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.


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!

Eric M. Jones.

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.


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.


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.


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.


I concur, some additional background information would be nice unless you are just looking for smart arm candy.


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.

Steve Nations

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.


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.

JP Morgan

But did she get an A in Real Analysis?


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


Could you perhaps include some more info on this woman? What does she like doing for fun? What are her tastes? Not all men are so shallow as to think beauty and a successful career are all that matters.

Some Random Economist

I don't believe there's such a thing as a woman who is so beautiful she doesn't get asked out. There are only beautiful women who don't like the quality of the men who ask them out, or aren't comfortable talking to men who approach them in public.


So interesting! Is this a start of a new business or is it part of a PhD thesis?


I am a heterosexual female student and even I want to date her. Get on it, gentleman.

Caleb B

I tell the single guys I know in their late 20s to be patient. "your stock is only rising. You have a good job, a full head of hair, and no criminal record. A pretty girl is going to find YOU."

In my early 20s I knew a lot of very nice "catch" guys that couldn't find a nice girl. I'm 31 now and that situation has completely reversed.


Ain't necessarily so. I am... well, let's just say some decades past my early 20s. no criminal record, still a full head of hair (& at least 4-pack abs), and not only a good job but a considerable degree of financial independence, but she hasn't found me yet.

So I can't help but wonder: yesterday a job advertisment, today this... Are we to expect the opening of the Freakonomics dating site shortly?


It's Kelly Goldsmith. Cute, but not that hot.


Being extremely attractive and completely focused on work are not great assets in a possible mate. Intimidation is a plot device turned urban myth. The greatest reason people stay single is they are overly picky.