Does He Need to Be a Bad Boy to Attract Mrs. Right?

Posted by in dating after divorce, first date success, love after 40 | 2 comments

Have you ever wondered what a guy was thinking after a date? Today’s letter comes from a thoughtful, bright, guy who claims he’s a great catch. Like most of my readers, he’s divorced and frustrated with dating. I think it’s helpful for women to hear what’s going on for men. They get just as frustrated as we do with the confusion and lack of success in finding a special mate. Please read what Les has to say, and feel free to share your thoughts below.

Hi Sandy,

First off I’m a guy. I’m 36, been divorced 6 years, and have 4 kids. I am way over the ex, we are friends and good parents, but that’s it. I am in a strange place. I really enjoy being single. I ride my motorcycle, hang out with my friends, come and go as I please, have crazy fun with the kids… life is great in general. I REALLY want someone to share in the fun, a best friend, a partner. I’m a bit lonely, but not what I would consider desperate. I know I am a great guy, and someone’s perfect catch.

I am a travel nurse so sometimes my job makes a social life hard. I am old and wise enough to be able to “hook up” with any young, vulnerable fluzzy I wanted, but I have no interest in that. I want real. Which leads me to the point.

The “wrong” girl is easy to attract. I could play mind games and attract anyone with a planted perception of someone I wasn’t. I guess my question in a nutshell is “Where are all the good girls?” The ladies. The women of character?

When I find someone I think might be a potential match, I get brushed off and the usual reason is chemistry and attraction. I’m good looking as I have been told by many women. 6’2″ 205 lb., fairly muscular, with a little bit of teddy bear upholstery, but I’m very active, and in great physical condition.

I fall victim to the “nice guy” syndrome. If I act like a thug or a jerk, women want to jump in bed with me. I have experimented with this as a social exercise. I read columns like yours, and hear all these women go on and on about finding Mr. kind hearted. Yet kind hearted gets you curbed as weak, and unattractive.

I have 4 kids and work critical care so it isn’t a lack of take charge, or knowing what I want, and like. I can date a woman for 2 months and be aloof and dismissive, and she will blow my phone up texting, and calling, and want to go out 4 times a week. If I show the least desire to connect, or go deeper, actually be friends, BAM! Dear John letter within a week.

I refuse to compromise who I am. I am strong, competent, confident, and happy. I am also intelligent, flexible, and sensitive. Women over 50 adore me, and try to match me up with their daughters. Who are of course completely uninterested, and evidently not done with the “bad boys.”

My ex-wife is re-married to a really nice guy, and I think she’s happy, but before she re-married she wanted desperately to reunite because she dated for a year or two, and no one was even close to as “whole package”(her words) as I was.

I make crazy good money, I am responsible, stable, and well established, but also have a fun loving, adventurous side. Basically I work hard to play harder. I know there is a great lack of good guys, I listen to the “locker room” talk all the time, and it disgusts me. I’m afraid there is an equally large deficit of good women. Am I just being impatient? 6 years is a long time. Why does “the game” work? Why do women say they hate game players yet that is all they will date?

If I wear my old wedding ring and pretend I’m married, women flock and flirt. If I admit I’m single they scatter like rats from a sinking ship. I hear every single woman say “I want a strong, kind, sensitive guy.” Yet you couldn’t pay them $100 to go out with one? Act an ass, and they won’t leave you alone. Sorry that isn’t me.

How long does it take to find a woman mature enough to recognize that strength and manhood is not defined by boyish bragodocio and false machismo? A real man is not selfish, and knows how to lead while considering their partner, and compromising.

Yet selfish jerks get all the uhm… “action” so to speak. In my experience most women want self absorbed jerks. They eat them up.

How do I attract Mrs. Right? Honesty and openess darn sure doesn’t work. Do I just need to wait until I’m older, and in the age group that is finally mature enough to appreciate a real man and not just a horny boy? The 30s and early 40’s isn’t looking so hot.

My apologies that this is rantish, and ventilatory, I really am a positive guy, and extremely blessed in life. I am usually having so much fun it should be illegal until I think “Wow, I wish I had a significant other to be laughing and screaming this loud with me.” You would think it fairly simple to find someone who wanted to share in that.

I LOVE my life, someone else out there has to feel the same way. You seem wise, mature, and well informed, I really would like your perspective, and perhaps correction.


Dear Les,

Thanks for sharing your dating questions with me. It takes a courage to reach out to a dating coach, so kudos to you. You sound like a guy who’s smart, articulate, fun, and responsible with a great attitude about life. Those are some of the items on my ‘Mr. Right’ list, and I’m sure I speak for tons of women out there who are looking for a guy like you.

Yet, you can’t seem to find a woman to share all of your life’s blessings. I think you hit on a very important dating dilemma – the majority of women want to date a bad boy. And you’re nice guy.

