Street Smart Chicago

To Where You Are

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onlinedatingilloWhen I discussed the idea with my girlfriend Sarah, we agreed it would be an interesting exercise to both sign up on the site, compare our test results, inspect our matches together and, finally, see if we are actually matched up through the service.

Why we thought this was a good idea, I’ll never know.

I’m not as hard on online dating services as others; everyone knows it’s difficult in the singles sphere anyway, even if you do have the time to frequent events and bars. We’re all getting older, and the more time passes, the more difficult it feels to meet people. Plus, I have some friends who’ve had great success with sites just like, and hey, they seem really happy and have met some great people, so whatever works. Read the rest of this entry »

Romance Profiling

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The topic came up a few weeks ago, when a friend mentioned he met his last wife and current, very foxy girlfriend via online personals. I was stunned that the flirtatious, compelling, mischievous fellow who befriended me on the Metra platform would need or choose to sift through profile pages for a date. At any rate, the pump was primed, the process legitimized and the assignment timely. Sure, what the hell? I’ll give it a shot.

I logged in, agonized over a photo and headline (odd, considering this was just for kicks) and jotted a few notes on the personality test administered by the site. What struck me most was how clinical the whole process was; after determining my personality type—incidentally, a more accurate measure than my astrological sign or the free online Briggs-Meyers tests I was hooked on two years ago—I indicated the desirability of certain traits and habits on grids and slide rules. This was scientifically calibrated navel-gazing—even the color scheme of the site was institutional white. Read the rest of this entry »

The Perfect Match

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When my girlfriend came home almost an hour late from work one day last week, I greeted her by saying, “Don’t worry, I’m just signing up for a dating site.” She gave me a look of shock/confusion, like she couldn’t believe I was calling it quits—it was only the first time she was late and it wasn’t even her fault. But I explained it was for an experiment.

I’d never used a dating site before, unless you count making a fake profile to trick my friend Kevin in college into thinking he had a stalker or helping my straight friend Sarah find a non-douchey “meat and potatoes” kind of guy in Bloomington-Normal (no luck).

Signing up for was as excruciating as an actual chemistry test. It was high school all over again, but instead of multiple choice and equations, it was: strongly agree, agree, disagree, strongly agree.

Instead of straightforward questions, there were statements such as, “You enjoy the company of others.” I was stumped on whether to agree or strongly agree. Or maybe I should disagree? I mean, does it make me co-dependent if I like being around people? But I don’t want to be considered anti-social. I’m just selective. Read the rest of this entry »

Gone Fishin’

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The assignment intrigued me. Hang out on a new dating site called, create a profile, and write about my experience. In other words, waste a good chunk of time and try to make sense out of nothingness. Like “Seinfeld” and Sartre rolled into one. Cool!

So I signed up, took the personality test, and voila! I was live in the online flesh market, ready to be sold like a bag of clams to some lucky fish. Like Jodie Foster in a floppy hat and short shorts, I was thrust before the ogling eyes of potential male buyers. Only in place of Harvey Keitel, I was my own pimp—boosting my selling points of European breeding, international education, blah and blah.

According to the personality test, I’m a Negotiator/Builder. Like Bob the Builder. Perhaps I should buy a tool belt? Read the rest of this entry »

Chemistry Isn’t Science

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I really dig taking online personality tests. You know, like the ones you can find on Facebook: “What kind of tree would you be?” or “What ‘Sex and the City’ character are you?” or “If you were a fascist leader, who would you be?” Because, well, they’re a joke with questions and answers that never really pertain to me.

So when told me I was going to answer a few questions that would lead to my Prince Charming, well, I was ready to test it. Would I be paired with the athletic jocks because of my passion for kickball? Would I be joined with the intellectuals because of my infinite interest in “Star Trek”? Could my soul mate be just a generic answer away? Read the rest of this entry »

The Veil of Iron

City Life, Love & Sex No Comments » promises to navigate the tumultuous seas of dating for you. However, is online dating really that much easier than dating in the real world?

