Where Are All the Emotionally Available, Mentally Healthy Men?

A woman thinking

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!!!!!


A very honest letter, Joan, which is particularly timely, given yesterday’s thematically similar posting. 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. Moxie hit it on the head in yesterday’s post that successful, intelligent woman can often 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 ex’s, 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.com, JDate and Nerve. 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 subsecription, 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 in 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.

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  1. 221

    Im an older women in her 40s and I do prefer younger men the ones I’ve seen around my town and beyond my age look so old frumpy unkept and overweight. I do look like u am in my 30s and prefer to date guys in their 30s. No because of health issues long ago I no longer can even have hormonal issues as some men may suggest and I don’t require a lot of maintenance to keep my looks it’s in my genes. I take care of my self I don’t need a man to do that what I had wanted was a partner in crime. Now I have vowed abstinence and sweated off everything I fell for someone hard it took the life out of me cheers to all you still out there trying I’m done. I just wanted to let you men know out here don’t look all frumpy lol and don’t be so shallow and us older women are not hormonal as we at this age are more balance compared to the younger set and we know what we want in life and who we want and we know who we are. We just want to experience things with you!

  2. 222

    Can’t help it women like guys that are somewhat settled down and out of that bad boy stage. I do enjoy spending time with some of the younger generation. I think they appreciate guys that can go with the flow. Enjoy some of the simple things in life. Being a good listener is easy for me. I enjoy being a sounding board for my partner. Sometimes women just need to be heard. Being playful comes easy for a more experienced and wiser guy also. It’s so much easier to be content and I have found women really appreciate that in a guy also.

  3. 223

    Certainly l wanted my ‘ex’ to change, he was a tradie that would come home covered in crap and sit straight on the couch, l never ‘nagged’ but tried to negotiate an alternative arrangement like coming home and jumping straight in the shower to no avail, he just didn’t get ‘the change’ that l wanted, which is often code for grow the F. up,. after 20 years l gave up… He always said to me ‘ tell me what you want me to do because l just don’t know’ l mean seriously l’m not your mother! and this was coming from a kind and loving man, as an earlier post stated, ‘it’s what he DIDN’T do’ .

  4. 224

    I would like be with a older woman because they can teach u an shape you into a better person they can help you get jobs and help you in life I don’t understand why don’t more guys try older women they are way more mature.

    1. 224.1


  5. 225

    I beg to differ, 50yo plus women with great profiles,  qualities & looks, demand a age selection of +2 -10 years seeking men, so by numbers 50 plus average joe men needs to seek older women to have any chance.

  6. 226
    Mature Don Juan

    I am an early 50-something no-kids, never-married bachelor, and look even younger than the OP (I’m eligible to join AARP and when I go beardless, I get asked for my ID to buy beer).   I have a sister that has children.   A woman like the OP cannot give me children, so genetically speaking, I would have more genetic investment with my sister than with an infertile woman like her.

    OK, I could have sex with the OP, but still, it is in my genetic interest to pursue a younger, fertile woman – and as it turns out, evolution has made it such that us men are repelled by the idea of a woman with children not our own, and as well just non-young women in general.   I am an American, but as I am early-retired (easy to do when one only has to spend money on himself), I spend most of time abroad – like many of my countrymen, in places like Eastern Europe, Latin American, Southeast Asia, etc. – where young, childless women are abundant and woman like the OP are considered undatable, as it should be.

  7. 227

    Young women should beware of middle aged men spinning a web of lies to win them over.   They’re not all mature father figures.

    1. 227.1

      Exactly!   The are most likely guys who didn’t get caught in the webs of young women.   Now they are spinning their own webs and hold all the cards.   Now the young and old women want them.   Ah, the mid 30s power flip.   I love nature!

  8. 228

    A single male friend of mine in his mid-fifties only seems to want to date women in their early to mid-forties. He summed it up this way. Women his own age “look older than I feel.” While that may come across as shallow, here is an emotional reality that I did not see mentioned elsewhere. Most healthy, middle-aged men FEEL a lot younger than they actually are. In fact, most are shocked when they see themselves in the mirror. Who the heck is that guy? they wonder. Perhaps many healthy middle-aged women feel the same way. That may explain why many financially independent, fit, and desirable middle-aged women prefer younger men.

