Good girls love bad boys. It’s in our nature. We want to help them find their true potential. It’s not that we like troublemakers, per se, but rather that we like troubled souls. And as much as we want prince charming to ride in on his white horse and protect us from our own demons, we also want to be the nurturing hand that helps guide the leather clad Mr. Tall, Dark, and Mysterious with a troubled soul into the light of his bright future. We can’t really help it; nurture is in our nature. Heaven knows it’s in my nature, that’s why pretty much every show I can think of that I’ve obsessed over has had a lead guy who makes everyone sing, “I knew you were trouble when you walked in.” And, that’s why Rory Gilmore fell for the likes of Tristan Dougray, Jess Mariano, and Logan Huntzberger. She was a good girl with a good life and she wanted to help them find their true potential. It’s also part of the reason why she and Jess were so perfect together!
The story starts when a fatherless boy named Jess moves to a small town to live with his Uncle Luke, because his mom just can’t handle his troublemaking ways anymore. Luke drags Jess to a dinner at the house of his favorite girls, Lorelai and her daughter Rory. Rory, who is a well-behaved private school student, is Jess’ age and Luke believes that introducing them will be good for his nephew. Right of the bat, Jess is secretly impressed by Rory, but attempts to hide it by encouraging Rory to join him in his troublemaking ways. She’s stubborn, and obliviously naive though, so it doesn’t work. Still though, she does befriend him, because he’s interesting and much different than most of the other people she knows in Stars Hollow, or even in Hartford where she goes to school.
As their friendship progresses and they realize how much they have in common, they start to fall for each other. That’s when Lorelai Gilmore starts singing “I knew you were trouble when you walked in,” or at least she would have, had Taylor Swift been around at that time. Anyway, Rory starts to fall for Jess and everyone around her can see it, especially her boyfriend, Dean, and her mother. They don’t want to believe it though, not Lorelai, not Dean, not even Rory wants to believe she’s falling for Jess. So, instead of taking a step back to prevent herself from falling hard for Jess, she takes a step closer and builds her relationship with Jess into something more—so much more that when he takes off to New York without saying anything, she—a girl who hasn’t even been late for school before—skips school to spend the day with him in New York City. Even after this, and after missing her mother’s/best friend’s college graduation, she still denies her feelings for Jess until denying it for five minutes straight causes her to breakdown and cry to her mother about how terrible she is for falling for someone else when she has a perfectly kind and patient boyfriend already. Then, things go from bad to worse when Jess shows up at a wedding where Rory is a bridesmaid. To both of their surprise, she kisses him and he kisses her back before she runs off, realizing how not okay it is to kiss him when someone else is her boyfriend.
Flash forward to the end of a summer trip she takes right after kissing Jess and Rory is more confused than ever. She has all these letters from her boyfriend, Dean, but all she can think about is writing a letter to Jess. Back in Stars Hollow, Jess is kissing someone else and Rory can’t stand it, even though she’s still with Dean. At this point, you can’t even excuse Rory’s actions based on the premise that she doesn’t want to fall for Jess, because she already has and she’s taking action to keep him from being with anyone else, because she wants to be with him. While Jess is a jerk to Rory, Dean, and his own girlfriend Shayne during this time, he gets some points for at least trying to stay away from Rory while she’s with Dean. I mean, yeah, he’s only with Shayne because it makes Rory crazy, but at least he’s not trying to steal her from Dean anymore. After a while, Dean can’t take it anymore and publicly breaks up with Rory, because she refuses to make up her mind between him and Jess. This, of course, breaks her heart, but it also relieves her from the stress of choosing who to be with for herself, because Jess breaks up with Shayne and he and Rory pretty much immediately get together and that’s mostly the end of the toxicity of their relationship.
Once they get together, Jess and Rory start to be really good for each other. Since he moved to Stars Hollow, Rory has believed that Jess can do so much better than he does. She knows how smart he is and she believes in him, even though he doesn’t believe in himself. Even though he still slacks off in school, Jess slowly starts to become a better person because of Rory’s (and Luke’s) influence on his life. Rory, who was hidden in her shell before meeting Jess, also becomes a better person because of Jess. As much as Lorelai, Emily, and Richard Gilmore believe in Rory and as much as Luke believes in both Rory and Jess, no one believes in them more than they believe in each other. They know each other like the back of their own hands and often better than either of them knows his or her own self. From the moment he moves to Stars Hollow to the moment she tells him she’s written three chapters for her book, they believe in each other and encourage each other more than anyone else. When something good happens in their lives, they tell each other, and when they need inspiration because life is beating them down, they always have each other.
Eventually, because she believes in him so much that he feels guilty for not living up to the potential she sees in him, Jess disappears again and this time, Rory doesn’t go looking for him. In fact, when she receives a ghost call from him, she informs him that even though she thinks she was in love with him, she’s not going after him again. This time, she’s moving on with her life and as mad as she is with him, she still hopes for the very best for him. Because of this, he doesn’t return to Stars Hollow for a long time and when he does, it’s only to get back his car from Luke. He tries to avoid seeing Rory, because he knows he hurt her, but is forced to stay a few days while Gypsy works on his car. He almost makes it the whole visit without seeing her, but he does run into her. Then, he chases her down so that he can tell her he loves her. Afraid of what she might say, he drives off in his newly repaired car and doesn’t return until Luke hunts him down and demands that he return for his mother’s wedding.
