Deep Dish Discussions

The Windy City and Lake Michigan

I happened upon a pop-up flea market near the Michigan-Indiana border. Little booths sold objects and art. Each vendor would smile as I walked by. From food to jewelry to wood-carved sculptures, the selections were vast. The thought of buying a friend or family member a gift quickly vanished after looking at my overly loaded bike.

I purchased an apple from a local orchard and sat at a table in the center to people-watch. Children were running around chasing each other while their parents meandered around munching on the vendors’ food. A man in his 60s named Max asked me about my trip and for my name. “You must be an Orthodox Jew or something with a name like that!” I have received so many reactions like this to my name, I was unphased.

“I grew up Orthodox, but I’m not anymore.”

“I grew up Conservative, but now I’m Reform.” He continued to tell me about his opinion on denominations of Judaism. “I just don’t like how Orthodox Jews treat women -why can’t I shake a woman’s hand? What are you now?” 

“I don’t know. Just Jewish I guess.” I wasn’t in the mood to get into a theological discussion. I was questioned regularly about my uncommon name. People would make assumptions or express curiosity, but this rarely bothered me. I left the market with a smile on my face from the odd interaction I had come to expect. 

The mandatory state sign photo

With Michigan behind me, the Windy City was approaching. After foolishly ignoring Alex's (my host) suggestion to avoid the mostly flooded bike path, I arrived with soaked shoes and a good attitude. I spent only a single night in Indiana. Fueled on juicy cheeseburgers from the dinner before and eggs on avocado toast for breakfast, I entered Illinois. 

Was it worth riding through the puddle three times to get this shot?

Due to stupidly avoidable shattered glass in the middle of the road, which punctured my tire and tube, and intense pain in my left knee that caused me to only peddle with my right leg, I was making poor time. As I entered Chicago, I saw fewer smiling faces and more masks. I biked along the lakefront bike path for a few miles: Chicago to my left, Lake Michigan to my right.  

Nothing like glass on the bike lane

After a left turn into the city, I entered a path through a park and passed by two men not too much older than me playing frisbee golf. “You’ve got quite the load! Where are you headed?” said the shorter one. His name was Romeo, and his friend was Mark. Shocked and excited about my trip, they asked if I had a GoFundMe or Venmo so they could fund it. I couldn’t help but feel slightly uncomfortable–why would strangers want to give me money? If biking across the country could be a job, I would be the first to apply. After some suggestions on how I should spend the next day exploring the city, I said bye and headed north to my host.

Josh, my father’s friend from grad school, and his family were Modern Orthodox, like my own. He and his wife, Elisheva, showed me where I would be staying in the basement. I showered and went upstairs for dinner. They ate dinner as a family; all six kids helped set and clear the table. Like at my family’s home, the dinner was vegetarian, kosher, and delicious. There was a level of familiarity here. Josh and Elisheva’s voices felt soothingly recognizable, like the voices I’d heard my whole life. The conversation and sibling dynamics mirrored one I would expect to see at my own home. I felt a blanket of ease cover me as we moved to the backyard for a small bonfire with s’mores. While the familiarity comforted me, it didn’t make me long for home. Instead, it just gave me a little taste of home to keep me going. 

Thinking of my recent graduation, I wondered which of my college friends I would still stay in touch with in twenty years. Josh and my father would talk regularly, and then, because of distance and time, their relationship could not be maintained at the same level. Already, I noticed it had been harder to stay in touch with friends. In the future many would move far away. We would have different lives. What would stick from this stage of life, and what would slowly erode by the river of time? I fell asleep with these sometimes-worrying thoughts bouncing in and out of my consciousness.

The next morning, I took the train to Chinatown. Starting from the south, the goal was to slowly walk my way uptown to see as much as I could.

Apparently this is not a bean

I’ve never felt shorter

“Keep being on”

I started to approach downtown, on a mission to get some Chicago deep-dish pizza that everyone and their dog was raving about. Towers surrounded me with claustrophobic scaffoldings as I walked along wide streets made for cars. An older black man with shaking hands leaned against the building to my right. A month ago, I would have averted my gaze. Large cities invite isolationist behavior in me. But the trip changed my attitude a bit. This past month I relearned to talk to strangers and unlearned the unfriendliness I developed during the first year of the COVID pandemic. The guard I had up previously had dropped. I sought interaction with a wider variety of people than I had before.

