Jess & Rory: What We Can Learn from Their Doomed Love Story
When I was in 8th grade, I decided to watch the show Gilmore Girls, and I was immediately hooked. It’s been three years since then, and I would still tell you it’s my all-time favorite show. I love feeling like I’m growing up alongside Rory Gilmore, and I especially love watching Rory’s romances unfold. Rory has three boyfriends throughout the seven seasons of the show, and I’ve always found it so interesting the way that I as a viewer fall in and out of love with each boyfriend as Rory does. Out of the three boyfriends, I've always found Rory's second boyfriend, Jess Mariano, to be the most interesting. There's a lot to unpack in his relationship with Rory and so much that we as viewers can learn.
To start, let’s get a little background on Jess. Jess is introduced into the show in Season 2, Episode 5. Jess moves to Starshollow (where Rory and Lorelei live) to live with his uncle Luke Daines, one of Gilmore Girls's main characters.
Jess comes in as this super troubled and rebellious teenager who hates everything and everyone. But, of course, he quickly develops a soft spot for Rory and he really matches her intellectually in a way that Dean, Rory’s boyfriend at the time, doesn’t. Of course, Rory develops a crush on Jess (while she’s still with Dean, and a general lesson here is that if you fall for another guy while you have a boyfriend, you probably shouldn’t be with your boyfriend!). The “bad boy and good girl” and “I hate everyone in the world but you” tropes are beloved by many, and Rory and Jess would definitely fit into this category.
The Good & Bad of Jess Mariano:
As I said, I first watched Gilmore Girls in 8th grade, and I have to say, I was obsessed with Jess Mariano. Three years later, I still have pictures of Jess and Rory on my photo wall in my room.
With that being said, Jess is a pretty awful 17-year-old boy. He’s super rude to literally everyone but Rory, he rebels against any sort of parental or authority figure, and he ends up failing out of high school. When Jess and Rory officially start dating, it’s pretty clear that Jess isn’t ready for a relationship. For instance, he doesn’t call Rory when he says she will, and he lies to Rory about how he’s doing in school. There’s also a scene where Jess got mad when Rory wouldn’t have sex with him, and that’s something fans often criticize Jess for (rightfully so).
Shortly after that situation, Jess ends up leaving to go live with his dad because he failed out of school, and he doesn’t even tell Rory he’s leaving. At that point, it became pretty obvious that Rory needed to end things with Jess, and she did (you can watch this scene here). I actually made a TikTok sharing my thoughts on this breakup scene, so make sure to check that out!
So, yeah. From an objective point of view, Jess wasn’t always the best guy. I often see people online saying they can't believe anyone could be Team Jess because of the bad things he does. But Rory really likes Jess, and I can understand why.
Jess connects with Rory on a deep emotional and intellectual level, and I loved watching their conversations and overall connection. Soon after Jess and Rory met, they have a picnic lunch together and end up talking about books and really enjoying each other’s company (watch it here). One of the most iconic Jess and Rory scenes features them driving around town and having a deep conversation about their futures (watch it here). During this car ride, Jess actually crashes Rory’s car and Luke sends him back to his mom in New York City, so Jess and Rory’s friendship (because they weren’t dating at this point) abruptly ends. But, a short time later, Rory actually ditches school to visit jess in NYC, and this is very out of character for the perfect, rule-following personality Rory has. While in NYC, the two spend the day together and they share a sad goodbye when Rory gets on the bus back home (watch it here). There are many more romantic moments between them throughout Gilmore Girls that explain why Rory and fans of the show (including me) love Jess.
What We Can Learn:
Obviously, I’m not a Jess hater, but I still see clearly the bad things he does. I think it’s okay to love watching Jess on Gilmore Girls while still acknowledging he’s not always the best guy. In fact, I think this is the best way to view Jess. This perspective allows us to become aware that in many situations in life, we like or want something that isn’t actually the best thing for us.
When Jess and Rory break up, we see the reality of what can happen when you go into a relationship with someone who isn't ready. The show really romanticizes Jess, but eventually, we see the disappointing but inevitable ending. This doesn’t just apply to romantic relationships, though. Throughout our lives (and especially as teenagers), we will want to do things that we know will put us in bad situations. So, it’s important to know the inevitable pain and consequences those things will bring us so we can make better decisions.
What I love most about all of this, though, is how Rory views her relationship with Jess after the fact. Rory was very aware that things needed to end between her and Jess because of his immaturity and poor decisions, but she never looks back at her relationship with regret or annoyance. Rather, Rory appreciates the time she had with Jess while still knowing that their relationship was doomed from the start. Jess actually comes back in a later season and begs Rory to leave college to be with him, and she declines because she knows the relationship is not right for her.
I find this to be a really great example of how we should look at our pasts. There’s no point in looking at our pasts and criticizing our emotions and how they led us to certain situations (especially during the years of adolescence). But, it is really important for us to know when something is better off left in the past so we can move on to a better future, and this is exactly what Rory did.
So, not only can we be entertained by Jess and Rory’s romance, but we can learn really important lessons from it. When I first watched Jess and Rory on Gilmore Girls when I was 14, I loved their relationship and I completely ignored any criticisms of Jess or any of his wrongdoings. But, as time has passed, I’ve been able to keep this same love for Jess while being able to see the many flaws in their relationship. This has actually allowed me to get a lot more value out of watching their relationship and it really opened my eyes to the complexity of relationships and characters. Whether you are Team Jess or a Jess hater, I encourage you to get comfortable seeing the good and the bad of Jess and Rory together. At the end of the day, that is how we can learn so much from the doomed love story of Jess and Rory.
"I wanna be good, life's just not letting me."
Jess Mariano
Written by Peyton Price - Entertainment Values
