How You Can Get Everything Wrong and Still Find The Man of Your Dreams

How You Can Get Everything Wrong and Still Find The Man of Your Dreams

Karin is tall, thin and blonde. She’s a former dancer who makes a good living as a doctor. She’s a patron of the arts, an animal lover, and has a quick wit.

Karin is also 42, never married, and desperately wants children.

I took her on as a Private Coaching client because she’s highly motivated.

Yet the second we started working together, Karin began to dictate how our coaching would go — and thus gave me a small glimpse of why she’s single at 42.

“I’m not going to date online. Only weirdos who do that. What if someone sees me? I’d be too embarrassed. The kind of men I’m looking for don’t date online.”

“I think you tell women to settle. I’m not going to settle. I haven’t waited this long to find love only to be with a man who is beneath my standards.”

And so on. And so forth.

I reminded Karin that 50 million people have tried online dating. I reminded her that if a man sees her online, he can’t judge her because he’s dating online as well.

The first three weeks of coaching Karin, we literally didn’t do any coaching.

All I did was cajole her into putting her profile on so we could actually have, you know, DATES to discuss during the rest of her coaching.

I reminded Karin that 50 million people have tried online dating.

I reminded her that if a man sees her online, he can’t judge her because he’s dating online as well.

I reminded her that my wife, my mom, my sister, my sister’s husband, my wife’s best friend, my wife’s best friend’s husband and pretty much every other single person I know has tried it. And we’re not all losers.

Finally, Karin got her professional photos and professional profile up on Match.

It was like magic. Even though Karin was in a highly unpopular demographic (42 and looking to have babies) she still got tons of attention online. Scores of men. Attractive men. Successful men. Age-appropriate men.

Quickly, Karin realized that her fears were considerably overstated.

Within weeks, Karin found herself dating a good guy named Gary. They’d gone out 3 or 4 times and he always followed up immediately to see her again. Moreover, he was enthusiastic, cute, successful and very much interested in Karin as a girlfriend.

Naturally, Karin started second-guessing her own interest him.

“He’s too nice,” she said. “He always asks for my opinion on what to do on dates. Why is he so eager to please?”

Didn’t you complain that in your last passionate love affair, you never knew where you stood with the guy? That he wasn’t considerate enough?

“Yes, but–How about the fact that Gary is a teacher who drives a Toyota? How can he support me? What are my Mercedes-driving friends going to think?”

You’re a doctor; he doesn’t have to support you. And who cares what your friends think as long as you’re happy in your relationship?

“Yeah, well, the other day, in the museum, he made a joke about a modernist sculpture. I thought it was so classless of him to do that when an artist poured his heart and soul into creating it.”

He made a joke about a piece of art? And you want to break up with him for it?

“He apologized to me the next day because he saw how it upset me, but all I could think was: why did you make that dumb joke in the first place?”

Because it was funny? Because it was no big deal? Because everyone makes jokes about modern art? Either way, Karin, the fact that he apologized to you when he’s done nothing wrong means that you’re dating a saint. I wouldn’t be so quick to dismiss him.

After a half-hour of back and forth, Karin made her decision.

She was dumping Gary.

He was too safe.

He was too nice.

He wasn’t able to support her financially.

And if this wasn’t enough, Karin simply didn’t feel what she was supposed to feel.

Fair enough.

I told Karin that I didn’t care about Gary, per se, but that if she were going to achieve her goal of finding love, she should start giving men like Gary a closer look.

She’d spent 42 years chasing exciting, charismatic, unpredictable, wildly attractive men…and here she was with a dating coach trying to figure out where she went wrong.

“THIS is where you’ve gone wrong”, I told her. “THIS is your chance to correct it.”

But Karin’s mind was made up.

She broke it off with Gary and they agreed to “remain friends”.

She put herself back on and prepared herself for the flood of responses that she got in her first month online.

Two weeks later, Karin was crying to me on the phone.

“The responses have slowed down”, she told me.

“The quality of the guys has gotten worse,” she observed.

“I’m really worried that I made a mistake,” she whimpered.

