Over the years I have worked with a number of women who have been in relationships with so-called ‘Bad Boys.’ Relationships with men of this sort tend to be tumultuous and create a roller coaster of emotions. Unlike rides at the amusement park, however, this roller coaster has a nasty tendency to leave the passenger emotionally bruised and confused.

Recently a journalist asked me why women get into these relationships, or put somewhat differently, what is the attraction of the bad boy?

That’s a good question. After all, developing a solid grasp on what motivates one’s attraction to a particular type of person can be the first step in making changes that lead to healthier choices.

In a moment I will describe some of the reasons women are drawn to these sort of men. But let’s not get the proverbial cart before the horse. First, we need to take a closer look at the variety of fellows that fall into the bad boy category.

The Whitman Sampler ‘Bad Boy’ Variety Pack

1. Tough Guy: the chap with a menacing disregard for social norms and willingness to quickly escalate frustration to hostility, then hostility to threats, and finally threats to aggression. No one is certain what prompts this escalation. Lightning strikes are more predictable than his angry outbursts. But that is part of the appeal.

2.  The Misunderstood Loner: this is the guy who breaks all social norms, and follows his own path even when it leaves a wake of chaos, heartache and ill feelings among those who continue to care about him. His silent brooding presence causes otherwise busy people to stop and ponder what dark secrets must lie hidden below the surface.

3.  The Boy/Man:  in this fellow one finds an irrepressible immaturity that gives him a boyish charm, yet also causes him to be perpetually in trouble for minor legal infractions, or conflicts with the boss, family, friends and just about everyone but his dog (which invariably is a sweet mixed breed with soft brown fur, white chest and feet, wearing a bandanna around its neck).

4. Successful Narcissist: the man about town who assures everyone within ear shot that he is: A. an alpha male (Pro Tip: true alpha males don’t waste energy explicitly proclaiming their alpha status) B. incredibly, unimaginably, even indecently financially well off, and   C. expert at all things, especially those involving sports and women.

He is a rolling stone that trades girlfriends in as though they were last year's model of Porsche. His charm pours forth effortlessly, much like the effluence of a chemical plant run off, but it belies a wasteland of character flaws that is often more toxic.

The Siren Song Of The Bad Boy

So what are the reasons women end up in relationships with these men? Quite a number of possibilities come to mind, but from my experience in working with clients over the years I would say the following five stand out.

ONE: Let's get the easy explanation out of the way first... it was a mistake. An error in judgement. The man was charming, attractive, attentive and my client, seeing the good qualities and not yet knowing of the man's darker side, became involved. Once emotionally invested, and having established a very positive view of the man, she found it difficult to believe that the bad qualities were part of his core character. It just couldn’t be. “Say it ain’t so” whispers the voice in the back of her mind.

Women at this point will often stay involved with the fellow. The man gets a ‘do over.’ Sometimes they will even be able to sweet talk themselves into two or three extra mulligans. Why? Because the sweet and normally rationale woman who he is mistreating is still convinced, at this point in their relationship, that the good is truer to his character than the bad.

When involvement with the bad boy is driven by a rare mistake in judgement, most women eventually come to flip that equation around: the bad is truer to the man’s character than the good. Once that happens, they move on to greener pastures.  

TWO: Some of my clients have a wonderfully confident mindset that is similar to Chip and Joanna when they come across a 'fixer upper.' They see all the potential that can be realized once the problems are resolved. These women view "bad boys" as diamonds in the rough that just need a vigorous polish to smooth out the rough edges.

Once this is accomplished, all of the man’s wonderful qualities are bound to shine through.

Unlike a house in need of renovation, however, these men have a mind of their own. Most are very familiar with women who would like to bring out their finer qualities. They relish the opportunity to engage in that type of struggle wherein they ultimately determine the outcome. Seldom do they allow someone else's belief in them to precipitate positive change: that would be an act of submission. They would be showing weakness by giving in to the will of another individual.

THREE: The third reason some women become involved with these men is that they lack confidence. These women are usually aware of the man's flaws but overlook them believing that it would be difficult to do better. They question whether men without these flaws would really find them of interest.

Enter the bad boy: after one or two relationships with this sort of man the woman becomes even more convinced that she would be foolish to aim higher in setting standards for the sort of man with whom she hopes to have a relationship. Aiming higher, she reasons, would only lead to greater heartache.

FOUR: Less frequent than the preceding three, this next dynamic involves women who have a fear of intimacy. It is not that they consciously select men who are unlikely to form mature relationships, but nevertheless they find in the bad boy a certain a sense of comfort, and fit with their needs. Having a relationship with a "bad boy" is safe inasmuch as it seldom threatens the uncertainties that are attached to intimacy involving deeply rooted commitment.

Unfortunately, this trade off comes with a very heavy price.

FIVE: The last group we look at are those women who feel perpetually anxious. Life seems threatening... and for some, given their circumstances, that perception is correct. They have a strong desire to be with someone who is tough enough to face the world, and punch back when necessary.

In itself that is not a bad quality to look for in a partner or soul mate. In fact it’s a terrific quality. The Bad Boy, however, is the wrong applicant to select for the job. He is primarily interested in punching back at what disturbs him, not what disturbs the woman who has given her heart over to him. 

Selfishness is part of his makeup. It stems from the same sort of deep-rooted insecurities that animate his attempts to control the woman he professes to love. It does not take long before the woman finds herself constantly being questioned and controlled. She cannot spend time with girlfriends without being interrogated. Or, what should have been a romantic stroll in the park leads to heated accusations of a straying heart because she happened to glance at another man, or smile at the teenage boy who worked at the kiosk where they bought ice cream. 

The Dilemma And The Solution

Invariably ‘Bad Boy’ romances turn into dystopic love affairs. The woman who enters such a relationship often feels as though her emotions are bounced around like a ping pong: one week she is hounded at every turn, the next ignored in favor of the Bad Boy’s  friends, or other love interests.

Extricating herself from such a relationship can be difficult. She has begun to know the Bad Boy, seen past the tough guy exterior and glimpsed the frightened man behind the curtain. His hidden yet deep insecurities evoke sympathy from her… even pity. This creates a predicament. To leave someone who is so vulnerable feels like abandonment.

Even so, a woman who finds herself in a relationship with this sort of fellow will do best by making for the exit.... these fellows seldom change. To do so would require him to acknowledge the deficits that exist in his character. Making substantive changes would also require an honest admission, if only to himself, of the insecurities that drive much of his behavior. For the bad boy this type of self-reflection feels overwhelmingly threatening, and consequently change seldom occurs.

What to do then? Paul Simon said it well in 50 Ways To Leave Your Lover:

You just slip out the back, Jack

Make a new plan, Stan

You don’t need to be coy, Roy

Just get yourself free

Hop on the bus, Gus

You don’t need to discuss much

Just drop off the key, Lee

And get yourself free.