Why Women Date Assholes: A Case Study

Why Women Date AssholesJennifer is 24 years old and just moved from her parent’s house.

She’s happily tasting true independence for the first time and loving every minute of it. She goes to the gym regularly, takes yoga classes, reads often, and spends time with her growing circle of friends from work, college and every day encounters.

More and more she’s dating different types of men and while she isn’t looking for a relationship, she’s growing pickier about what she feels the dude needs to bring to the table.

The last guy Jennifer dated long-term was Jake. This was her college sweetheart of 2 years. He was sweet, gentlemanly, affectionate, considerate, attentive and very present. It didn’t work out though because the excitement and passion fizzled and they both grew apart.

Now she wants to try something different!

Because she’s independent, she expects her mate to be the same. A man “in-between jobs” is not acceptable, and the same goes for any man who’s not open minded like her or ambitious and confident about his career. 

So she starts dating Paul and she really likes him. When he first picked her up at a Café local to her job, she fell for him right away. Not only was he handsome, but he had a strong personality, was very outgoing and take charge. He didn’t take no for an answer.

Paul is an entrepreneur that fell into Real Estate and has his “fuck you” money so he doesn’t think twice about telling someone how he really feels- for better or for worse. She finds his brand of honesty refreshing compared with her old sweetheart Jake, who would sooner tell a white lie than to hurt her feelings in the smallest way.

Sure, Paul can be an asshole sometimes, but she feels safe and protected with him when they’re out. Because he won’t stand down from a confrontation and manages to stay cool when things go wrong.

But after dating 3 months, his jealous side grows increasingly unbearable. They fight more and more.

After 2 months of this, the relationship comes to a stand still. And worse, she wants to get closer to him but he’s busier with his career than with her. He grows distant, they snap at each other, resentment grows and she begins to wonder why they’re still together… even though their passion is as strong as it was on the first date.

One day, the relationship finally explodes after an epic fight, and the name calling reaches a point of no return. Paul completely shuts down emotionally and he won’t return her texts or calls anymore. So Jennifer decides he’s just another asshole and moves on.


A month later, Jennifer is dating Doug. He’s the opposite of Paul and is like a breath of fresh air! He’s sweet, laid back, non-possessive and affectionate. He reminds her of her old college sweetheart Jake.  And in fact, after just 2 months of dating, the attraction fizzles… just like it did with Jake.

Ladies, do you see the pattern here yet? Maybe you’ve experienced this first hand?!

Unfortunately, Jennifer doesn’t realize that she’s bouncing back and forth from the “Alpha male” type to the “nice guy” type, because she’s simply avoiding the worst qualities of her last relationship.

While she is attracted to the Alpha male, the passion is eventually overcome by their inability to build a deeper, healthy relationship.

And while she feels connection and intimacy with the nice guy, the relationship fails in the passion department… so Jennifer bounces back and forth, back and forth, over and over again… eventually believing “there is no such thing as a good guy”.

Because to her a good guy is a man that she is attracted to who can also be as emotionally available as the nice guy. The problem with this is that she can’t recognize what she truly wants is a man who is confident… not just a superficial confidence, but the kind of deep confidence in a man that allows him to be open emotionally and still shout “NO!” if he feels like his personal boundaries are being crossed (of course, this assumes he knows who he is and what his boundaries are!).

In short, Jennifer doesn’t KNOW the difference between a confident man and some dude who’s just another asshole.

So what is the difference, you ask?

This often takes the form of the classic “nice guy” versus “jerk” scenario.  And the challenge comes in recognizing not only the patterns of behavior but the motivation behind it.


Let’s take these two extremes and break them down together.

The man who acts like a jerk because “nice guys always finish last” is just as trapped as the guy who was a jerk and decides to be a nice guy. He’s merely trading one prison for another. Either way you cut it, he’s limited in a world that doesn’t allow him to truly be himself.

The nice guy is trying to please everybody so that he doesn’t get rejected. The jerk is rejecting people first and pushing people’s buttons to prove how much he doesn’t care because he doesn’t want to get rejected himself. The jerk fears intimacy. Otherwise, if it truly didn’t matter to him, why would he bother to resist it so much in the first place?

Human connection is not only natural, it’s our default mode. We’re pack animals that survived precisely because we’ve learned to survive together.