Instead of playing the “I told you so” card, I continued to support Karin’s dream.

I spend a lot of time writing about sad things: men who lie, men who cheat, men who won’t commit, etc. This blog doesn’t change the fact that these men are still out there.

I didn’t tell her she blew it with Gary; I did remind her that the Garys of the world — cute, smart, thoughtful, patient, relationship-oriented — were the type of men she should consider whenever they come along.

I told her that everyone goes through online dry spells and that a new guy will emerge in a matter of weeks. Promise.

Two weeks later, Karin revealed that she and Gary were “hanging out as friends” when he suddenly kissed her.

And after further reflection, she would give Gary — and their relationship – another shot.

Sure, it was a happy ending — another client who achieved her goal and got her money’s worth — but I didn’t have a warm and fuzzy feeling about it. Why?

Because Karin was still the same person she was before — neurotic, critical, unrealistic, and bound to dissect Gary and dump him in favor of a fantasy man who would never commit to her.

So imagine my surprise last week when I received this email from Karin:

Hi Evan!

I can’t believe it’s taken me so long to tell you this, but… I’m married! To Gary – the man about whom you were coaching me when we parted. We had an amazingly beautiful and intimate wedding with 50 guests. We honeymooned in Tahiti.

Needless to say, this is a dream come true for me. I am so happy, because I feel safe and secure with a man who is devoted to me. He is everything I was looking for – although it took you to make me realize that. Of all the thank-you notes I have written (and have yet still to write …), yours is the most important to me – because there is no way I would be a happily married woman today without you.

Gary is everything I need, and more – but I still couldn’t fully accept that when you and I finished off in February. At that time, I still couldn’t help looking for perfection, magnifying shortcomings, and not accepting what was most important: unwavering interest in me as a person, following through on commitments, and truly wanting the same things I wanted in a relationship. I still wasn’t appreciating Gary’s amazingly hot body, razor-sharp intellect, and unique life experiences he had created for himself. Or that he made me breakfast in bed, put up with my neuroses, and just wanted to be with me. All I saw was that he didn’t create a Fortune 500 company, drive a Tesla, or lunch regularly with Gavin Newsom. Yes, I am ashamed.

There is no way I would have gotten to that point without you, Evan. No chance I have found Gary and let him into my heart if it hadn’t been for you. You were instrumental every step of the way: from that incredible online profile, to actually getting me to put it online (an entirely separate step, as you well know), to coaching me through all those first dates, to helping me realize why Gary was the kind of guy I should be with … I can’t thank you enough.

I continue to read your weekly post, and I couldn’t agree more with everything you say (yes, pretty much everything). For any woman who wants a real and meaningful relationship but continues coming up short, you are the man for the job to figure out where the stumbling blocks lie and implement a personalized plan to overcome them. Or via the ebook – I bet it is just as helpful for those who want a more economical approach to coaching (although you were worth every penny 🙂 I plan on reading it once the dust settles on setting up a new household (and those thank-you notes are written …) because it will not only speak to my fascination with human relationships but also keep me abreast of how you communicate your wisdom. Regardless of how women want to go about finding the relationship they want and need, you are the one to help them find it.

You sure did it for me. I have a mature, supportive, satisfying, committed relationship (it’s even a marriage!), and I am so happy. Thank you so much for everything!!

All my best,


You know what I did when I got this email?

I ran into the kitchen to find my wife.

Tears were brimming out of my eyes.

I couldn’t believe that Karin found true love — much less gave me credit for it.

I know this is a long blog post.

I know that it can be interpreted as egocentric or self-aggrandizing.

But you know what?

I just think it’s inspiring.

I spend a lot of time writing about sad things: men who lie, men who cheat, men who won’t commit, etc.

This blog doesn’t change the fact that these men are still out there.

Still, I think Karin’s email is a useful reminder that you MUST have hope.

Karin didn’t believe in online dating.

She dated online.

Karin didn’t believe in compromising.

She compromised.

Karin didn’t think she had to accept anything less than a perfect man because she’d held out for so long.

She accepted Gary.

And she WON.

