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Confessions of a High School Disaster

Freshman Year



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About The Book

In the tradition of Bridget Jones’s Diary, a lovably flawed high school student chronicles her life as she navigates the highs and lows of family, friendship, school, and love in a diary that sparkles with humor and warmth.

I’m Chloe Snow, and my life is kiiiiind of a disaster.

1. I’m a kissing virgin (so so so embarrassing).
2. My best friend, Hannah, is driving me insane.
3. I think I’m in love with Mac Brody, senior football star, whose girlfriend is so beautiful she doesn’t even need eyeliner.
4. My dad won’t stop asking me if I’m okay.
5. Oh, and my mom moved to Mexico to work on her novel. But it’s fine—she’ll be back soon. She said so.

Mom says the only thing sadder than remembering is forgetting, so I’m going to write down everything that happens to me in this diary. That way, even when I’m ninety, I’ll remember how awkward and horrible and exciting it is to be in high school.


Confessions of a High School Disaster
Monday, August 10

Mom’s gone. Not forever, obviously. For four months at the most, she said.

She came in here all shaky, with swollen eyes, and pressed her forehead into my forehead. Her breath smelled like pad thai. She was like, “Please know how much I love you.” We both cried. She explained everything: She’s going to Mexico to work on her novel. She knows it’s sudden, but she also knows I’m mature enough to handle a little surprise. We’ll be in touch all the time. We can Skype and chat and talk on the phone whenever we want. Maybe I can go visit her.

She gave me her blue-and-white porcelain rabbit, which I’ve always loved, and a journal, and said, “If there’s one thing I want you to remember, it’s the importance of creating memories.” I don’t really want to remember this, actually. Plus I already write in this diary every day, but it seemed rude to tell her that.

Tuesday, August 11

Dad made me breakfast before he went to work: banana pancakes, bacon, and a strawberry smoothie. He sat there watching me eat. So did Snickers. I never give Snickers food from the table, but he never stops hoping.

“This is really good,” I said.

“You don’t have to finish it,” Dad said, but I did, because he looked so sad.

“Don’t worry,” I said. “It’s not for very long.”

He unscrewed the blender from its stand. He wasn’t looking at me.

“She has to work on her novel,” I said. “It’s impossible to get anything done here. She needs a room of her own.”

He laughed, but not a real laugh, and said, “Right.”

Wednesday, August 12

Things I love about Dad:

1. His dad jeans

2. His crinkly eyes

3. He sends me cat videos

4. He never yells

5. He still wears the fugly brown tie I got him for Father’s Day when I was eight

6. He knows all the words to every ’80s song

7. His dad smell (peanuts and limes)

Thursday, August 13

I try to forget that I’m starting high school in a few weeks, but sometimes the fact rushes into my mind and I get sweaty with fear.

However bad it is, it can’t be worse than junior high. My theory is, they put the two most evil grades in one building to keep them from infecting everyone else with their awfulness. Basically all I did in junior high was text, straighten my hair, add to my Benedict Cumberbatch shrine, and worry about how to be more popular. Thinking about it makes me cringe.

I want to be different in high school. Like a new person.

And I want to make out with someone. It’s so humiliating that I’m a kissing virgin at this advanced age. Everyone halfway normal in my grade had their first kiss at, like, age 10. I’ve never even gotten a peck on the cheek (I’m not counting my parents or Uncle Julian). And the longer I go un-smooched, the more freakish I feel. If I graduate high school without being kissed, I’ll be too embarrassed to kiss anyone during college, and then I’ll most likely die without ever even getting to second base. Something has to change fast. This I vow: I will kiss a guy before New Year’s Eve. Or maybe it’ll happen on New Year’s Eve. OK, this I vow: I will kiss a guy before New Year’s Day. Vow taken.

Friday, August 14

Before Dad left for work, he said, “Don’t just sit online all day, OK, kiddo?” so I invited Hannah over, and we went to the pool. She put on SPF one billion because she’s so pale she’s basically light blue. She wouldn’t shut up about how scary the first day of school will be. Finally, to get her to stop, I told her my mom left for Mexico on Monday. She gasped.

“It’s not a big deal,” I said, irritated.

“It seems like kind of a big deal.”

I put my sunglasses on.

She said, “What’s going on with her and your dad?”

