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?

Join our conversation (127 Comments).
Click Here To Leave Your Comment Below.


  1. 21
    Evan Marc Katz

    To all the “I’m perfectly happy being single” people:

    Most everyone I know has a rich single life but very much desires a relationship. All of them, in a quiet moment with me, lament how tricky and frustrating dating is, and wonder when, if ever, they’ll find a suitable partner. So…

    The question is not whether it’s fine to be single and not looking. It is. No one’s arguing with you.

    The question remains: is it harder for more impressive people to date because they raise the bar so high that almost no one can jump it?

  2. 22
    Curly Girl

    In answer to that question: Nah. People are drawn to “impressive” people. If they aren’t in a public-facing couple they probably have something else going on.

    And not-so-impressive people can raise the bar pretty high, too. (Delusional!)

    But thanks for the question, EMK! It’s a good one, and I’m glad to hear that non-loser singles are getting some blog space. (Weren’t you once a non-loser single? 🙂 )

  3. 23
    Curly Girl

    Oh, and one of the things that happens when you are single is so many of the married/encoupled people want to cry on your shoulder for hours about how crappy their exclusive relationships are, as if you’ve got nothing better to do than listen to their all-important relationship problems (narcissism, anyone?). So I guess the lamenting goes both ways….

  4. 24

    Is it harder for more impressive people to date?

    I think it’s harder for anyone – impressive or not – in their 30s and 40s to date. The dating pool is smaller. Your identity is more “fixed,” which makes compromise with anyone more difficult. In addition, you’ve spent so much time not being with someone that you have filled your life with other things – work, hobbies, friends, volunteering, etc. – which makes it harder to find the time looking for someone & dating, because it means cutting back on the stuff you’re already involved with.

    To test if what you’re seeing is a function of impressiveness or simply age, you’d have to compare your group to:
    (1) younger impressive people; and
    (2) non-impressive people in their 30s-40s.

    You suggest that maybe these impressive people are mostly maximizers. But do you know that they are? They are your friends, so maybe you do. Without more info, I’d suggest that maybe some of them are satisficers who have made good choices, because they don’t hold out waiting for the best (which may or may not come along). As a result, they have advanced in their lives and become the impressive people you see today. It’s not clear the maximizer theory holds up.

    Last, I think the comments above about dating pools and statistics make a lot of sense. It’s harder to find a “match” when you want to match across different levels of impressiveness (looks, intelligence, humor, etc.) as well as other concerns (geography, religion, etc.). I used to enjoy teasing friends who believed that there was “the one” out there for them the chances that this one lived in China.

    It’s easy to set the bar “too high” if you choose to narrow it based on one specific category, rather than an aggregate.

  5. 25

    First of all — if my group of friends is a group of impressive single people, I’m much less likely to feel the need to seek out a relationship. Instead, I get a lot of the personal interaction from my friends. That can be a good thing–not feeling desperate or alone, but that can also be a bad thing if there’s no strong impetus to find a compatible someone.

    That being said, it does make sense that it’s harder for ‘impressive’ people. There’s less reason to ‘settle’ or have a ‘Mr. Right Now’ kind of relationship if you’re fulfilled in other areas. Plus, it’s only natural to want someone who doesn’t bore you and can understand where you’re coming from. It’s not an issue of narcissism or ego, but of finding someone simpatico. For example, as a woman with an impressive set of degrees* it’s ‘easier’ for me to date a man with a similar background. Not because I’m a snob, but because he would be more likely to understand the hard work I put into earning them. Plus, I wouldn’t have to deal with HIS insecurities. Or someone with an ‘impressive’ career would understand the amount of time and energy it takes to keep such a career going.

    *It’s impossible to claim to be impressive without sounding egotistical, so I apologize. And the idea of being ‘impressive’ is pretty subjective and must vary from social circle to social circle.

    1. 25.1

      very eloquent and well -expressed!       As a fellow single  woman, dating I identify with you!
      best wishes to all of us,

  6. 26

    It’s a numbers game. If you only want to date someone who is in the top 10% in terms of intelligence and the top 40% in terms of attractiveness then you’re only talking about 4% of the population. (If only 10% are intelligent enough, and then only 40% of that 10% is attractive enough, then you get 4%.) And this is only looking at two factors. And there’s no way of saying that people will all find a similar mate in those key respects.

    For example, how often do we find that a higher earning man will go for a woman with less earnings, but more attractiveness? So that automatically means that some higher earning women aren’t going to have an equivalent partner and will need to make a choice to go with a lower income man or to have no man. Is this settling?