If you’ve been sitting on the sidelines, wondering why love isn’t finding you, ask yourself if you’re willing to do what Karin did: look within, challenge yourself, and open up to a whole new way of thinking.

Who knows? You could be next.

Join our conversation (113 Comments).
Click Here To Leave Your Comment Below.


  1. 41

    Ria — EXACTLY — until you get the the point about choosing Gary, which I see as “well, I can’t get what I want, so I’ll try to want what I can get.” But trying to want, as K points out, ain’t the world’s most successful strategy. People used to live with it because they were more dependent on each other, but it wasn’t terrific, and they’d just go have affairs and be miserable with each other.
    I think the real question here is: what did she want more, man or child? (I’m biased, but I think “child” is usually the better bet.) And if she wanted a child more, she’s in a rare position. She’s actually in a good spot to have one on her own. If her family’s not supportive, she can buy support. She’s got a recessionproof occupation. And she’s well-established in her career, no doubt insured up the wazoo. She may even be nearly done paying off student loans.  
    You have to ask, of course, whether that’s fair to a kid. But if she’s near family, and has a loving and supportive family, well shoot, that’s more than lots of two-parent kids get.
    Karin’s something of an outlier because she is so successful, and that changes the whole baby equation. A woman who doesn’t make much money’s in a much more secure spot, having a child. In a divorce, she’ll likely keep the child and collect child support. But a high-powered woman will likely take the man spot in divorce, and see her child move out, eventually to be raised by another woman. That seems to me a searingly painful scenario, definitely to be avoided. Which, when you look at it, makes Karin’s initial impulse to go for the alpha male and avoid Gary extremely sensible.

  2. 42

    I LOVED this story!   Thank you very much the inspiration and your well-written and substantive blog postings.
    Unlike others who have posted on here, I don’t think you are totally off base.   Obviously, you’ve made some major assumptions about Karin and Gary based on stereotypes and generalizations regarding occupational choice.   That’s fair game given that you have very little information about each of them.    
    I think your assessment of class values between Karin and Gary is dead on.   Essentially, you’ve classified Karin as identifying with upper class values and Gary as solidly middle class.   Your proposed future for Karin and Gary based on a values clash seems plausible based on what I know of research on American class values.   Despite the criticism you’re garnering, I think you’ve done readers a favor by hopefully getting them to examine their own value systems in the context of long term relationships.
    Your proposed scenarios reminded me a lot of my own life.   I am an ambitious person who married my second husband, an alpha male, in my early thirties.   I loved my husband, I didn’t see him much.   The tradeoff was that I got to run our household however I wanted and was firmly in charge of all of the parenting.   I wanted to give my children the best and always strove to do that.   After our kids were in school and   I went back to work, I found out my husband was cheating, which I   couldn’t tolerate.   Long story short, the alpha male side of my ex-husband came out during our divorce and he demolished me financially.   He now is now involved with a woman who is uneducated and unsophisticated woman whom he is using trying to raise our children with his financial advantages (but with a different value system) , while I struggle financially to give our children the same educational and social opportunities I sought to give them during our marriage.   Honestly, that part really kills me.    
    The reason I share this story is that I think that Karin is no worse off with a “nebbish,” than with an alpha type.   In fact, I think if Gary can get along well with others (which is fair assumption if he’s a career educator), she is far better off with someone like him rather than an alpha.   Divorce is always a possibility, but divorce with an alpha vs. a normal guy is a like night and day.   Many   males don’t pursue support from women out of sheer pride, but if Gary has high emotional intelligence (which would could infer), he will likely be motivated to make the relationship work instead of seeking divorce.   In summary, I think a woman like Karin would be better off with a nice “beta” in marriage and — worst case scenario — in divorce, too.
    Finally, to address your concerns about the values clash between Karin an Gary, I think you have to acknowledge other competing values and needs within the individual.   While the Upper Middle Class/Upper Class strata tends to value money and financial security, research in the behavioral sciences has always shown us that personal happiness and well-being is directly correlated with the quality of our relationships.   Karin may have Upper/Upper Middle Class values, but she’s also still a warm blooded human being with emotional needs.   At some point, intelligent, lonely people may evolve and consciously decide to re-examine their values and adopt new, more adaptive ones.   That is exactly what Karin decided to do, which is why this article is so inspiring.   I understand your cynicism at the possibility of this happening, but my guess is that both Karin and Gary value education and self-improvement and this might serve as a bedrock of shared values on which they can build their relationship.