“Nothing. She’s working on her novel. That’s it.”

“Chloe, I’m so sorry.”

“Ugh! Don’t be sorry! She’s writing, not dying.”

I know I shouldn’t be mean to Hannah, but she seriously drives me insane. The more intense and touchy-feely she gets, the more I turn into a block of ice.

Saturday, August 15

I pulled all my boxes of fall and winter stuff out of the closet, and I. Hate. Everything. It all says, I have no identity of my own, so I’m going to wear the most generic clothing possible in a desperate quest to blend in. My flowered sneakers from Hannah I love. The rest I would burn if I could.

I need a makeover. No, not a makeover—that sounds like some gross magazine. I need to dress like the person I really am. Which is . . . what? Hipster. Hippie. Stoner. Emo. Preppy. None of those.

Sunday, August 16

The first thing I do in the morning, lying in bed, before I’m all the way awake, is check everything on my phone. I don’t even want to; it feels like I have to catch up on what happened while I was asleep, so I don’t fall behind. I’ve tried to do a phone cleanse before, but the longest I’ve lasted is three hours. I don’t understand why it feels so good to click while you’re doing it and so disgusting after you’re done.

Monday, August 17

I just talked to Mom!!!!! It wasn’t for very long, because her phone was dying. She’s in a small town with cobblestone streets and a bullring. She rented a one-room apartment that looks out on a courtyard.

“I miss you like crazy,” she said.

“I miss you, too!”

“I can’t wait to show you my place, babe. There are these Argentinean kids staying downstairs from me, and they have drum circles under my window 24/7. This morning, a stray cat showed up on my doorstep. She’s orange, with one white paw. Doesn’t that seem lucky?”

I asked if she wanted to talk to Dad, but she said she had to go find cat food before the stores closed, and she’d call him later.

At dinner, I told Dad everything Mom said. He nodded and smiled. He looked like he had a migraine, but when I asked him if he wanted an Advil, he said he was fine, just tired.

Tuesday, August 18

Things I love about Mom:

1. Artistic

2. Did yoga before it was cool

3. Genius writer

4. Lets me skip school all the time to hang out with her

5. Lets me watch and read whatever I want, because you can’t shield your children from the world; you have to introduce them to it

6. Beautiful

7. Compliments me a lot

Wednesday, August 19

Hannah’s mom drove us to the mall. She was wearing a pink short-sleeved cardigan and cork wedges with pink straps. On the way there, we talked about Hannah’s older brother, Brian, who just left for his first semester at Dartmouth, which according to Mrs. Egan is the best school in the world.

“I’m telling you, Chloe, it’s all about the family dinner. Eating together as a family is scientifically proven to raise your SAT score, did you know that?”

Hannah hissed, “Mom, stop.”

“Oh, honey,” Mrs. Egan said, looking at me in the rearview mirror. “Hannah told me about your mother.”

I gave Hannah a look of death.

“She’ll be back in December,” I said.

“Of course she will!”

I refused to talk to Hannah in the mall until she bought me a soft pretzel and a Diet Coke. Even then I was being a total B. I went to all the stores with her, but I wouldn’t try anything on. I sat in the armchairs they put there for boyfriends and husbands and pretended to fall asleep.

Even when Mom was here, we didn’t have family dinner. Usually Dad would make something for him and me, and we’d eat while Mom worked upstairs. Then she would eat carrots and hummus standing up at the kitchen counter. She can’t be on a regular schedule, because she’s an artist.

I’ll do way better on the SAT than Brian. He’s the kind of guy who says “She’s driving with Mike and I” because he thinks “I” sounds fancier.

Thursday, August 20

There’s nothing better than going to the pool. Here’s what to bring:

* Sunglasses

* Beach towel decorated with a picture of a New York City taxi, to help you dream up ways to escape the suburbs

* Pencil case with house keys and money for the concession stand

* Book

Then lie in the sun for hours, and do some breaststroke when you get too hot. Don’t feel like you’re being lazy, because you’re reading and working on your tan. I know it gives you wrinkles, but what if you die in a terrorist attack when you’re 20? Then you’ll regret wasting your time worrying about sun damage when you could have been living it up and looking cute.

