Search the Site

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

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.