Street Smart Chicago

411: Juicing the Pickle

Events, Love & Sex No Comments »

“STEP HIGH STOOP LOW LEAVE YOUR DIGNITY OUTSIDE.” That was the sign posted outside Chicago’s legendary “Dil Pickle Club,” a Bohemian club/speakeasy/cabaret/theater that played host to various radicals, artists, anarchists, authors and socialites throughout the twenties. It was a place for self-styled free thinkers and sexual libertines, one of the few public places in the city where it was okay to be openly homosexual. And while the original club faded into memory in the mid-thirties, its message of political and sexual expression and spirit of meeting high culture with lowbrow is gaining resurgence some ninety years later.

“It was a place where you had hobos next to housewives,” says Fred Sasaki, one of the co-founders of the revived Dil Pickle. “You had doctors and lawyers mingling with tramps and prostitutes.”

The fifth installment of this incarnation of the group, entitled “LOVE/DEATH,” takes place February 10 at The Hideout (1354 West Wabansia). More than just a simple art event, the evening promises live music (with the band weaving in and around the crowd, not on stage), a tattoo artist giving out temps, a Day of the Dead shrine complete with group ritual, a St. Valentine’s Day Massacre-themed photo booth, talks on both serial killers and Precious Moments figurines, and algorithm-aided matchmaking. Read the rest of this entry »

Velo Love: Popping the question at Bum Island

Bicycling, Love & Sex, Wicker Park No Comments »

It’s a frigid Friday night and forty bicyclists have convened on Polish Triangle, aka Bum Island, the three-sided plaza at Division/Ashland/Milwaukee, populated by homeless guys and a hotdog vendor, and carpeted with pigeon droppings. It’s a bigger crowd than usual for the Wicker Park Critical Mass, one of several “mini masses” on the first Friday of the month, that also take place in Pilsen, Evanston and Oak Park. A female cyclist dressed as Santa passes out fleece balaclavas, while a dude on a recumbent in a spiky orange motorcycle helmet puffs on a pipe. Then a young couple, Aaron and Katie, ride up to the plaza and stand before the group, in front of the Nelson Algren Fountain. Aaron presents a small red box to his surprised girlfriend and drops to one knee as five of his helmeted pals unfurl signs reading “KATIE / WILL YOU / MARRY / ME ?” She runs forward and kisses him passionately as the crowd erupts with cheers, honking bike horns and ringing bells. After passing around bottles of bubbly, the mass of bicyclists saddle up and pedal off into the sunset. (John Greenfield)

Naked Politics: Democracy Burlesque puts skin in the game

Andersonville, Love & Sex, Politics No Comments »

Nelly’s club anthem bumps along the purple walls and gold-plastered ceilings in Mary’s Attic. “It’s gettin’ hot in herre, so take off all your clothes” seems fitting for a group that calls itself Democracy Burlesque. But while the name fools, the players don’t tease. The audience gets a little skin, but nothing unpalatable and nothing overtly naked (except the politics—that’s their tagline).

Democracy Burlesque is more sketch comedy than dance, more sharp wit than easy laughs. Many of the actors double as writers and directors, and that multifaceted involvement exudes a bud-to-blossom continuity throughout each sketch and the production as a whole, as if the company members all slept with each other and raised their babies at Hamburger Mary’s, divulging in free-range mini-burgers and spouting political quips left and right. Read the rest of this entry »

Cub Scouting: Surveying the field at the Cougar Convention

Love & Sex 1 Comment »

Miss Cougar America, Amy Roberts

A thin tan blonde in a sparkly top, jeans and high heels holds hands with a guy in shorts and a polo as they attempt to surreptitiously run through the Embassy Suites Rosemont O’Hare parking lot to the car. It is a moment right out of high school, but this isn’t prom. It is the 2nd Annual National Cougar Convention. This woman is probably twice the age she was when she went to the big dance. Her new date likely still gets carded at the liquor store.

If you stumbled upon the convention, you might think you were at a bar mitzvah: the DJ’s futile attempts at music that appeals across the generations, the awkward guys standing by the wall and the moms breaking it down on the dance floor. But then you would realize the guys aren’t quite that young, and while the middle-aged women might be moms, they aren’t dressed—or acting—like it. These are “cougars,” in all their red-stilettoed, tan-legged, leopard-print-wearing glory.

The event, with upwards of 200 attendees, aims at bringing together cougars (older women interested in younger men) and cubs (younger men interested in older women), but attracts a wide audience that also includes younger women and older men. While some cougars and cubs seem to be in their natural environment, most look curious, surprised and somewhat uncomfortable to be at such a unique singles event. Read the rest of this entry »

Love & Sex 2010

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In acknowledgment of Valentine’s Day, we present our annual Love & Sex issue, featuring three tales of those two very distinct pieces of human existence. Three stories directly from the trenches, full of lust, longing and heartbreak. Full of life itself.

Enjoy. And for dining specials linked to Valentine’s Day weekend, visit

Look at Me

The Bitter Taste of Amy

A Break-Up

Love & Sex: Look at Me

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By Jessica Meyer

I barely knew this woman, but I liked her, she was brash and witchy, so when she pulled me into the bathroom at a party I was too old for, brandished a compact full of dope, and asked me who I was fucking, I wanted to tell her something scintillating and mysterious, but the boring truth was this: I was freshly raw over the end of a serious relationship and hadn’t had any action in months. I tell her how long it’s been, how much I just want to rub up on these sexy young men with swaggering egos and tight pants, they are writhing so close and smirking through the beer, and I’ve been dancing, and here, I admit, I get a little breathless, going on while she cuts up lines and nods, solemn and intent.

