When I was first reading over the list of 50 challenges in the Pop Sugar 2015 Reading Challenge, there was one book I knew I had to read. It fit with:

a book that became a movie
a book you were supposed to read in high school
a book you started but never finished
a book based on a true story

and most importantly of all:

a book that scares you

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In 11^th grade English we had a vibrant assistant teacher. She was a movie character come to life: the optimistic young white women sent to get the kids to realize their potential. She wanted to get us excited about learning, excited about English literature. She wanted us to try new things and experiment. So we didn’t just write book reports – we made art and journals and brought in songs and did all sorts of insanity none of us really appreciated at the time. And we didn’t really appreciate her either. I think at most I had a sort of objective appreciation. I felt like I knew who she was – the dreamer who hadn’t yet had her spirit broken by a thousand terrible school board decisions. I somehow felt like I knew more about how the world worked than she did, like I had already outgrown the naiveté that causes a person to believe they can change humanity through education. I was cynical and sixteen, and I respected her for being something else.

I remember talking a lot about the supposed American Dream in that English class, and at some point in the year we were assigned On The Road by Jack Kerouac. We learned about Stream of Consciousness writing and fell in love with it, as I assume all 16-year-olds do. We got our copies of Kerouac and we all underlined that same beautiful passage near the beginning of the book. The one I assume is underlined in every used copy of On the Road in existence.

“because the only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones that never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars and in the middle you see the blue centerlight pop and everybody goes “Awww!””

I wrote in books back then. I didn’t when I was young, but my best friend Sarah did all the time and somehow she convinced me it was something free spirits did. Sarah convinced me of a lot of things that free spirits did, because that’s what we both powerfully needed to be at that time. We were middle-class white girls who didn’t do drugs or have sex. But we were smart, and we had to use our minds to form our rebellion. We liked making jokes no one else understood. We liked being obsessed with things other people found old or dull. We listened to lyric-intensive songs and wrote our own poetry and once tried to convince our whole 10th grade English class that “Stopping by Woods on a Snowy Evening” was about Santa Clause.

We were outright brats.

I always had trouble finishing books in school. From elementary through college, I struggled with getting my reading done on time. This was strange, since as a child I always tested above my grade in reading. But as I grew older I never wanted to read what they assigned in class. And I quickly learned that I didn’t have to. I had perfect attendance, good notes, and I picked things up fast. I finished few books, but received many As.

Sarah loved On the Road, I think because part of her longed to be a drug-addled madman. There was something exotic and enticing about being a true deviant, not just playing one from the back of the class. I liked the idea myself. The drugs didn’t hold much fascination, but the dangerous and winding jog across the country did. What an amazing thing to do, being free like that. Freedom is all that matters when you’re in high school and oppressed by everything at once yet nothing in particular.

I started to read On the Road. I really loved it. I loved the way Kerouac could start a sentence with monotony and end it with poetry. I loved the way the whole thing flowed, never telling the reader what was and was not important, and glossing over what felt like monumental events. It was beautiful. I got through 72 beautiful pages.

I can’t tell you what interrupted me the first time. School work I suppose. Watching TV late at night. Being in a play. Whatever it was, I wasn’t able to finish the book before whatever test or paper concluded the unit (I did fine on that test or paper by the way. I don’t remember it of course, but I know I did fine because I was an honor student and I always did fine).

With the pressure from class gone, love of the text wasn’t nearly enough of a reason for me to keep reading. It never was. Life went on and other books I never finished came and went. That summer Sarah and I went on vacation together and I brought along my copy of On the Road with the intention of finishing it. Months had passed so I had to start at the beginning. This time I got through 98 pages.

There was a third attempt about a year later. Another vacation, another chance to convince myself I could read a book in my free time. When Sarah saw me pull out the same beat-up copy of our high school text, she laughed.

“You are never going to finish that book,” she said.

I don’t know what it was. Something about her tone. Something about being high school girls and by definition as much friends as we were enemies. Something about her expectations of me and her expectations of herself. Something. She was so sure of my failure. And she was right.

I made one more attempt a few years later before finally taking Sarah’s curse to heart. I was never going to finish this book. And if I did, it would most certainly kill me. My ignorance of the ending had turned into some demented horcrux – if I destroyed it I would destroy myself.