    So once you figure out how great you are (i.e., what percentage of the population is like you, or better) then try and figure out how likely it is that you can find one of those people, and then how likely is it that they would be interested in you back. So if impressive people are in the top 2% of the population and they’re only seeking someone in the top 2% of the population then they’re going to have a harder time simply because that’s the way the numbers work out.

  7. 27

    Ah but the numbers are not weighted equally! How a woman looks factors more to a man that how smart she may be. Also personality and just being easy to get along with counts. So many impressive people are high maintenance. I remember when I was younger and I bragged about being hard to please and an old man said to me: being hard to please means you go through life not being pleased often.

  8. 28

    While I agree that on some level, we all want to love an be loved and we can enjoy a satisfying life in or out of a romantic relationship, is it possible that “impressive” people find difficulty in being motivated to find someone? For instance, look at how many discussions there are about “why are women this?” and “why are men that?”. We can’t get around the preferences of others and change their wants and desires, so could it be more difficult for impressive people to date because they don’t want to jump through all the hoops, so to speak? If they’re enjoying their lives well enough, is that motivation really there? For some perhaps; maybe not so much for others.

  9. 29

    Had another thought about “maximizers”; I consider myself to be impressive on a few fronts, i.e. I’m continuing my education, I own a home, I have a good career, I’m raising good kids, and I’m spiritually grounded. But my fatal flaw is my weight. I just put myself on Weight Watchers so I’m doing something about it, but it’s a process and doesn’t happen overnight. But that one thing knocks me off of 99.9% of anybody’s “list” of who or what is acceptable. So, until I lose some weight, I can pretty much forget dating. Now as far as being a maximizer, I’m not looking for the best looking or richest guy, but the best I can do – even with the “impressive” qualities I possess is a guy who MIGHT be able to structure a complete sentence or all of his teeth, or some guy who has a wierd fetish for BBW chicks. That doesn’t even rise up to “settling”. So until I have reached the goal of weight loss, I’d rather not mess with trying to date.

    1. 29.1

      Sister, there are lots more men than you think who like round women. Work on loving yourself and all the rest follows.

  10. 30

    I’m in my early 40’s. I was married right after college, and thrown back into the dating pool a few years ago. I have many single friends in their 30’s-guys and girls. All professional, good looking, smart-and alone. I searched for love and kept looking for that spark-that spark with someone intelligent enough to hold a conversation. It was hard. Very hard.

    I finally got Evan’s Finding Love Online. It opened my eyes to give the guy who was a 5 or 6 a chance for a second date. A 5 or 6 that was smart and met my “other criteria.”. It has worked. My friends were amazed that I went out with him again, and I have to say, the “spark” and love has only gotten better with time. It has been over 6 months now. And my friends love him. Because he is a great guy who meets all my needs. He just doesn’t look like what I expected him to. But that’s okay. I’m happy.

  11. 31

    I’d venture most people are drawn to, and fall in love with, those who are most similar to themselves in terms of attractiveness, intelligence, humor, inner and outer measures of success.

    EMK: “The question remains: is it harder for more impressive people to date because they raise the bar so high that almost no one can jump it?”

    No. They aren’t raising the bar any higher than anyone else hoping to find someone who complements them, that they can *relate* to.

    I agree with A-L that it’s a numbers game. If you are in the 2%, (or 10%, or 20%) of a particular catagory of impressiveness – your pool of similar potential partners is going to be correspondingly as small.

    Think about European royalty historically: there were only so many monarchies in existance, therefore to marry within your class meant marrying someone who was related to you by cousinship to one degree or another. The smaller the pool, the fewer the choices.

  12. 32
    Evan Marc Katz

    Thank you for the feedback, Suzy. It means the world to me.

    In case you’re wondering, the product that helped her meet her boyfriend was http://www.findingtheoneonline.com.

    If you’re finding it hard to meet a great partner – online or off – this 7 hour CD series could make a big difference. Let me know what you think!

  13. 33

    I’d like to add another point or two. Evan said that his friends are in the 30-40 age range. I think alot of people who are smart and career-oriented, and perhaps not necessarily as child focused, are delaying getting married or finding a partner. I often wish that I’d been more ready to settle down while in my twenties; it would have made finding a partner much easier. Some of my friends didn’t get married until they got into their forties, and some have simply given up on dating. They always say they’re too busy with their careers, but when pressed, they admit that they’re afraid of getting hurt again. Perhaps when you’re doing well with career/friends, all the difficulties associated with dating can be pretty devastating to the ego, and you can feel like a loser in that arena.

