Just Gilmore Girly Things: Learning About Relationships Through Rory's Exes

Just Gilmore Girly Things is a blog series on my inexplicable obsession with the CW/WB series Gilmore Girls that aired from 2000-2007. This series explores the personal and social connections I’ve made in my repeated watch-throughs over the last 23 years that nobody asked for. 

I think the best lesson we can take away from Rory’s (Alexis Bledel) love life is that how we feel about our exes often reflects how we felt about who we were at the time that we knew them. We see that with Rory with how she idealizes the exes she feels she did wrong but can only see the negatives of the exes she was wronged by.

For example, I used to think Logan (Matt Czuchry) was the worst of Rory's boyfriends but it's actually Dean (Jared Padalecki). Like I personally think that Logan is an ass but he never tries to hide that fact. Dean is controlling and manipulative but he never owns up to any of it. And the thing is that at no point in time does Rory ever feel like Dean was a bad boyfriend. 

It begins with the typical telltale signs in their high school romance. Like in S01E14, “That Damn Donna Reed”, he hangs onto his irritation at Rory and Lorelai (Lauren Graham) for poking fun at early TV portrayals of American housewives. In the end, Rory finds a way to come around to his perspective and he gets a home-cooked dinner out of it.

He also has a pattern throughout the first two seasons of getting angry with her every time she prioritizes school over him. He claims to be supportive of her educational aspirations, but any time she flies into a panic over her future, his first reaction is, well what about him? He ends up breaking up with her every time he feels insecure—first when she struggles to reciprocate his “I love you”, the second, publicly, when he senses she’s grown feelings for Jess (Milo Ventimiglia), and third when he sees her coming out of a party with a bunch of upper class boys while they looked on—even though he never brings those feelings up to her any time before then.

After the second break-up, after Rory begins to date Jess, he approaches Jess after work and tries to intimidate him while admitting that he's staying friends with Rory to try to steal her back to retaliate. 

All of this alone, I’d have dismissed as adolescent immaturity and part of how we learn to be in relationships as we grow up, but then he proposes to Lindsay, his next girlfriend (Arielle Kebbel), to make her jealous and as an attempt to make her regret choosing Jess. He even goes so far as to trap her into agreeing to attend the wedding, despite, as revealed in a drunken stupor at his bachelor party, that he’s still completely hung up on her. 

Again, that might’ve just been emotional immaturity, but continues to find excuses to stay in her life and sustain emotional intimacy with her, becoming her emotional support as she begins to feel more and more insecure at school. He only ever brings up Lindsay, now his wife, before convincing Rory to sleep with him by implying that he’d already broken off the marriage. But it’s later revealed that Lindsay is still determinedly trying to figure out how to make him happy as a wife, and not only does Dean gaslight her out of guilt, he begins to yell at her as a way to deflect responsibility from himself until she concedes. Their marriage only ends when Linsday finds out about his cheating, which is the only reason that Rory ends up back in a relationship with him again. 

But again, because Rory feels like she’d been the one in the wrong for not being happy in the relationship, she always looks back at him (as evidenced in the Netflix revival, A Year in the Life) as being safe and good and a relationship that she regrets not appreciating more.

Now Jess, on the other hand, is a shitty boyfriend for sure. He struggles with communication, he gets jealous and insecure, and he disappears without telling her twice. He reappears with grand romantic gestures that are centred around his own needs and then disappears again. But, in the incident where he ambushes her at Yale with a proposal to run away with him, when she says she’s saying no because she doesn’t want to be with him, he accepts it and walks away. 

The next time we see him, he’s come to give Rory credit for getting his shit together, resulting in a short novel he writes. He clearly still has feelings for her, but when he sees that she’s making choices in her life that don’t align with who he thought she was, he shares his feelings and then walks away for his own good. It’s this tough love moment that forces her to re-evaluate her life and go back to school. 

He owns up to all of his shit eventually, both with Rory and with Luke (Scott Patterson). When Luke visits Jess at the open house for his small independent press (oriented around supporting local independent artists no less), he pays Luke back for the damages he owed the family he got into a fistfight with Dean (that Dean started) and thanks Luke for trying his best to figure out how to support him, even if he made mistakes along the way. He’s also the one that gives her the entire idea for her book in the revival.

