing and ascension in this area of your life.
All I can do is present the opportunity to you.
But don’t expect it to be around forever… especially at this price point.
2025 is coming. And with it a very different business, at a very different scale.
– Pat
