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I’m a 42 year old single mom who is very attractive (I look about 7 years younger), fun, has a great smile and laugh (and does both a LOT), emotionally stable, and not looking to race to the altar. And I definitely fit the definition of a “cool chick” – and my guy friends will confirm:-).”

Unfortunately, the pool of men that I’m dating from (early to mid 40s, usually divorced) are pretty messed up. A number of them want younger women (never mind that I look much younger) – didn’t anyone tell these guys that women hit their sexual prime over 40:-)?

I’m besieged by the 50+ set even though our lives are completely different (like my kids are young and theirs are grown and they don’t want anymore). A number of gentlemen I’ve met shouldn’t have been dating at all because they are still grieving. And the most surprising phenomenon that I’ve witnessed in this pool of men is that being a pretty, happy, vivacious “cool chick” is a big negative strike against me. I’m amazed at how many of them fall for the psycho Bs and drama queens.

My last (short-term – I can’t find one healthy enough to become long term!) boyfriend told me I was the first mentally healthy woman he dated in 3 years. But although I had everything he wanted in a woman, he didn’t feel any “chemistry” for me – so he went back to a younger woman who had serious enough issues that she lost custody of her kids. And he is not the only guy I’ve encountered like this. Another date, who didn’t feel chemistry with me but we became friends, I’ve watched him fall for all the women who don’t want to give him the time of day. He gets his butt kicked time and again and then cries on my shoulder.

I’ve tried all the big dating websites and I go out a lot (that is another weird phenomenon – men my age sit home on the weekends and don’t go out and do anything so I never meet anyone by just going out and having fun). So Evan where can I find the emotionally available mentally healthy men who will appreciate a woman like me? Thanks!!!!!

Joan

A very honest letter, Joan. I anticipate that you speak for a lot of readers out there – quality woman who are frustrated at their ability to meet quality men. I can tell, from your tone, that you’re speaking your truth, based on your experience, and I would never attempt to negate it. However, I would like to expand on your truth. Maybe put it into a different perspective.

If we take everything you wrote at simply face value, you’re pretty close to the perfect woman. Young for your age, emotionally stable, cool, etc. This is good news. Now, by your estimation, there are no men out there who are either a) interested or b) qualified for a long-term relationship. Let’s analyze both of those things. And let’s delve into the assertion that “being a pretty, happy, vivacious ‘cool chick’ is a big negative strike against you. Because that’s simply untrue.

What is true is that your options are unfairly limited. This is a dilemma that faces any woman on the far side of 35. Your value goes up – your self-awareness, your experience, your wisdom, your sex drive, your income – and yet, to men, your value goes down. And the main reasons it goes down are because he wants to have kids or because he’s still a slave to the Maxim aesthetic. One reason that women rarely want to consider (and I’m not necessarily applying this to you, Joan), is that with their experience comes a darker lining. As fellow coaches and bloggers have pointed out, sometimes successful, intelligent women can also be anxious, self-righteous, negative, and entitled. These are not the adjectives women use to describe themselves; these are the adjectives that men often use to describe you based on their own dating experiences.

A relevant aside: Last year, it dawned on me that for every “crazy girl” dating story I had, there was a woman on the other end who was telling her own version of the story, except that in her version, she’s the heroine and I’m the bad guy. We all have myopia when it comes to dating. It’s much easier to find fault in others than it is to find it in ourselves. Studies have shown that people in couples overestimate what they bring to relationships – their generosity, their emotional availability – because they are exclusively inside their own heads. We remember our good deeds more than others’ good deeds. We don’t keep track of how many times our partner kept his/her mouth shut for the sake of harmony. But our partner does. Each of us thinks we’re the martyr.

So am I saying that you, Joan, are anxious and negative? Not at all. What I am saying is that you’re only seeing things from your own perspective. Which is limited. If you’ve gone out with a handful of guys who ended up with drama queens, that brings up a very obvious question: why would any man prefer a drama queen over you? If you think it’s because men like drama, I’ll have to respectfully disagree. I wrote about this in Why You’re Still Single. Once a man reaches a certain age, he prefers easy relationships. When we’re younger, we may tolerate craziness, just because we’re lonely or desperate for sex. But as we mature and value ourselves, we tend to court what makes sense for us in the long term. I’m not suggesting that the drama queens make sense to your exes, per se. I am challenging you to consider why he’d choose them over you at all. We’re largely rational beings. There has to be some reason, right?

I was on a plane two days ago and found myself seated next to an attractive and wealthy 59-year-old man. We got to talking and I learned that, not surprisingly, he had a predilection for younger women. In addition to the obvious physical attraction reasons, this man emphasized that it was so much EASIER to go out with a younger woman who has not yet been scarred by life. Someone who is up for anything. Someone who doesn’t judge. Someone who doesn’t tell you how to act. Keep in mind if you’re reading this that a younger woman doesn’t have to be a sycophant or a brainless chimp (although some insecure men are just fine with that). But for the men you’re interested in, the younger woman just has to be open and fun and easy to get along with. This is one of the things that women often ignore when they question the tastes of men. Every time I hear a woman saying that she “intimidates” men, this is what comes to mind. First of all, you don’t want to be with a man who is intimidated by you. Second of all, the greater likelihood is that not that he’s intimidated, but that he doesn’t want to be challenged by you on every little matter. This doesn’t mean he wants you to “dumb it down.” It means he wants you to “take it easy.”

That said, men ARE impossibly shallow. I struggle with it in my coaching every day. Clients who tell me, as they show me their lists of hot, underaged favorites, “I can’t help what I’m attracted to”. Yeah. There’s not much we can do about that. It’s why the 50+ set is interested in you. Just know that there ARE men out there who are looking for peers. My 60-year-old Mom married a 60-year-old guy. I’ve had single parent clients find the love of their lives on Match, JDate and every dating app. It happens all the time.

But one thing I’ve learned from years of dating and dating coaching is that there’s nothing to learn when placing the blame squarely on everybody else. I hear your pain in your email, Joan. It’s frustrating out there. I completely agree. But I assume your question was not simply looking for validation: “You’re perfect. Men suck. Don’t change.” A question seeks an answer. And if you’re not arriving at the answers yourself, it’s useful to get another perspective. In this case, a male perspective.

Listen, if you’re dating online with a great profile, great photos, healthy flirting technique, and a long-term subscription, great. If you’re going out and doing things you love and putting yourself in the position to meet like-minded men, great. If you’re still finding that there isn’t one quality man in the world who wants a quality woman like you, I have to question something. There are quality men out there – even if they’re few and far between. Most of them want to date someone younger – because they can. But if you are all the things you say you are, I have no doubt that some quality single dad is going to grab you and never let you go.

Just don’t make the mistake of assuming that there are no emotionally available men, that men prefer drama, or that men don’t want “cool” women. Because that type of false thinking doesn’t lead to anything positive.