After confessing to Luke that his proclamation of love to Rory was why he didn’t want to come for the wedding, Luke encourages Jess to work on his communication skills. Taking Luke’s advice, Jess visits Rory at Yale and begs her to run away with him because, he’s “ready now,” he “wasn’t ready then,” but he is now. He’s ready to be the man she needs and deserves, but she turns him down flat and he respects her feelings while walking away with one of the most heartbreakingly dejected looks on his face that I’ve ever seen.
Approximately two years later, Jess surprises Rory while she’s living with her grandparents in Hartford and explains to her that he wrote a book because of her belief in him. Per Jess Mariano style, he plays it off like it’s no big deal, essentially claiming it’s nothing to be proud of, because he’s it’s not that good. Of course, Rory is more than ecstatic and beyond proud of him, exclaiming that she knew he could do it. “I know you did,” he tells her, letting us see a little peek of how proud he is that he was motivated enough to write a book and prove to himself and Rory that she was right for believing him in no matter what.
This time, while he’s in a very good place in life, he observes that Rory is not. She’s dropped out of Yale, is fighting with her mom, and dating a jerky rich boy that she would have used to mock with Jess. He calls her out on how unlike her she’s behaving and she nearly falls to pieces, but is unwilling to admit to him that he is right about everything and that he does still know her better than anyone. Not wanting to fight her, Jess suggests that they catch up at a better time and leaves after wishing her a belated happy birthday.
Several months later, after Rory has mostly cleaned up her life, she receives an invite from Jess to come to the opening of a business he has started with a couple of other guys. As usual, they are both quietly thrilled to see each other. After taking the time to catch up, Jess kisses Rory and she kisses him back before pulling away confessing that she’s being unfair to him, because she’s still with the guy she was with last time they saw each other. As brokenhearted as he is to know this, he’s also beyond understanding and tells her that if it helps, she can tell him that she cheated on him with him. He seems to be touched by the fact that when she was in trouble with her boyfriend, she ran to him for comfort. This moment shows how much they’ve both grown. Before, Jess would have given into his own feelings for Rory and ignored the fact that she had a boyfriend, but he didn’t. This time, all he cares about is Rory, who also would have given into her feelings for Jess before, but doesn’t this time. However, it also shows just how much Rory has actually lost some of her maturity as she’s grown older and since starting to date Logan. With Dean, she at least tried for a while not to allow her feelings for Jess to grow, but with Logan, she runs straight to Jess for comfort when there’s trouble in paradise. Mature or not, right or wrong, it still is kind of sweet that Jess is where she ran to when she needed comforting.
Finally, over ten years later, when Rory is failing in pretty much every area of her life and Jess is succeeding in pretty much area of his life, he shows up again at just the right time to give her the support she’s always given him. Jess has become a very well-rounded and successful man, largely in part because of Rory’s (and Luke’s) constant belief in and support of him. Rory, on the other hand, is currently at rock bottom. There are very few ways in which she could sink any lower in her life than she is right now and yet, Jess believes in and supports her anyway, because he’s seen her at her best and knows she can be even better than the best he’s seen her. He also knows that she just needs to believe that herself, so he encourages her to write a book about her life with her mother. Rory realizes that this is a brilliant idea and, after some fighting and thinking, Lorelai agrees, so Rory sets to work writing “Gilmore Girls” and excitedly rejoices to Jess once she’s written three chapters and has received Lorelai’s full blessing. Luke is present during this brief rejoiceful moment between Rory and Jess and questions Jess’ feelings about Rory. Jess claims to be over it, but longingly looks through the window at Rory after Luke walks back inside shortly after she does.
By the end of the series, Rory finally seems to be on a healthy path in life—even though it’s possible she may not know who the father is of the baby she’s carrying—and she can thank Jess for that, because he’s the one who reminds her that she can and will make something of herself if she’ll just stop fooling around and set her mind to it. Throughout their whole relationship, even during the toxic moments when she’s emotionally cheating on her boyfriend with him, Jess and Rory are as good for each other as two imperfect human beings can be for each other. Through thick and thin, they believe in each other and encourage each other to be the very best versions of themselves that they can be. I’m no fool, I know good and well that neither of them are perfect, but I also know that “love keeps no record of wrongs.” Both Jess and Rory have screwed up a lot, but they’ve also succeeded a lot and many of their successes have come from the encouragement, belief system, and love they have for each other.
Also, at the end of the day, Rory has succeeded in every good girl’s dream–she’s helped a bad boy see that he can be good. She’s helped a troubled soul see the light. And she’s helped a slacker become successful. Despite all her personal loses, I’d call that a win! 😉 Plus, he becomes her Prince Charming who swoops in on his white horse to save her from demons too! 😁