Why the Most Impressive People Struggle in Love


I had a Memorial Day barbecue yesterday and got a chance to connect with some amazing friends. As the day wound down and the sangria pitcher drained, I started musing about dating and relationships, which is the kind of thing I do whether I’m sober or not.

It occurred to me that all of our friends are demographically similar: Attractive, fun, 30-40 years old. Writers. Directors. Marketers. Professors. Artists. MBAs. Just a solid bunch of folks.

And yet there was only one other couple at our party – everyone else was single.

So if the common denominator between my friends is that they’re single and impressive, is it possible that the reason that they’re single is BECAUSE they’re impressive?

When you have everything going for you, does it become that much harder to compromise on looks? Intelligence? Humor? Money?

So if the common denominator between my friends is that they’re single and impressive, is it possible that the reason that they’re single is BECAUSE they’re impressive?

Without psychoanalyzing any of my friends (since a. they didn’t ask me, and b. I’m not a shrink), I’d have to at least pose the question:

When you truly are an 8 in looks, a 9 in intelligence, a 7 in career, an 8 in humor… is it imperative to find someone as impressive as you are? Is anything less “settling”?

Believe me, I’m not one of those people who became an expert when he put a ring on his finger. After all, for most of my career, I was the single guy. Plus, it’s quite evident that married people aren’t necessarily smarter – they’re just more committed to one relationship.

But maybe it’s not just a coincidence that the cream of the crop is largely made up of “maximizers” as described in Barry Schwartz’s “The Paradox of Choice”. These folks have so much self-worth that they feel that the grass is always greener. And if they have 90% of what they’re looking for in a mate, maybe they just won’t rest until they find 94%.

Alas, as Schwartz points out in his amazing book: maximizers are rarely happy. In fact, “satisficers” – the people who are content with “less” – tend to be happier people overall.

So, is it harder for the most impressive people to find love? Would they be wiser if they learned to compromise? Are they holding out for something that doesn’t exist?

What do you think?

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  1. 41

    All the work you do for yourself is for yourself, but it will change how you operate/communicate in the world and therefore change the response you get from others. A kind of domino effect.

  2. 42
    Senior Chick

    I enjoy reading your blog and the various comments. Most of you are much younger and as you get older, different things take priority. What I wanted at 20 when I got married and raised a family, is very different than what I want at 65. I know I don’t want to be a “nurse” or a “purse”- Desire for intelligent conversation, thoughtfulness, loyalty and physical desire and activity doesn’t disappear. It just changes form. Physical appearance becomes less important because- let’s face it- men lose their hair and women fight gravity and we all shrink a little.

    Does that mean we no longer consider ourselves “maximizers”? Does the desire for companionship fade? I don’t think so. Those of us in the middle part of our latter years still have levels of acceptance. Those who were delusional in their 40’s and 50’s are in their 60’s and 70’s still alone and looking for a 10 who is 20 years younger.

    Evan, I bought your tapes after being offline for six months I decided to try it your way. According to what you teach-I made every mistake in the book. I’ll let you know how it goes. If you think the pool at age 40 is small-try 65 even in Southern California.

  3. 43

    It’s a numbers game, pure and simple.
    If you’re in an “exceptional” or “definitely not the average” category of any kind (the far end of the bell curve versus the middle), whether it’s looks, intelligence, money, talent, political ideology, hobbies and interests – whatever – it’s always going to be more difficult to find some one who is similar to you. Even harder if you’re aiming for “better”.

    As we get older, the number of singles in the dating pool drops and (usually) we’ve gotten wiser re: the proverbial B_S out there, so we won’t put up with some of the B_S that we might have done 10+ years earlier.

    In total, when you do the math, the odds are not the best.

    So…. Do we sanitize ourselves into some sort of “average” package that is more “acceptable” just to boost our odds of finding a mate?
    I think not. That’s a fool’s errand that will lead to tragedy sooner or later.

    I’d rather be alone than in a relationship with some one who doesn’t truly understand and appreciate the “real me”. And the “real me” is not going to fundamentally change anytime soon (but the odd rough edge is always up for smoothing off).

  4. 44

    Ah, see Robyn, that’s my problem: dating is a numbers game. I hated accounting.

  5. 45
    Karl R

    starthrower68 said: (#29)
    “my fatal flaw is my weight.”
    “the best I can do – even with the impressive qualities I possess – is a guy […] who has a wierd fetish for BBW chicks. “

    What’s the problem with dating someone who prefers large women?

    About 10 years ago I dated a woman who preferred skinny men. Back then I was about 5’11” and 145 lbs (182cm, 66kg). Most women thought I was “too skinny”. That girlfriend thought I looked terrific. I see that type of situation as ideal, not weird.

