Despite the awkward Texas weather, it’s officially Gilmore Girls season! Though I am not joining the many who are rewatching the Gilmore Girls series this year, I continue to embrace Gilmore Girls fall with cute outfits, coffee, and lots of studying! While I could talk about Gilmore Girls for hours specifically about the messy but truthful “A Year In the Life” has, or Rory and her downfall, I wanted to talk about Rory and her boyfriends.
The analysis of what each of Rory’s boyfriends represents, in parallel to Lorelai’s life, as well as who treated Rory better just to find that Rory is the problem, has always been one of my favorite topics so I wanted to share my opinion on who I believed to be the better boyfriend.
First Love: Dean
Dean Forester was introduced as Rory’s first boyfriend and eventual first love. What had originally started as a cute relationship, soon turned into a dramatic mess (thanks Jess).
While Dean and Rory had first initially clicked due to their equal importance in movies, the viewer starts to see the differences. Rory is the girl who likes to stay in, study for fun, and read a good book whether she be in line at the grocery store or at her own winter formal.
Dean on the other hand was more focused on going out, playing sports, and overall doing other things besides studying and reading for fun. While the difference is more transparent in season two, I think this greatly exemplifies a girl’s first relationship. We don’t initially have experience so we date someone with who we share similarities, and can effectively communicate creating a strong emotional connection. This is revealed when Jess asks Rory, “What do you and Dean talk about,” also adding he thinks Dean doesn’t seem like “her kind of guy.” This leads to Rory realizing that she and Dean aren’t very similar and begins to outgrow him which usually happens in a first relationship; the outgrowing of a person.
Despite the upsetting way Dean’s character was ruined from season two to his last appearances, on the show, Dean though not the best boyfriend was certainly not the worst. He was just the “canon” event in Rory’s life who exemplified a girl’s dream first relationship.
Intellectual Equal: Jess
Jess was a better boyfriend when he wasn’t Rory’s boyfriend rather than when he was Rory’s boyfriend. And that is probably a hard pill for many to swallow. Don’t get me wrong, I love Jess and believe that he was the only one who truly understood Rory. However, this doesn’t hide from the fact that he was a boy who, due to his lack of communication and stability in life, treated Rory wrongly. Instead of being together with Rory, he should’ve focused on himself.
Though Jess was presented as the charming bad boy in season two with whom Rory finds interest due to their similar intelligence in books and characters, as soon as he gets with Rory he stops putting effort into their relationship and instead leaves Rory in confusion!
A simple recap/summarization of how Jess treated Rory:
Dating:
- Left Rory alone with unclear hang-out plans
- Disrespected her mother and Luke
- The Party scene
- Never communicated with with Rory
Not Dating:
- Motivated Rory to go back to Yale
- Pushed Rory to write a book about her and her mother’s life
Eventually, Jess works on himself but by that time, Rory is in a relationship with Logan. Jess was what could have been but just didn’t happen due to timing, but it’s easy to say, he is not the better boyfriend.
Prince Charming: Logan
While Dean and Jess happened during Rory’s teenage years, Logan came in during Rory’s early adult life. Initially starting as just a casual relationship, Logan and Rory both come together as an actual couple in which they both show the realities of a relationship as well as the growth within a relationship.
Though the likes and dislikes for Logan are evenly split among the Gilmore Girls fandom, Logan like Jess, pushes Rory to be her best self. The difference, however, was that Logan also kept Rory in check. An example would be when Rory and Logan started arguing about Rory’s article piece on Logan’s party in which she made fun of the guests seeing herself as “morally superior” among the rich. In response, Logan reality-checks saying she is no different from them:
“Wake up Rory. Whether you like it or not, you’re one of us. You went to prep school; you go to Yale. Your grandparents are building a whole damn astronomy building in your name.”
To which Rory then responds with her not living on a five-million-dollar trust fund set up by her parent, keeping her in check he says, “Yeah, well you’re not exactly paying rent either.”
Many fans claim that Logan never changed and his being wealthy and proud of it clouded him from that change. However, after a fourth rewatch, you see Logan go from this selfish rich kid to a more caring and humbling person. Logan and Rory both showed how two people in a relationship always have each other’s back to get through struggles. For example, when Rory drops out of school, Logan doesn’t do anything to push her back into something she feels conflicted about. On the contrary, he lets her figure it out on her own as she understands she is capable of her actions. When Logan made a bad deal losing millions of dollars, Rory didn’t let him quit and encouraged him to get back up from his setback.
Logan and Rory showed the good and the bad, but their talks make their relationship stronger. They really showed what a love relationship consisted of, even through their rough patches, and how they overcame them together. Logan was the better boyfriend because he not only committed to Rory but also supported her when needed, trusted her judgment in making her own decisions, and corrected her when needed.
Additional notes: “Rory is the problem”
Unfortunately, Rory never recognizes her privilege and constantly denies it making her the unlikeable character she soon turns out to be. This leads to many fans quickly turning the once-loveable character into what many consider “the problem.”
However, to say that Rory was the problem is completely unfair in the context of her relationships. Yes, Rory does not become her best self, but she just shows we are all humans and as humans we all make mistakes. The difference is Rory is too stubborn to see this but she shouldn’t be the only one blamed for each ending of her relationships, her breakups happened on mutual faults.
Dean
- Rory: Denying and failing to communicate her feelings for Jess to Dean
- Dean: Constantly being threatened by any other guy, having a short temper, and yelling at Rory
Jess
- Rory: Leading Jess on
- Jess: Miscommunication, impulsive, ghosting Rory
Logan
- Rory: Wanting to build her career
- Logan: Wanting to move on to marriage