by Chessy Prout
“All right, Chessy, we’re just going to rotate around positions,” Doc said, towering over me with his toothy grin. “Relax and give it your best.”
I started in the back row and lasered my eyes on the ball. I could hear Dad cheering in the stands, like he used to when we played sports at Sacred Heart. I tuned him out when I saw Lauren Rusher—Lucy’s roommate from last year—go for the ball on the opposite side of the court.
Lauren was one of the biggest and fiercest girls on the team. She hit the ball so hard she’d supposedly given several girls concussions, earning her the nickname Rusher the Crusher. Lauren had a wild look in her eyes as she lifted her arm up and smashed the white sphere, knocking the moon out of the sky.
It was heading straight for my face in what was sure to end with a broken nose. I took a step backward and stuck my arms out. The ball hit my skin so hard I felt like I’d been stung by a thousand hornets. I wanted to collapse, but if I moved, the ball would shoot sideways. I clenched my jaw and returned the missile to Lauren’s side of the court. Not an ideal bump, but at least it didn’t land on the floor next to me. Doc looked impressed.
Moments later, when I rotated to the front row, I was face-to-face with Lucy. We jousted at the top of the net and I blocked her spike. Lucy beamed with pride. Sweat was pouring down my head by the time the scrimmage was over.
Dad rushed off the bleachers onto the squeaky parquet floor as if I’d won an Olympic medal. He put one arm around me as Doc ambled over.
“Chessy’s got a spot on the team next year if she wants it,” Doc said to Dad. “I’ll make sure to put in a good word with admissions.”
“Oh my gosh, thank you so much,” I said. “It was such an honor to play with the team.”
“That’s our newb,” one of the varsity players called out to me.
I was elated. The volleyball team was like Lucy’s second family. The girls ate dinners together, walked to classes, and hung out on weekends. I was beginning to see this as my community, my new home.
A few weeks later Dad and I visited Lucy to see her compete in a New England semifinal match. I imagined myself on the court playing next to Lucy and Rusher the Crusher. Some boys on the bleachers were shirtless and covered in red body paint. I couldn’t help but gawk at one guy who had written PROUT MAKE ME SHOUT across his back.
Unfortunately, St. Paul’s lost, but Lucy was still in a good mood when we headed out to dinner with her boyfriend, Brooks, and their friends Duncan and Jackson. Dad had been a year ahead of Brooks’s father at St. Paul’s, but the two hadn’t known each other well because Dad mostly hung out with the minority scholarship students.
Lucy’s friends piled into our rental car, and I ended up squished in the back between Duncan and Jackson. They started teasing that they’d “watch out for me” when I got to St. Paul’s and walk me to class.
“We’ll take you out,” Jackson said. I turned cranberry red with embarrassment and giggled nervously. Lucy rolled her eyes at their blatant attempts to unnerve her.
I leaped out of the car when we arrived at our destination, the Common Man. It was a two-story restaurant that looked like a charming New England home, with dark wooden beams and rooms with upholstered couches and floral curtains. There were quotes from politicians and athletes painted on the bathroom walls, like John F. Kennedy’s “Forgive your enemies but never forget their names” and Vince Lombardi’s “Winning isn’t everything. It’s the only thing.”
At the dinner table, I was sandwiched again between Duncan and Jackson. We played hangman after we ordered food, and Duncan tried unsuccessfully to get the phone number of our waitress. What was up with these boys?
I looked over at Jackson, who was wearing a burnt-orange Texas Longhorns baseball hat backward on his head. He started in with Lucy again and suggested that he’d date me next year, and then she could go out with one of his younger brothers when they enrolled next fall.
Lucy burst out laughing. “She’s in middle school. Don’t even think about it.”
On the drive back to St. Paul’s, Duncan put his arm around me and Jackson stuck his thumb up in front of my face as Lucy snapped a photo. I pressed my lips together and smiled. I was flattered by the attention but didn’t exactly feel comfortable. I was only thirteen and in eighth grade, after all. And they would be seniors by the time I got there next fall. If I got there next fall.
