I’m on a Greyhound Bus, en route from Des Moines to Chicago, back in the Midwest for about a month to visit my parents (who moved to Iowa from our hometown, Milwaukee, the previous year) and a few friends dispersed among three other states. Having just finished grad school in Boston and very much burned out on academia, I’ve spent “A Summer Wasting” (to quote a then-recent Belle and Sebastian song), filling my days writing in coffeehouses, biking along the Minuteman Trail and methodically weeding my way through Zen and The Art of Motorcycle Maintenance (which I never finish.) I have no real prospects or cogent ideas as what to do next, so I’m living off my dwindling savings, prolonging the real world for as long as I can.
This six-hour express route has one stop along I-80 just outside Davenport at a large facility frequented by truckers and fellow travelers. I sit in a white plastic booth amidst the bleeps and blare of a nearby video arcade, sipping an Orange-Mango Tang juice box, eating fresh grapes from a plastic baggie and a cinnamon bagel generously spread with Smucker’s Strawberry Preserves. My bus driver’s in the booth behind me, downing black coffee and greasy Wendy’s potato cakes. After popping in my contacts in the men’s room, leaving the sink a saline-soaked mess as others line up behind me, eager to take my place, I return to the bus. It’s muggy outside and also unseasonably cool for mid-August.
Crossing the Mississippi River, a sign proclaims THE PEOPLE OF ILLINOIS WELCOME YOU. From there, the road stretches on, the landscape pancake-flat with endless fields of nothing, flanked by the occasional tree, decaying farmhouse, string of power lines, crop duster or road sign like NEXT EXIT 36 MILES. With Sheryl Crow’s The Globe Sessions on my headphones, I attempt to write in my journal, but it’s too bumpy a ride, my pen involuntarily jerking all over the page.
Eventually, cornfields give way to strip malls and subdivisions. Off in the distance, I make out the faint visage of the tall, thin, severe Sears Tower. We pull into downtown Chicago a half-hour ahead of schedule. I look around the crowded station for Dana, a friend from high school; she’s currently working on her graduate degree at Loyola. I don’t see her, so I schlep my luggage outside onto Harrison Street, along with a dozen other folks also waiting for rides. A lanky, 68-year-old black man insists on divulging his age repeatedly to an uninterested eight-year-old white boy. I’m not certain that they actually know each other. The man then does a few push-ups for him, showing off his impeccable-for-his-age strength, I guess.
Finally, I spot Dana down the block walking towards me. She wears bulky denim overalls and her braided blonde hair’s far longer than it was the last time we got together, about eight months before when we met up over the holidays.
“Hey old person,” I call out.
“I’ll never be older than you,” she replies, deadpan. She is a year younger than me, but we maintain this running joke.
Pleased to see each other, but not overly excited, we don’t hug (we never do.) The punishing late afternoon sun, along with the concrete-heavy surroundings somewhat casts a pall on our reunion. We walk for two blocks, then enter the subway deep into Chicago’s bowels and take the L outbound to the far North Side. Her neighborhood consists of long rectangular blocks dense with five and six story pre-war apartment buildings. It’s also close to Lake Michigan, where there’s a number of post-war high rises along the coast (one of them was likely Bob and Emily Hartley’s in the 1970s.)
We take a manually-operated elevator up to her fifth-floor studio, during which I had to follow one rule, due to Dana’s fear of elevators: Stay Still. Her studio apartment is cramped but cozy, densely packed with her canine figurines and an assortment of Pez dispensers. Not wanting to be cooped up in this shoebox on a hot August night, we get in her Blue Tercel and drive out to the ‘burbs for an early dinner at the Cheesecake Factory. Although we have our pick of an array of cosmopolitan cuisine in this mighty city, we’re both poor grad students and it is our tradition to dine out on reasonably priced Navajo Chicken Sandwiches at our favorite chain restaurant.
Returning to her neighborhood, we look for a parking space, circling her block (and adjacent ones) over and over until something opens up. We spend at least 20 minutes completing this task, which, according to Dana, is less time than usual. After a quick freshening up, we hop back on the L inbound to Wrigleyville. There, among all the other people in their 20s and 30s enjoying a Friday night out on the town, we check out an immense store specializing in leather jackets, Doc Martens and other “alternative” clothing. Curiously enough, it also sells plenty of unpainted stone gargoyles.
We head up North Halsted over to Boystown, a “gayborhood” flanked by rainbow beacons. Lots of guys out that night—we see one young man wearing tight leather pants. This prompts Dana to ask me, “I don’t get it – why would you wear something just to show off your package when you don’t really have much of one to show off?” I honestly don’t know the answer to that. She’s still fixated on it as we consume two-and-a-half pots of coffee and a slice of cherry pie each at a nearby IHOP (this one still in its classic A-Frame design.)
As with most of my Midwestern friends, I came out to Dana in an email the year before. She wrote back, “Frankly, Chris, I was more surprised when you said you were dating a girl.” (Yes, that was a thing only two years before, and a story for another time.) Presently, I hadn’t dated much or even slept with another guy; Dana, on the other hand, was actually engaged, having met her fiancé Marc while attending the U of M in Minneapolis. It was clear our lives were heading on divergent paths. Dana, oddly enough, was who’d encouraged me to check out Boston for grad school, her having visited relatives there. I’d secretly hoped she’d even come out there for school as well. Instead, after getting her master’s in social work the following year, she’d move back to Minnesota and get married. We talked about all of this and seemingly every other little thing that came to mind, from our waitress’ hot pink lipstick to how neither of us had ever found a scone as buttery and moist as those we use to regularly get at Gil’s Café, our haunt of choice back in Milwaukee.
The rest of that weekend passed by unremarkably: we watched movies, walked along the Lake and all over the Loop, had the requisite Chicago style hot dog (topped with seemingly every condiment except for ketchup, of course) and sought occasional breaks from the relentless late-Summer heat (contrary to the popular expression, it was not all that much cooler by the Lake.) Monday morning, we took the L all the way out to O’Hare so I could catch a United Limo bus to Milwaukee. This trip took ninety minutes—roughly the amount of time it would take to drive from her apartment to Milwaukee. Our parting mirrored our meeting: no hugs, just a pat on the back, a “Stay outta trouble” and a “Maybe we’ll met up at Christmas”; we’d next see each other at her wedding.
As much as I enjoyed spending a weekend with Dana, I admit I was seeking something in Chicago that I did not find—a sense of direction, perhaps, a reason to relocate again and reconnect with the region I came from. All I felt was ambivalence, a city that was essentially a supersized version of my hometown, less than 100 miles north.
Go here for Part II.