    BeenThruTheWars said: (#13)
    “What’s frustrating is being a genuine ten in intelligence, maturity, career, wit/charm, kindness and all those other important intangibles – but only a 5 in looks. No matter how great you are head- and heartwise, all those narcissists Steve mentioned won’t give you a second look.”

    I’m a bit skeptical of values places on intangibles … probably because my job involves valuing intangibles. Intelligence and career can be quantified to an extent. Looks can be loosely quantified, but we all have lots of practice making qualitative judgments about looks.

    If someone is a 10 in maturity, wit/char, kindness, humor and other intangibles, it will be difficult for anyone to tell. This makes it a lot easier for us to inflate our values in these categories.

    I don’t think narcissism causes people to reject someone as a 5 in looks. At least it’s not the sole cause. I can evaluate someone’s looks long before I can evaluate their wit & charm.

    And if you’re a 10 on all the internal qualities and a 5 in looks, don’t you think it should be possible for you to find someone else who is roughly your equal: 9s and 10s on all the internal qualities and maybe a 3, 4 or 5 in looks? And if you’re unwilling to give the guy who is a 3 a second look, how are you different than the “narcissists”?

  6. 46

    @starthrower68 – Not a problem, I didn’t take it that way. And I did join a gym and lost a few lbs as well at the beginning of my journey. It was for me, but it also had the side benefit of bumping me up a notch on the attractiveness scale. Also, I started guitar lessons at the beginning of the year before I met my current girlfriend, because I wanted to learn a new instrument (even at 28 you can learn new tricks), but it did factor into my dating life, as I was able to play a few songs during our first few initial dates.

    I gotta tell you, the girl I’m with is far more impressive than I am… if I had to rate both of us, I’d be a 7 in looks, she’s a 10, I’d be a 9 in intelligence and she’s a 9, I’m a 6 in career (a MBA would bump me up to a 7) and she’s a 9, I’m a 7 in humor and she’s a 6 (hah, got her beat there ^_^), this girl outrates me in pretty much everything. But we’re together because of the chemistry we have, plus our similarities, plus we’re crazy about each other, and so forth.

    @vino – Interesting post! I can relate because my girlfriend has told me similar stories about when she goes out with her friends from work. They’re all doctors, and have the same expectations. And because one of them married a investment banker, the others want the same thing.

  7. 47

    I think Evans right. Impressive people do have a harder time. There is a whole sea of average people out there with other average people that are extremely happy whoile a lot of us are sitting on the sidelines trying to achieve what they have. I also think that settling is not an option…people who think that are they shouldn’t settle, largely, that are the single ones. You HAVE to settle in life in just about everything you do. It’s the word “settle” itself that has a bad rap…it’s almost like it’s politically incorrect. I find it odd that in a land of people that are “individuals” and who are “independent”, there is so much sheep like thinking. If you don’t think you have to settle in life in just about everything you do, you’ve got a head on collision with reality coming! Especially with the opposite sex! Change the word “settle” to “compromise” and everyone nods their head. And guess what…that person that might not have seemed all that attractive but you get along with great, that’s the one you should be with…not the more attractive one you have to walk on eggshells around. And I’m totally guilty of trying to find a perfect 10, or a trophy woman, when I’m in fact not one. I fit Evans mold of the typical guy (sometimes – working on it) who is a 7, who thinks he’s an 8, and who is going after 9’s and 10’s! How stupid! Do I really think making love to a 30 year old hard body is going to be that much different than a 40 year old typical women? Not that much. The best relationships (and lovers) I’ve ever had have been with ladies who are more or less equal in apprearence, or less, than me. So, after educating myself with the extreme help of Evans blog (thanks btw!), I’m lowering my lofty standards and “settling” more and it is working out very well. Besides, some of the best things about relationships, like forging traditions together for example, have nothing to do with physicality anyway. Besides, I’ve found that most good looking women can’t cook their way out of a paper bag! What are you going to do on Thanksgiving?

  8. 48


    You took the words right out of my mouth regarding getting wiser to BS as we age. While it does make it statistically more difficult to find a match, we don’t waste as much time on people who are wrong for us from the get go. I think it’s actually an advantage.

    I would add that gaining wisdom with age isn’t guaranteed across the spectrum of intelligence. I suspect smarter people lean a little more towards learning from their mistakes than do their less intelligent counterparts. I have a neighbor, for example, who is not exactly a Rhodes Scholar. She doesn’t seem to get it that she is making the same mistakes over and over again with men, always with relation to personal boundaries and self-esteem–not that I have it down perfectly either, mind you. But she also isn’t interested in pursuing any dating advice or reading self-help books that might point her in the right direction–she prefers bodice rippers. That points to the biggest factor in the acquisition of wisdom, regardless of intellect: the willingness to be introspective and make changes if you don’t like what you see.

