Gilmore Girls (an analysis on Rory's boyfriends)

If you are anything like me, longing for teen and coming-of-age 90's and 2000's shows, you definitely know we're about to dive into a (personal) analysis of one of the most talked-about shows of that era, and some of the most talked-about and debated on-screen couples.

Gilmore Girls is an all-time favorite show about life in a small town, mother-daughter relationships, growing up, and figuring yourself (and life) out. We're shown different family dynamics throughout the seasons and the characters: if you were young enough, you could've learned about growing up and literally coming of age alongside Rory, and one of my favorite things I learned about through the show: academic burnout.

But I'm not here to talk about any of that today.

I'm here to talk about Rory's boyfriends and her relationship dynamics.

This isn't meant to sound like relationship advice, or anything you should base your relationships or standards on; I know I definitely don't.

Puppy Love: Dean Forester

I personally describe Dean and Rory's relationship as puppy love. Yes, there was toxicity in the relationship,  and yes, there was cheating, but they were real.

No matter how much you hate Dean, you cannot say he didn't love Rory. He loved her deeply; he did everything she wanted to do, compromised, built her a car (even let Richard check it a bunch of times), did everything she liked even if he didn't really enjoy it because he just wanted her to be happy, and he paid attention; that boy loved her for years. He even wanted to look past her cheating because he wanted it to work; he wanted it to be forever.

Yes, he was flawed, but he was absolutely terrified of losing the love of his life.

Dean never stopped loving Rory. Not when they fought, not when she cheated, not when she dated Jess, not when she went away for school, not even when he tried to move on. 

He married Lindsay, trying to move on, as Rory did.

Rory wasn't intending to break his marriage just because she wanted him back or because she loved him (to be completely honest, I'm not sure she still did, as deeply as before, at least); she went back to Dean because she needed him, she needed a safe space, and that's what Dean gave her from day 1.

Dean gave Rory a space where she felt safe and loved, a space in which she knew that, no matter what, she would always have someone waiting for her with open arms.

They were a big codependent overthinker trying to be realistic and an incredibly avoidant person living in a fairytale.

Teenage Rebel: Jess Mariano

I'm sick and tired of people defending their hateful posture towards Jess behind a lame "he was better at yearning for her than at actually being her boyfriend".

Jess was a messed-up kid; he had his problems, but none of them were related to Rory. Almost every problem in their relationship was a direct result of Jess trying to protect her from himself. All of the getting closer to her just to run away wasn't with the intention to hurt her; it was just a kid trying to protect the person he liked, the person he felt so much for, from his own darkness and tormented mind speaking louder than his heart and touching her light. 

He wanted Rory so much that when he finally got her, he couldn't handle it, because it meant she would see all of him, and he was used to being superficial and staying in the shadows to protect those around him.

Like it or not, Jess was a very introspective and pensive person. Even if he didn't know how to deal with his thoughts and feelings, he knew the one thing he could do to protect the people he loved was staying at a safe distance and putting on this sarcastic, mean mask.

Let's also remember that a lot of what we think of when we think of Rory and Jess is pre- and post-relationship; this is where the "Was it casual" questions come into play, in my opinion, about these two.

Was it casual when Jess stole Rory's book when they first met, just to give it back to her with his own notes written in the margins?

Was it casual when he spent the night knocking down every snowman in the contest just so Rory's would win?

Was it casual when he spent $90 on Rory's picnic basket just to be able to sit with her?

Was it casual when Rory managed to cheat on two of her boyfriends, but never on Jess?

Was it casual when Rory ditched school and missed her mom's graduation to go see Jess in New York because he didn't say goodbye, and he was happy to spend the day with her?

Was it casual when he wanted Paris to like him because she was Rory's friend?

Yale Heartthrob: Logan Huntzberger

Logan is there to represent Rory's shift into adulthood; he's the shift from teenage innocence to adult dynamic realism. He represents adulthood with its complexity, compromises, and learning about maturity; he brings into question Rory's life and the privilege she doesn't realize she had, from his own privileged perspective.

We first meet him as this fun, single, heartthrob, privilege hurricane, which either makes you love him or hate him, but I objectively think that it helps us understand that Rory and her background fit right in his world, even when she doesn't realize that herself.

He's everything that Rory's not, personality-wise at least. Or maybe he's just the contrast of what Rory could've been had Lorelai stayed with Richard and Emily, but because that didn't happen, Logan's relationship with Rory is meant to explore how family expectations and class affect partnership.

Logan is the man who helps Rory build her confidence little by little and find her own voice, while also being a remaining part of the world that almost made her lose herself.

Not everything can be good, and we all know Logan is most definitely not perfect. 

He is the perfect example of a toxic elitist upbringing. If we were to list his flaws, I'd say some of them (and maybe some of the reasons he is not the one) could be: 1. his arrogance, which could be perceived as hot by some or annoying by others. 2. His carelessness towards other people's feelings; he makes Rory go through hard times several times, and other people too. 3. His inability to break free from the Huntzberger's expectations.

The Logan Huntzberger Flaw List could probably go on for way longer if you find a Logan hater, but I'm not one of them.

I do believe that Logan and Rory's relationship is like watching A Series of Unfortunate Events (relationship version), just break-up after break-up, but at least they managed to solve some of their problems along the way.

Which of Rory's boyfriends is your personal fave?

Thank you for stopping by!

xoxo, Bluu✨