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What Dating After 40 Is Like for Men (Advice for Women)

I love men. I’m often asked whether I offer dating and relationship coaching for single men dating after 40. I don’t. But I DO help men by helping women who are dating after 40. (It really is ALL about you, ladies!)





One of the most transformational ways I support women is by helping you better understand GROWNUP men. The vast majority of these guys are not the self-centered, testosterone-led, immature boys you met (and maybe married) in your 20s or 30s. Like you, the men you’re dating have lived and learned. They have matured. (Thank goodness, right?)


If you’ve read 100 Dates and A Wedding, you know that Stephanie talks about men she dated just after her divorce. She relates the good and the bad of the London dating scene. But, this is just one side of the story. What about men? Here are some of their stories of dating after 40; dating that never turned into relationships, this is. (Guys, if you’re reading this…get in touch if you want to share!)


Below are the common types of women single grownup men have told me about.


The Princess

The Princess is confident, well put together, and very attractive. She easily lures in men. She still follows “The Rules” and requires that her man do what she wants when she wants. He needs to make all the right moves. She’s a scorekeeper, and she alone decides when he’s given enough to satisfy her…or when he hasn’t and is history. The Princess has an “I deserve it” attitude and has little or no concern for how she can make the other person happy. She insists he gives and gives with little or no reciprocity; after all, he’s The Man and she’s his prize!


The 18 Year Old  

The 18-year-old dates – sometimes a lot – but she doesn’t have relationships because “she doesn’t want the men who want her, and the men she wants don’t want her.”  She doesn’t know what will make her happy and has not yet learned how to communicate and relate to grownup men. By default, she clings to the same type of guy she wanted in high school or college. He’s often the “Bad Boy” because he excites her.


The nice, relationship-minded men get quickly discarded by the 18-year-old. Try as he might, the 60-year-old fabulous guy can’t measure up to her expectations because she’s looking for a man who doesn’t exist. She gets stuck in affairs with men who never commit, and it’s often the nice guys who are interested in her who bear the brunt of her hurt and anger.


The Scaredy Cat

The Scaredy Cat has been emotionally wounded by men in the past, and she can’t let go of it. She mistrusts men and often blames herself for the rejection she’s felt, believing that she just wasn’t good enough. She says things like “I need him to say he wants a relationship, and then I’ll open up,” or “Once he gets to know me, he probably won’t like me.”


The Scaredy Cat may put her guy through lots of tests before she feels confident that he’s truly interested. When he passes those tests or shows he has feelings for her, she questions it and might up the ante. She picks fights, picks the wrong guys, or maneuvers relationships to end because it gives her control.


This “I’m never going to find a good relationship” gal leaves men unable to get any traction during courting or in a relationship. The wall she has erected is just too high for him to climb in order to get to the other side. Since trust and affection are what men yearn for from women, he usually does her a favor and leaves…hence rendering her “right” once again.


The Wow Me Woman  

The Wow Me Woman is a midlife gal who still thinks that excitement is the key to judging if a guy is a good match.  She’s looking for her guy to be interesting, keep her laughing, ask her all about herself, and give her butterflies…all on the first date. If she’s not swept away, there won’t be a second.


The Wow Me Woman leaves many good men in her dust. Men sense her quick judgment, which leaves them feeling deflated, unattractive and powerless. That man then makes a poor impression (understandably), and the date is chalked up to another “he just wasn’t right for me” experience. The Wow Me Woman is often single for a very, very long time.


The Bitter Gal 

The Bitter Gal is angry — usually about everything, but especially about men. She’ll find fault with every man she meets. A guy never has a chance, even he is the nicest guy in the world and really likes her. (Which usually doesn’t last very long since, no matter how pretty and smart she is, she is no fun to be around.)


The truth is that The Bitter Gal has been playing the victim for most (if not all) of her life. Her life isn’t going the way she wants and she just can’t figure out why. With men, she might complain that they just “don’t get her,” but the truth is that she’s giving them every reason to head for the hills with her off-handed comments and negativity. She hasn’t mastered the life skill of introspection, so she’s blinded by her bitterness. It doesn’t occur to her that she might be the problem even though every date and relationship seems to end the same way. Though a nice guy might try to break through and prove her wrong about men, he will give up out of exhaustion.


The Sexpot  

The Sexpot is all about putting out the sex vibe. She believes her sexuality is the only way she can attract a man, or she wants this point in her life to be a series of sexual experiences. Either way, she’s not connecting with men. She posts a provocative picture on her online dating profile, invites him over to her house on the first date, shows too much skin (especially for a woman over 40), and is overly familiar with her affection.


The Sexpot offers herself up on the first date and is offended if her date doesn’t partake. Men who are looking just for sex will say yes. Relationship-minded men may also say “yes” even though they may feel somewhat emasculated or turned off by her aggressiveness. (They are men, after all.) She won’t get a call from either of these guys and forever wonder why since she thinks she gave him what he wants.


You know that dating after 40 (or at any stage of life, for that matter!) is not exactly a rose garden every moment. When you appreciate the same is true for the men you date, it will go a long way toward building compassion and, in turn, building relationships.


Oh, and girlfriend, you can learn a TON of really brilliant things AND some that will drive you to drink from the comments men have left below.


And, hey ladies…I want to know what you think! Which of the Femitypes do YOU see in YOURSELF?


#love #datingtips #humanconnections #matchmakinginlondon #introductionagency

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