  9. 229

    I think Marc Katz’ response was spot on. More than not, single women over 35 develop a sense of entitlement, judgement and expect the world be handed to them by a man (not any man, a man who fits their unrealistic expectations)   . I say this, as a 52 year old woman. I am long divorced. No kids. No relationship in 10 years. Admittedly men do stop looking at you past an age. For me it became obvious mid 40’s. If I am to be honest, I WAS at one time a great catch…but, I screwed up by dating men I knew were not marriage material or even good relationship material. Then I got old.

    The only men Ive encountered who are single, in the last few years, is Bob, a 60 year old, handsome, church going man. Sounds great, except, hes been married/divorced 3x. He will tell you on of his ex wives filed rape charges against him (he says while she was having an affair) and then his daughter (with the same wife) also accused him. He claims they both dropped the charges, and he has court documents stating that, but, he claims, it will never be off his record. Next, he lives with his 90 year old mother, because her house is paid for. She cooks, launders, and pays his car insurance. A married woman hes been hung on since HS, and he had affairs with during all his marriages (which I believe he said caused all his divorces) still buys him cell phones and pays his phone bill. I could go on about men I meet who, like Bob, have similar lives that eliminate them as relationship material. I would say older men who have their act together and find themselves single will have the full spectrum of single women young thru old to choose from. I have my own emotional baggage now, well, because I spent my life dating lots of men and making the same poor choices and causing damage to my mental and spiritual health. I now suffer chronic illness (severe disabling migraines, arthritis) as well as anxiety/traumatic related disorders that pose their own challenges for me and for anyone who dates me. What I look for in a man now? Is he honest with himself about himself? Bob has no idea why he is alone. LOL.

  10. 230

    One other thing I hear from every 35+ single “I look 5 or 10 year younger” My response to you is  “Chances are you dont”

    Further and more damaging, making forthright statements about looking younger than you are….shows you are preoccupied with your age, yet, feel your match should not be.

  11. 231
    Chris St Pierre

    “Every time I hear a woman saying that she ‘intimidates’ men, this is what comes to mind.”   Dead on.   Absolutely.   Women who think of themselves as “intimidating” to men are usually simply unpleasant to be around and they will have not time for you because they are out there proving to the world – and themselves – how great they are.   If they were men, we wouldn’t want to hang around them either.

    1. 231.1

      I find this to be a very combative perspective. Maybe it’s not that they are “unpleasant” to be around, they just may not know how to attract that intial interest because she may not have great communication skills or know how to be open.

      Men and women are not judged by the same standards. Strong men are usually given compliments for their strong, independent demeanors. Women are usually criticized. Which is why male leaders are given props and female leaders are usualling called the “b-word”.

      1. 231.1.1
        Chris St Pierre

        I don’t agree that a woman is labeled by men as a bitch simply because she is a strong leader.   Reference: Indra Nooyi, head of Pepsico; Pat Woertz, head of Archer Daniels Midland ; Madeleine Albright; Oprah; Angela Merkel; Queen Elizabeth; Margaret Thatcher.   I don’t think I have ever heard these female leaders referred to by a male as a bitch.   I think most men respect these women as strong leaders and formidable opponents.   You have to have other negative qualities present to end up with that label as a common occurrence.   Just as bullying, derisive, Machiavellian male leaders end up being referred to as an a-hole – and rightly so – and not looked as positively for their strength.   But, what we’re talking about here are intimate relationships.   What person, male or female, wants an “intimidating” person as a partner?   I certainly don’t, and I bet this is true of most men.

  12. 232

    I’m a 65 year old man and have been looking for a similar age female partner.   But after 2 years, I have decided to give up and will begin a new quest to find a younger non mentally damaged women.

    Ironically on web dating services, I was contacted 9 out of 10 times by women from 30 to 45 that want a relationship with an older stable man.   However, I wanted a same age partner, I did spend some email time trying to learn why they wanted a relationship with an older man, most comments related to instability of their same age available men, they wanted to focus on relationship building with older me and had written of their same age men as viable partners.

    The consistent problem I have run into is that my  same age women have forgotten how to be a life partner to a man and act like competitors or want to dominate the relationship.    Further I am not interested in shoveling your horse stables or clearing the yard every day from your 6 at 90 pound dogs leaving 2 dozen at 2 pound piles all over the place per day.   I’m looking for a relationship with a women and not interested in funding or being stuck with a  massive collection of animals.