Both the jerk and the nice guy are living in reaction to fear, yet both will adamantly state “I am just being myself!” – I can assure you, they are not.

The woman who goes from one extreme of dating a nice guy to the other extreme of dating the modern asshole also begins to feel the frustration of not having the deeper connection along with the passion that she really wants: because he’s not being himself in the first place (and perhaps, neither is she).

True confidence in a man comes down to his being comfortable enough with himself, with who he is and is also mature enough to be vulnerable.

The first half (being himself) is what allows him to set strong boundaries, while the second half (being open and vulnerable) allows him to develop intimacy and connection in his relationships. It’s like a glass of water. It may be fluid and clear, but it can’t be enjoyed without the boundaries of the glass that holds it in the cup. 

The common ancestor in both these qualities is that it comes from a proactive way of being. It’s non-reactionary. It doesn’t revolve around the fear of how others might react to him.

A truly confident man has the freedom to be both the nice guy when appropriate and a jerk, when appropriate. But in both cases, he’s acting from within HIMSELF… and of course his core, his sense of self, beliefs and identity is already pre-defined.

Likewise, a man who chooses to treat people nicely – because that’s how he chooses to live his life, regardless of what people think –  is coming from a place of strength. He’s strong enough not to care if he gets criticized for it and derives personal pleasure from what he believes is doing good.

But if a man can’t stand up for himself and what he wants when it counts – when something is important to him – then he’s still trapped in his way of being. He’s still losing the freedom of not being nice because of his fear of rejection.

And a man who isn’t strong enough to be vulnerable and open, or admit when he’s wrong, is nothing more than a scared little boy.

Being vulnerable demonstrates a significant level of emotional maturity and inner strength. It shows a healthy self-acceptance and self-love. Without this self-acceptance, no love or acceptance is available for her.

Today’s woman wants a man who is truly confident. Superficial strength will always show it’s weaknesses and insecurities over time and she recognizes that no matter how attractive he may seem at first, if he doesn’t have enough inner strength, a healthy long-term relationship is unlikely.

Of course, women aren’t completely innocent when it comes to keeping their guard up! But it takes a much more subtle – and deadly form –with them, which I’ll cover another time.

As you date more and more, keep this in mind and you’ll begin to recognize what true confidence is and begin to grow attracted to a new type of man… a man who’s strong when it comes to issues important to him, but is otherwise sweet-as-pie with you… and it’s not based on outside approval.

In other words, you’ll be attracted to a man who’s truly confident inside and it won’t be because he’s an asshole.

Big goals, I know.

3 Dating Lessons for Men To Be More Attractive NOW!

3 Lessons for MenIf there’s one piece of dating advice for men that’s most universal, it’s this: be more confident!

And if you’re like most men, that only makes you feel even MORE INSECURE than normal. But it’s normal to feel insecure and the truth is, it’s only a piece of the great man-puzzle that is dating a woman.

First, you have to understand why confidence is so universally accepted as an important aspect for attracting women.

Because women want men who can be confident AND vulnerable, be funny AND serious, be adventurous AND her rock of security,  be focused AND in the moment, be passionate AND emotionally stable… and that’s the short list! It seems impossible at first – until you realize that behind all of it is a woman who just wants to feel and she needs your help.

Most men chase the laundry list of what women say they want (i.e. funny, serious, confident, vulnerable, passionate, focused, emotionally even-keeled) in a futile attempt to grab the prize… like a dog chasing its tail… sometimes never realizing that they ARE the prize.

So let’s take confidence and break it down.

To put it bluntly, they want you to be a leader. They want you to lead them to all the emotions they want to feel. BUT… they want you do it in a way that speaks their language.

This one powerful concept is brought to you in 3 simple lessons, in order to immediately improve your dating life.


Lesson #1: Why is leading good?
She WANTS you to succeed stupid!

Let’s be real here.

How many women do you really think go out every night saying to themselves, “Let’s see how many men’s souls we can crush tonight?”

No, it’s not even close to how many you may think.

I’m not saying they’re not out there. There are a handful of true ice queens out there who go out for the sole purpose of shooting down boys for its own sake. It makes them feel better about themselves. 

But those are the rare exceptions.

