My Midlife Crisis (And Your Most Important Question About Understanding Men!)

young sweet couple kissing in the garden

I have something to confess:

I’ve been struggling recently.

My struggles are probably different than yours, but they’re real nonetheless.

I wouldn’t say I’m in a midlife crisis, per se. I’m happily married. I’m crazy about my kids. I have a healthy work/life balance.

In fact, most of my anxieties stem from my career as a dating coach.

“What is this all for?”
“Am I doing exactly what I want to be doing?”
“How can I do this better?”
“How can I reach more women?”
“How can feel more connected with my community?”

Believe it or not, these are serious existential dilemmas. And when I look around at some other coaches with their Bali retreats and their book tours, I have to admit, I get a little envious. I am an extrovert who leads an introverted life, and it’s been a great source of frustration to me for many years.

For over a decade, I have worked over the phone with a handful of women.

While I’d like to think I have a grasp on women’s needs after listening to you for 12 years, I’m humble enough to realize there must be SOMETHING I’m missing.

Even as my knowledge grew, even as my status grew, even as my practice grew, it has always bothered me that I didn’t feel more connected to my clients.

The worst part was that there was nothing anyone else could do about it.

I had to do something different to get a different result.

That was scary and daunting.

For the past year, I have been working on reinventing my entire business, with the purpose of offering better coaching at a more affordable rate.

Something easy.
Something fun.
Something comprehensive.
Something that gets results fast.

I read books. I watched other coaches’ video programs. I took reams of notes. I reached out to mentors who kindly explained how to run a business that made me feel more connected AND served women more effectively.

I’ll admit: I was thrilled with all my progress. Then it dawned upon me:

Who did I forget to ask for feedback?


And while I’d like to think I have a grasp on women’s needs after listening to you for 12 years, I’m humble enough to realize there must be SOMETHING I’m missing.

So, to make sure that I am covering all the right material in my new coaching program, I would really appreciate it if you can tell me:

What is the single most burning question you have about understanding men?

I suspect I already know, but, hey, that’s why I’m asking the question.

Maybe you’ll verify what I’m already thinking.

Maybe you’ll surprise me.

Either way, I’m asking you to help shape my new coaching program. By listening to your needs, I can craft a curriculum that addresses what YOU want to learn.

So click here to tell me your main question about understanding men.

Fire away. This is gonna be fun!

Warmest wishes and much love,

Your friend,

P.S. It’s not easy for me to be publicly vulnerable, but I gotta say, it does feel good to let you in to what I’ve been feeling privately for a long time. So thanks for listening and thanks for telling me the one thing you want to understand about men.

Join our conversation (32 Comments).
Click Here To Leave Your Comment Below.


  1. 1

    I live by your words Evan, and follow you faithfully!! You are right on the money when you say to pay attention to a man’s actions more than his words but as a 51 yr old divorced woman I am struggling to find a normal, kind man to have fun and date. A man who puts effort into planning a nice evening or wants to do something fun, or even take a nice long walk. I’m pretty easy to please but feel that 90% of the men I date put zero effort into planning in advance or even presenting themselves in any sort of appealing manner. They are so jaded by their marriages/ex wives that they are clueless in the dating dept. (unless they are a player or looking for younger women).
    I am in good shape, take care of myself, can pass for early 40’s and surround myself with wonderful friends..and I have a pretty awesome social life (with my girlfriends). I do make time for dating but it seems that it is just one disappointment after another over the last few years. I don’t have 2-3 hours a day to devote to looking “online” and I tend to reply to the men who contact me (which is probably 20-30 a week but I typically narrow down to 5). Out of the 5 I may get one or 2 dates if I’m lucky but I realize that is what online dating is about. Persistence and effort. Perhaps I’m not putting in as much effort as I need to (will work on that) but it gets overwhelming and disappointing when you get your hopes up and then he turns out to be shrek (I nicknamed my latest lol). Our phone conversations were great and was so promising but he has showed up on each date (4) in old ratty sneakers, baggy jeans and wrinkled rugby shirt!!! Really???? I made some nice comments on what I find attractive and he laughed and said he was dressing up to impress me. This man is a 50-year old management consultant, he is smart and funny but looks like he hopped out of bed and can’t walk 10 feet without his back or legs hurting as he is 50 lbs overweight (I even gave him that benefit as he was working on losing weight). This stuff you can’t see online or over the phone. I had to let him down nicely yesterday as he already considered me his girlfriend after only 4 dates. I probably gave him more chances than I should have but I thought there was really some good potential through our phone conversations prior to meeting him.