  3. 43

    Geez, since when are doctors and teachers that far apart on the class spectrum? I get SarahRaRah’s point about upper class and middle class, but I don’t feel that the divide here is all that great. I’ve known schoolteachers with more generosity and sophistication than some doctors, that’s for sure. If Gary were more blue-collar, then, yes, that would be a greater difference. The most offensive thing to me about amy’s posts are how classist they sound, how absolutist, and stereotypical, not to mention that she has already mapped out all the particulars of Karin’s inevitable divorce before the wedding has even taken place. But I hear that a lot on this blog: if a man isn’t alpha, he’s beta. Winner/loser. There are never any shades of gray.  

    I might have sounded like a disbeliever in my previous post, but in Karin’s email, she sounds really happy. Who are we to second-guess that at this stage?

  4. 44

    I realise this is slightly off topic, but I would like to say something in defence of alpha males, having been married to one for 15 years and having had a subsequent LTR with another. Yes, these guys were assertive, highly intelligent, always thought they were right,pain in the ass and selfish at times,   and their my-way-or-the-highway, failure to compromise attitude to relationship differences eventually led me to leave both of them, but being an alpha male does NOT mean a person lacks morals and will wipe the floor with you in a divorce or break-up. Both of my exes behaved with respect towards me at all times during and after the break-ups, and financially behaved in a fair and decent manner. Both continue to exhibit concern for my wellbeing and offer support and encouragement for my dreams and ambitions, albeit from a distance. Neither of them has any interest in getting back together with me, one has even remarried, so this is not the motivation for their behaviour. I agree wholeheartedly that alpha males have their serious downsides, but they are called alpha for a reason – they do have many highly positive attributes, and in my view are generally   morally stronger  that their more easily-led B brothers.

  5. 45

    Still-Looking: Thanks. I appreciate it.
    Gradient: I’ve never dated a teacher. I’m involved in sales to them, though, and have spent years on teachers’ forums and lists. All the guys I’ve been involved with have been highly ambitious, one way or another, and a few have been wealthy. But there are enough people telling their stories in the world these days that you don’t have to base things on personal experience anymore. Just go listen to what people tell you about their lives.
    About upper/middle etc. — I see what you’re saying, but that’s not really how I see this. Think of what it takes just to get into and through med school v. what it it takes to get a teaching license. Med school requires considerably more planning, brights, discipline, organization, and work. For a woman, it’s also a battle in a boys’ club. Once you’re out of med school, the hours remain grueling, the responsibility doesn’t get much more serious, the review is unrelenting, and you’re forced to reckon with business realities. Oh, and odds are good you borrowed $200K to get there. I don’t begrudge doctors’ pay. If Karin’s a doctor at 42, she’s almost certainly brighter, harder driving, better organized, more ambitious, more of a planner, harder working, more attuned to business realities, and more responsible than Gary is. I’d even wager she’s got a better driving record. Like I said, if she was looking for a wife, then bingo. There’s a reason why so many male doctors have schoolteacher wives. The part where Karin loses out, though, is that the schoolteacher wives don’t generally come with male egos, and those have consequences.

  6. 46

    Oh, and Gradient, re materialism: I drive a 24-year-old car and live in a modest house. But money is serious business. If you don’t believe it is, ask your parents.
    I accept that men will in general devote their entire lives to playing king of the mountain, and that the currency they use for showing each other who’s boss is money. Okay. So if a guy is serious about me, he can court me, and he can do it appropriately. Let me see that he means it, and that he values me. Talk is pleasing but cheap; courtesy is appreciated; but let him woo me with something he had to go out and fight for.

  7. 47

    Hi, Amy, thanks for a point, love it! There is, however one thing that is dingleing in my mind. Which is   – if there was such a need just to have a baby, there are options  like   (IVF) or (short-fling-with-alpha-male and …you know.)

