A Chance to Date One of The Most Eligible Bachelorettes in Chicago

(Photo: tracy ducasse)

We’ve had this blog for seven years.  This is the first time I have ever tried to use it play cupid.

Here’s the deal.  I have a close friend here in Chicago.  She is in her late twenties.  She is really smart. She has an extremely successful career.  She is incredibly pretty.

Here is a true story.  The first time my wife Jeannette met this friend, she was so shocked by my friend’s beauty that her jaw went slack, and she temporarily lost the ability to speak.  My wife later described her as the most beautiful woman she had ever seen in person.

Why, if she is so great, is she still single?  I don’t have a good explanation.  Partly, she works really hard so she doesn’t have that much opportunity to meet people.  Also, I suspect a lot of potential suitors are intimidated by her – I know I would have been.  She’s got a Ph.D. from a top university, she’s on top of the world professionally, she’s pretty. A man would need to be very self-confident to ask her out.

So, with her permission, I’ve decided to take things into my own hands, using the blog to find her a boyfriend.

Here are the rules.  If you think you have the right stuff, or you know someone else who does, send the following things to lindalevittjines@gmail.com:

  • A paragraph (or several) describing yourself (or the person whom you think would be perfect for our bachelorette). This can and should include your/the bachelor’s age, state of residence, educational background, current profession, hobbies and interests, marital history, and anything else that you think someone who’s considering dating him would want to know.
  • A current photo, if possible.

My sister Linda, who claims to have a sixth sense when it comes to ferreting out prospective love matches, has agreed to cull through the submissions, do some pre-interviews, and set up the dates. Linda is also a close friend of the eligible female friend I’ve been describing, so she’s going to be like a cross between a mother hen and “The Mentalist” (meaning cautious and intuitive – she says “playahs” need not apply!).

Here’s hoping you, the Freakonomics readers, can provide leads to “a few good men.” Without revealing any names or other personal details, I’ll blog in the future to let you know what happens when the crowd plays Cupid.

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  1. fotios says:

    What about those eligible but not requesting a date also send in their paragraph and picture and then you can test what are the characteristics of someone self confident enough. This should answer the question of why such a great woman is single. What about those that are suggested by others? Are they different from those putting themselves forward? Is self opinion of suitability better than what others think? Glad to help with the analysis, not the dating!

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    • Agustin says:

      I would actually be very interested in such post. Who answered ? What is the profile of the not intimidated men who dare to be considered for the “most eligible” bachelorette in Chicago. (yet, those men ALSO remain single)
      I would love to answer myself actually, the woman seems fantastic, but I live in China and soon will move to Norway. No long distance relationships for me.

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  2. Eric M. Jones. says:

    In my single years, I dated a stunning, smart, talented beauty. The only reason I ever dated her was that she and I had some history because years earlier she had dated my best friend. So after a few dates, I asked her…”How on God’s Green Earth is it possible that you are single and available?”

    She remarked, sadly…” ’cause I scare the piss out of normal guys”. Sociopaths and various players would ask her out, but regular good guys always thought she was out of their league.”

    My advice to your friend in Chicago….You’ve got all the cards in this game, girl. Find a guy who approximately measures up to your standards and just ASK HIM OUT!

    The above stunning woman ASKED ME out and most of my guy friends hated me for it…HAH.

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    • twobeef says:

      I know a guy online who says he has the same problem. This guy was kind of a skinny nerd when he was younger, but he dedicated himself to weightlifting after high school and ended up getting a lot of modeling gigs. He also went into programming and ended up pretty well-off after the startup he worked for was purchased by a large corporation. From what I can tell, he doesn’t have a terrible personality or otherwise drive people away.

      And his biggest complaint about dating is that he goes up to women at the bar, gets to know them, has long conversations and such, but he never gets any phone numbers, saying that once he asks a woman to hang out that they shy away and feel embarrassed for trying to hook up with the guy. I haven’t gone barhopping with him personally, so take that with a grain of salt, but he has been single for quite a while.