You’re faced with a choice:

Do you act the part of the bad boy (which you have in the past, with great success)?

Or, do you remain the nice guy and possibly stay single for a long time?

I don’t believe in using games and manipulation to snag the woman of your dreams. If she were your special woman, I don’t think she’d want a guy who used trickery and suave macho tactics to win her over.

You say that you can remain aloof for up to two months and then she flees when you become Mr. Nice Guy. Don’t bait and switch a woman. Be yourself. But be careful what you reveal of yourself too early on in the relationship.

You don’t want to appear needy in any way. Sharing and being vulnerable are wonderful character traits. But timing is crucial. Wait until you’re in a committed relationship before revealing too many of your deepest darkest secrets.

While it would be easy to just blame the opposite sex for all your troubles, that wouldn’t improve your dating success. The only person you can improve upon is yourself.

I don’t know you, so I can’t tell you what you may or may not be doing on a date that might be turning women off.

Here are some possibilities:

1) You might be attracting the wrong women. Do you date the same type over and over? Are you clear with the type of woman with whom you would be most compatible?Are you leading with strong physical attraction and going a little mushy in the brain when it comes to choosing a good match? Start by making a list of five things you can’t live without in a woman. Be very focused on that list when sifting and sorting through women. If they don’t make the initial cut, move on and find someone else. Lust can be a deterrent to making good choices. Having your list will cut through the mushy brain syndrome and help you find a better match.

2) You might not be showing your manliness enough.┬áMost women like a manly man. Let’s be clear; there’s a big difference between acting like a bad boy and acting like a nice guy who’s manly. Let’s define manly. This is a guy who takes charge, makes plans, has a sense of purpose and passion, initiates each stage of the initial courtship phase. In the workplace, both women and men are stereotypically ‘manly’ in their pursuit of power, money, and control. But in the dating world, most women and men are happiest in old-fashioned traditional roles. This was a revelation to me as a woman dating again after a 25-year hiatus (marriage).

Neither sex should compromise their personality. What this means is that in the initial stage of dating, a woman who is receptive will attract a man who is an initiator.

I have had many men who defer to me to take charge from the start, such as asking me to call them, leaving the ball in my court as to when to go out, where to go, when to be in touch again. This is a turn off to me and many other women.

If any of what I just wrote above resonates with you, all you need to do is make those few tweaks and you should increase your dating success exponentially.

Deep down, I don’t believe women really like jerks. Some women might be attracted to men who treat them poorly because they themselves have low self-esteem.

But a quality woman who has an intact ego and self-image will be attracted to a good guy like you.

Hold out for the good ones. They are out there. Make sure you are dating online and socializing in places where you might meet a woman who is a right fit for you.

Best of luck, Les. Let me know how it goes…





  1. Thanks Sandy! Very informative. I think my issue may be transitioning too quickly from the initial phase. I don’t think I have an issue being manly. I do have a soft side, I mean C’mon I’m a nurse, but I’m not soft, or weak. I’m a big “teddy bear” looking guy with a beard, and I drive a Chevy Z-71, ride a Harley, and not for the image my grandfather rode Harleys in the 1940s before it was “cool.” I have actually gone on 3 dates with a very nice multiracial woman since I wrote you, and she is fascinating, and beautiful. The whole “Be yourself, but hold back.” thing feels like game playing a bit to me, but I shall defer to your wisdom in this, and see how it goes. I have actually been told by platonic female friends that I may intimidate women sometimes by getting too intellectual.
    Maybe a few pointers on cues from her that’s she ready for transition?

  2. Hey Les,

    Glad you found my response helpful. Like I said, without knowing you, it’s hard for me to know what the exact issues are. As for being yourself but holding back, I’m referring to the heavy stuff, not the wonderful personality stuff. Like dark stories of your past, big illnesses, parent issues, anything that might give her the idea that you’re a burden before she grows to love you.
    A classic story I heard was about a guy whose girlfriend was about $100,000 in debt. She didn’t share that with him until they were dating for 9 months and he was in love with her. He says he would have definitely broken up with her had he known in the early stages of dating. But he listened to her story. Turns out she wasn’t reckless with money. Quite the opposite. She was a kind soul who lent a friend in need a lot of money out of the goodness of her heart. He ended up marrying this woman, but timing was crucial in revealing the hard stuff. Not a game. Just good timing. Got it?
    As for transitioning to the next phase, again, try and take things slowly. She sounds like a quality woman. Escalate the relationship from week to week, seeing her on weekends (which shows that you’re serious), but not being ‘stalkish’ in your contact with her via phone/text, etc. (I’m sure you’re not).
    A woman values a man that she thinks is a catch. Let her know your value by taking your time. Both of you should be sitting in the ‘chooser’ seat. And enjoy the ride! Dating should be a lot of fun.

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