Street Smart Chicago

Oh Captain, My Captain: Chicago Blog Inspires Worldwide Community of Awkwarders

Love & Sex, News etc. 1 Comment »
jennifer peepas

Jennifer Peepas

By Megan Kirby

In Baltimore, look for a girl with blue hair in a Batman t-shirt. In Washington DC, find the red balloon at the coffee shop. In London, seek out the table with the Cthulhu plushie perched on the edge. You’ve found the Awkward Army.

These are fans of massively popular advice blog Captain Awkward, and they are meeting up worldwide. The Captain herself, Chicago-based filmmaker Jennifer Peepas, never expected such an active global audience. Today, self-proclaimed “Awkwarders” plan meet-ups in coffee shops and ice cream parlors from Boston to Tokyo, gathering with coloring books or knitting projects or stacks of fiction and graphic novels for impromptu book clubs—essentially, getting together to just hang out.

When Peepas first launched Captain Awkward in January 2011, she just hoped she’d have enough readers to never have to fabricate a reader question herself. Now, she gets so many emails that she can’t answer all of them. At the end of 2013, Captain Awkward’s page views hovered just under eleven million. As of March 2014, 557 reader questions have been answered. (Everything from “How do I deal with my abusive family” to “My crush might be a furry.”) Posts garner hundreds of comments with readers’ advice and stories (and tangents about books, TV shows, vacation plans and any other topic). The most dedicated Awkwarders even started a fan-run forum, Friends of Captain Awkward, to keep up with conversations off comment threads. Read the rest of this entry »

Perception vs. Reality: The Sex Workers Outreach Project Reaches Out to the Public

Love & Sex 2 Comments »
Two Cassandras

Two Cassandras

By Michael Workman

Late March and it’s still like walking through a meat locker outside, cold enough that the fabric of my jacket stiffens as I lumber and linger outside the cab, tussling with the straps of my camera bag and satchel. Too many straps. Finally I get sorted as the cab pulls off, and I raise my gaze, take a moment to study the unassuming gray corporate slab of a building where the Sex Workers Outreach Project meeting is taking place at the Test Positive Aware Network (or TPAN) offices.

I’m in Uptown, a short hike down the avenue from the Green Mill. I’ve only ever been in the neighborhood for events, music and poetry mainly, and tonight it’s activism. I’ve known of SWOP for years, but didn’t feel qualified to attend any of the group’s private membership events, but they are holding their first-ever public event. It’s called, “Understanding Sex Work and Allyship” and I’m curious what this national organization will contribute to the public dialogue about at-present forms of outlawed sexuality, and afterward, find myself reflecting on the social support system they wish to foster, their institutional outreach efforts. And they represent their constituencies well. Read the rest of this entry »

Walking on the Wild Side: A Former Prostitute Recalls Life on the Street

Essays & Commentary, Love & Sex No Comments »


Illustration: Kady Dennell

Illustration: Kady Dennell

By Anonymous

I am standing in front of The Closet, a gay bar on Broadway between Addison and Belmont. It is a warm summer night. I am twenty-four. I am going to get in the first car that stops. I am a sex worker, but right now, in the 1980s, we are called prostitutes and streetwalkers. If we do it in a hotel we are call girls. Interesting how long it took for people to realize this is a job and work.

Neither the johns nor the sex workers realize that in a few years a lot of our cruising will be online. We will be using Craigslist and cell phones to screen out nuts and psychos and cops. Hopefully. But the Internet has not been invented yet. Right now, if you are selling it or buying it, you have to rely on your street sense.

When you are out here, you don’t think about the danger. For one thing, I am high as a kite on meth. These guys are rude and repulsive, but I can enjoy myself because I am high. People without addictions don’t understand that there are three highs: the high; the high of knowing you’re going to get high; and the high of doing risky things while you’re high. Read the rest of this entry »

Crazy Love: Memoir of a Marriage Gone Queer

Love & Sex 1 Comment »

Photo0229By Lawrence L’Amour

Marriage has changed a lot since my wife and I walked into a River North church on a Friday nearly fifteen years ago. It’s a few years before 9/11. We’ve been waiting four years for this day, and it feels like we’ve done everything right. Planned perfectly. My family is here from Indiana, hers from Michigan, even the elderly ones we’re surprised are willing to travel, especially to the city. Tons of friends. It’s sort of a party. And it’s all for them, really. Admirers point to the brocade work on her dress, elaborate but plain. “We deserve this,” Marla says, smiling. Proud. My mother is here, fascinated with taking pictures of the weeping, bleeding Saints flanking the nave in rows between the stained-glass windows of the Assumption. In one of them, Saint Frances Xavier Cabrini—the first American saint, who lived and worked in Chicago, and after whom the eponymous (and infamous) housing projects were named—is shown landing in New York. Marla’s parents are here too, trying to keep out of the way, beaming and apple-cheeked. I nod at her mother, for whom I mainly agreed to a Roman-Catholic wedding. I’m more or less atheist, but Marla requested it out of respect for her mother’s deeply-felt devotion to the church. Afterward, we’ll go get stoned with our friends, drink too much, collapse on the bed, order pizza and watch old black-and-white movies, too exhausted for any wedding-night consummation. It isn’t important. We’ve always agreed on this, that there’s something more important than the fallen reality we’re forced to inhabit, with its continual suffering and loss. Our love for each other transcends it, stands for something greater, something transformational. I look over at her as we walk up the steps, and we share fleeting smiles. Her salmon-colored lips pull back over white teeth, the light at pinpoints in her eyes as they turn from me to our red-frocked priest, who beckons us down with a slow, calm motion of his hand. It’s our secret, this shadow of a smile as we kneel before God. Read the rest of this entry »

Dime Stories: For Those in Love

Dime Stories, Love & Sex 1 Comment »
Oh Baby-This Ache_100

Illustration: Tony Fitzpatrick

By Tony Fitzpatrick

Love is a slippery fish. People perish every day for want of it, or a pantomime of it, as if they were on fire. Nothing has been lamented more than lost love, love gone wrong, or the making or unmaking of the human heart. It is written about ad nauseam in every annoying love song, each one being “someone’s song.” Makes you want to blow chunks. When your friends fall in love, they are disgusting—the cooing, the walking around with a simpleton look on their face, the spring in their step, the flush in their cheeks, the chipper-ass good mood they are always in. You want to slap the shit out of them.