  9. 49

    All good points, but I truly think most people would be so much better off if they just got the hell over themselves. Impressive? 10? Maximizers? Mensa? Who’s the judge here? Who’s doing the defining and establishing the criteria to be met? Personally, I find it all just a little, er, creepy. I’m single & in my 50’s, post-long term marriage, post-childrearing, and have always had my own career. I also happen to be fit, athletic, smart, informed, political, artistic, blessed with a young-looking face & good health, but – luckily – I’ve always had the good sense to realize these “impressive” traits are 99% the result of dumb luck. A gift. This is what I think a lot of impressive people forget, and the result is they wind up feeling entitled to nothing but the best by virtue of simply possessing all these wonderful traits. Kinda like they’ve earned it, or even DESERVE it. But I don’t think that’s how life works. Sure, I’m initially as impressed as anyone else with a good looking guy who carries himself well, but when the sun goes down, I’m always going to choose a great personality, warmth & wit over looks. Just speaking from my own experiences with my age group, I think the older you get, the more you realize how essential compromise is IF you’re serious about finding an in-depth intimate relationship(s). But compromising is different than settling. I can compromise in one area and still remain true to myself & be quite happy. If I stay with a man who disregards my boundaries, disrespects me. or takes advantage of my good nature, then I’m settling. Another harsh reality is that being a hottie at 28 doesn’t guarantee you’ll be desirable at 58. You might have been solidly within the ranks of the impressive crowd in your salad days, but sooner or later you find yourself face-to-face with the realities and practicalities of aging. It’s sort of a blessing and sort of a curse. In many ways, age is the great equalizer, the leveler. Overall, I believe there is an incredible amount of narcissism in our culture, and it’s encouraged in our media and advertising from a very young age. But IMHO someone who is truly self-loving is not someone who is narcissistic, just content. And they don’t require mini versions of themselves to keep them company & make them happy. While it’s true that we do tend to gravitate towards people who share our economic background and world view, that’s very different than feeling like you’re settling if you accept anything less than the “cream of the crop.” Not only does that sound limiting, to me it sounds pretty boring.

  10. 50

    Assuming that you’re on the “better” part of an extreme in terms of the bell curve (wealth, intelligence, attractiveness, etc.) then nobody is saying that you should dumb yourself down or try to make yourself more “average.” What I suspect Evan is saying is that you might want to consider being more willing to accept someone who is more average than yourself in that area. For instance, if you’re in the top 10%, you’re willing to date someone who’s in the top 30%. This doesn’t decrease your value, but it increases the pool from which you get to select.

    But if everyone is trying to meet someone their equal, or better, then doesn’t that mean that if our potential partner is actually better than us that they are then dating down? So when is it okay for someone to date “down?”

  11. 51

    Perfect is the enemy of good…and of happy.

  12. 52

    Dear EMK and others, I’m not sure this is a problem only related to the most “impressive” people. I guess with the most impressive crowd it is just a little more peculiar? The way I see it, love is hard, and everyone but the most fortuitous struggle with it at some point. I have several very impressive friends who are coupled, as well as impressive single friends and the same of both who would fall in the more “average” category. What I’m saying is that isn’t it difficult for most people to meet that special someone? For argument’s sake, let’s say that the top 2% of people want to date others in the top 2%. But what about the bottom 2%? As some others have said, it’s not just about who you want to date but whether or not that person will want to date you. I think it can be difficult for everyone, not just the cream of the crop.

  13. 53

    This question is asked all the time and it makes me almost as sad as it does angry.
    You are quantifying people. People are not numbers, they are a complex mix of many, many things both fortunate and unfortunate.
    Why assume a rich, successful, charming man is more likely to find love than a shy guy with an “ok” job or no job at all? Or that a gorgeous, intelligent babe is a better lover than her plainer sister with less education?
    What does any of this have to do with anything?
    Finding “the one” is a needle-in-a-haystack proposition for everyone who’s honest about it. The crucial difference is attitude and effort.
    People who always assume the grass is greener have problems far more serious than finding a significant other. This is the attitude that prevents people from being happy no matter what they have.

  14. 54

    I don’t think it is unreasonable for someone to WANT an equal when it comes to intellect/looks/success, but the chances of it happening so perfectly are slim.