“The boys were acting really weird,” I said to Lucy at the end of the night.
“Yeah, don’t worry about it,” Lucy said. “They’re just being dumb.”
Boys will be boys, I guessed.
I didn’t think twice about Jackson or Duncan once I was back in Naples. I’d been dreaming about Dean, a boy in my grade with chocolate-brown eyes. We loved playing basketball and watching TV with Zach and Scott. Dean understood my sarcasm—somewhat of a rarity—and we binge-watched episodes of Impractical Jokers together. By Thanksgiving, a fuzzy more-than-friend feeling enveloped me whenever Dean was around.
I mostly ignored it until we ended up at a bonfire party after Christmas. I stuffed my face with marshmallows and chocolate from the s’mores supplies and swung wildly from a rope hanging off the trees. When I finally sat down, Dean gently took my wrist and slipped his hand into mine.
At school the next week, Dean picked me up after class and kissed me in front of our lockers. We were officially boyfriend and girlfriend. Our science teacher scolded us for kissing in the hallway.
Dean had an infectious laugh, and when I was with him, the hamster wheel of anxiety in my brain slowed down. I was still seeing Dr. Sloane and had started taking medication to treat my depression and anxiety. I told Dean a little bit about what I’d been going through, but I tried to keep things light and fun.
I wasn’t ready for anything super serious, so I liked having Zach and Scott around as buffers. My friend Jackie was close with Dean, and she constantly wanted relationship updates.
“Chessy, do you love him?” Jackie asked.
“I dunno,” I said. “He’s not family.”
“Chessy, he really loves you.”
Yikes. Was I in love? What did love feel like?
I was too embarrassed to ask Mom. I knew Mom had had serious boyfriends in high school and college, but she didn’t talk much about them. She grew up in a very Catholic household—sex before marriage was forbidden—and her own mother wouldn’t even acknowledge some of Mom’s relationships. There was no real sex talk yet, and that was fine by me. That felt like light-years away.
But with Valentine’s Day fast approaching, I felt pressure to tell Dean how much I enjoyed being around him. While I was sitting in French class, I wrote Dean a note on a stray index card, and it was kind of mushy. I cringed when I took it out later that night and read it again. I worried about putting myself out there too much and getting hurt. So I tucked the note into my diary and wrote him a new, toned-down card.
Dean showed up on Valentine’s Day with roses, a box of chocolates, and a picture frame with a photo of us in it. I kept the roses for weeks, until they were wilted and blackened around the edges. I worried that our relationship would soon look like that, because it was seeming more likely that I’d be heading off to boarding school.
Decision Day—when St. Paul’s emailed its acceptance letters—was in early March, and it was marked on the kitchen calendar with four exclamation points!!!! I’d be in Colorado for a national volleyball tournament, possibly my last one with my team. I was excited because one of my old friends from Sacred Heart was supposed to be there playing with her new school.
Dad was meeting me in Colorado—his job was now based in Atlanta, so he commuted to Naples on weekends. I didn’t feel well when I boarded the plane in Florida. I started sweating and shaking. Everything I touched sent pain shooting through my veins. It had to be the flu or some wicked virus. When we got to the hotel in Denver, I collapsed in bed. My teammates tracked down some medicine, and I fell into a NyQuil-induced haze.
I woke up in a
pool of sweat, my eyes crusted shut. I rubbed away the sleep, but my vision was still blurred. It took a while before I could make out Dad smiling at me from across the room, with an iPad in his lap. It was March 9, he reminded me. Decision Day.
“Check your email! Check your email!” Dad yelped as he handed me his iPad.
A video popped up featuring admissions officers, students, faculty, administrators, and the school mascot, the Pelican, dancing in various picture-perfect settings on campus and waving red-and-white signs imploring me to SAY YES TO SPS!
I looked over at Dad, and he had tears in his eyes.
“This is so wonderful. We’ll be on the same reunion-year cycle, sweetie,” Dad said. “This is going to be a lifelong bond for us.”