Friday, August 21

Hannah came over seriously crying about our so-called fight. I felt like saying, “I have bigger fish to fry,” but I didn’t say it, first of all because that would be mean, and second of all because it would be a lie.

I said, “It’s not a big deal. Sorry I wouldn’t try on pants with you.” She almost fainted with relief. It was raining out, so we ate a bag of cinnamon-flavored pita chips and I told her about my kissing vow. She doesn’t understand how much I’m suffering, because she kissed Matt Welch last summer at Kayla Price’s birthday party, and so now she is a normal human teenager rather than an unkissed freak. No matter how much I ask, she can only describe kissing Matt as “too wet,” “kind of strange,” and “not what I thought it would be like,” which is so frustrating, because I’m dying to know every detail about nose placement and tongue texture and post-kiss facial expressions.

“Don’t overthink it,” she said, breaking off a corner of a pita chip. “When it’s meant to happen, it’ll happen.”

“No, I need a plan, Hannah. I need to take matters into my own hands. Now help me come up with a list of prospects.”

After hours of internet research, we had a list of three guys who are single, reasonably cute but not out of my league, popular enough but not Popular, not too druggy, not too mean, not too cocky, and not too player-y:

Zach Chen. Sophomore. Has a man bun (sexy, IMO), sings in an a cappella group (kind of dorky), and plays guitar in a rock band called Deposed Monarchs (again, sexy).

Luke Powers. Junior. Hockey goalie. Has a beautiful flowing hockey mullet like it’s the 1970s. At least 6'2" and ripped. Hannah thinks I’m punching above my weight class on this one, but not everyone appreciates his hair, plus his Twitter reveals he’s suuuuuper into Settlers of Catan, which, again, is not everyone’s cup of tea.

Griffin Gonzalez. Fellow freshman. Has the best name in our class by a mile. Reads a ton, like me. Does a lot of eye rolling and sighing in English class when nonreaders talk. Gives off a vibe like he’s counting the days until his PhD program starts. I’m scared of him and think he’s a snob but desperately want him to like me.

Little do these guys know that one of them will make out with me before the year is over.

Saturday, August 22

I went to the pool alone. I like doing stuff by myself. It’s easier to observe the world when you’re not trying to keep a conversation going.

When I went to the concession stand to get a rocket pop, I had to pass this big bunch of older boys. They got quiet as I walked by, but I didn’t look at them, so I’m not sure if it was a natural pause in the conversation or if one of them was, like, making a hand job gesture in my direction while everyone died of silent laughter.

After I got my Popsicle, I turned around to head back, and there was one of the guys, in line behind two shivering kids wrapped in striped towels. When he looked at me and I looked at him, I felt like a key sliding into a lock.

“You didn’t get me anything?” he said.

“What? Oh, no, I didn’t, um . . . Sorry. I don’t—”

“Calm down,” he said. “I’m messing with you. Wait for me, we can eat together.”

While he ordered a SpongeBob ice cream, I studied him. I don’t think Hannah would consider him cute. He has a face like bread dough, with raisins for eyes. Plenty of zits on his chin. His hair goes down to his shoulders, and I’m pretty sure it’s in dreads. He’s extremely tall and about the size of a riding mower, and he has big muscles in his arms and legs. I’m not talking about gym muscles either. Baling-hay muscles, not that there’s any hay to bale around here.

I waited for him to pay, and then we went and sat on the bench by the sign-in sheet. It seemed weird that a few seconds earlier, I had never seen this person, and now we were sitting side by side and acting like it was normal. Maybe it was normal. I don’t know, because I never meet any new guys. I’ve known everyone in my class since kindergarten.

“Do you go to MH?” he said.

“I’m starting in the fall.”

I must have looked petrified, because he said, “There’s nothing to worry about.”

“On a scale of one to ten, how horrible is it?”

“Two.” He was biting his ice cream instead of licking it, which looked so freaking manly.

“You must be popular,” I said. “Otherwise you would never say two.”

“Oh God.” He waved SpongeBob in the air. “That stuff is so stupid.”

“You are popular!” I said.

“You’re not?” he said.

For a second I considered lying, but I realized he would find out the truth on September 2—that is, if he even deigned to notice me at all.

“Nope,” I said. “I’m not, like, a loser, but I’m not famous, either. I’m just kind of there.”

“I find that hard to believe,” he said. I’m pretty sure he was being gallant.