    Sorry same age ladies, but that’s not what an older guy wants >> we want a companion and partner to do things together and not dealing with your inability to focus on a new relationship while you are still stuck in your past.   I’ve been OK with some level of overweight for the women as long as they were willing to eat and exercise and burn it off.   But to date, I have not found one single same age over weight female that had any desire to implement a healthy life style.   And stop drinking the wine, all it does is add up to 20 pounds a year of excess sugar to your diet that converts to fat, when you don’t exercise to burn it off.

    And most ironic of all, is that many of the same age women, after a month of discussion with me, have stated that I should look for younger women that have a more flexible attitude towards men.

    Note that my only Must requirement  was to work with me on healthy food choices (organic, non GMO, plenty of minerals, vitamins, etc), and to go walk 4 to 5 times a week.   Everything else wold be done to help each other as required.   I would ask them what they see themselves doing in the next year.   This resulted in “I don’t know, I have not given it any thought”.   Well, why are you even bothering to be on a dating site if you don’t have any future goals.   Why waste your time and the time of the men looking for a female partner if you have no idea what you want with a new relationship.

    Bottom line for me is the same age women (60 to 70) seem to be stuck in their prior lives and do not seem to have the ability to walk away from past life / relationships and start over.   I’m OK with you having kids, but I’m not interested in your children’s problems.    My children are all in their 30’s and working.   They call me once in a while and don’t waste my time, and are off my payroll.   I’m not interested in your 25+ year olds that want to live at home, do nothing, play video games, spend all day glued to their smart phones, and waste our  time.   Kick them out, get over it.

    Somewhat interesting is that the 30 to 45 year old women that I have emailed with point out that their same age men appear to have the same problems I’m experiencing with older women.   I think this is why the younger women are looking for the older men.    Somewhat of an interesting social conundrum.

    30 to 45 year old women cannot find 30 to 45 year old men and looking for older stable men.   An persistent comment from the younger women was that they wanted a man that would treat them as good as their father treated their mother, and they can’t find that with same age men.

    older men have difficulty finding  same age women and give up and start looking for   younger women that want older men.

    When I would meet women in stores / events and talk with them.   I would ask if they have older women friends or family members that might be interesting in dating / creating a new relationship.   What I would often hear from these younger women, is ‘I am single, I can’t find a same age man, I am OK with dating a older man, and I not happy that I am putting on weight and want to learn how to be on a  healthy living diet / live to achieve proper body weight “.   Sadly, I did not pursue them, but will do so in the future.


  13. 233
    Susan Young

    I hear a lot of anger from some of those that have posted. Bob says that no man wants to be romantic with a woman that is fat. Does he think a woman finds a man with a huge stomach romantic? What it comes down to is one needs to find a partner that is similar:   background, weight, finances, age, values etc. Because that person will be able to relate to you and understand your imperfections therefore be empathetic and compassionate. Bob obviously isn’t compassionate. Woman and men are not over weight just because they let themselves go. Some people are stuck on medicines that increase weight for example.

    I think that people place far too much importance on high income and big houses they don’t need. Working for the big bucks just causes a more stressful life and less time with family. Also they place too much emphasis on their partner having a perfect body etc. When you really have chemistry with someone; not just looking for a trophy partner, they are beautiful inside and out. I am personally looking for a man that is similar in age, is stable financially (not loaded), has chemistry, is warm, friendly, affectionate and wants to nurture a relationship. Just an average guy that will value me as much as I value him.

    It is very important to understand what is important to your mate and remember to do it. Otherwise it is all about you and that is what you will end up with in the end- just you.

    1. 233.1

      Yes that’s what you’re looking for now.   But is that what you were looking for at 25?   I will give you the benefit of the doubt but most women aren’t.   They only come to these conclusions once they have no cards left.   The smartest guys will figure this out and just wait till they hold all the cards (later in life.)   Women love to criticise men for what they desire once they aren’t THAT anymore.   Is it any better for a young, beautiful women to desire a rich, powerful man?   Again, I’m not saying this is you, but it seems to be most women.

  14. 234

    Why would any smart, upwardly-mobile guy get serious or marry a woman these days?   There’s too much to risk and it’s not necessary.   Society has gotten so crazy that the smartest guys are opting out.   No marriage, no kids, no charity, no mentoring, no getting involved in politics, etc.   Why take the risk?   Why waste your time?   Work on your education and career.   Travel, buy nice things, have hobbies.   Unfortunately, the people you need engaged the most, are the first to figure out it’s just not worth it.   If you wonder where all the good guys are, this is where their headed…if they’re not already taken.

