CTA Orange LineValerie is running late. We were supposed to be on the Red Line by 11 but of course Valerie is running late, probably in line at Starbucks with the rest of the Big Ten-sweatshirt-clad scrunchie-wearing young things because, come on Reilly, I need my tall half-skinny half-one-percent extra hot split quad shot latte with whip, probably sending inane three-letter text messages about meeting, like, The Hottest Guy at the Cubs game, Valerie, you better—

A voice snaps me back to reality. “There you are,” Valerie says.

“Where were you?” I ask. “We’ve got work to do.”

Valerie sighs. “Reilly, it’s 11:01. Relax.”

Relax, I think. Who can relax at a time like this? Today, Valerie and I are going to explore, to conquer, to embark on a quest into the holy land. Today, we are going to walk. All the way. Down Archer Avenue. South Side by Southwest Side, land of White Sox bars and distant neighborhoods and all kinds of awesome, freaky establishments I can’t even imagine; a spiritual search for reminders of why I like this city; Valerie instead anticipates an afternoon of death and danger, brought on by her spaz friend’s psychotic ideas of how he wants to spend a Sunday.

“Reilly,” she asks, “are you taking me to the ghetto?”

“No,” I say. I lie. I have no idea what’s waiting for us. But finding out, I remember, is the whole reason for going, and I refuse to let her become a liability.

We hit the ground walking at Archer and State, and BAM!, we make a friend, maybe in his mid-thirties—hard to tell through all the dirt and grime on his face, hands, and sweater.

“Excuse me, sir,” he says, “can I talk to you for a minute?”

“Of course,” I say, leaving out that I know exactly where this was going.

“Let me just say – and I mean no disrespect – that she is a beautiful lady,” he says, motioning to Valerie. “You, sir, you should marry someone with such pretty eyes.”

She smiles at this, and I couldn’t help but chuckle a little to myself as well. Not that he was wrong about Valerie, but if he knows of any pretty-eyed woman that actually wants to hang out on that particular stretch of State Street I would not mind being introduced to her.

“How about a picture?” he asks. We have this trick on the North Side too, but Valerie, either trusting or just oblivious, hands her camera over—Jesus, Valerie what are you doing—“It’s the button on the top,” she says. When he runs away with your camera, I think, my knees are are going to hate you for making me chase after him.

And that word again: liability.

He takes a step back, I tense up but then, instead of taking off, he just takes . . . our picture. “Two lovely people,” he says handing back Valerie’s camera. “Have a lovely afternoon, alright?” Valerie smiles.

Just south of Chinatown, gutted factories stare down anyone bold enough to enter the invisible border around the neighborhood, but these few steps outside of the dragon statues and waterfall plazas, we look up at brand new banks and boutique shops, gorgeous condominiums-to-be announcing their arrival onto half-empty lots.

“Who are they trying to sell these to?” I wonder aloud.

“Duh,” Valerie says. “Us.” And to the casual observer, we probably did look like the perfect young homebuyers: matching gray fleece pullovers, telltale north suburban vocal inflections, confused looks at every street corner we came to. Farrell. Lock. Broad. Bonfield. She’s never even heard of any of these streets. Then again, neither have I.

Valerie says she needs something to drink. “Do you think we’ll find a Starbucks or a Caribou down here?”

I forcibly contain my laughter. “Are you serious? Do you know where we are?”

“So what?” she asks. “People drink coffee on the South Side too, you know.”

“Not for $5 a cup,” I inform her.

“Well, I would if there was one.”

“But there isn’t one,” I say.

“Well,” she retorts, “maybe that’s why I don’t live here.”

She mentions how all three of her apartments have been within falling distance of either of those venues—not a convenience, but a reliable amenity. I imagine the listings:

FOR RENT: 2bd/1bth, close to trains, buses, Starbucks, w/d in bldg, must see!

We find the strip mall at Ashland Avenue but, alas, merely a Dunkin Donuts.

“No,” she sighs, “that won’t do. I’ll just go without.” Yes, I think, life can be so cruel sometimes, can’t it?