We walked back to the pool together. All his friends stared at us like we were on fire. One of them yelled, “Ask to see some ID!” and they all laughed.

“Ignore those idiots,” he said. He walked me back to my chair and said, “What’s your name, by the way?”


“I’m Mac.”

We shook hands while a group of young mothers watched us through their big sunglasses. I hate this town. It’s teeming with snoops and gossips.

I pretended to read for about an hour, and then Mac and his friends left, and on his way out, MAC BLEW ME A KISS.

Sunday, August 23


I was in the midst of an intensive search for Mac online, which wasn’t working, because I didn’t know his last name or even his real first name.

And then, as I was looking, he added me.

His full name is Macintyre Brody, and I think he has a girlfriend.

He has one of those annoying profiles with no posts of his own, a thousand posts from other people, which he never responded to, and about 10 pictures. There’s one of him in someone’s basement, wearing a gray T-shirt with the sleeves cut off, holding a red cup. There’s one of him in his football uniform, running onto the field and flipping off the camera. And then there’s a really beautiful one. His arms are stretched out, and he’s laughing. He’s just thrown a girl off a dock, and she’s hanging in the air like a star, with her long hair flying up behind her. She’s wearing cutoffs and a white wifebeater. No bra. She hasn’t detagged herself, even though you can see her nipples, so I know her name: Sienna Ross. Underneath the pic, she wrote, dude i WILL get u back. If I were Mac’s girlfriend, I’d probably call him something boring, like “sweetie.” But Sienna calls him “dude.” So confident!

I couldn’t stalk her profile, because she has super-strict privacy settings, but from the one picture, she looks very athletic and outdoorsy. The kind of person who would survive a zombie apocalypse and who doesn’t even need eyeliner to look halfway normal.

Well, that’s that.

Monday, August 24

Texted Hannah, Met a guy named mac at pool. Hot but has gf. Meh.

She called me immediately and made me tell her every detail. When I sent her the link to his profile, she was like, “He’s very handsome,” and even though I could tell by her voice that she didn’t mean it, I could also tell she was trying her hardest to sound convincing. She really is a good friend.

Tuesday, August 25

I do miss Mom like crazy, but it’s kind of nice, being here with just Dad.

They’ve always fought a lot. Mom throws stuff, not at Dad, but not NOT at him. The week before she left, she winged a wineglass at the backsplash and it broke into a thousand pieces.

Maybe everyone’s parents are like that. I don’t know. It’s not really the kind of thing I talk about with Hannah. I saw her parents get cranky with each other once because they were about to go to the movies and when Mrs. Egan asked how she looked, Mr. Egan said her pants were “not my all-time favorite.” She sighed and rolled her eyes, and he said, “What?” in a rude voice. She said, “Being kind is more important than being honest,” which I think is true. He said, “Honey, if you don’t want to know, don’t ask,” and it went from there. When they left, Hannah said, “I hate it when they fight,” and I said, “Yeah,” even though I was thinking, That was nothing.

My parents fight about:

1. Whether Dad respects Mom’s need to be an artist (Dad says yes, otherwise he wouldn’t work to support her while she writes; Mom says no, because he’s always throwing his job in her face, like being a lawyer is harder than being a mother and a writer)

2. The state of the house (Dad says it’s a pigsty; Mom says he should get evaluated for obsessive-compulsive disorder)

3. Mom’s online shopping (Dad says she’s spending my tuition money; Mom says he’s being melodramatic and controlling)

4. Mom’s friends (Dad says they’re a bunch of losers; Mom says he’s intimidated by anyone who cares more about art than money)

They think I can’t hear them because I’m in my bedroom with the door shut, but our house was built in about 1700, and the walls are thin. I could listen to loud music, I guess, but I feel like I have to eavesdrop, to know the worst.

Other times they do disgusting stuff like slow dance in the kitchen with their hands on each other’s butts, or sing songs from musicals. That almost drives me crazier than the fighting.

Wednesday, August 26

Dad took me to CVS to buy school supplies. I got highlighters, fine-point pens, notebooks, and a bunch of folders with unicorns on them. I meant the unicorn folders as a joke, but now I’m worried that everyone will see them and think I seriously love unicorns. Ughhhh.