    1. 234.1
      Karl R

      Tyler said:

      “Why would any smart, upwardly-mobile guy get serious or marry a woman these days?   There’s too much to risk and it’s not necessary.   Society has gotten so crazy that the smartest guys are opting out.”

      Let me unwind this a little….

      You believe you’re a smart guy (and you probably have some evidence backing that up).   You’ve opted out of marriage.   And clearly, all of the rest of use would agree with you … except we’re a little bit slow and dense … compared to you, of course.


      I’m not going to say you’re less than intelligent.   But let me point out, that if you’re beginning a persuasive argument, that’s not the manner which is most likely to bring people around to your way of thinking.   (If you’re just preaching to the choir, it may get a few “Amens!” though.)


      Tyler said:
      “If you wonder where all the good guys are, this is where their headed…”

      And when you’re talking about good guys, you’re clearly referring to yourself.   Right?

      I apologize for rehashing things you’ve said already.   I’m married, so I’m clearly a little slow on the uptake.


      Tyler said:
      “No marriage, no kids, no charity, no mentoring, no getting involved in politics, etc.”

      Um … okaaayyy….

      If you’re trying to convince other people that you’re one of the “good guys” (your choice of words), where does “no charity” fall into that?

      All of the major world religions agree that charity is a good thing.   Same with secular humanism.   Philosophies like Utilitarianism also feel the same way.

      I’m trying to think of a belief system that would equate “uncharitable” with “good,” and the only thing that’s springing to mind is LaVeyan satanism.


      But I’m one of the married guys, so clearly I must have overlooked something.   Please enlighten me.


      Tyler said:

      “Travel, buy nice things, have hobbies.”

      I’ve done most of my traveling since I met my wife.   (With her.   I wasn’t traveling in order to escape her company.)


      If you’re trying to buy happiness, the return-on-investment for “nice things” is terrible.   The happiness from a new thing wears off very, very quickly.   Invest in experiences instead.   They’re an appreciating asset (from a happiness standpoint).

      And when I go on a trip or to a show, attractive companionship often doubles my enjoyment.


      I hate to cut this short, but my wife and I are going out dancing.   (Even the dull, boring, and slightly less intelligent married folks still have hobbies.)


  15. 235

    i think the hub of this, is if your confortable and mortgage free, and can travel or do what you like, as i am. you say whats in it for me? and its difficult to really know why i should take a risk, divorce is terrifying, and i see older women with kids seeking a resource mate firstly and a partner second. so goodbye to that.

    i do give something back, but on my terms, and do give to charity. men and women are predatory to some degrees, and men seek younger women perhaps in a more casual sense, take the lyrics of  Ariana Grande’s new song states   – men are to be discarded, and its only my current turn with this women….and then….Thank you, next –Thank you, next,  Thank you, next –Thank you, next.    

    i wont ever get married, i’d rather be happy. – but good luck to those who believe you will find that rainbow coloured unicorn.

  16. 236
    John Gabriel Otvos

    There was a comment about how shallow men are.  Without blame or shame, our culture has created this dumbed down lack of emotional, intellectual and spiritual situation.  This consumer culture is always trying to sell us something, especially that which there is no need for. Why else would humanity be in the 6th mass extinction?

    One of the things we can do during our brief time here on E-air-th is to learn.  It’s a choice to look at the many sides to questions, topics and POV’s. We put all this data through our filters paying attention to how our intuition and inner feelings take in this information. Or, we can go to the bar, hang out, watch dumb shows and reality TV, rather than create our own rich reality by being present and eschewing boredom.

  17. 237

    I can’t be bothered addressing most of that, but I will say about the ‘I am so amazing that I intimidate men’ thing – you don’t, and we are sick of fucking hearing that tired old nonsense. Women who say that don’t intimidate us, they irritate us. As soon as I hear it I just avoid her.

  18. 238

    Too many women everywhere nowadays with their very high super standards.

  19. 239

    I definitely understand the frustration and hurt out there- and its affected a lot of people. Instead of fighting, though, and attacking each other based on gender and on the worst behaviors of SOME of the opposite sex, l think it would be really great -and potentially healing- to assess our experiences with individuals and try to be supportive of each other. To try to understand and learn from each other. Bitterness and anger are simply signs of having been hurt and I get the impression that everyone here understands what it feels like to be hurt; Lets not become each other’s enemies. Life is so hard for us humans as it is. Keep hanging in there, everyone, I’m sincerely rooting for you ❤

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