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. 101

    Trying to find love is like trying to win the lottery, and the odds are really against you. Especially for us men since today is totally different than years ago which it was so much more easier.

  2. 102

    Almost all of the “impressive” people I meet are already taken or they don’t want to date anyone. The rest of them are generally like you describe here and let it be known upfront, as well as that they’re not looking to “settle” for anyone even remotely different on any one measure (this is what I find with online dating), which, even if you match that person, is intimidating as hell and even kind of unattractive to be told upfront that this person thinks she’s all that and you better be good enough or you’re wasting everyone’s time. The latter, I see why they’re single. But all three groups show why it’s not really a matter of not wanting to settle. At least half the time, it’s more so having been beaten to the punch, and it’s usually a lot more than half the time. Not all impressive people are single.

    I’d also have to say impressive people don’t generally hang out in groups together because they are fairly hard to find in the first place, unless they work together. With the job market being like it is and education helping less and less in boosting career opportunities, a lot of impressive people are lacking in the career department, which makes it harder to find each other once we graduate. Then when we do find someone who interests us, they’re in one of the three categories I mentioned, and the snobs in the third category will eliminate you ahead of time for not equalling them in career.

  3. 103

    Most career women have really destroyed many of us good men already do to their greed and selfishness that they carry around with them everywhere they go unfortunately since so many women nowadays really want the best and will never settle for less at all which many marriages today have ended over this.

    1. 103.1

      Take your own advice and settle for less then.

      1. 103.1.1

        To Adreana, oh by the way it is very true what i have said with my last comment since most women today are Nothing at all like the good old fashioned women were that were so much Nicer and much easier to meet with a much better personality than today which certainly does count too. Today many women are very selfish and greedy which i have just mentioned since they want it all today unfortunately which is the real reason why many of us good men are still single today when there is no reason to blame ourselves anyway since many of us are not single by choice.   Many career women really think that they’re very high and mighty which many of them will just grow old their cats since many of the women with their very high salary do have such a very bad attitude problem that i have noticed which my friends do agree with me too.   It is very obvious how the women of today are when years ago most women had to struggle along with their men to make ends meat since they hardly had any money at all to begin with since most i would say had to live with their parents anyway.   Most high salary women unfortunately cause more divorces since many of these women are very likely to cheat as well which is very sad.   And if i met a woman that makes much less money than me so what big deal since money is not every thing which being very compatible with one another would be much more important anyway.

        1. Adreana

          I don’t know if “old-fashioned” woman are any better or loyal than modern-career women..but they surely had  less options. When you have more options /can take care of yourself you’re less likely to settle or stay in an unhappy relationship…the same goes for men. But NO quality, sane person who’s  NOT in survival mode is willing to put-up with someone’s bad behavior, or actively choose someone they know they would struggle with. Don’t you want to be happy? Or are you ok with  just being “ok” in a relationship to fill the loneliness?

          IMO if the man or woman has dignity , they will not get married and drag another person into their problems before they fix their issues. If they do, they will soon become like those old, miserable couples who stick it out just to be loyal ( while dying inside)…

          Walk a day in those miserable couple’s shoes and you’ll start thinking how lucky the career, cat-lady is. BTW, the old-fashioned women with options also wanted the very “best”. Take my grandmother for example-she wasn’t a high- earning CEO ( or whatever), but she was very beautiful  , had a good career as a nurse,  and a charming, ladylike demeanor.     She had many suitors but who do you think she chose at the end? The   good-looking man with a great career, lots of land and a good reputation..and yes, they did fall in love so it wasn’t just based on status or beauty. ( I know other women from older generations had different needs/ wants than my grandparents, but I’m just sharing what I know).

          I’m not saying this to discourage you-I’m just saying   whether now or then, desirable people with options tend to be a lot pickier. There is nothing we can do about it other than improve ourselves or look for a person with less options.

  4. 104

    I am a 31 year old female, medical student planning on becoming an anesthesiologist, have an interest in learning languages on my down time, have been told I’m a pretty good cook, love to write and hope to publish a book one day, and actively travel the world. I’m 5’7″, size 4 and in terms of looks I’d say I’m a 7 or 8.

    Unlike a lot of medical student counterparts, I have spent a huge chunk of my 20s being directionless and jobless. I used to be a shy and my lack of networking skills really hurt me when I graduated college and was looking for employment. I just didn’t know how to put myself out there so I bounced around from deadend job to deadend job barely breaking 24K in annual income. Then it struck me one day that I couldn’t live like this forever and pursued medical school in my late 20s.

    I consider myself a straight 7. 7 in looks, 7 in career, 7 in intelligence, and 7 in humor. I have my own flaws like anyone else and have learned to own them. I’m slightly tall for a woman and have been open to dating someone shorter. I also understand that someone doesn’t need a graduate degree to be considered smart, but I do value education and highly prioritize men with college degrees. Because I struggled so much with finding a job myself, I don’t judge a man for what he does for work as long as he has long term goals that are realistic. The only thing about income that bothers me about guys that I meet is that they fail to live within my means. For example, I’m still currently a student so I have to budget away for food, rent, and utilities. I limit going out every weekend and even what I order at restaurants. I don’t drink often, for health reasons as well as the added benefit of saving money.