When I got home, I took my school stuff to my room and spread it out on my bed. There’s something so satisfying about new, juicy highlighters and notebooks with crisp edges. They make me feel hopeful, like maybe the school year will go great and I’ll suddenly understand math.

Thursday, August 27

After dinner, Dad and I watched Midnight in Paris. The point of the movie is, everyone idealizes the past, not realizing that their own era is pretty great and will be idealized by future generations. After it was over, I said, “I still think I’d be happiest in the Jazz Age,” and Dad said, “You wouldn’t last five minutes without your phone,” which doesn’t make sense, because if I were born back then, I wouldn’t know about smartphones, so I couldn’t miss them, which I said, thereby winning the argument. For dessert, Dad had whiskey, and I had a lemon Italian ice, which I flipped over so I could eat the mushy super-sweet part first.

Friday, August 28

Email from Mom!

Dear babe,

¿Que onda? (What’s up?) I’m writing to you from the public library. This is the only place I can get an internet connection, thank God; you know how it enslaves me at home. I had to come all the way to Mexico to escape the siren call of Twitter.

I discovered that if I open the window next to my bathroom and clamber along a sloped portion of roof, I can get to a flat section perfect for sunbathing. I’ve been sitting out there for hours every day, tanning and writing.

I’m getting a tremendous amount of work done but am missing you horribly. Email soon and tell me everything.


Your old mom

I wanted to chat her, but she wasn’t online, so I emailed back instead.

Dear Mom,

I miss you! Dad does too. I met a guy at the pool, Mac. I’m trying to be confident and calm, like you say, but it’s hard because he’s so cute and I can’t tell if he likes me or not. He added me on Facebook, but I think he has a girlfriend. Thoughts?

Well, adios for now!

xxoo Chloe

Saturday, August 29

I’m at Hannah’s. We just sobbed our way through The Notebook. I was mostly faking it; I think she should have married the reliable guy with bright-blue eyes and a jaw like a box—what’s so bad about him? Now Hannah’s online and I’m writing. I feel lonely at her house today. I’m dreading this sleepover. What’s the point of sleepovers, anyway? There’s all this pressure to stay up until 5 a.m., and you eat too much candy, and the next day you feel disgusting and you usually cry about something dumb because you’re so tired. Even when you go to bed at a normal hour, you can’t sleep, because Hannah’s house smells wrong, and there’s a ticking clock in her bedroom. Then in the morning you have to eat with the Egans, who have eggs for breakfast, a thing with which I cannot deal.

I’m going to kick Hannah off her phone and make her talk to me about my kissing campaign. Should I go for Griffin Gonzalez first, since he’s in our class and the most similar to me? Or should I aim higher? And if the latter, does “aiming higher” mean starting with Luke Powers or Zach Chen? These are the important questions Hannah has to pretend to care about, because she’s my best friend and that’s how it goes.

Sunday, August 30

The landline rang this afternoon. I let Dad get it, like I always do. I hate answering the phone if I don’t know who’s calling. A few minutes later, I heard him raising his voice, so I snuck upstairs to eavesdrop. The door was closed, and I couldn’t hear much. “. . . If you think I’m going to . . . ,” “mind-bendingly irresponsible . . . ,” “. . . Eat, Pray, Love, it’s your real life . . . ,” and “. . . of course she’s upset; she’s just hiding it.” That’s the one that made me feel guilty for listening, so I snuck downstairs again. Snickers was hanging out by the sliding doors, keeping an eye on the backyard. I sat next to him and scratched his neck, which he wasn’t in the mood for, since it was distracting him from his important squirrel-watching duties.

Eventually I went back upstairs. The door to Mom and Dad’s room was open. Dad was taking Mom’s clothes out of the closet and throwing them on the bed.

“I wanted to talk to Mom,” I said.

“She had to go.” He yanked her long green dress off its hanger and tossed it onto the pile.

“What are you doing?”


“Are you throwing out those clothes?”

“Mom asked me to donate some things.”

I couldn’t see his face, but his voice sounded funny.

“Can I have them, then?” I said. “If she doesn’t want them anymore?”

He turned around to look at me. “Well, I guess,” he said. I could tell he didn’t want to let me, but he couldn’t think of a reason to say no. Too bad! That’s what he gets for lying.