    I am attracted to alpha, take-charge men (aren’t we all). I spend 50 hours a week working and doing for everyone else, taking care of a house and 2 teenage boys, I just want a man to step up, make a plan, and look presentable!! Is that too much to ask??? I’m beginning to think that it is. My expectations are not that high as I know I’m in that bracket where the field of available men is pretty narrow. Thanks for letting me vent.

    1. 1.1

      “I just want a man to step up, make a plan, and look presentable!! Is that too much to ask???”

      It is certainly not too much to ask. My peers embarrass me with their dating ignorance. Post-divorce guys ask me for advice often and I say two things: Dress better and get out of the house to be more social. As well, a man must be making the dating plans. Simply showing up isn’t enough for a man.

      Many women complain of the exact same thing about middle-age guys.

    2. 1.2

      Nicely said LC!

    3. 1.3

      LC, you’re not alone. I am 33, divorced with 2 small children and I experience the SAME EXACT THING. Men just want to “casually date” which means friends with benefits. They want it all with no effort. Or expect sex after a half ass first date. It’s very disheartening and disappointing.

    4. 1.4

      Just wondering .. did you ever consider that maybe he too works 50 hours/week, doing for everyone else, taking care of a house kids, etc … but still you insist it’s his obligation to “step up, make a plan, and look presentable”? OK, so yeah the “presentable” part is a reasonable expectation .. look, it’s 2015. Women and men are supposed to be ‘equal’, right? Or maybe you believe some are more ‘equal’ than others? Cherry-picking only those ‘traditional’ obligations that suit you (and tossing those that don’t) isn’t very reasonable .. or attractive. BTW, most people just roll their eyes when someone claims they look 10 years younger .. just don’t. It’s embarrassing.

      1. 1.4.1

        Didnt mean to embarrass you. I dont believe you read my full post though. I Never stated I was a beauty queen or a cougar looking for a much younger man (although my inbox is full of them every day). I know the field is narrower in my age range. I’m very understanding if a man is very busy and has a house and children to take care of. That is not the case here however. It only boiled down to pure laziness. He did admit that he has not worked out in many years and has become very lazy. Not my job to train and teach a 50-year-old man how to date a grown woman.

        1. Morgan Hill

          Great job in making the case that the men you dated are losers.
          Consider this reality: You are not the catch as you think you are since these are all the men you could pull.

  2. 2

    Evan: this is a site where many of us women come and “spill our guts” to you… as well as to other countless, faceless strangers. We write of cheating husbands and sexually abusive step-dads; of falling for ONSs and continuously driving men away with our nit-picking; of grief for waning fertility and fear of dying without having ever known true love.

    Thank you for honouring our confidences by sharing a few of your own personal struggles.

    1. 2.1
      Evan Marc Katz

      It’s my pleasure, it’s my honor, and, of course, it’s my job.

      I’m always looking to improve my services and effectively help more women, so if you’re a lurker who is looking to change your life in 2015, ask me your question at the link above and I’ll do my best to answer it, somehow, in the future.

  3. 3

    Morgan Hill, I don’t recall me saying anyone that I dated was a loser. Obviously you have a lot of anger inside of you to have interpreted it that way. In fact all of the men have very good jobs and are all very upstanding men and fathers. Just more of the friend zone connection than romantic one.

    1. 3.1
      Karmic Equation

      But they didn’t know how to “present” themselves. And that was your complaint about them, along with the stepping up and making a plan.

      Did they dress better in their profile pics and then came to the date in track suits?

      Or did they not know how to dress (as in short sleeve collared shirts with a tie and pen in shirt pocket?)

      Or did you choose to date men without profile pix? If this is what you did, you are definitely a better woman than I. I don’t trust profiles with no pics. And I no longer trust profiles with tightly cropped face pics (the guy had longer, though stringy, hair than me). And once a guy I dated ONLY had pics from 5 years and 50#s ago, so checking all the pix in a guys profile is still not a guarantee they’re correctly representing themselves. And the guys I’ve dated online have the same complaints about women.