    I still find it hard to date. Most guys I meet  don’t have long term goals. It’s just that I have struggled so much and have really pushed myself into doing something and I really wouldn’t want someone around me that is going to drag me down by having bad finances, bad habits (drinking too much, smoking too much), and making poor choices (driving drink, consistently overspending).


    1. 104.1
      Sharon Reddy

      Everything you want sounds realistic. I think you should be clear in your online profile. That you are not looking for a high income but a man who has completed college,   lives within his means doesn’t smoke or drink a lot, is disciplined , has long term goals , and understands that you are willing to pay your way but you are still a medical student so cannot live an extravagant lifestyle at this point. Perhaps you should work a little on your grooming and self esteem. Also make it clear that height doesn’t matter to you as shorter men may not contact you. Perhaps even look for other doctors as they may have a similar mindset, professors, accountants, pharmacists, IT professionals, lawyers. I am sure you will find someone. I think a match making agency may work well for you, if you can afford it.

  5. 105
    Sharon Reddy

    One thing does strike me though, you sound so serious for such a young lady. I know you have struggled to get where you are, but also show you are able to relax and have fun. Even without drugs or alcohol.

  6. 106

    Hi, Just my two cents. I could be one of the friends you describe… Maybe 9 intelligence, 7-8 look,(I do not think I am beautiful… just being told so. I keep in shape, dress nicely….maybe 5-6 career as at the time I am pursuing a second (medical) degree and I do not earn money. 8 humour? What’s the problem? I was googlinf around to get the answer. First of all I think that intelligent people can be intimidating and demanding. I had a long complicated relationship which lasted about 12 years (until I gave up) and well while he was quite rich, I was better looking and for sure more intelligent which… I think made me complicated to handle and more demanding (?) that he wanted me to be? We are still on very good terms and good friends though so I could not have been such terrible girlfriend and I was told by third parties that he misses me but… no thanks. He hurt me (psychologically and emotionally) which made me be even more afraid of fallin in love with someone. But… it happened and when I least expected to happen… he was/is extremely smart   even though he just attended highschool, I’ll give him a 9, great humor (I’ll give him a 10), maybe 6 for career and 6.5 7 for looks… But I felt at home with him… He is not perfect at all but… perfect for me… and we now are stuck somewhere. I have been a little clingy last   year I admit (but we live thousands of miles away so… a couple of text a day well….). Then I realized he did not like this and returned to be the same ld independent me…. but now he sends mixed signals, gets hot and cold…. One of the things he told me is that I was way above him in terms of looks, education, lifestyle….. and well while I honestly do not think so… he seems to be convinced. Pretty disappointing uh? So, stil to figure out why smart+pretty+sense of humour puzzles men… As for me, what I can say is that I really want to be with a person I like a lot….not just a person to be in a couple

  7. 107

    If you’re impressive, you have worked hard, you may go to the fit club every second day, read and educate yourself a lot,   have become quite knowledgeable in politics, History, … you need someone who can challenge you. Put you up. So if you find someone who wakes up at 1pm, spends her/his life in front of the tv, or whatever is not empowering and doesn’t give you this feeling to move forward, to make something out of your life, it won’t work.

  8. 108

    How about when you aren’t terribly picky, just looking for someone kind and self sufficient and active enough to adventure, but people consistently stop being attracted to you due to your intellectual traits?

    Because I’m there. I study Physics as a major, speak German fluently, read classic literature and philosophy for fun, and otherwise I play rugby, travel, or climb walls in my free time. Im overachieving not for anyone but myself. I don’t have commitment issues. Im probably about an 8, and I get a lot of male attention, but only until about 4 months in. I honestly believe I will spend 80% of the rest of my life alone.

    1. 108.1
      Evan Marc Katz

      Perhaps you should reprioritize. Build in more time for dating and less for overachieving.

      You sound impressive, but most men don’t need an impressive partner, they need an AVAILABLE partner.

  9. 109

    I’m in my early 30’s, looks-wise I’m a 10, career wise 8, intelligence wise 9, humor is relative, so I’d add emotional maturity instead, and for me I’d say 9-10.

    What I’ve learned from dating an assortment of different people over the years is that appearance is not something that is all that important to me. The best relationships were with people that were maybe 5-7 on the looks scale, but 9-10 in emotional maturity, 9-10 intelligence, and 9-10 career. I find that the “spark” happens over time and have thus applied it to my dating habits. As a result, I have been on a surprising number of dates with men who really don’t come close to me in terms of looks, but that wows me with our conversation.

    Still, I recently separated from a person who is much older than me, late 40’s. He was plagued by this problem. He had almost married two other women in his lifetime, and so for him, he’s looking for that unicorn. We broke up because he didn’t feel the strong “spark” anymore while admitting that I had all the qualities in a partner that he was looking for and valued. He has expressed regret in his relationships and job pursuits of the past. Indecision is a trait of his.

    So it is probably a likely problem for those who have left previous relationships in search of better. The grass *has to be* greener, it’s not that it is.

    At the heart of it, for some: The grass *has to be* greener, it’s not that it is.

    They’ve invested so much time, are afraid of feeling regretful, that they will keep passing over future opportunities to commit because the possibility of regret looms.

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