As the man’s eyes turned to me, I, in turn, made eye contact and smiled as I began to walk past. Taking the in I gave him, he said “I’m hungry, can you buy me a burger?” pointing at the fast-food chain behind him. 

I thought about how I had been trying to budget for my trip. I’d been frugal and saving for a big adventure since I graduated high school. But I had a lot saved, how much difference would this one meal affect my wallet? “Sure, let’s go, I’ll buy you some food!” I told him.

We walk into the restaurant behind him, and I ask him which burger he wants. “That one,” he pointed to the board. I buy the food and continue my deep-dish quest. 

It must have been tourist season because the lines at all the pizzerias went far out the door. I was determined to get a pie but had no interest in waiting for an hour. I bit the bullet and found Pizzeria Uno, which didn’t have too long of a line. I only learned later that this was a huge country-wide chain. I made my way to the bar since I was alone. I ordered a medium pie for $23, more than I would like to spend on a single meal. I had almost passed on the meal when seeing the price, but I figured I would have leftovers, and this was a cultural experience people swore I needed to have. 

I needed to capture this cultural experience

The bartender, a big clean-shaven man with a burly voice, asked where I was coming from. As I had done countless times before, I explained my trip with the same enthusiasm of the first time. Eyes wide, he expressed how impressed he was with the trip. Then a woman and man, both with graying hair, confidently approached the bar to get some beer while they waited for an open booth. 

“Can I tell them what you did?” The bartender’s teeth shined with pride for me. 

“Sure,” I replied, slightly embarrassed, but mostly proud. The bartender enthusiastically explained my trip. The couple now shared the bartender’s impressed face.

“That sounds amazing!” the woman exclaimed. “We’ll take his bill,” she declared, this time facing the bar. She said it with such certainty I didn’t even begin to put up a fight of politeness. They made their order and then a booth became available. “Would you like to join us?” 

Excited by the unexpected company, I agreed and brought my freshly made pizza to the booth. The booth gave little legroom as they both sat opposite me. It was a tight squeeze, so our knees touched awkwardly, but we laughed away any discomfort that could have otherwise brewed. We slowly ate our deep-dish pizza over deep discussions about life, travel, and the future. Wendy and Greg were a recently retired couple on their way to their new home in Florida. They were taking a large detour through Chicago, one of their favorite cities that they visit every year. They applauded me for taking the time now to travel before I settle down and don’t have the same chances anymore. 

“Don’t just get a career for yourself,” Greg shared his wisdom from only recently finishing his career. “Do something you are passionate about, something you believe in, and something you will stick with. But also understand that it isn’t for you. It’s for your family or some other greater purpose, whether that be providing financially or making an impact in something important.”

I spent the past week since graduation thinking a lot about what to do with my life. Did I want a traditional career? What was the point of work? Was it about money, meaning, something in between or was I missing the point entirely? I was on a trip about myself and self-exploration as much as it was about external exploration. The idea of dedicating my life to something else stressed me out. But I felt Greg was right in a way, I just wasn’t there yet. 

“You need to work with people.” Wendy suggested potential career paths for me. “You’re not shy, you’re very friendly. You’d be great with people.” I found this encouraging and hopeful because I never thought this about myself. How much had I been in my head? It had been almost a month since I stopped taking my ADHD medication and was thrown into this new world of travel. Maybe I changed. Their first impressions of me are very different from what I thought of myself. I recognized that I was changing, and becoming a better person, but I worried about reverting when the trip was done.

The sauce and cheese seem to be in the wrong order

With a belly full of pizza and leftovers in hand, I headed to the train. By the station, a man was begging for money. I had already given money to two people today, so I said no. I boarded the train and began to immediately feel regret. My lunch was paid for entirely and I had leftovers, but I rejected a guy begging for food-money because I filled my niceness quota for the day. I received almost immediate karma for my choice to give charity to strangers earlier that day. The money Wendy and Greg spent on my pizza was more than I had given for the burger and train ticket. I had been benefiting off the kindness and generosity of strangers, but I hesitated when paying more than a fraction of the kindness forward.

On an adventure, I could ignore the realities of the world I found uncomfortable, but visiting Chicago forced me to recognize my obliviousness. However, traveling through rural towns for the past month shook away the numbness that had grown in me from years of city life. By stepping away, I viewed what had previously been normal in a new light. The next day, as I headed north to Wisconsin, the State I was born in, my mind filled with thoughts of the Windy City.