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Riding the Roller Coaster with Sinatra

by Elaine Soloway

His name was Tony and he sat in the last row, last seat of my sixth grade classroom. He wasn’t the brightest, or the dumbest boy in our grade, but as soon as I learned his name was Tony -- so much more lyrical and exotic than the more familiar Sheldons, Marshalls, or Melvins -- I was intrigued.

Tony’s last name escapes me now, but I know it ended in an “A,” just like Sinatra, who was my favorite crooner in 1950, the year I turned twelve. It could have been my crush on Frank Sinatra that spilled on to Tony, for I had mooned over the singer ever since I first heard him on the radio. And when I saw Sinatra’s skinny, vulnerable self on Bob Hope’s television special, The Star Spangled Review, I was hooked.

On the evening of Sinatra’s appearance, my parents sank into the sagging cushions of our upholstered couch, while my brother and I sat cross-legged on the carpet -- the recommended six feet from the television screen. When Sinatra sang, “I’m gonna love you, like nobody’s loved you, Come rain or come shine,” I ignored eye doctors’ warnings and scooted closer, certain the young man from Hoboken was singing directly to me.

Tony showed interest in me earlier that week in the schoolyard. “How did you get to be such a brain?” was his opening remark. I was surprised by his attention, because with his black hair brushed back into a ducktail, blue eyes circled by long lashes, olive skin, and pretty smile, he was a dreamboat. And to be honest, there was nothing special about me. I wasn’t the prettiest or the ugliest girl in class, but I was the shortest. My black hair had body, and when I wasn’t wearing my thick glasses, you could say I had nice green eyes. I did have an out-going personality, but I wasn’t “fast” like a few of the girls who applied Hazel Bishop Tangee lipstick in the girl’s bathroom. And my chest was flat -- no buds had sprouted yet to warrant a visit to Marshall Field’s lingerie department.

After a few days of small talk on the way to our third floor classroom, Tony said, “How about going to Riverview with me next Tuesday? It’s a school holiday and Two Cents Day.”

As I considered Tony’s offer, I took in the portrait I had been sketching in my head each night. I could also smell garlic, a mouth-watering scent that in my family’s grocery store was married to kosher deli, but at Lafayette signaled Tony.

I hesitated a response -- not because I wasn’t ecstatic to be asked to go to Chicago’s popular amusement park with this lovely Italian boy -- but because I was trying to figure out how I’d get my parents’ permission. Besides being an age which they believed too young to think about boys, Tony was a shaygitz, not one of our own kind. And although I had never heard either of them bad-mouth our Italian customers, I understood that if and when I would be allowed to date, it would be with “a nice Jewish boy.”

“Go to Riverview with you?” I repeated, stalling for time. When Tony nodded “yes,” I replied, “I’d love to.” To myself I thought, how are you going to pull this off?

I knew that if I wanted to blissfully stroll the Riverview midway with Tony, crush myself next to his slim body in a roller coaster, and watch him toss at a target to win me a panda bear, I’d have to lie. This would be difficult, for I never lied to my parents, or rebelled in any way. Now I could barely recognize this new me, this brazen girl contemplating a deception that could break my parents’ hearts, but also make mine sing.

After school that day, when I entered our store, my mother was dusting some canned goods that were lined up on a shelf. Except for a radio news program announcing the number of U.S. military lost in the Korean War, there was no other sound in the place.

“Hi honey,” Mom said, turning her rouged cheek to catch my kiss. I stared at the cans of Libby’s, Savoy’s, and Campbell’s. In playful moods, I imagined them to be soldiers standing at attention, waiting for General Mac Arthur’s review. I saw their brightly-colored labels as war medals. But unlike men engaged in combat, our store’s tin soldiers hardly moved, rarely left their posts on the shelf, never were set “at ease.” Month after month they stood, their expiration dates coming dangerously close. Poor peas, peaches, and pineapple chunks in heavy syrup, I would think, forsaken by customers who are now pushing carts along supermarket aisles, or shopping in better neighborhoods far from Division Street.

“Ma,” I said, turning from my illusion and placing my schoolbooks on her counter. “A bunch of kids from my class are going to Riverview on Tuesday. It’s a ‘teacher’s something or other day,’ so we’re off and we can get into the park for two cents.”

“Who’s going?” she asked.

I was prepared for this line of questioning, and offered up six names of Jewish classmates, more girls than boys. Satisfied, she gave her okay.

On Tuesday, when I arrived at the gate, Tony was waiting at the gaudy entrance. Dwarfed by the giant archway with minarets at each side, my swain looked like the kewpie doll I hoped he’d win for me. The calliope sounds of the carousel, shouts of, “Wait up!” and the clanking gears of carnival rides met me, too. “Hi,” Tony said, taking my hand in his. “You look pretty.”

It was a hot day, so I had convinced my mother that my white batiste cotton midriff blouse with an eyelet ruffle would be appropriate clothing. When I had exited our grocery store, the elastic top of the blouse sat demurely on my shoulders, but by the time Tony laid eyes on me, I had pushed the ruffle down two inches.

