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.

7 Dating Lessons for Women In the New Year

dating for modern womenDo you remember that viral graduation speech given by a student to his class where he gave the best advice he’s ever learned in just a few simple steps?

It played everywhere and it was even turned into a song. Many versions were born from it. 

But ultimately the idea was that it was just some good, simple advice: reminders about living according to the things that are important to us, as we often forget what they really are along the way.

So when it comes to dating in the new year, I’ve thought of how many of us will be embarking on this new journey of love, dating and relationships and all the joy, heartbreak, frustration and just “meh…” that comes in between.

I’m proud to say I’ve graduated from MANY of these painful cycles. But I’ve said this before and I’ll say it again… at the end of the day, I still think of myself as a student first, a teacher second. And really, it’s more fun being a student, if for nothing else than the crazy drama and the volatile 90210 moments that abound!

Before digging in, I think it’s fair to say we’re all graduates.

We’ve all graduated from a tough economic year in our lives. We’ve all graduated from a life filled with heartbreak and disappointment, inspiration and indomitable faith, working harder than ever, only to find that success is still not enough. And of course, we’ve all graduated from having it all and losing it all – and now, here we stand, with another year behind us.

Another year wiser, another year of experiences and perspectives, ready to face the new, the unknown. The New Year.

So I want to take this moment to share a few of my own words of wisdom as we kick off the new year and pause to reflect on what we hope to gain from what’s to come.

This is where you’re supposed to imagine some graduation music, playing triumphantly in the background…. (and here’s a link to help with that: http://www.youtube.com/watch?v=0HDM3eYp4KQ  )


STEP 1: Just like a new year’s resolution puts you in a reflective mood, always take time to know who you’re dating.

When you don’t get to know him – or he doesn’t have the privilege of getting to know you – then you leave behind a golden opportunity to find the love of your life or better still, to learn a new lesson about yourself…because very often, we learn the most about ourselves thru others. And if you don’t know yourself then chances are, he doesn’t either.

But hey, at least you’ll have found a good friend… maybe?


STEP 2: Try to charm the poor bloke, at least a little bit?

Too many women (AHEM… city girls…) are so used to being hit on and getting wined and dined while the investment banker of the month is blabbing on about how awesome he is because of this deal and that – but wait a tick.

There’s a girl on the other side of this table that’s just as awesome as he is, inside and out. Unfortunately, in this crazy dating world she’s forgotten how to talk about herself beyond the superficial “I went to the gym, I got some coffee, and I hate Lady Gaga right now.”

It means opening your mouth more, and making it talk about the many things you have going in your life and the conversationally elusive WHY it’s important to you.

Pretty soon, he’ll shut up. And if he doesn’t like it, find the guy right behind him that does want to know more about you… and he’ll be taken in by you before he even notices your spectacular C-cups.

No, it’s not love, but it’s a START.


STEP 3: Take it one day at a time.

If it’s going to happen, he’ll make it happen. If it’s not going to happen, he’ll do nothing about it. If you’re having fun, keep going. And if you’re not having fun, try laughing at him a little.

You’re only as limited as your imagination…especially if you’re imagining junk punching him. But you probably want that part to stay in your head so another girl has a chance to laugh at him and maybe someday, to laugh with him.


STEP 4: There are the assholes and then there are the nice guys.

If that’s all you date, you’re insecure. Yea, they are too, but real human beings have strengths and weaknesses and normal people that are really honest with themselves will recognize it’s healthy in other people too. And most importantly, it’s desirable.

Because if you can’t be real at times… if you can’t drop the need to seem perfect around him, or he’s a meathead jock right out of the Jersey Shore who sees your tears as a sign of weakness, or he’s so nice that you’re afraid to laugh when he farts loudly, then don’t just walk away… run!

And start back at Step 1.


STEP 5: You know it’s coming (that’s what she said)… but, love yourself.

Love yourself enough to keep dating new people, even though you told yourself on the last date that it’s all a waste of time. Love yourself enough to stop dating if you feel like you’re breaking his heart only because your heart was broken before.

And love yourself enough that you can actually believe it when he says that your eyes sparkle bright, like two Pikachus battling it out with a mighty Volt Tackle. (Oh, it’s true girlfriend!)

And if you keep your eyes open, you might learn something about yourself… something new that you can love yourself about. It’ll go into your next date.

And love yourself enough to stop dating if you feel chicks are starting to look mighty good to you about now… unless you have enough love to go around, of course.

The lesson is you have to give back to yourself before you have yourself to give.


STEP 6: Be your sexiest self.

When a girl goes out of her way to look good, or look sexy, it goes without saying he’ll probably be more attracted. But if you’ve done the first 5 steps right, then chances are he already knows how awesome you are on the inside.

And because you made sure he knows what makes you so special, being hot eye-candy won’t work against you. But just remember to take it, as always, one day a time.


STEP 7: Get out there more!

Don’t geek things up by obsessing with endless dating listicles (and by endless, I mean more than 7). Because you can’t meet someone from your couch…unless you’re on those dating sites, I guess. Which in that case, get a profile up and start swiping a few guys!

And who knows, maybe one day you’ll be one of those few lucky women out there with a guy you can “tolerate” this Valentine’s Day.

So Happy New Year to all you lovely ladies!

And remember that as long as you can learn something new, no moment is ever lost in the world of dating and relationships. :-)