If you are around my age and you spent your high school or college years watching Gilmore Girls during its original run in the early 2000s, I already know you have an affinity towards Rory Gilmore. Her personality resonated among us book nerds because we thought—or hoped?—that she was the type of girl we were headed towards becoming.
For instance, in one of the earlier episodes, she had an argument with Lorelai about what books she needed to bring to school, noting that the book she read during lunch was different from the book she read in the bus on the way to school and it couldn’t possibly be two different novels, one has to be a memoir. When she delicately tried to explain the difference and importance of reading nonfiction as a break from reading fiction, I knew she understood me. I was 18, I just started my first year as an English major, and already I was drowning in required book readings. But I was also stressing out about making time to read the books I wanted to read.
There just wasn’t enough time, I would whine. I had to develop a system. Easier-to-digest books are for bus rides to and from school because I could easily pick up from where I left off. Books that needed more focus and concentration a.k.a. Pushkin or Joyce—would only be read on school grounds or at home without the pressure of being interrupted.
I wish I could say that the fascination with Rory’s character stopped there. But Jess Mariano made an entrance in the second season, with his unruly but gorgeous hair and that scowl he wore except for when he was with Rory. Dark, well-read, and witty, Jess was a trap not only for Rory but also for us viewers. Who could resist a boy who not only could recommend the best books and music but also made an effort to be friendly with just you? He zeroed in his interest in Rory and, in turn, us. He cared only about what she thought, he showed his soft side only to her, and he was unpredictable which made him seem more exciting. And there was something irresistible about a bad boy who was good only to you. At least that’s what I thought when I was 18 and didn’t know better.
More than a decade later and I’m re-watching the entire original series on Netflix. And it truly has been a revelation to learn how much I’ve grown as a person. Rory’s character doesn’t resonate with me as much as before, because I realized how narrow and limited her interests are. She doesn’t like sports, and I was varsity player in volleyball when I was in high school. She’s very judgmental when it comes to music, and I basically listen to everything. She judges Lane for joining the cheerleading team and Dean for initially not wanting to go to college, and she separates herself from others in many instances by saying that she’s “not that kind of girl” with a condescending tone. While smart, she’s extremely elitist and divisive in her own way.
The first time I loved Rory’s character, it was because I didn’t know a lot of people in real life who liked the same things I did. She represented the kind of person I thought I was and I thought I wanted as my friend. But my interests have evolved since I was 18, so it wasn’t difficult to accept that Rory and I have grown apart over the years. And there is more to a person than the books they like.
Jess Mariano, on the other hand, was wilder to unpack because he represented all the bad decisions I’ve made in my early 20s that had to do with boys and relationships. Liking a fictional bad boy transcended into liking non-fictional bad boys. Unfortunately, there is no script to follow in real life. You can’t rely on an episode of Gilmore Girls to learn what to say next to your real-life Jess who hates your friends, or who acts out in anger when you say you’re not ready to have sex for the first time. It’s cute in the beginning when he pays attention to only you, but in reality, all the toxic attention gets exhausting after a few months. The unpredictability will soon become the main trigger for your anxiety. And you can’t really expect to talk about music and books for the rest of your life. I’ve held on to the image of dark and interesting Jess all those years without fully realizing that I looked for some of his qualities in the boys that I liked. The most dangerous of which is looking to them for the same redemption arc that Jess had after being with Rory. But it wasn’t anyone else’s job to save Jess from himself.
I’m not putting the blame solely on Jess for having a lousy, virtually non-existent dating life in my 20s. But he was one of the strongest imprints on my impressionable young self. And watching the series again now is seeing all the red flags shine so brightly like Christmas lights on that beautiful, troubled face. I romanticized that to the point of dismissing safe and sure as boring. I fell in love with instant and fleeting encounters and took them in as legitimate relationships. As much as Jess wasn’t someone to save, Rory wasn’t a savior. Neither was I. And this has been the bane of my twenty-something life.
I believed that being troubled gave Jess a more profound perspective on life and that hating on Rory’s friends made Rory all the more special, but I ignored how it could also have been a cry for help from an emotionally stunted intellectual. As a child of the 90s and worshiper of Spice Girls, what a blasphemous thing to have forgotten the mantra that every 8-year-old girl had when Wanna Be was released: If you wanna be my lover, you gotta get with my friends.
Through the emotional roller coaster of realizing what Jess truly meant to me, I can’t bring myself to resent him or the boys like him that came into my life. The Jess Marianos of our lives won’t necessarily make a comeback to us years later to prove us right for believing in them, validating our judge of character. It’s not how real life works. Nonetheless, I’m a believer of mistakes being made to fuel our own emotional growth. And Jess had been my personal litmus test for that.
Is it a rite of passage to fall in love with the proverbial bad boy? I don’t know. I’d like to believe it isn’t. So much can be said about recognizing that someone is good right away. But people are more complex than that and we are all wired differently. I’d like to believe, however, in our capacity to learn, reflect, and adjust.