Dad had left his home in New York City in the fall of 1979 and arrived at St. Paul’s as a sophomore, a lanky scholarship kid excited about the school’s strong athletics program. He was the fourth of five children from an Irish-American father and a Japanese mother whose own parents were pioneers, attending college in the United States—Mount Holyoke and Harvard. Dad was really tall and towered over his siblings. He liked to joke that he got his height from all the milk he drank as a kid. Dad guzzled the stuff because he was collecting as many cartons as possible to exchange for free tickets to Yankee Stadium, his favorite place on earth.
At St. Paul’s, Dad was not part of the prep-school legacy crowd—the many students who had generations of Paulies in their blood. But he found a core group of friends through sports.
Mom hadn’t heard of St. Paul’s until she met Dad. She was the daughter of public school teachers from a small working-class town in Connecticut. She got her first glimpse of the campus when Dad brought her to his ten-year reunion. They were newly engaged—after meeting on a flight from Tokyo to New York—and Dad linked arms with her as they walked in the alumni parade along a path that cut through the emerald landscape.
“Do you think we could send our kids here?” Dad asked.
They weren’t even married yet, and he was already asking to give up their future children? She thought boarding school was where kids were sent away as punishment. Mom crossed her fingers behind her back before answering.
“Maybe,” she said.
Dad’s job in finance led us to Japan, and Mom set aside her career in marketing to take care of us girls. But Mom always wanted us to have an American education before we attended college. Months before the earthquake, Dad lobbied Mom to open the door to the family nest and let Lucy apply to St. Paul’s.
Her acceptance a day before the earthquake seemed like a sign—here was a stable and safe place that could care for Lucy the way Sacred Heart had. Two years later, as Dad prepared for another transfer abroad, Mom felt confident entrusting me to the St. Paul’s community.
“This is so great, Chessy,” Dad said as he replayed the St. Paul’s video acceptance over and over.
All I knew was that my head needed to meet the pillow or else the world would end. I started to close my eyes when Dad shook me: “Call Mom! Call Lucy!”
It barely rang once before Mom and Lucy picked up the phone together and squealed with excitement. Lucy was home for spring break, and Mom promised a proper celebration when I returned to Naples.
I was laying in the hotel bed and scrolling through Instagram when I stumbled across a cryptic posting from my boyfriend:
Through God all things are possible
Please pray for my family.
I tried calling Dean, but he didn’t pick up.
I texted Jackie to find out what was going on, and she responded that Dean’s brother was hospitalized in the intensive care unit after trying to hurt himself. It didn’t make sense. Was this a NyQuil hallucination? The room was spinning, so I pulled the covers over my head and fell back asleep. I never made it onto the volleyball court.
When I returned to Naples, Mom, Lucy, and Christianna presented me with a gluten-free cake they’d baked themselves, canvases with CONGRATULATIONS and SPS YEA! CHESSY ‘17 DAD ‘82 AND LUCY ‘14 painted in red, and crimson-and-white balloons to match the St. Paul’s school colors.
My family was ecstatic, but I was having trouble matching their excitement. I was worried about Dean’s brother and anxious that my friends at CSN would ditch me when they found out I’d be leaving. Arielle usually did not get emotional, but she teared up after I broke the news.
I refused to let Arielle out of my sight when we took a school trip to Washington, DC, a few days later. I even made her sit between me and Dean on a two-person bench during a bus ride back to the hotel. Dean wasn’t talking much about his brother. He was acting distant, and I couldn’t tell whether he was upset about his family stuff or my acceptance to St. Paul’s. I wasn’t sure how to navigate this.
It didn’t help matters when I left with Mom for New Hampshire in early April 2013 for St. Paul’s Revisit Weekend. The trip gave prospective students one last look at the school before deciding whether to go.
When we arrived on campus, I picked up registration materials at the Lindsay Center for Mathematics and Science. It was a massive brick structure named after an alumnus and had a greenhouse, a solar observatory, and a Foucault pendulum that hung down a stairwell. Mom quickly made friends with a family who had an older daughter, Allie, starting in the fall. I hoped I could make friends that easily.
