9 Brutal Reasons Successful Men Fall For Chaotic Women

The deeper, generational reasons so many men are attracted to women who appear to be so different from them on the surface.

By Mitzi Bockmann — Written on Jun 05, 2023

Photo: calcassa / Shutterstock

When I think about very successful men who I have encountered over the years, they all share a few important personality traits.

Successful men are leaders. They are self-confident. They are intelligent, creative, ambitious and strong.

One other trait that I always associate with successful men is deliberate — that habits and routines are a key part of how they accomplish their goals. It would make sense that a man with these personality traits would be attracted to women with similar constitutions, right?

Well, no.

Interestingly, it often feels like successful men are more likely to fall in love with chaotic women instead of steady ones.

The Oxford Dictionary defines chaotic as “complete disorder and confusion” and/or “behavior so unpredictable as to appear random, owing to great sensitivity to small changes in conditions.”

Keeping this definition in mind, know that I am not talking about a so-called "crazy" woman, one with issues and neuroses, but a woman who is much like the Tasmanian Devil, whirling about, leaving chaos in her wake.

So, why do successful, deliberate, men fall in love with chaotic women? The reasons are numerous.

Here are nine reasons so many men often fall for chaotic women

1. They were raised by chaotic women

Whether we like it or not, we are often attracted to people who are like our parents and men, especially, find themselves in love with people who are like their mothers.

And, for those men whose mothers caused chaos in their childhood, being attracted to a chaotic woman makes sense.

A chaotic mother is one who is highly emotional — and those emotions change on a dime. They are unpredictable, they can be angry and anxious. They don’t create a calm space to raise their kids. Instead, kids with chaotic mothers are raised in an atmosphere where they never know what is going to happen next.

A man who has been raised by a chaotic mother will never be attracted to someone who creates a safe space. They might want to but, subconsciously, they seek an environment like the one they were raised in.

And that environment is exactly what a chaotic woman brings to the table.

2. The desire to fix them

Many sons of chaotic mothers have a tremendous capacity for empathy. They are naturally inclined to be caregivers. They tend to see someone with a broken wing and want to fix them.

And, while this might be an excellent trait for someone to be successful in business, it’s not so much when looking for a stable relationship.

For a man who is in love with a chaotic woman, what they see is a project. Someone who can be fixed. Much like they are able to bring about positive change in the office place, they see a chaotic woman as someone they can tame and make into the ideal mate.

Unfortunately, unless she actively wants to change, a chaotic woman will not do so, no matter how successful her man is.

3. Like wants like

I know that the image of a successful man is someone who is steady and directed and, in many cases, they are.

But there are successful men who got that way because of their own chaotic ways.

According to the University of the People, men who thrive in chaos “are outside-of-the-box thinkers and often produce the most original and creative ideas, and their superior energy means that they can achieve more and work harder and faster than others.” Richard Branson, Jamie Oliver, and Leonardo Da Vinci are examples of successful men who found success amid chaos.

Despite the old notion that opposites attract, Indianapolis-based social psychologist Justin Lehmiller, who is a research fellow at the Kinsey Institute and author of Tell Me What You Want, says "People naturally gravitate toward people who are familiar, even though the whole process is likely subconscious."

So, one reason successful men fall in love with chaotic women is that they might be chaotic themselves.

4. Distraction

The lives of successful men are often pretty habitual. Every day looks much like the next. People around them treat them the way they think they deserve to be treated. It’s all great but it’s pretty humdrum.

Imagine your first date with a chaotic woman. They most likely showed up late, maybe really late, perhaps dressed like a gypsy. They want to show you something on their phone and they realized they left it at home. You suggest going to a bar after dinner and they take you to a speakeasy where they drink martinis and flirt with you, and everyone else at the bar. They call you the next morning and ask you out, or tell you that they are engaged to someone else.

Chaotic women are ever entertaining, in both good and bad ways, and can provide a very fun distraction from the everyday routine and boredom of the life of a successful man.

5. The excitement

Chaotic women are never boring. And it is rare that a successful man who wants someone who is boring.

Howie Blaustein, a 36-year-old New York lawyer, tells the New York Times that “even a simple dinner becomes a game of conversational chess, without all the pieces. Normal women tell you about their day. Crazy women spin fantastical tales or blurt out cryptic nonsequiturs. They're like a puzzle. You’re always trying to figure them out.''

Successful men thrive on the new and exciting and often choose the thing that is extreme over the thing that is simple. When it comes to dating, they can look outside of themselves and find a chaotic woman who can bring them the excitement that they crave.

6. To hide from their own issues

We all struggle with issues in our lives. Whether they are born from our childhood, our traumas or something else, we all have broken parts of us that would be best served dealt with.

When they get involved with a woman who is all over the place, who is exciting and unpredictable and ever-changing, men can lose the bandwidth to deal with those issues.

Instead of focusing on themselves, they spend their time trying to manage the whirling dervish that is their woman and therefore don’t need to dig deep into what they might be dealing with.

Even more, if a man has a chaotic woman by his side, it’s very easy to blame anything that he might be struggling with on her and how difficult she can be to manage.

7. Commitment issues

Many successful men have commitment issues.

Whether they stem from their own childhood chaos, their fear of giving themselves to someone else completely, or their discomfort of not having options or needing to change for someone else, many successful men go out of their way to not commit.

Chaotic women are the perfect dates for men who have commitment issues.

Why? Because men can explain their lack of commitment to that chaotic woman. That a chaotic woman’s wildness, her unpredictability, and her need for drama are all things that no one would want in a lifelong partner. They might love them but they will never marry them.

So, they don’t have to commit and it’s not their fault! After all, no one can blame them for that!

8. The challenge

According to Dr. Herb Goldberg, a psychologist in Los Angeles, has written several books on male psychology including, The Hazards of Being Male. He wrote what men really want, "in his view, is a ''magic lady'' who challenges their limited attention spans. ''Achievement-oriented, aggressive, dominant, success-driven males have a very low tolerance for boredom and passivity. The crazy woman keeps them on their toes.''

A chaotic person is someone you can’t pin down. Someone who is unpredictable and fearless and neurotic and sexual. Someone who can be one person one minute and another the next. Someone who can surprise a man who has seen it all.

If there is one thing that any man wants is a woman who keeps him off balance. Who they aren’t always sure of. Who they can chase like a hunter and who they can never capture.

The chase is in a man’s nature and a chaotic woman is exactly the person who can give him that.

9. To be something that they are not

Women process our emotions 24/7. We can talk about them until the cows home and we want to! A chaotic woman especially. It’s not unlike them to jump from one thought or emotion over the course of a single sentence.

Dr. William S. Pollack, a psychologist who teaches at Harvard Medical School and is the author of Real Boys, says ''In extremis, a woman is pure feeling. Very exciting, obsessionally involved, very willing to cry one moment and be funny the next. This is not only attractive to a man because he doesn't have it, but because it's a part of himself he's not.”