    These high achievers need to find balance in a partner. I am dating a man who is pretty successful, cute, and a literal genius. I am attractive, smart, and have a decent job in education, but i’m no genius, and i’m far from rich. I am, however, way funnier than he is. We talk about intellectual interests and pursuits, but probably not as much as we would if I were a complete brainiac. He has super-smart friends to talk about his geeky interests like that, and he is satisfied.
    People who go on dates with these great catches might feel intimidated that they are not as rich or smart, and that is where I think a lot of the problem lies. The successful person is spending the whole time sizing the person up, and that person is intimidated and may begin to feel badly about themselves. No one wants to date the dude with low self-esteem.

    Perhaps the successful folks should relax a bit in their assessment of their dates, and try to just have a good time. If you spend so much time thinking about yourself, and how wonderful you are, you will miss the good qualities in someone else.

  15. 55
    Karl R

    Dana asked: (#53)
    “Why assume a rich, successful, charming man is more likely to find love than a shy guy with an ‘ok’ job or no job at all?”

    For the same reason I assume that Michael Phelps will win if we race a couple laps across the pool. The odds are stacked in his favor.

    “Or that a gorgeous, intelligent babe is a better lover than her plainer sister with less education?”

    The plainer sister may be better in bed. But if my past relationships are any indication, we spend more time talking than having sex. Therefore, the amount of importance I place on stimulating conversation should reflect that.

    “What does any of this have to do with anything? […] People who always assume the grass is greener have problems far more serious than finding a significant other.”

    True. But this is a dating blog, so all those more serious problems fall a bit off-topic.

  16. 56

    Did we even ask these questions before internet dating came about? Seems to me the more choices you have, the less choices you have. Dating has become one big smorgasbord of one person after another online. It makes it seem like the supply is endless when maybe, it really isn’t. Being able to push a button and see people that you may be attracted to on a screen is so one dimensional. Maybe if people were able to meet more people in person things would be easier. Everyone thinks they are in the top 2%. So why shouldn’t they? Everyone is good at something. Everyone thinks they are so entitled to everything. At the end of the day snuggling up with entitlement isn’t going to keep you warm or take care of you when you are sick. Relationships are built on one person really taking the time to care about someone else. I don’t see as much time taken for caring, kindness or compassion in this world anymore. Everyone is too busy being their “true selves” in the top 1% of the world.

  17. 57

    Well – in response to sjz – At first glance, I felt your comments were slightly cynical. However, after re-reading, I agree. Unfortunately, the dating world has become multiple choice – better for some… not so much for others. Sure, it would be great to meet someone “live”.. However, I don’t do the pub crawl anymore and my workplace has exactly one man – and he’s married… I go to a gym – mainly family oriented. So – for me, online dating is where its at. I’m divorced, early 40’s and have kids…. Honestly, people are people… Human nature will take its course… I like your statement about Relationships being built on one person taking time to care about the other… A lot of people aren’t in in for the long haul-but if you really care about someone – its not a chore – its a joy and a privilege….

  18. 58

    Hi Karl,
    I was talking about finding “love,” not snagging a date or a mate.
    Of course a rich, successful man and a gorgeous, intelligent woman will get more dates than the national average, if you will. That doesn’t guarantee either will have a successful relationship.
    Maybe the fact that a lot of people look at this as a competition rather than a quest for mutual happiness is why so many people end up unhappy.

  19. 59

    I’m not going to rate myself on a scale of 1 to 10, but I will say that I have a decent career–I am a professional and have a master’s degree, I’ve been told that I’m attractive, intelligent and funny, and I don’t think that I present myself as narcissistic or snobbish in any way, ….I’m quite the opposite, infact: I’m very down to earth, genuine and sincere and have no sense of entitlement whatsoever (infact that’s one of my pet peeves with others); I’m not looking for a man who is a “10” or in the top 90% of the male population and believe that I am extremely realistic when it comes to what I am searching for in a relationship, ie: compassion, kindness, thoughtfulness, honesty, integrity, a good communicator, having a good sense of humor, etc; physical appearance to me is not extremely important, what is more important is the chemistry I have with the person; the problem that I continue to experience is finding a man who possess these traits, that I really don’t feel are out of the realm of reality……I’m not looking for someone who is my equal necessarily, but someone who compliments my strengths and weaknesses well…..so I don’t consider myself “picky” in my search for a partner, but I’m not finding the ones with the right characteristics, just the ones that seem to have intimacy issues, who are scared of having someone who has “it all” I guess….

  20. 60


    I completely agree. The great thing about internet dating – the chance to meet lots of people you wouldn’t have access to otherwise, is, oddly enough, its greatest curse. It feeds into our consumer mentality that there is always going to be someone better looking, younger, thinner, taller, or richer out there.

    I’m curious, Evan, given your profession, have you ever asked your fabulous single friends why they’re uncoupled?

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