“Thanks,” I said. “You look nice, too.” Tony was wearing a short-sleeved, button-down shirt and I could see a gold cross dangling from his neck. Why hadn’t I noticed the religious symbol before? Was it cross hidden beneath polo shirts, or was I so blinded by adoration that I missed it? Now, with my guilt clinging to me like my damp cotton blouse, I stared at the jewelry and pictured my parents wailing into their stained aprons -- “oy gevalts” punctuating their tears. But once again, Tony’s sweet smile, warm hand, and Sinatra-like voice pushed my parents’ heart-wrenching images back behind the counters of our store.

“So where to? Aladdin’s Castle, the Tilt-a-Whirl, Shoot-the-Chutes, the Bobs?” he asked.

I was relieved he had omitted the Old Mill Tunnel-Of-Love, because the thought of the darkened cave, and the moans of tangled couples in slow-moving boats was scary. I may have been bold enough to deceive my mother, but this passageway called for skills and courage I hadn’t yet mastered.

“The Bobs,” I said, “let’s go on the Bobs.”

“You’re not scared of roller coasters?” he asked, a look of respect lighting up his olive-colored face.

“No, I like them,” I said. I wasn’t insulted Tony had thought me too timid for the wild ride -- I was surprised at myself as well. For a girl who had been afraid of the dark just a few years earlier, I had blossomed into someone who loved roller coasters. Their sharp curves, shortened dips, and perpendicular climbs and drops thrilled me. I liked the Comet and the Blue Streak, too, but the Bobs was my favorite, and I would happily scream with the rest of the riders as we’d screech along the roller coaster’s tracks.

The ride on the Bobs was just as I had pictured. At the start, Tony and I sat rigid, our hands on the bar in front of us, our eyes fastened on the upcoming hill. But after the first deep drop, we scrunched up against one another. Tony left one hand on the bar and wrapped the other around my bare shoulder. After several trips (Only 5 Cents To Ride Again!), we stumbled off the roller coaster. As we walked hand-in-hand to the Pair-A-Chutes, I heard a familiar voice behind us. “Well hel-lo Elaine. And hel-lo Tony.” It was Melvin Bronstein, a classmate and neighbor whose parents shopped in our store. His small eyes darted from my face, to my off-the-shoulder-blouse, to Tony’s Italian face, and to our entwined hands. I quickly untangled my fingers and said, “Hi.” Tony narrowed his eyes, but didn’t say a word.

“Have fun,” Melvin said, in a voice more like a threat than a blessing. “See ya back on Division Street.” Then he turned and ran towards the exit. Was he racing to tell my parents about my shaygitz boyfriend? I better get home and confess before the rat has a chance to blab. Maybe honesty will bring a lighter sentence.

“This has to be the last ride,” I said to Tony.

“No problem.”

At the Pair-A-Chutes, I grasped the ropes attached to the parachute seat while the gears hoisted me up 212 feet. I freed one hand to touch the Jewish star I wore around my neck. Closing my eyes, I prayed, “Keep me safe,” more for my homecoming than the drop to come. The seat swayed as it poised at the top of the tower and in the thinner air of the carnival ride I felt lightheaded. I glanced at Tony, separate and fearless in the seat next to me. Unlike my worried face, Tony’s was alive. Instead of squeezing the ropes as I was doing, Tony’s arms were spread wide and he rocked his seat to make his position even more dangerous.

The parachute suddenly dropped and my stomach flipped over and over until the ride slowed in its last feet of descent. Tony and I unbuckled ourselves from the protective harnesses, and walked silently to the Park’s exit. At the streetcar stop, Tony bent down and kissed me on the cheek. “I had fun,” he said.

I touched the spot his Sinatra-lips had marked. “Me too,” I said. “See you in school.” Sweating in the streetcar, with my forehead pressed against the window, I composed a speech I would offer my parents, “There’s this boy in school, he’s very nice,” and continue listing invented virtues. And when they would ask the inevitable, “Is he Jewish?” I would bravely tell the truth.

After arriving home, with the elastic of my blouse now up over my shoulders, I walked into our store ready to face my inquisitors. But the sight of my two parents standing with their arms crossed in from of them warned me that Melvin had beaten me to it. Before I had a chance to launch my speech, my parents said in unison, “You’re not seeing the Italian again.”

As much as I adored Tony, I loved my parents more. And with our grocery store’s dim prospects, I figured they had enough tsouris without adding a rebellious daughter to the mix.

“Okay,” I said, all bravery evaporating into the store’s stifling air.

The next day in school, I was prepared to tell Tony goodbye, but he was absent. Days went by without his appearance. Then, I learned Tony had been joy riding in a stolen car, got kicked out of Lafayette, and was shipped to Montefiore -- the public school for troubled youth. When I heard this, I felt a mixture of sadness and relief. Sad because this short, brainy Jewish girl was not thrilling enough to lure Tony from petty crime. And relief, for without Tony’s swaggering presence, my remaining journey at Lafayette -- though ordinary and predictable -- would be easier to navigate for a girl ill-suited to danger. For the time being, I’d have to confine my crush to Sinatra, and any desired thrills to the roller coaster rides of Riverview.

The End

* * * * *

Elaine Soloway is a freelance writer whose essays have appeared in the New York Times Money & Business, Chicago Tribune WomanNews, ActiveTimes Magazine, Today's Chicago Woman; and Web Sites:,, and Elaine’s memoir, THE DIVISION STREET PRINCESS, a coming-of-age-story of a girl, a store, and an old Chicago neighborhood, will be published in the Fall of 2005. This story is an abridged version of one of the chapters.

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