She meets eyes with me in the mirror, checks her nose for residue, and tells me, with conviction, “I know someone.” I follow her out, amused, protesting a little—”I’m not really that kind of girl!”—but then I get swept up by the DJ, he’s playing Prince, and everyone is going nuts and it’s fun, even if I’m older than everyone here, I’m having a good time, and I really am that kind of girl, who am I kidding.

I’m only 27, my heart is broken, but my desire to fuck attractive men is not.

I see my wild new friend through the crowd, she’s talking to someone and soon enough a boy with sweaty hands and a pretty smile is sidling my way and grabbing my hips. He says he loves my hair, does this endearing move with his face in my neck, and my weak resolve is thoroughly ruined. Yes, I say, I will go home with you.

We are both only vague friends with our matchmaker, and have, in fact, met before, but briefly, and without the maelstrom of desire that seemed to engage every person at the party we had just left. He drives us to his house, furious kissing at all red lights, and by the time we get there, I am so ready I have already unbuckled my belt, removed my coat, unbuttoned a layer.

There is something cinematic about struggling up flights of stairs while trying to sustain a passionate embrace with someone; eventually, though, this feels ridiculous and it’s a relief to get in the door and out of my clothes. Read the rest of this entry »

Love & Sex: The Bitter Taste of Amy

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By Pete Bailey

She pukes.

All over the car door, the passenger door, my car’s passenger door, as we sail north up Damen Avenue, New Year’s Eve. We’re only two drinks into the evening—I’m driving, after all, and we’re heading to a place we can crash for the night—and she vomits a great awfulness all over her side of the car. Two friends are in the backseat, a couple, Jane and Fred. Amy, my date, looks mortified in embarrassment. She’s got puke on her pink shirt.

“I puked.”

“I know.”

I turn, pull over, stop in front of Nick’s Beer Garden, and Jane takes Amy inside to help her clean up in the tavern’s bathroom. Fred and I sit in the car; I’m furiously wiping away the two-drink upchuck on the interior. Fred repeats “Dude” over and over again, each utter more and more dramatic, until the women return. Read the rest of this entry »

Love & Sex: A Break-Up

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By Lisa Buscani

When we started, I was thin. My face was a diamond, all clean walls. I was weightless but I had control, like astronauts after they learn to swim properly in space.

Our conversations used to overlap and dovetail and interweave and occasionally we’d stop to breathe. When we made love, we knew how to forget ourselves. That, I’m convinced, is passion; to kiss him so hard and hold him so hard that the act itself is forgotten and all that is remembered is skin and hair and warmth, that’s a gift. That’s something that we kept for a long, long time. Read the rest of this entry »

Worldwide Pants-less: Skybar hosts a trouser-banned party

Events, Lincoln Park, Love & Sex, Pride No Comments »

GoddesShe-01-bigThe time-honored tradition of The Fourth Annual “No Pants Party” makes Lincoln Park’s Skybar transform into a girls-for-girls paradise. From the sidewalk looking up to the second-floor window, two very scantily clad young ladies—with no more than pink lingerie and white fluffy boots—shake what their mammas gave them and hope their fathers aren’t aware of it.

A skinny, mustachioed hipster in maroon boxer shorts and suspenders dances to the muffled beats from inside the bar next to the uncomfortable valet attendants. Sunday at Skybar is designated Gay Night, and tonight is no different. Chicago’s strong and vibrant lesbian community is out in full force making the best of their last few hours of the weekend before returning to the Monday morning grind. The place looks like a normal party with loud house music and strobe lights until the adorable—and unfortunately unattainable—waitress, wearing American Apparel briefs, strolls over. She’s holding trays of fluorescent shooters, claiming they have the elixir for a time you’re sure to forget in the morning, only to remember as your head falls below the rim of the toilet upon crawling out of bed. Of course she didn’t actually say that, but we all know the result of glow-in-the-dark booze.           Read the rest of this entry »

Love at First Byte: Six writers, a dating site and a weekend…

City Life, Love & Sex No Comments »

newcitydatingserviceDuring the site’s highly advertised “free weekend,” six Newcity writers decided to sign up for online dating service, sister site to, and each write about our experiences. Launched in 2006 and featuring the famed scientific personality test created by Dr. Helen Fisher, the Web site has more than five million members and helps set up more than 15,000 dates a week. We liked our chances.

First you take the personality quiz, which asks you an abundant amount of questions pertaining to personal preference and background. You’re assigned two of the four possible personality types: explorer, builder, negotiator, director.

You write a description of yourself for your public profile and include a headline, comparable to an outgoing message on Facebook or a headline on MySpace. Once everything is submitted—including a photo of yourself—you receive “matches” from the service, from which you indicate the ones in which you’re interested. (You archive your various rejections.) Meanwhile, your profile is being sent out to members, and they indicate if they’re interested in you. If you’re both interested, you take additional steps—which include comparing “relationship essentials,” like if it’s important to you that your partner loves pets, and an additional “Short Answers” portion—until finally there’s an email exchange, and from there you go. Needless to say, the testing and screening process is rather intensive.

We chose because we imagined its free weekend would inspire some fresh, new profiles, maybe even people who were first-timers to something like this. Also because the commercial advertising the event was constantly on MSNBC while we were trying to watch our Rachel Maddow.