  14. 34

    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? <– This is a interesting question. Last year I decided after getting my act together to try online dating, and I went on 54 first dates last year (plus multiple second dates). I just had this feeling that I didn’t want to settle, that I wanted someone who I was attracted to, who was attracted to me (very key), who was intelligent, Christian, had a good relationship with their family, and so forth. But then early this year I went on a date with a girl from eHarmony, and she’s a medical doctor (and used to model too, but that’s merely icing), and we’ve been together four months now, and we’ve planned out dates till the end of the year. Basically, things are going fantastic. So I’d say that it’s not imperative that you find someone who is impressive as you are, but you should know first what you’re attracted to, what your potential is for attracting a mate (Kevin James and Hitch notwithstanding, shorter guys have it tougher, and heavier girls have it tougher too), and what your plan is for meeting people in your range.

    Because, let’s be honest, there are a LOT of attractive intelligent women online. The trick is meeting them.

    And man, do I have some crazy online dating stories! It’s good stuff, let me tell you.

    If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.
    – Sun Tzu

  15. 35

    Another reason “impressive” people in their 30’s are single? Speaking for myself… I didn’t start reading EMK’s blogs until now. I’ve always been a serial monogamist. I spent many, many years investing in men that weren’t serious enough about me, or when they said they were, they suddenly got cold feet after 3 years and left me for a different woman. Really, being alone isn’t something many people choose. Sometimes it’s the luck of the draw, but sometimes it’s putting too much stock in a worthless investment! Now that I know some of the warning signs and bad characteristics, I can clearly recognize patterns in my own dating mistakes and make healthier choices for future relationships. That is key… recognizing the roles we play in our own singledom.

  16. 36

    Interesting reading. I actually agree with nearly everyone in some way, shape, or form.

    A couple of points by way of a story.

    Recently, I was out of town and met up with a friend of mine who’s a doctor in residency. We met up for dinner, then out to meet a friend of hers from work. It was a challenge scheduling meeting up due to her schedule. She was a bit of a late bloomer, and is highly intelligent, nice, funny, and attractive. Her friend is also.

    Both shared with me their challenges regarding dating. No time was number 1. Something else one mentioned was that a certain birthday was approaching. Of course my usual barrage of over-the-hill jokes ensued. I think, but didn’t want to blatantly state, that concerns over starting a family were behind the birthday concern.

    The discussion ensued with several points being raised:

    – They’re in the top 1% or better.
    – They have little time, if any for really building a relationship
    – They want someone in top 1% or better (someone who brings as much or more to the table)
    – Many in top 1% or better are married
    – The time (years), effort & energy to create that career is not to be underestimated
    – They’re perfectionists

    Notice the gender-neutrality of the points. The overriding I mentioned was patience. It will take more time to get to know someone, let alone find someone who may not mind them having an 80+ hour workweek. Also, I mentioned perfectionists are more likely to focus on the supposed imperfections rather than all of the great things in others.

    Plus, people in 30’s & up are likely to have a few dating battle scars. Sometimes people are so cautious about being wounded they self-sabotage in dating to avoid placing themselves in a vulnerable position.

    On a more gender-specific point, they expect to marry or date up. I brought up the point that if both genders applied that criteria, there would be no dating at all. I guess I just tried to get them to see that they have to somehow reconcile all of these things and choices they make. And sometimes, you can’t have what you want when you want it.

  17. 37

    After reading your thoughts on compatability v. chemistry rating, putting it into practice and posing some questions to my single friends, I have come to understand this. People have a rating scale they default to. Wants and expectations first, needs last. It really doesn’t matter if they have great qualities to offer, most folks EXPECT to find a partner with great qualities. I think even more so with those people who do have a lot to offer. If we become more concious about what we NEED as we look for potential partners, this would put us in a place to find someone truly compatable. However, the other factors that influence our success are our feelings about being vulnerable, relationship fears, an ability to be open minded and what we feel we deserve. Often, even the most successful individuals are unaware of the underlying groove that drives them, and in the end, may sabotage their best efforts unknowingly.

  18. 38

    Mr. Right,

    A slight veer off the topic, but I’m working on myself and perhaps I’ll give dating another shot. But I want the work I do on me to be FOR me, not because I’m trying to get a date. And even when I hit my goal, I’ll never be a supermodel. I might be a 7 or 8 when I’m dressed up, have the hair & make-up, etc.

  19. 39

    Not saying you did that Mr. Right. That’s how my comment came off and I do apologize.

  20. 40

    @ Terri,

    Interesting points, espcially “what we deserve”. I think what we miss is that it doesn’t matter how much we “deserve” to be desired, loved, etc. by someone. The right person will be with us even when we don’t deserve it, with given the nature of human behavior (myself included) is not daily.

Leave a Reply

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