I had to make six trips to my room to move all Mom’s clothes in there.

If I had to describe her style in two words, I’d say SCARVES GALORE. Picture a gypsy yoga teacher, and then add more bangles than you thought, and that’s Mom.

Monday, August 31

Thank God for Snickers. I was lying in bed crying last night and he jumped up and stared at me with a worried look on his face. Then he burrowed into the sheets, headfirst, and fell asleep. If only he didn’t fart on me all night long, he’d be the perfect dog.

About The Author

Photograph by Amanda Castle Photography

Emma Chastain is a graduate of Barnard College and the creative writing MFA program at Boston University. She lives in Brooklyn with her husband and children.

Product Details

  • Publisher: Simon & Schuster Books for Young Readers (July 10, 2018)
  • Length: 368 pages
  • ISBN13: 9781481488761
  • Grades: 7 and up
  • Ages: 12 - 99

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Raves and Reviews

"Chloe Snow's Diary goes far beyond the expected awesomeness + angst of a freshman in high school, though it has both of those qualities in spades. But Chloe Snow, in all her hilarious brilliance, will also break your heart and make you bawl those "happy to be alive" tears. Amazing."

– Lauren Myracle, New York Times bestselling author of The Infinite Moment of Us

As if starting high school wasn’t daunting enough, Chloe Snow has to do it without her free-spirited writer mother—who bolted to Mexico to find her “muse”—and alongside her religious best friend, Hannah, and Hannah’s judgmental, picture-perfect family. Fortunately, Chloe has a caring dad; a new best friend, Tristan; and the lead in the school’s musical! In the spirit of Meg Cabot’s The Princess Diaries series, Chloe’s daily diary serves as the book’s format. Encompassing an overwhelming majority of Chloe’s record is her obsession with Mac, a senior boy with a girlfriend and Chloe’s secret hookup. Chloe, Hannah, and Tristan all have intense relationships with senior boys, which, aside from seeming a little improbable, starts to become how they define themselves. But despite Chloe’s dominating obsession with Mac, and the book’s abrupt ending, Chloe is refreshingly honest and unfiltered about very real issues facing high-school students: unsteady family dynamics, drinking at parties, balancing old and new friends, and the stigma of slut shaming. — Caitlin Kling

– Booklist, January 1, 2017

Chloe Snow wants nothing more than to be kissed by New Year’s Eve. She is a typical high school freshman, ready to take on the challenges of leaving middle school behind, and her dad is predictably embarrassing. Her mom, however, is another story: she has recently left for Mexico in order to concentrate on herself and her writing. At the pool, right before school starts, Chloe catches the eye of the school bad boy—never mind that he already has a girlfriend. But when she gets cast in the leading role of the school’s musical, instead of the most popular girl, the drama really begins. Writing in a diary format, Chastain captures a spot-on teen voice that would feel at home in an updated version of the film Mean Girls. Underlying the humor and angst of high school life, though, are Chloe’s ache for her mother and her confusion and anger about her parents’ relationship. Readers will hope for the heroine’s continued adventures in future volumes. VERDICT An above-average purchase for readers who love comedic, realistic fiction about high school.–Deanna McDaniel, Genoa Middle School, OH

CHASTAIN, Emma. Confessions of a High School Disaster. 352p. ebook available. S. & S./Simon Pulse. Mar. 2017. Tr $17.99. ISBN 9781481488754.

Gr 9 Up–Chloe Snow wants nothing more than to be kissed by New Year’s Eve. She is a typical high school freshman, ready to take on the challenges of leaving middle school behind, and her dad is predictably embarrassing. Her mom, however, is another story: she has recently left for Mexico in order to concentrate on herself and her writing. At the pool, right before school starts, Chloe catches the eye of the school bad boy—never mind that he already has a girlfriend. But when she gets cast in the leading role of the school’s musical, instead of the most popular girl, the drama really begins. Writing in a diary format, Chastain captures a spot-on teen voice that would feel at home in an updated version of the film Mean Girls. Underlying the humor and angst of high school life, though, are Chloe’s ache for her mother and her confusion and anger about her parents’ relationship. Readers will hope for the heroine’s continued adventures in future volumes. VERDICT An above-average purchase for readers who love comedic, realistic fiction about high school.

– School Library Journal, February 2017

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