WARNING: SPOILERS AHEAD!
Dean, Jess or Logan: who matches Rory the best?
Gilmore Girls is a classic TV show from the early 2000s about a mother and her daughter, who live in the fictional town of Stars Hollow. This series is very popular and features Rory Gilmore, (played by Alexis Bledel), who has three major boyfriends over the course of the show: Dean, Jess and Logan.
People who love the show argue about this online, or with friends, and most people are either Team Dean, Team Jess or Team Logan. But only one of these boyfriends is the overall best option for Rory.
Dean Forester (Jared Padalecki) is Rory’s first boyfriend, and they date while they are both in high school, for roughly two seasons of the show. Dean is the perfect first boyfriend, but he has his weak spots.
Most of the arguments between Rory and Dean are because of Dean’s insecurities and Rory’s growing ambitions in life. For their anniversary, Dean builds Rory a car, which seems like the perfect gift, but this leads to them breaking up, because Dean tells Rory he loves her and she remains speechless.
At the beginning of Season Two, Rory and Dean break up. Later on in the season, they make up and get back together, but soon afterwards, Jess moves into town.
Jess Mariano (Milo Ventimiglia) is the classic bad-boy who has an immediate liking for Rory. He constantly tries to get under Dean’s skin, like his actions during the town’s basket-making fundraiser. Jess outbids Dean in buying Rory’s basket, and by doing so, he is entitled to sharing the basket with her.
Dean and Rory eventually break up for good at the town’s twenty-four-hour dance marathon, but this not only ends their relationship. It also ruins Rory’s chances of winning the marathon with her mother. Both times that Rory and Dean break up, they choose to do it publicly.
Eventually, Jess and Rory get together, although Rory still feels guilty about it. Rory is not the best girlfriend for Dean towards the end of their relationship, and it is obvious that she likes Jess. She starts acting worse and worse towards Dean, and she even kisses Jess at one point.
Once Jess and Rory get together, Jess seems like such a downgrade from Dean, but he is just different. Jess and Rory have a lot in common, and they both love to read. Jess is a troubled teen, and he has to move in with his uncle because his mother cannot handle him anymore.
Jess really does try to be good for Rory, but he has his own problems to deal with. One famous moment from the show is when Rory asks Jess how he was able to calculate the distance between Yale, the college she is going to attend, and Stars Hollow, and he says, “Do you Yahoo?” This is one example of how Jess is better than Dean, because every time Rory would bring up college to Dean, he would just put her down.
When they are about to graduate high school, Jess finds out he won’t be able to graduate. His uncle says that if he wants to stay and live with him, he needs to retake his senior year, but instead Jess decides to live with his father, whom he’s never met before, without telling Rory.
This is the end of their relationship, even though Jess comes back to Stars Hollow a few times. In another memorable episode, he tells Rory that he loves her, and then he leaves again without waiting for her response. At another point, Jess asks her to run away with him, but she refuses.
In Rory’s first year at Yale, she had no major boyfriends, except her disastrous affair with Dean, who is now married and decides to cheat on his wife with Rory. At this point, they have become friends again, but Dean’s wife, Lindsay, doesn’t approve of their relationship. Dean and Rory only date for a few months after this, and they break up publicly once again.
Once she’s in her sophomore year of college, Rory meets Logan Huntzberger (Matt Czuchry), a rich boy who has a new girlfriend every day. He is first introduced as a “trust fund brat” who doesn’t seem like a good fit for Rory at all.
One of Rory’s friends hates Logan, but Rory still decides to date him. The original plan for their situation is to date other people, as if they aren’t in an exclusive relationship, because Logan doesn’t want one solid girlfriend. Even though they have this arrangement, Logan still gets jealous each time Rory goes out with someone else. Eventually, Logan grows up and they start an official relationship together.
Soon afterwards, Rory decides to drop out of Yale, because Logan’s father, a famous veteran of the newspaper industry, tells her that she doesn’t have what it takes to be a journalist. She gets into an argument with her mother over this and moves into her grandparents’ pool house. Logan supports Rory in dropping out of school and doesn’t try to get her to go back, even though he knows that what his father has said isn’t true.
Later Jess comes back to visit Rory again. He is a changed man who has gotten his life together, and he now seems like the perfect fit for Rory, but she is now with Logan. They ultimately decide that they will just remain friends, but Logan is still jealous.
After a dinner with Rory and Logan, where Logan is extremely rude to him, Jess leaves and Rory runs after him. This is when he says his famous line, maybe the most famous of the show, “Why did you drop out of Yale?” At the end of the show, Rory and Logan decide not to stay together.
Overall, Jess is Rory’s best boyfriend. When they first start dating, Jess is not the best fit for her, but as he grows older, he is able to put his life together. This would have been the perfect time for him and Rory to get back together, but they don’t.
Fans of the series know that Luke is Rory’s mother Lorelai’s boyfriend, whom she marries in the Netflix revival of the show, called A Year in the Life. Christopher is Rory’s father, and no matter how many times he and Lorelai try to be together, it never works out.
In the end, Logan is Rory’s Christopher, and Jess is her Luke. And we can all be lucky to find a person like Jess in our own lives.