I decide to test the waters and sign up for an account. Writing my online bio is supposed to be fun, but instead it throws me down some sort of existential rabbit hole that I am yet to climb out of. Now I’m plagued with all sorts of doubts and nagging questions about moral relativism. Who am I?  Where have I been, and where am I going with my life? Read the rest of this entry »

The Air Down There: The 2009 Air Sex World Championships reach Chicago

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Amongst slightly creaky hardwood floors and below rotating fans from protruding circles on the ceiling, an audience gathers in the Logan Square Auditorium with beers in hand to view a sexy spectacle. The 2009 Air Sex World Championships are about to take place, and viewers prepare for a sight that many of them have never seen before-think an air-guitar contest, but different.

The competition starts. Seven contestants, all ready and willing to show their best O-faces on stage in front of a crowd of strangers to songs of their choosing. First: Long John Silver. He moves slowly and sweetly, but is just as short as he is sweet. Second comes Vaughn Quee-Quee, who seduces an imaginary woman three times his size. He begins by tossing his aviators to the floor and ends with a peace sign to the audience. “I’ve been practicing my whole life for this,” he tells the us as he leaves the stage. Jade is third, and he climbs his way into his woman and starts swimming, telling the audience later that his song of choice had been “Under the Sea” from “The Little Mermaid,” even though the DJ had played something else by accident. “The uterus is the origin of our existence, and sometimes you just wanna get back in it,” he says of his swimming. Crunchy McVibe, feigning inebriation, undresses all the way to his boxers. Curvy Shaft starts with a cigarette and relaxes as his partner does all the work. Pair of Jugs, the first female contestant, makes do with a small member and awkwardly gyrates to the theme song from “Full House.” Dr. Leonard McCoy wraps up the first round with a perfectly choreographed routine in a green one-piece jumpsuit.

After a round of finalists, Crunchy McVibe is deemed winner by the audience. Apparently, being fake-drunk helps. (Micah McCrary)

Naughty Words: challenges your filthiness

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It’s not every day that you walk into the Empty Bottle and see condoms by the bowlful strewn across the bar. “No need to get all crazy and put your hand in the bowl, just take one,” Pretty, one of the founders of, shouts to everyone from the venue’s stage. For the Web site’s launch event, Pretty and co-founder Cheeky have successfully transformed the Empty Bottle into a den of debauchery during “The Birds and The Bees X-Rated Spelling Bee.” Read the rest of this entry »

Sex School: The Burlington offers everything you’ve ever wanted to know

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strike-a-poseWhere can you find six women in one room who would happily don a strap-on and take on a guy? Or a bar full of men who shout out the maximum distance they’ve managed to shoot a load?

Logan Square bar The Burlington is home to the monthly Sunday Night Sex Show, where creators and hosts Allen Makere and Robyn Pennacchia infuse your mind, libido and sense of humor with any and all things sex-related. Read the rest of this entry »

Sex on Display

Events, Love & Sex, News etc., Wicker Park No Comments »

At Wicker Park’s Debonair Social Club, Wednesday nights have become a “weekly sex-capade,” featuring live performances by local entertainers ranging from burlesque performers like Red Hot Annie to Elvis impersonators. Titled the “No-Tell Motel,” it’s slated to be raunchy and rowdy, causing a stir right from its inception. “We’ve had some burlesque events at Debonair over the last year with a couple of different companies and have always had a really good response,” says operating partner and Debonair owner Steve Harris. “It seems the clientele likes it because it’s different and new and not just another DJ. We’re trying to pick points of bringing in new fun things to Debonair.” And where’s the inspiration behind the “No-Tell Motel”? “We wanted it to be sexy and kind of provocative and have hidden meanings,” Harris says. “We wanted to make it a little bit clever and fun and just keep people on their toes. We try to put a twist on everything we do at Debonair.”