You were walking west on Armitage. Faded skinny jeans, red handkerchief and brown sweater. Thought you were cute…

If you just happen to be the girl, boy or done-up accessory dog that applies to this ad, then boy-oh-boy did fate work in your favor.

Now I’m a firm believer in all things fate. I find it a much more relaxing way of being. But this relatively recent phenomenon has really got me questioning the parameters of what we consider “destiny.”

Riding the coattails of Facebook marriages and Google-ing is a intriguing phenomenon known as the Craigslist “missed connections” ad. For those of you who have been too busy scrolling through the more honest portions of Craigslist (yes, searching for the right used coffee table consumes most of my time as well), I will briefly explain. Directions for posting are pretty simple: You see girl/guy, fail to muster the guts to introduce yourself, go home and in a moment of “what have I got to lose?” you post a short line about noticing said person, list one descriptive feature, then wax remiss about not saying hi when you had the chance.

Now these posts can run from vague to utterly charming to downright creepy. And in the style of most things Internet, this romantic outlet has seemingly grown not only in acceptability, but in popularity as well. More and more are people actually reading and posting, infinitely upping your chances at a second chance.

Here’s where my liberal arts college late-night munchies with a side of philosophy come in handy. Fate vs. Free Will, or rather, Fate vs. Craigslist. In the not-so-distant past, you passed a hottie leaving the drugstore as you went in, and if you got a look or a smile, you were lucky. If Fate did not bump her into you, or send you both reaching for that last tube of toothpaste, then that was the end of that.

Until now. Fate can deny us a phone number and we have the opportunity to go behind Its back and try again via modern technology. Have we evolved into fabricating our own fate?

Now I am fully aware of the mind-bending arguments that surround this philosophical conundrum, and you’re welcome to get as meta as you want on me… but I have to wonder if this whole new method of finding love is all that natural. Sure, it’s dandy now, but I shudder to think of the handfuls of soulmates that passed me by, before a few double-clicks destined them to meet me at a well-lit, populated coffee shop. What did we do before missed connections? Just missed out? Now we have a new fate to depend on. If it’s meant to be, our posts will be answered.

And I do have to admit its convenient—you hardly have to leave the house. No drinks need to be bought, no risky pick-up lines, instead a mutual attraction agreed upon over email. Sure, you could muster up the balls and introduce yourself in person, but why risk rejection and humiliation when you can place your bets on an ambiguous MC post?

But does it work? So far, I’ve had a couple of friends find themselves/the object of their desire on an ad, and one of them is now dating their connected connection. Surprisingly heart-warming, no?

Of course that’s an exception to the rule; the majority of posts seem more akin to half-hearted scrawlings on a Catholic school lavatory stall. Yet the odds don’t stop any of us from looking, or holding that eye contact on the train a second longer, in the hopes of securing a post of our very own. Because after all, fate is fate, no matter how you spin it. As for me, I think I’ll attempt a fleeting smile at this fellow cafe-goer next to me and try my chances later on tonight. You were drinking a macchiatto. Reading your law text. Thought you were cute…

What did you think of this post?

To start your own Chicago neighborhood or topical blog on The Windy Citizen, write to us at windycitizen@gmail.com.