      Anyway, as to the stepping up and having a plan part, I normally provided my dates with my likes: karaoke or pool. If we could do one or the other, I was happy. As were they, since it gave them something to start with. So if you have masculine hobbies (cooking class or yoga won’t be well-received) or neutral (karaoke) hobbies, and say if you could do one or the other, that would be awesome that guy will try to find those places. On a first date with a guy, I mentioned that I love Beef Wellington but the only time I’ve ever had them was on cruises and I’d never had any on dry land. On our second date, we met in Boston, cuz he found a place that served Beef Wellington.

      Anyway, in defense of Morgan, you did make it sound like you were only getting “losers” to respond, and he was reacting to your implication, however, unintentional.

    2. 3.2
      Morgan Hill

      Like you, I am in my early 50’s. My professional life in the high tech industry was very rewarding which enabled me to retire early. My two sons are in their twenties. One just got his J.D. from NYU and one is in graduate school. I have the financial means and freedom to do what I enjoy. I am dating women close to my age. But unlike you, my dating experience has been very positive.

      “jaded by their marriages/ex wives that they are clueless in the dating dept”, “50 lbs overweight”, “put zero effort into planning in advance or even presenting themselves in any sort of appealing manner”, “pure laziness”, and you nicknamed the latest guy “Shrek”. Those are your words verbatim. If in fact all of the men have very good jobs and are all very upstanding men and fathers, i.e. basically nice men according to you now, and yet you badmouthed them with such umbrage, you must be some drama queen.

      Water seeks its own level. You should work on developing some self-awareness.

      1. 3.2.1

        Mr. Hill, as I mentioned in my post, I was merely venting to Evan and tried to do it with some humor but obviously my passionate side got the best of me and it was misconstrued. I had no intention of starting a war ..and I certainly don’t appreciate being personally attacked by someone who knows nothing about me. Further, as a man dating women, there is no comparison as you are in a completely different place. I was married for almost 20 years and was in a relationship for 2 years after my divorce. Only during the last year or so have I noticed that some men in their 50’s have become a bit lazy in the way they dress and/or plan for a date. Again, I am not alone in noticing this..and again I am not speaking that every man is this way! They certainly are not. My good friend’s husband was going to start a website for divorced men/women over 40 and the survey results from women happened to reflect it was a major complaint about the middle aged men in their dating pool. I have not given up hope and will continue my search…as a 50 yr old woman, I have never felt better in my life : ))

        I am an open, honest, caring woman and look for the good in everyone and wish that everyone would do the same.

  4. 4
    In Not Of

    To LC’s detractors, no doubt YOU are dating women who are homely, overweight and out of shape, and making no effort which is why you have the pretext to be so critical of her.

    1. 4.1
      Morgan Hill

      Why are you so vitriolic? Homely, overweight and out of shape women can be emotionally generous, kind and loving. They probably have a better chance finding love than you do. The level of anger you exhibited is like hell hath no fury like a woman scorned.

  5. 5

    Dear Evan, I find Your website very informative and well written, thank You, keep up the good work! To answer Your question, what is the single most burning question you have about understanding men, I have to explain a few things first. I come from an Northern Europe country called Estonia that is near Finland. We are calm, do not like to show our emotions very much etc. Therefore the dating scene is also pretty much nonexistant, I ´d say. Recentely even two well known female actors made a comedy show about how hard it is to be a young Estonian female in your late twenties – how on the one hand there seem to be those silly excpectations that one should be married by now or at least most definitely have a boyfriend, otherwise there is most definitely something very wrong with you, and on the other hand, single women can ´t often even remember when was the last time they were asked on a date because it was so long time ago as men tend to be shy. Many people in Estonia seem to meet their partner mostly in their early twenties, live together for a long time, have babies. Even then many Estonians never marry – we have one of the highest percentage of people cohabitating. To my mind people are just trying to avoid commitment and mask it by saying things like “what does this paper that states that we are married give me”, “what would it change if we married – nothing” etc. We have quite high divorce rates too. I was concentrating mostly in my studies when I was in the university and I almost never went to parties, went to a few dates, and was very satisfied with myself. It seemed like a very good choice. I now have an excellent job that I like and I am very happy about it, but its ironic that I really regret not socialising more when I was a student. I ´m still amazed how I could make a bad decision while consciously being sure, and even feeling in my heart that the choice made, to concentrate only on my studies, was the right one. It never bothered me and somehow I thought that I would find someone, that it would just happen – because it seemed that it had happened to many others. Now I understand that it does not work like that. Almost all men in their late twenties, thirties seem to be married or cohabitating. It seems that a man in their late twenties or early twenties is much less likely to live alone than a woman. I hate generalisations and I am aware of the fact that there are many men who make a conscious choice and love their partner. However, can some sort of a generalisation be made that it is harder for men to live alone? Do therefore many men sometimes settle for less just to have a partner, when the are aware that this is not exactly woman of their dreams and it will most definitely end some day?