You want to tell them: In a year, Bunky? She’s going to hate you! All of the witty repartee she giggles at girlishly now are the anecdotes she’ll be rolling her eyes at in a scant eight months. The lingerie? A year from now she’ll be washing the windows with it.

She’ll make sure you know, in no uncertain terms, what an annoying asshole you are, how disgusting your habits are, how you snore and fart and smell like a zoo animal, and how all of your friends are mentally deficient as well. Read the rest of this entry »

Miss Rose: The Life and Times of the Gold Coast Madam

Chicago History, Gold Coast/Near North, Love & Sex 1 Comment »

Rose Laws with friends.

By Harrison Smith

Rose Laws stands five-feet four-inches, with red hair, glasses and a strong Southern accent she’s retained from a childhood in Tennessee. She once had thirty-six-triple-D breasts, which she lost purposely because they were too big, and a tiny waist, which she lost with age because that’s how things go. She looks and talks like a grandmother, is gracious and warm like the best grandmothers, and at age seventy-seven is, not surprisingly, a grandmother.

Tonight she is without her grandchildren, though two of her sons are with her at the Everleigh Social Club on West Randolph. The club is pretty empty this early in the evening, and most of the people who are there—just about all of whom are friends or family of Rose—are sipping the night’s signature drink, a “Gold Coast Madam” cocktail mixed specially for the occasion. Read the rest of this entry »

A Spring Awakening in Summer

Love & Sex No Comments »

By Jenny Yoon

I woke up freezing, groggy and very naked.

I had no idea where I was. The most I knew was that I was under a thin, blue sheet—like Michael Fassbender’s character was in the opening scene of “Shame”—only without the sex addiction. The self-loathing was there, however.

Wiping at my watery eyes, I turned my head to regard the figure next to me. Face in the pillow, a mass of dark curls, an errant arm placed in such a way that I saw one closed eye, sooty lashes against ashen skin. It took me too long to recognize the guy lying next to me. Read the rest of this entry »

Love Hurts: An Unconventional Romance

Essays & Commentary, Love & Sex 1 Comment »

By Lawrence L’Amour and Cinnamon Smidge

“Sex and Violence go together like Bacon and Eggs.” –David Cronenberg

Nothing terrifies people more than male sexuality, especially violent male sexuality. “Fuck off,” I whisper to my own fear and shame as I push open the door to a privately owned downtown loft. It’s midnight on a Saturday four years ago. The place is packed. Smells like wet hair and fresh leather. Cigarette fog. Long dark halls and even darker corners. Shadows move, sniffing each other. Slags and slag hags, both male and female, people decked out in leather fashion, gay and straight mingling. Then, as today, this party is the go-to party for deviants. Women stuffed into rubber dresses, leather vests hanging off men’s bare chests. Racks strewn with whips, floggers, cuffs, gags and blunt striking tools line the walls. I unhook a short wood bat, feeling its heft in my fist, and imagine slamming a partner in the stomach and thighs with it. I pass sex furniture made of wood, well-secured mounts in the walls. BYO alcohol is allowed (recently limited), and people are swilling it down, shuffling past, beers and the occasional highball glass in hand.

Read the rest of this entry »

Cereal Romance: Adventures in the Brave New World of Online Dating

Love & Sex No Comments »

Illustration: Beryl Chung

By Michael Workman

Breaking up is hard to do. It’s made even harder when it happens in the grip of a new social reality. I’m sitting on a window barstool at Café Selmarie on the Lincoln Square strip, where I’ve been summoned via text message through a flash downpour for the bad news, and I’m totally blindsided. How did this happen? It’s absurd, something out of an episode of “Bored to Death”: just three days earlier we were lying in bed discussing plans for a friend’s wedding two months out. I rotate my gaze floor to the ceiling. What did I miss? Everything slows down, then pauses a beat. My clothes are dripping wet, and I’m sitting with (let’s call her) Ramona, who I met through an online dating site called OkCupid. It’s a service I’ve been on for nearly two years now, since my wife and I split up (amicably) and after hundreds of therapy sessions, when I found myself confronted with a dating scene that has changed pretty radically. Read the rest of this entry »

Wrigley Field’s Summer of Love: Welcome to the best pickup venue in sports

Lakeview, Love & Sex, Sports No Comments »

By Scoop Jackson

It’s Year 103 of the Drought and by the initial look of things, nothing’s changed. It’s cold, raining, damp, wind blowing… perfect baseball weather for opening day on the North Side. Baseball’s “other” worst team has come to visit, but the place is still packed.

Like Carnival off the Lake.

For the fairweathered, non-diehard, quasi-apathetic Cubs fan, this is simply the best time of the year. It’s when Wrigley Field turns into the Playboy Mansion East. When some of the most beautiful women this side of South America­—or LA, depending on who’s asking and who’s telling the stories—migrate to one place for the next five months, treating the national pastime like Fast Times at Cooley High.

When everyone gets to enjoy Wrigley Field for the “second best” thing it is known for: Welcome to the best pickup venue in sports. Period.

Read the rest of this entry »