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Why You Should Try the Gilmore Girls Book Challenge

Books & Writing

Mon, February 19

From the infamous Bell Jar to the still more beloved Daisy Jones and the Six, the Rory Gilmore Book Challenge is not a contest you should miss! This contest is one of a kind—it's a race against your own time clock. Let me walk you through how I completed (most) of the books on the list.

When I started the challenge three years ago, back when I was a teeny, tiny freshman, my reading level was not on par with the eloquent words of Jane Austen and Louisa May Alcott. So, I started with the more modern books.

I ate up (and left no crumbs) from The Song Reader, which was so evidently written in the 2000s that I wasn't sure whether I wanted to laugh or scream, and I bought my copy of The Bell Jar—it was too good not to have my own copy.

Newhouse from Pexels

I slowly started to ease into Edith Warton, starting with her classic The Age of Innocence and leading into Ethan Frome. Both were wildly interesting—my previous distaste for the old "unreadable" classics was slowly starting to fade.

The Catcher in the Rye came next for a bit of word breather, and I LOVED all the hilarious teen angst—the book was dripping in sassy teeenager-ness.

I started reading a little bit about the Beatniks and then read On the Road and Howl, which, let me tell you, was so deliciously scandalous for the 60s that it was AMAZING!

Now, you might be under the impression that all of the reading was easy, that I had all the time in the world to read. In reality, I spent maybe only about 20 minutes a week devoting time to reading—instead, I read mainly on the train.

I treated the books like levels in an athletic sport—even if sometimes I didn't feel like practicing (reading), I would still push myself to do so for the fabulous reward of grabbing an old pen and checking off another book from the list.

I can't say I enjoyed all of the books—for instance, I spent a million months reading the giant biography of Colette with only some vague interest every twenty chapters or so.

I can't say I didn't pay attention—the reading was fun, but the content was boring. From this challenge, I learned that it makes all the difference!

For instance, A Confederacy of Dunces was the strangest book I've ever read, and had any other written it, I would have never finished it (or picked it up). But John Kennedy Toole's writing is terribly immaculate and disgusting—he would take that as a compliment, I'm sure. The number of gory details about the hot dog stand and the main character's pathetic ineptitude at just about anything made me cringe in exactly the same way I can imagine the author had intended, which, for me personally, makes a book good.

If an author was thinking about the audience when they were writing it, they knew their craft. I see the opposite sometimes in my editing work for a literary magazine—authors get so caught up in the work's lyricism or the content that it becomes unreadable to anybody else. This book felt designed to make me cringe and laugh nervously—which it did!

Interestingly, many of the books Rory reads are pretty dark, which seems unsatisfactory with her character at first but makes more sense once you think about it. Her favorite book was, after all, Anna Karenina, which hardcore fans will remember Dean's views as ‘extremely depressing.’ I believe the book was somewhat spoiled for me by the knowledge of the ending—I honestly just kept waiting for Anna to die. I imagine Rory probably told Dean about the book long before he opened it, so perhaps we were in the same boat.

Speaking of Rory, one of the best things about this book challenge is the cute reminders of Gilmore Girls at every turn of a page. I was reading the Valley of the Dolls and wondering how innocent little Rory, who wanted to see the world and become an international reporter, would feel reading such scandalous stories.

As I turned the pages of Daisy Jones and the Six, I wondered how Rory reacted to the band's terrible addictions and habits. I don't fully comprehend the depth of her character, but her personality seems so at odds with many of the books. She does, however, strike me as the kind to read classics for the sake of their being classics.

Beyond Rory's book choices, the list also has a certain musical quality—I'm instantly reminded of the Velvet Underground and the Distillers as I skim through the pages of Rosemary's Baby, and the Smiths practically leap out of the pages of The Perks of Being a Wallflower.

I suggest grabbing a massive pad of sticky notes for every book of this challenge—the number of song references became overpowering when I got to Girl Interrupted. So, I immediately made a playlist for all of the songs I wanted to listen to in the future.

To tell the complete truth, the books changed my entire music taste. When I started the challenge, I was mostly listening to the radio, which featured pop and rap, but the books began introducing me to Pavement and Joey Ramone, and before I knew it, I was hooked.

My 2023 Spotify Wrapped said that this year was quite the flip—a gradual flip, but still a major one. Even if you don't necessarily like rock, being introduced to new music is always exciting!

For my 17th birthday, I bought myself a CD player. No one can prove it had anything to do with the number of 2000s books I was now reading that all feature vinyl and CD players, but it did. My CD player is a bright bubblegum pink, and I currently own three CDs of albums by Abba, Belle, and Sebastian, and the Velvet Underground and Nico. I also have my mom's old CDs from the '90s, all featuring Ukrainian rock artists that fit perfectly with the Gilmore Books vibe.

I've been converted into a hardcore Gilmore Girls fan, and I'm proud!

Marinkovic from Pexels

With the reading of these books, the incessant rewatching of Gilmore Girls is, as you might imagine, unavoidable and imminent. Over winter break, I rewatched most of Season 2-3 due to Jess's stellar book references. For the first time, I understood the majority of what he said!

Overall, knowing what book to check out every time I went to the library instead of wandering for hours on end and checking off every book I had finished was truly satisfying—I would highly recommend this challenge to any Gilmore Girls fan who loves to read!

Bianca Mints
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Bianca is a junior from Massachusetts. Outside of The Teen Magazine, Bianca is a reporter for Teens In Print, Boston's citywide high school newsletter. Outside of writing, she enjoys reading, spending time with her friends and family, and listening to Taylor Swift.