The misunderstanding is that she doesn’t want to be your mother, or your therapist, or your best friend. She wants to be your WOMAN. And it’s up to you to make her feel like one.

In the end, men and women want the same basic things. Love. Sex. Companionship. Excitement. Intimacy. Vulnerability. Acceptance.

It’s the specifics that have been lost in this age of gender equality. Your generation- our generation of men – is suffering from the delusion that female attraction somehow works exactly the same as a man’s.

We’ve been raised to think that if only we do everything she tells us to, THEN she’s sure to want us, right? You don’t need to be told how wrong that is.

And if you didn’t already know, you’ll find out soon enough.

Lesson #2: You Must Lead By Example…
You can’t REASON women into being attracted to you.

 Before you can learn anything else, you need to understand this. You can’t talk a woman into feeling attraction for you.

This is the biggest mistake you can ever make with a woman, and yet, night after night, MILLIONS OF MEN across the country try to reason women out of their panties.

You see it in clubs and bars, on the street and on the internet… men deluded into thinking that the way to a woman’s heart is through a well-reasoned argument. I call it the “lawyer’s defense.”

They throw around their money.

They throw around their status.

They throw around their huge biceps, hot cars and hipster threads in vain attempts to convince women of their worth in quantifiable, masculine terms.

Does this work sometimes?

Thankfully, it does! Or there wouldn’t be nearly as many people in the world as there are now.

But, like monkeys with typewriters, success seems entirely random, and way outside the control of your average, non-rockstar, non-millionaire guy. After all, it’s called “getting lucky” for a reason, right?

Yes, women are generally wired to seek alpha men or men with alpha-status amongst guys available to them.

But emotionally speaking, being alpha is not an external thing. For women, it’s internal.  

Why do women like to dance so much?

Ask a girl and she’ll tell you. No matter what’s going on in her life, no matter how bad her week was, she can always go to the club, and lose herself entirely to the music. It’s just her and the rhythm of the music washing over her body. And everything else is just… gone. The logical part of her brain shuts down, and she lets herself sense of self go.

Women are attracted to men who can give them these feelings too.

With shockingly few exceptions, women aren’t gold-diggers. They aren’t status-seekers. They aren’t heart-breakers, ice queens, ball-busters, or any of the other things that unsuccessful men call them after a long, hard night of strikeouts. Just like you, they just want to have a good time.

The men who succeed with women know how to engage their feelings, not their mindsSo if you’re not going to try to reason a woman into attraction, what do you do?

Throw away the sales pitch. If you really want to connect with her, you must go there FIRST. Lead her to the emotions you want by connecting to those feelings first and then allow her to follow you.


Once upon a date, Sam was on sharing a cab ride with a girl named Ophelia, but she was acting standoffish. So instead of trying to convince her to open up, Sam opened up to her.

He thought about the positive feelings he wanted them both to connect with and decided that it was affection and warmth – because that’s what he remembered most fondly about the girls he dated before…

And as they’re riding in the cab together, he shared with her the story of Nikki, his last long term relationship.

Sam: The thing about our first date was we got along right away. You could just tell when you’re with someone that you feel totally comfortable with and you’re having a great time.

So that night we had this amazing connection that naturally became physical – and sure enough, we liked each other so much that we continued dating for like a year and a half.

And on our one-year anniversary, I asked her, “you know how I knew that we were gonna get along right away? 

Ophelia: How?

Sam (looking into Ophelia’s eyes): Because you were so affectionate, so open and warm that it just made me WANT to open up to you. And I just knew we’d be together for a very long time.

I LOOOOOOOOVE affectionate girls!


This is way better than just qualifying her with “are you affectionate? Because if you’re not then we can’t hang out, cuz you’re not cool enough for me… NYAH!”

Instead, Sam felt those emotions first and then used what in NLP terms is called process language. He used those details to really immerse both her and himself into the experience.

Speak to her as a woman. Paint a picture with your words. There’s poetry in every woman’s heart. Meet her there… 

And no matter how little money or status they have, notice how artists and musicians have always gotten beautiful, smart and successful women.

Because communicating in powerful feelings is second nature to them.

So one final time, put away the sales pitch. Learn how to engage a woman’s imagination, and her world- as well as other things- will open up to you.