    1. 5.1
      Evan Marc Katz

      Hey, the questions were meant to be asked on the survey, not in the comments section. 🙂

  6. 6

    @Evan: how are these questions to be used differently than all the other questions that people send to you?

    1. 6.1
      Evan Marc Katz

      There are the random questions I get to answer on the blog on Mondays…and there are the questions I get from this survey, which I’ll answer in a series of videos next week…

      1. 6.1.1

        All right; thank you.

  7. 7

    You are following in the tradition of the matchmakers of the days of yore. Perhaps there is a clue for you there. How did those matchmakers work? They focused on the sacred, essential qualities that make for happy marriages long term–they were able to assess the potential compatibility of two people because of their years of accumulated wisdom. It looked fast and easy, but it only looked that way because of their many years of learning. Fast and easy is a bad hookup. Wise and accurate is a meaningful union. I saw a flyer today posted on a light post in midtown Manhattan: A man’s name and his picture. “I am looking for a real relationship. This is serious.” Then his website address. I believed him. I wondered how different his life would be if he had someone who could help him find a serious relationship in this world of online superficiality and status-seeking partnerships. This guy needs wise and accurate. So does his future mate.

  8. 8

    I am happily married but know a lot of 40+ single women. I am going to say something harsh, but please take it to heart. Women need to let go of being so picky about the wrong things. I know women who will refuse to date and smoker without a college degree, saying they need a professional with a college degree. Then a “hot” (read: emotionally unavailable) smoker with no job and no degree comes along and they are head over heels, making all kinds of excuses. They overlook the shy guy in the suit with the good job because there is no chemistry. This what women do in high school and it has no place if looking for a partner. The bottom line is, throw the list of superficials away. Look for the core qualities of kindness, unselfishness and integrity. Who cares if the guys looks are rough around the edges and who cares if he doesn’t bring flowers. Women also need to get past wanting to be treated like Princesses. How about instead of always looking for what he can do for you, look at what you can do for him. To have a successful relationship, sometimes we must give more than we get. And when we give unselfishly the getting always takes care of itself. But, I see so many single women who believe they are so special that a guy needs to be like something out of a movie. And if he doesn’t sweep them off their feet within minutes, these guys get overlooked. Well the guys who make the best husbands are the quietly supportive types. The ones who sweep us off our feet and charm our socks off are generally narcissists. While narcissistic men make for great entertainment at social gatherings, they make the most terrible partners. Evan, try to deprogram women from judging men solely based on initial chemistry. Wild chemistry is not love and it always wears off.

  9. 9

    Ariella , you are preaching to the choir with me. I discovered Evan after reading the book Marry Him, which makes the points you made. When I date as a late 30 something woman , I keep all of those points in mind.

    1. 9.1

      Hi Josie,
      I wish you the very best of luck in finding someone wonderful. My best friend is in her 40’s (like me). It took a while and a lot of dates, but it has paid off because now she has someone wonderful. She also used the tips in that book Marry Him. But she has also had success with the tips in the book Why Men Love Bitches. I read that one just for fun and that author has an incredibly entertaining style. She made me laugh a lot. Good book. 🙂

  10. 10

    Hey Evan,
    Another thought. You mentioned that you have been happily married since 2008 and have kids. Maybe start another blog for us married folks on how to make marriages work. With the divorce rate at 50%, it’s a thought. Plus, the people who lose the most from divorce are the innocent children who did not ask to be born into a broken family. While there are legitimate reasons for divorce, too many people get divorced because they are bored or lost that “spark”. So the blog would be written for those folks.