Years went by. Sarah and I became closer friends. Then roommates. Then things got difficult. She had troubles I couldn’t save her from. I loved my friend so much I thought maybe I could fix it all if only I stuck around long enough. It took me months to realize our relationship didn’t exist anymore. I left. It was terrible and I felt like a monster. It tore her apart and I knew it would, but I had to get out. I had to get out before it got me.

I moved into a new apartment, then a house, then a studio, then another apartment. I still had the book. The book with my notes in it. It had her notes, too. She used to scribble on my copy in class when she wanted to make it clear she wasn’t paying attention to the teacher. Alongside the underlined passages were our inside jokes. Stupid, immature, inside jokes that don’t make me laugh anymore. And that one dumb line about falling in love with the mad ones.

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The beginning of On the Road was just as captivating this time around as it had always been. As narrator, Sal Paradise is the best mix of idiotic and wonderful. He does the stupidest things, the bravest things, the strangest things. And with each paragraph you meet a new and unusual character, the mad people that populate his life on the road. And the whole time you’re feeling that same anxious desire he feels: you can’t wait to see Dean and the gang.

But then you meet Dean. You meet the gang. And after some time with them and California you go back across the country, away from the mysterious West. And you’re outside New Jersey for awhile, and then back driving across the country, and the whole thing has so little purpose, no course to pin your anxious desires to. You start to wonder what Sal’s problem is, why he never seems to want anything enough to go after it.

As I read through the endless travels, I was driven by my own benchmarks: the old bookmarks that I’d left between the pages. There was a receipt with nothing itemized, a sad letter I’d received from a friend, an old ticket to the Tomb of the Unknown Soldier from 1999 that was in the book when I first bought it. With each piece of paper I got one step closer to my goal of reaching the end of this damn book. With each piece of paper, I had done just a little bit more than I’d done before.

It was difficult. Every time I sat down to read it felt like a slog. I couldn’t get into it. I wasn’t fascinated like I was when I was young, like I was when I read those first glorious chapters. I told my boyfriend about my sneaking suspicion.

“I’m starting to think maybe I just don’t like this book,” I said.

He laughed at me. “I could have told you that,” he said, “It’s taken you ten years to read it.”

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As I muscled through the last 100 pages, it was becoming very clear what I couldn’t stand about On the Road. Dean and Sal aren’t just unsympathetic, they are the poster children for oppression nostalgia. It’s that feeling you get sometimes when you read about how things used to be and find yourself looking back with longing, completely forgetting how grateful you are to live in a world without polio. If you want to look back at the 1950s with affection then On the Road is the perfect book for you. If you want to remember a time when people were free and loved life and roamed the land and weren’t all stuck up in cubicles, then Sal Paradise has a story for you. But a requirement for reading it is forgetting that one man’s rebellious youth often comes at the cost of another man’s liberty. To enjoy On the Road you need to be willing to overlook the powerful stack of inequalities that allowed Dean Moriarty to blow through life like a petulant three-year-old while the rest of the world suffered for his benefit. You have to assume that the 1950s were just a safer time, rather than acknowledging that men like Sal Paradise could go wherever they liked, wrapped in the secure embrace of unspoken privilege. You have to do that to enjoy On the Road. And I can’t do it anymore.

I can’t feel for Sal when he wishes he were born a ‘negro’ because they apparently live such simple and beautiful lives, while he’s stuck having to actually think about who he is and what he’s supposed to do in the world. I can’t sympathize with Dean when he goes from one woman to the next, making promises only slightly faster than he can break them, and leaving in his wake a trail of broken marriages and fatherless children. I just can’t be on their side.

I could do it back in high school because in high school I didn’t really know oppression. I didn’t know systematic injustice. In high school sexism was on the way out and racism was defeated sometime around 1959. But the person I am now has trouble revering a story about pushing the limits of human decency in the name of celebrating the straight white man’s freedom. I can’t enjoy Sal’s story because all I can see are the “colored girls” he fetishizes and abandons, all the times when he should have ended up in prison instead of my high school classroom. Liking On the Road required a certain ignorance on my part – an ignorance I am anxious to outgrow.

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On an unassuming Saturday morning more than 12 years after I first read the opening lines, I finally finished Jack Kerouac’s On the Road. In the very back of my copy was a post-it note, folded in half so it wouldn’t stick to the pages. On it were the words “You were right Sarah, I never finished it.” I’d signed my name at the bottom. This note was my insurance policy in case I died without telling my dear friend that she was right all along. I took the note out from between the pages and threw it in the trash. Not all dreams are meant to be admired. Not all prophecies will come to pass.