Lesson #3: Being Powerful Is Attractive
It’s no secret women are attracted to confidence but there’s also a psychological reason…

Here’s the last lesson.

We talked about leading by example and bringing her with you on an emotional journey to the positive feelings we all crave.

And while you may never get “rejected” for talking about your poor little kitten named Fluffy that was caught in a tree one time but then got freed and was so extremely happy and grateful and super cute….

Sometimes, you gotta take a little chance.

Don’t get me wrong. It’s great to be in deep rapport. But when it comes to gaining attraction traction, sometimes you’ll need to go further.

This is a moment where you have to put yourself strongly and powerfully on the line by moving in a bolder direction – and where she’s likely to respond in a yes/no fashion within seconds.

The good news is, if you do it right, the answer will be yes most of the time. :-)

What’s the trick?

Understanding that everyone naturally carries some doubt and insecurity to varying degrees. Our mind is always looking for meaning in the noise and make sense of the world. That way we can go about our world “knowing” that we can handle any surprises…

That is, until I come along while you’re on your way to work and smack you upside the head and then gleefully run away.

“WHAT THE HELL? Why… did this happen?!? How can I prevent this from happening again???”

When the brain is seeking answers, it will always create an answer – even if there is no answer.

And THAT is the bottom line, my friend.

Because people want to feel safe, secure, comfortable and protected so they can enjoy life without fear – but women ESPECIALLY value this. And your confidence gives them that.

Your confidence is sexy to them.

Ever hear a girl tell you she wants a tall guy because she can “feel safe in his big, strong arms”? Well, if he’s not confident and you are, she will get that feeling from you and not from him.

Taking this a step further is called the bold approach.

When a person is taken by surprise, the mind goes into a state of confusion – and I bet you didn’t know that in hypnosis, confusion is considered a form of trance-like state. In the face of the unexpected, we drop our guard temporarily and leave space for new information (i.e. you). 

Because it’s unexpected! And a bold, powerful approach does this. 

It’s as if you went into a luxury store and the salesperson immediately walks up to you and says “can I help you?” Almost everyone says no, but it’s purely out of habit. It’s a knee-jerk reaction and sometimes we forget that and have to make a conscious effort to return to the salesperson to ask for help (I know, it’s horrible).

The saddest part is that’s how girls are often reacting too – from all the moments where they’ve had to suffer the cat calls, the comments about how slutty she looks, the stupid and downright stomach turning pick-up lines from guys who seriously have no clue what to do, besides point at her and grunt.

And – big shocker! – she may even say no to that cool, laid-back guy she found really attractive, purely out of habit and then REALLY regret it later on.

The point is a bold confidence allows you to be attractive. It gives her a sense of comfort AND it gives you a chance to interact with her on a more real, genuine level. And the more confident you are, the easier it will be to lead her into those positive experiences.

For some, this is probably stretching you a bit in terms of your current beliefs and experience, but it’s just one of those things you can only believe once you’ve gone through the journey a bit.

Keep in mind, when we say “bold and powerful”… it doesn’t mean you should be jumping at her from behind the bushes, or blasting her eardrums with your new Harley that has red flames on it. Use your head, OK?

Ok. One last example to close this out.


One night, Alex goes out to a really nice salsa club. The dance floor is filled with women, but the walls are packed with clueless men. So, Alex decides he has to get moving quickly. He spots a beautifully dressed girl from behind, who’s sitting with some of her friends. 

Guys are coming up to her, one after the other, and she’s shooting them down like a machine gun of rejection, one by one.

So, he takes the lead.

He goes up to her and places a hand on her shoulder. Looking down he asks, “You don’t want to dance to this song right now, do you?” After turning down a dozen guys in the last 15 minutes, she of course, automatically says no.

Then after a brief pause, he smiles and nods saying, “But we should dance to the next one, right?”

She didn’t expect to agree with him by saying no. And while she’s thinking about that, Alex is already asking her for the next dance and nodding his head.

Afer a moment, she breaks into a smile. “You’re alright,” she says… and as the curiosity grows inside her, she can’t help asking him, “what’s your name?”


So, what’s the lesson here? Be the man. Surprise her with a bold approach, and confidently take the lead.


Because she wants you to succeed, stupid!