I opened a glossy crimson folder embossed with the St. Paul’s crest: a pelican ripping meat from its own breast to feed its young. Yikes, what a horrific image. I wasn’t sure why they would choose that.
I met my student host in the common room of Coit, one of the dorms attached to the main dining hall known as the Upper. My host was friendly and gave me a tour of her dorm, including the laundry room. Most kids paid to have their clothes cleaned and delivered in neatly folded piles—a negligible expense when you considered the annual $50,000-plus price tag to attend St. Paul’s.
I met other girls who told me how fun the school dances were and that they never got in trouble for violating the dress code. Apparently, female students at nearby Phillips Exeter Academy were always complaining about how faculty forced them to change clothes because they were wearing something too revealing or “distracting.”
The girls here seemed so sophisticated. I thumbed through one of the brochures in my folder etched with the St. Paul’s motto: “Freedom with responsibility.” That sounded right up my alley. I could choose when I woke up, what I ate, and when I did my homework.
I was in awe of famous alumni like then secretary of state John Kerry and cartoonist Garry Trudeau. Who wouldn’t want to be a part of this exclusive club?
Later that night the students put on a variety show, where all the different a cappella and dance troupes performed. I could already imagine myself singing on that stage. After the show, Lucy found me along with Jackson and Brooks. Jackson introduced me to one of his younger brothers, who would be in my grade.
“Hi,” I said shyly.
“Hi,” he said without looking at me. Neither of us could get out any more words. Awkward.
I started scrolling through Instagram to check in on my friends back home. I saw pictures of Dean with his arm around a girl from my school. My stomach dropped to my feet. I showed Lucy the photos and asked her what she thought I should do.
“Forget about him,” she said. “That’s not a real relationship anyway. When you come to school, you’ll realize what a real relationship is.”
“Yes, it is real,” I insisted.
Lucy annoyed me when she played that older sibling card—the one where she knew better because she was soooo much more mature than me.
“Lucy, we’re only a few years apart,” I said.
“You’re going to break up soon because you’re leaving,” Lucy said. “All these boys here are interested in you. I’ll get a picture of you with them to make Dean jealous.”
When I got back to Naples, I learned that Dean had cheated on me with the girl in the photo. I unleashed my fury at home. I thoug
ht about setting fire to the picture frame he’d given me for Valentine’s Day, but that seemed like more effort than Dean was worth. Instead I ripped up our picture.
A wave of calm washed over me when I saw him at school. Dean walked over and tried to give me a bullshit explanation. I cut him off midsentence.
“You know what? I don’t want to hear it. I’m leaving,” I said.
His mouth twisted with sadness, and then I softened my tone.
“I want the best for you. I want to make sure you’re okay,” I said. “But we’re done.”
I walked away before he could get another word in. I was done with Dean, done with CSN. As much as I had tried to make Naples my home, I had never truly fit in. It was small and homogenous and closed off—the opposite of my world in Tokyo. I had so much hope for St. Paul’s to provide a place of love and stability and community that I sorely needed.
While Mom and Dad packed for Hong Kong, I spent the summer getting quality sister time with Christianna and Lucy. We biked together to the beach and splashed in the water. Lucy had recently gotten her license, so she drove us around Naples blasting country music at top volume on Gator Country 101.9.
Mom helped me pick out a pretty blue-and-white comforter for my bed at St. Paul’s and shop for posters for my dorm room. She also got me a few prep-school essentials: black Hunter boots, a navy Longchamp bag, and a forest-green Barbour jacket.
I filled out a roommate questionnaire for St. Paul’s that asked me about my living style: was I clean or messy, was I quiet or loud, did I go to bed early or late? Lucy really wanted me to room with Ivy, the little sister of her roommate, Georgina, and so I put down the request.
One night Lucy sat down next to me on the glider couch on our patio as the warm gulf breeze swept over us.
“Chester, I’m so excited for you to come to St. Paul’s,” she said, and squeezed my hand. “We’re going to play volleyball together and have sister brunches on Sundays.”