    So let us portrait Gary, then. He is stabile in what he does (he has been in his job position for long l assume) and he does not have this Hamlet syndrome a la to be or not to be, meaning questioning his path of life (and belive me, that is VERY important). I belive Gary is one of those guys who is happy with the way he is, no matter of the missing big bank account and BMW. And thats cool. Did l read Gary was a teacher?10 points to him because do you know how big responsibility lies on teachers? That to me shows, that Gary is able to take full responsibility and he is doing it.

    What else is Gary – he is loyal  and man of words.    And now a  short  sentence from Evan ´s article: “Moreover, he was enthusiastic, cute, successful and very much interested in Karin as a girlfriend.” Note – enthusiastic, cute and successful.


  8. 48

    @ amy — In California it takes two years beyond the bachelor degree to become a teacher and the requirements are more rigorous than those for community college instructors.    I also frequently encounter secondary educators in my work and most do not seem to be the “bottom of the barrel. ”
    @helene — I’m glad that your alphas didn’t treat you like garbage the moment you split with them.   I think the great danger of being with an alpha is that they follow their own rules.   If they are a highly ethical person, great.   If not, you had better watch out.

  9. 49

    I’d also like to add that the apparently ethical alpha males are not always the ones that most vocally proclaim their own ethical status. Take it from someone who watched at close distance a situation where a supposedly ethical alpha male had severe cognitive dissonance over his marital affair, which was not consistent with his image of himself as a moral person, and then dragged out his divorce in a extremely bitter and venomous way in a (sublimated) attempt to self-justify his behavior, and in this process alienated everyone in his immediate and extended family. This sublimation was patently obvious to everyone else watching, of course.

    Probably the best predictor of this is whether or not the alpha male has ultimate respect for you as a female and a partner, and whether or not he has high EQ. The lower his EQ is, the more likely he is to resort to these sorts of tactics.

  10. 50

    not going to last

  11. 51

    @ Amy #49: while becoming a doctor may be a battle in a boys’ club, becoming a teacher is a battle in a girls’ club.

  12. 52

    Amy’s argument is a valid one.   Also, I like the way Amy has chosen to not to make personal insults at  opposing commenters.   I agree with Amy.   Not too many women who have overcome tremendous obstacles to become successful want to marry a man without the same initiative.   Personally, I will NEVER give a man money or provide for him in any financial way.   That is his job – provide and protect.   I’m not saying that he has to make the same amount of money, but he would need to have some goals and past successes in his chosen endeavors.   Karin, in my opinion, settled.   But I wish her the best.  

  13. 53

    Nadia @ 56 – You stated that you will never give a man money or provide for him in any financial way because it is a man’s job to provide and protect.   What are you providing?   Do you really feel that a “what’s yours is mine, what’s ours is mine, and what’s mine is mine” attitude is fair?   I’m just trying to make sure I’m reading your comments correctly, so if you married you would expect your husband to pay for the house, the groceries, the car, etc. and you would not even pay for your pedicures??

  14. 54

    @57 – I’m talking about providing food, shelter, and basics for a man.   No way, no how.   I am fully capable of taking care of ALL of my financial needs by myself.  

  15. 55

    Hi Evan!

    I love this story and I don’t believe the negativity about it not lasting.   It sounds like Karin is a woman who has not only worked on some of her own issues but is planning on continuing to work on them in order to have the happiness she has sought for so long. Aren’t there tons of highly successful women who are beginning to re-evaluate what they want and need out of a relationship – i.e. not money but love?

    I also wanted to tell you that I have been reading your blog for a while and LOVE how you spout out mini-truths that are pretty blunt but absolutely true.   Some of us need that shock therapy to see how our own choices have brought us pain, but in the end they are our choices.   We can choose better.

    I have recently started dating a really, really great guy that I probably would not have given a second glance before reading your advice. He is smart, kind, funny, attentive, family-oriented, and a really good match for me. The reasons I wouldn’t have chosen him before? While historically a responsible provider, he is currently going through a career move and is not financially well off because of it…and he’s not “hot”.