Like I admit, I might be biased because he's the brooding sensitive artist boy and a major influence on my own conception of gender, but he also never cheated on or with Rory and to be fair, his life was really fucked up! He grew up poor, abandoned by his father as a baby, with an insecure mother who cycled through toxic relationship after toxic relationship while emotionally neglecting him. He had good enough excuses, but he still grows up and learns how to be better and apologizes!

And my theory is that if he stayed with Rory or if she did end up running away with him, he'd never have figured out his shit and found his own path. I think she saw him as a project instead of a person. I think it might’ve resulted in Rory developing further as a writer and politically, much in the way that Jess does, but he would end up hesitating on the decisions he needed to make for himself. Really the red flag should’ve been when she tries to convince him to read and enjoy Ayn Rand despite agreeing that Rand’s political beliefs were incongruent with his own. 

Rory continues to benefit from her relationship with Jess as she enters into adulthood, but she doesn’t hold him in the same idealistic light that she holds either Dean or Logan. 

Speaking of Logan, I can’t stress enough that he is one of the marks of Rory’s divergence from Lorelai’s path. He also represents her fascination and glorification of rich-living. 

Logan is your typical elitist rich kid: He’s arrogant, reckless and views emotional discussions as intellectual debates that he can always find a way to win. All these traits make Logan repulsive to her initially, but she also meets him while she’s trying to convince herself that she wants to be back with Dean. 

Logan provides her with everything that Jess did—the intellectual stimulation mixed with the bad boy thrill and a shared joy of mockery—with the social palatability of Dean. But he also comes with the added promise of adventure and luxury that she craves. 

I used to relate to the appeal of Logan’s literary prowess, especially as she’s confronted with the very reason that she first fell out of love with Dean as he can only muster up a general, “I liked it!” in reaction to her latest article (featuring her new love interest anonymously). But their relationship thrives on the access to the lifestyle that Rory wants to live and the status that he holds. 

And to be able to enjoy that lifestyle, Rory has to continually tweak her values until they begin to align with Logan’s and his pals. She pretends to condemn his friends sexually predatory antics, but she continues to hang out and take them on as her own friends—to the point of not actually making any of her own. It comes to the point where after his parents’ disapproval of her status threatens her future with him, she takes on a rapid transformation into the model of the perfect corporate housewife, as demonstrated by her grandmother, Emily (Kelly Bishop). Once again it’s Jess, hero to the wayward starving artist, that sets her back on her original path. 

But to Logan’s credit, he knows who he is and he’s not ashamed to admit it. When Rory returns to her more “blue collar” roots as she writes an incisive social critique of the attendees at his business (pre-)launch party, Logan is the one who points of her hypocrisy in criticizing the upper class while taking advantage of the access the both he and her grandparents have provided her to the privileges of the upper class. It’s also a reality check that has a bumpy landing with her, but results in her returning to the cheap crumbling apartment she shares with Paris (Liza Weil) and her boyfriend.

In the end, Logan becomes the partner that Rory’s father took too long to become for Lorelai, but like her father, it’s Logan’s insistence on settling down with her that breaks them up. Another theory of mine is that her unwillingness to let him go, even after he gets engaged to “some French heiress” as revealed in the revival, is a part of why Rory struggles with finding herself as a writer later in life. He provides her a sense of comfort and safety that keeps her settling instead of striving to grow and be better. 

Another boyfriend revealed in the revival is Paul. Paul (Jack Carpenter), deemed unforgettable, is Rory’s boyfriend of two years, resulting from Rory putting off breaking up with him as she pursues her own goals. While she finds him unremarkable, he’s also consistent, present and supportive, representing the “dullness” of healthy relationships. 

It’s Paul who ends up breaking up with her for her lack of communication and inconsistency, but since he doesn’t have the social status of Dean or Logan, it barely even registers for her that she’s the toxic girlfriend. 

But once again, that’s the beauty of Gilmore Girls. It’s a world where everybody kinda sucks but nobody sucks enough to have psychologically scarring consequences. Well at least for the on-screen characters.