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Stoop-Sitting for Singles

Yep, that’s me from 11 years ago. Something my Chicago blogging brethren probably don’t know about me is that, like windy citizen Jasmine Davila, I’m one of the Interweb’s charter bloggers. At the beginning of 1999 I began scribing the Brooklyn local site for (I can’t believe they still exist) For most of the following three years, I wrote weekly articles about life in the “Mother Borough,” as I liked to call my former NYC home. I used to have an archive of all my old content, but a hard drive crash in the early 2000s put an end to that.

Or so I thought. Tonight while goofing through the Internet Archive Wayback Machine, I ran a search for my former About blog. I can’t believe I didn’t do it sooner. I can’t believe the site was right there all along. That link takes you to the archive that blew my mind tonight. Clicking through years 1999, 2000, and 2001 will bring up lots of content I barely remember writing.

Actually, I barely remember writing so much of it. But it turns out I was as prolific a blogger back then as I have been in the past five years with the more than 600 posts that currently populate the pages of Chicago Carless. I covered a lot of ground familiar to regular readers of this blog: city hall silliness; public art controversies; public transit; tech issues; profiles of local residents. I truly had forgotten Chicago Carless was not the first time I had been an online urban gadfly.

Much more amazing to me, though, is the tone and tenor of the posts. Many of them are still there in the archive. Though I never truly believed I could write well until I began writing Carless, I’m amazed that the online voice that has become so familiar to me from being a Chicago blogger was right there all along back in Brooklyn.

Best of all, the one post that was my favorite from my years as the “ Brooklyn Guide” was right there, too. “Stoop-Sitting for Singles.” It was my most popular post from my Brooklyn blogging days and for years I have regretted losing it. I’m thrilled to have found it again. Here’s an unedited peek at the blogger I was more than a decade ago, shared with the joy of finally realizing that the writer in me has been there all along…


by Michael Doyle, Your Brooklyn Guide
Dateline: 09/04/99

I admit it, I never use my backyard. And if you’re single, neither should you. Who are you expecting to meet back there? This is Brooklyn, and we have some of the most interesting and eligible people walking down our streets. Love – or lust – might be waiting for you on your very own front steps if you’d just take the time to sit there. You know of other people who’ve met their Ms. or Mr. Right out on that urban porch. Here’s how to improve your chances of it happening to you.

Before we begin, don’t fret if you live in a building without a stoop. If you grew up here, you’d know that real New Yorkers will sit on anyone’s stoop, at least until they’re chased off (and how often does that happen?). So do like us natives: go find a pleasant stoop. Keep in mind that your chances of being shooed away will lower dramatically as the number of doorbells on the building rises. Now, on with the show.

First, step selection is prime. Blow this and you might as well go back inside. You want to be able to make eye contact with passersby. If you like to hold court near the top of your stoop, this will never happen – although you will see everyone walking by, no one will see you. Savvy stoop-sitters opt for the second or, ideally, third step up from the sidewalk, easing the flirtation process for all concerned.

Those in the know also know not to wear sunglasses. I don’t care how bright it is out there. If your eyes can’t be seen, you might as well migrate back to the top step. Wear a cap, instead.

Next, bring along reading material that telegraphs your personality, or that you think would be read by the type of person you want to meet. If you want him to know you’re gay and available, be there with the latest issue of Out. If you want her to share your interest in finance, you better be sitting there with the Wall Street Journal. Just remember, these are tools of the hunt. Read, certainly, but notice the people passing by as well.

You’ll no doubt want a beverage out there. Avoid beer. It’s illegal to drink it on your stoop, but, more to the point, it ain’t attractive either. Think water, or soda, or coffee. A real glass or ceramic mug will tell people that you live in the house attached to this stoop, but a plastic travel mug or a cardboard cup with a lid will keep the ants and leaves out of your liquid refreshment.

Sitting on the stoop so far is you, your reading material, and your beverage. Unless you’re the owner or sole resident, try not to spread across the width of the stoop. Make yourself noticed, but always make sure you leave a path for your neighbors to go up and down.

You shy pies out there won’t like this next piece of advice, but it’s essential. Smile at people. Even better, say hello like you’re the official greeter for your street. Be friendly. You’ll be surprised at how many people will smile and say hello back. And those who are really interested will pause to talk. And there you go, you’ve just met someone on your front stoop. If it works out, I expect an invitation to the wedding or commitment ceremony.

Finally, for those of you with lots of junk and a yen for instant gratification, there’s a sure-fire way to practically guarantee tons of immediate and friendly conversation: have a stoop sale! You’ll turn that spouse hunt into a money-making endeavor and the worst that can happen is you’ll end up with uncluttered closets. Just remember, the above rules still apply. Don’t block the entire width of the stoop with your junk. Do prominently display those items which personify your interests and personality (history buffs, make sure those Civil War biographies don’t go unnoticed; Mac addicts, plop that aging Centris on the front table).

Of course, while many Brooklynites have hit the jackpot of romance on their front steps, your results may vary. If at the end of the day all you have to show for your stoop-sitting efforts is a sore bottom, it’s time to get up and go for a walk. First, to Junior’s to take-out one of their legendary cheesecakes, and then back home via your nearest video store.

Sorry, for the fork and VCR you’re on your own.


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Mike Doyle

I’m an #OpenlyAutistic gay, Hispanic, urbanist, Disney World fan, New York native, politically independent, Jewish blogger in Chicago. I believe in social justice, big cities, and public transit. I write words and raise money for nonprofits. I’ve written this blog since 2005. And counting...

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3 replies

  1. One thing that amazes me looking back at the old posts that I didn’t think about last night is the way the mechanics of writing for the Internet have changed. Eleven years ago, asked its “Guides” to post a short, annotated list of “web resources” with links at the bottom of every article. Who would do that today? Modern web copy simply includes hyperlinks within the body of the writing, with the context, itself, telling readers why those links might be important. We’ve come a long way in ten years. Also, I’m fatter now. It’s not germane, but it is annoying.

    1. You should write a “letter to my former self.” It’s cathartic and will show you how far you’ve gone in your writing and observation skills.

      Oh, I hear ya about weight. I look back at my 1990 self in photos and wish I bitch slap those triple quarterpounders and double orders of fries out of my hands.

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