    The funny thing is, all of his wonderful qualities just keep getting brighter and brighter and outshining any of the superficial reasons I would have rejected him as a partner And while I couldn’t tell you just yet that he is “the one”, I can say that he is pretty great and if he’s just an example of the kind of man I am open to now then my romantic prospects are a thousand times brighter then they were just a few months ago.

    So, keep up the good work!   You’re a match-making guru!

  16. 56

    @ Nadia: if you’re fully capable of taking care of your financial needs, WTF do you care whether the guy is an alpha (i.e. an intiative-taker), as long as he can take care of his own shit?

  17. 57
    Christie Hartman

    I’m pretty surprised at how many people here think Karin “settled.” How is it settling to marry a cute teacher, who you love and who treats you great? She’s a physician, he’s a teacher. They’re both educated professionals who work in helping professions. What exactly is the problem?
    I’m also surprised at how many assumptions people are making about both Karin and Gary’s attributes, based on little more than their chosen careers and a couple of examples. And this is probably the 3rd time I’ve heard people insult teachers on Evan’s blog, which is utterly insane considering the huge responsibility it is to teach others.

  18. 58

    Christie… I’m late to this thread, but you said it all. I find the whole teacher = near loser dichotomy rather amusing really. Then again, I find that a lot of the readers of this board are coming from a coastal perspective where the super-alpha type professions (whether held by men or women) are in great supply… while here in Peoria, your average doctor with his family practice rubs elbows with the average high school teacher and maybe even the cop or firefighter… and all have about equal social standing, heaven forbid!
    (I don’t really live in Peoria, but I am from one of your average Midwestern mid-sized cities of about 100,000 or so!)
    My father taught elementary school. So did my mother. Both had master’s degrees. Their income combined put our household over the six-figure mark and income-wise, my brother and I would have probably been considered upper middle class and “advantaged” compared to many of our peers.
    Oh, and my father was a military man first before he settled into the wild world of elementary school. To this day, young boys (now men) he taught thank him for being a father figure to them and teaching them what it meant to be a good, upstanding example of a man and providing that type of guidance when they needed it. For taking them to their first ever baseball and basketball games. For teaching them about life. Etc., etc.
    So when I was dating and met men who were teachers, I was thrilled… because if they were anything remotely like my father, I would be a lucky woman to be with them and so would our future children.
    But hey, to each her own…

  19. 59

    Re teachers and doctors: I mean no disrespect to teachers. I couldn’t do their job (not on the K-10 level, anyway, and certainly not in the admin/legal environment they work in). They’re often trained as great classroom managers, and they’re usually warm people who really get kids.
    But I’ve worked with teachers, and worked with doctors and med students, and as far as intelligence, stamina, and drive go, i don’t think there’s any contest. Docs, hands down. Keep in mind that this is a group of people who generated lots of complaints at a labor-board ruling restricting residents to working 80 hours a week *on average*. They thought it wasn’t enough. And if they’re not working in hospitals, they’re also small businesspeople; they’re not relying on a union to negotiate contracts and a board/admin to take care of running all but the doctoring part. It’s considerably harder to get into med school than it is to get into ed school, and you have to be a gambler: you’ll likely be $250K+ in the hole by the time you finish your education.
    I’m not saying anything about relative niceness, decency, any of that. Just saying that if you stack up a random hundred docs and a random hundred teachers, I’m pretty sure the docs will be brighter, harder-driving, and have greater stamina.

  20. 60

    Many of my friends are artists and writers who also teach to support themselves. Granted, most of them teach at the college level, so maybe amy’s not referring to them, but some of them teach high school also. They are extremely smart and hard-working, although I’d grant that they may be more dedicated to their creative careers than to their teaching. But teachers are not all cut from the same cloth.

    Someone who works 80 hours a week probably pulls in a high income and is certainly hard-working, but might not be the best choice if you want a husband who actually has some time to stay home with you and your children, and who might be in a better position to support your own very demanding career. That sort of dedication to one’s job can come at the expense of a more balanced life.  

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