Archer, 35th and Hoyne. Valerie points out a hulking, vacant triangle-shaped building the size of a airplane hangar. I take a closer look and vaguely make out the words SOUTHWEST TRUST AND SAVINGS. “Looks like a bank,” I said. “And a big one.”

“What’s in there now?” she asks.

“Who knows?” I ask, and I motion that we keep moving. Valerie shrugs, and onwards we march.

Suddenly, just past Pershing Road, Valerie stops and lets out this awwwww sound: in the front window of Netty’s Furniture, a tiny cat plays in the front window, and Valerie has just fallen in love.

“Hi kitty! Hi kitty!” She puts her hand to the window and the cat reaches back out to her, rolling over and rubbing its tiny paws against the glass. “It’s so cute! Reilly, come look at it!”

“I see it.” And I think of that word again: liability.

“Reilly! Look at it!” The animal has her hypnotized. “Hi! Hi! You are so adorable kitty!”

I don’t have the heart to tell her it probably can’t hear her through the glass. And that cats don’t speak English. “Valerie, let’s go.”

Stepping away from the store and the cat, she keeps waving and smiling at the animal, and it reaches back out to her as she leaves; she reaches back, fading away and even I have to admit it’s a nice moment.

“Why is that store closed today?” she asks. “It’s the weekend. That’s when people buy furniture. Wouldn’t you want to be open when people want to buy what you’re selling?”

“Let me get this straight,” I say. “You just bonded with a strange and random housecat through the front window of a closed furniture shop. You’re not even remotely thrown off by a five-pound kitten guarding an empty store, but you are bothered by the fact the owners might want Sundays off?”

She pauses for a moment. “Reilly, you don’t get it. That cat was just too cute.”

She’s right: I don’t get it.

47th Street. Home stretch. I remark out loud how hungry I’ve become. “Let’s stop somewhere then,” Valerie says.

“Can’t,” I say. “We’re almost there.”

Valerie stops in her tracks. “Okay Reilly,” she asks, “what is with you today?”

I shrug, not understanding the question.

“You wouldn’t shut up about seeing the Southwest Side, but now we’re here and all you want to do is leave. You wanted to look at weird empty buildings but as soon as we find them you won’t go near them. You wanted to find new places to hang out but how many bars and restaurants have you even thought of stopping in?”

And I say . . . nothing.

“There’s miles’ worth of fun back there,” she adds. “And what have you done with it?”

And the thing is, she’s right. She is the one asking all the questions; she is the one noticing all the interesting things; she is the one connecting the dots. And here I am—the one saying “forget it,” the one saying no, the one ignoring why we came here, my only contributions to the day being variations of “Come on, let’s go.” So now who’s the liability?

At the intersection of Archer and Cicero Avenues, Chicago briefly ends before beginning again just a few blocks later and I tell her to stop.

“What is it? Are you okay?”

“We’re here,” I say.

“This is it?” This is it.

“This is like a movie,” she says, “where it just ends without warning.”

And yeah, after all that, standing on this unremarkable street corner does seem so entirely anticlimactic. The diner on Cicero is closed; the only traffic is the stream of cars roaring towards Midway Airport just down the block. We had seemingly trekked across the world, only to end up here alone.

We head into the airport and up to the ‘L’, its ride away from the sunset showing us the other side of the places and things we had spent the day looking at and looking for. On the train, we are just two people leaving an airport, but on that lifeless street that reached out across the city, I was a rich man and she the object of every stranger’s affection. Banks lived forever without money, and coffee was the stuff good neighborhoods were made of. The guy who took Valerie’s camera didn’t take her camera, there was nowhere to eat because it’s always time to eat, and my Starbucks friend is totally psyched to go hang out in strange places along weird roads. For one gray afternoon on the Southwest Side of Chicago, life was entirely strange and strangely wonderful. We step onto the train, lumbering back the way we came, steadfast iron and steel making its way through the city. To the city. To our city. To home.


– Chicago, IL / April 28, 2008 & November 21, 2011