    1. 10.1
      Evan Marc Katz

      Thanks, Ariella. There’s not gonna be another blog since we have so many readers here, but if you search this one, you’ll get LOTS of information on how to make marriages work. Click the Marriage, Relationship or Communication tabs on the right. And look for the New York Times article that points out that the divorce rate is closer to 1/3 than 1/2…and if you’re over 30 and college educated before you get married, it’s closer to 1/5. Things aren’t as bad as they seem – if you make the right choices.

  11. 11

    This is a tangent and maybe even mischievous of me, but I think you should write an article and a programme telling women to get out there with the main objective of failing.
    Us women, we hold on to the “idea” of a relationship that’s just not there so in preparation for your pivotal “walk away” article, where the emotional stakes are actually high, I suggest a training course of dates where you KNOW you aren’t very interested and you KNOW you have the upper hand and basically practicing saying goodbye in a calm and honest way. Because when the time comes that there actually IS something on the line a lot of women stall… I think because they’ve never practiced before. Just like men may need to practice approaching women, I think women need to practice putting their foot down. And meaning it. It might seem counter-intuitive but my group of fit, professional 20-something friends have more experience being broken up with than doing the breaking up.
    I’m 28 and I have 5 knock-out gorgeous friends recently-ish married to boorish men who take them for granted because of what essentially amounts to the fact that they didn’t shop around enough, and they are equally incapable of expressing their needs within the relationship now. I hate to be Cassandra, but I feel like they’re heading for being 40, divorced, and child-free.
    Just some food for thought. Breaking down the bigger objective of “happily ever after” into “obtaining the skills to maintain happily ever after”.

  12. 12

    I really appreciate your advice and it’s already improved my love life!
    There’s a problem with sharing your advice with others though – most of my friends and people I meet are totally put off by the marketing. I can see past it because I see that a lot of the public expect it. You have to find a way to get past their indifference   or disinterest by offering the ‘one secret to getting a man to love you’ (for example).
    Trouble is my friends or people I meet at yoga or at work or whatever, who I’d like to recommend you to just groan or close the email as soon as they read something like ‘getting a man to love you’. It’s not even true as you totally don’t recommend ‘tricks’ which such a phrase implies.
    I can see this is a bit of a catch 22 as all the self help books I ever pick up seem to have the same ‘solve your life in a second’ book jacket blurb, even if the true advice inside is meaningful.
    The advice works for me and I was happy to buy your downloadable books. But the endless realms of marketing blurb I do find off putting. I’m on your email list, and find the same with the emails. There’s useful stuff but about two thirds of it seems like padding or hard sell. And I really dislike emails with my name in the subject line – in the same way I dislike spam.
    So I would love content with less overt hard sell in it – I would find it easier to recommend you which I’d love to do as I meet women who I can see have given up and would really benefit.

    1. 12.1
      Evan Marc Katz

      Frankie, appreciate your feedback but nothing’s going to change over here.

      I’ve been giving free advice in this blog and via email since 2007.

      If you never choose to buy a product from me, you can learn a ton.

      But the only way for me to make a living or to get you to buy a product from me is to ask, as opposed to you volunteering to maybe possibly go to my website and maybe find the page where I sell things.

      You’ve bought my books and enjoyed them, so the decision is yours: no longer buy my products and refuse to share me with your friends who need me, simply because I ask you to click a link at the end of each email, or keep reading the volumes of free information I give you, not buy my products and keep me as your little secret.

      My life will not change either way. But yours might.

      1. 12.1.1

        Oh hi!
        Yes I do mention you – but I get scrunched up very skeptical faces in response.
        Maybe they secretly read you : )
        I do really appreciate the free material – thank you. Really it’s because I appreciate it that I took the time to write the above message.
        I work in marketing myself so I’m not against it on any kind of principle. I get that it’s about finding the people who need you. It just seems to work the other way sometimes too.

  13. 13

    i thought of a better way of explaining it.
    Say you were selling elephants, and I said but why don’t you sell giraffes, I want giraffes!!
    And you replied ‘look I’m not going to be selling giraffes any time soon – that’s not what i do.’ Ok fair enough.
    But what if the elephants were wrapped in penguins. So I say to my friends ‘there’s these amazing elephants’!!! And they’re like ‘well they look like penguins to me’.
    See clear as mud : )

Leave a Reply

Your email address will not be published. Required fields are marked *