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      • James says:

        I may be pointing out the obvious here, but I long ago figured out that if you go to bars to meet women, you have a very good chance of meeting women who like to hang out in bars. (I suppose this is likewise true for women.) If you’re not really interested in hanging out in bars, that means you have a very small chance of meeting anyone with common interests.

        I’ll offer your friend a suggestion for meeting interesting (at least by my standards) women: learn to ride a horse. From my observation, about 95% of riders are women.

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      • Jorge Borges says:

        Hidden due to low comment rating. Click here to see.

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    • David says:

      I hear stories like this and I love them, probably because of the same reason I love hearing about people winning the lottery or making a hole in one in golf. I know they are possible and it happens but they are so hard to believe. Where are all these beautiful single women that are scaring away men?

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  3. Matthew says:

    It might have been nice if you had given some indication of her field and/or course of study. A person with a PhD in biochemistry is a very different person than one with a PhD in French. In addition, a relative of mine with a PhD in History does work in television documentary production, a job not necessarily associated with academics. While “Smart & Beautiful” would certainly interest most successful men, a little info about that which she is interested would be helpful.

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  4. JP says:

    Are there geographic restrictions on this? Does the potential suitor have to reside in the Chicago area? I am in St. Louis and looking for just the type of girl you described.

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  5. Steve Nations says:

    Isn’t the question “why is she single” an economics question? And hasn’t the question been studied? (Not specifically in this case of course). I believe it has something to do with asymmetrical bidding. If the beautiful women see themselves as a great catch, they wait too long to “bid”, and then eventually all the good men really are gone, snatched up by women who jumped into the “bidding” early.

    By the way, my wife is beautiful.

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    • Steve S. says:

      This obliquely relates; one of my favorite quotes from “Moneyball” by Michael Lewis (it didn’t make it into the movie):

      “Every form of strength is also a form of weakness,” he once wrote. “Pretty girls tend to become insufferable because, being pretty, their faults are too much tolerated. Possessions entrap men, and wealth paralyzes them.”

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    • Eugenia says:

      What does it mean for a single eligible woman to “bid”? I don’t prefer to ask men out because, as a single career woman myself, I prefer men who are more assertive. I’ve done the asking out a few times and predictably, I end up with men who are not as assertive as I would like my partner to be.

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      • Brad says:

        Women are hardwired to not like the kind of guy that isn’t assertive enough to talk to them. They may like a guy they see, but unless he signals his interest she will not make the connection. I have a few friends who are gorgeous accomplished women who have this issue, as well as plain Janes (though guys don’t seem so concerned with approaching them).

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    • Carolina says:

      Does everyone now assume that it is the woman who has to do the bidding? Maybe that is the problem.

      Like every woman I know, I want the man to make the move. Why? Because if a man is sufficiently motivated, he WILL make the move. If he doesn’t, he was not sufficiently motivated. He should go find a woman that DOES motivate him. And then we can all watch as he goes after her relentlessly.

      Yes, I know there are exceptions, blah blah, but who cares. This is overwhelmingly the rule.

      I am not interested in a man that won’t act.

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  6. Jack says:

    Without referring to any specific person, people who are given excessive advantages (whether it’s excessive money, fame, or looks) often face a much more difficult time developing a good personality.

    Of course, a ‘good personality’ is culturally defined by what the average person aspires to so there is an inherent gap between someone who has average assets and someone who has extreme assets but that’s another story.

    And there are definitely exceptions. And they are even more impressive for having a good personality despite the liability (from a personality viewpoint) of their advantages.

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  7. JP Morgan says:

    But did she get an A in Real Analysis?

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    • Cathy says:

      Believe it or not…I am one of the above mentioned women….most recently three men I hanged out with told me I am attractive and intimidating. I am having the same problem finding a match now…

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      • Peter says:

        Are you really one of these women when you “hanged” out with three men? :)

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  8. Eric says:

    I wonder if this is a prank to get your sister flooded with emails from single guys?

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