Ever since Netflix announced the return of Gilmore Girls this Friday, one question has been on everyone’s minds: Who will Rory end up with? Which team will win? Will it be Dean, Jess, or Logan?
Team Dean
Rory bumps into Dean during the pilot of the series. She drops her school books and gets annoyed at the towering figure in front of her, until she sees his face. Dean moved to town from Chicago, and was intrigued by Rory from the beginning. Rory can’t stop thinking about him, and Dean can’t stop himself from casually bumping into Rory.
Pros: He’s adorable. Dean is clearly the boy-next-door type. In their first encounter in the hallway, Dean picked up on Rory’s movie references right away. Why is this a plus? Because, Rory and Lorelei spend most of their days doing just that. He’s on good terms with the people in Rory’s life, which is great in a relationship. He’s undeniably in love with her, and would have done anything for her. He even built a car for her. In all, he’s caring, sweet, and in love with Rory.
Cons: While Dean was a great first boyfriend for Rory, there isn’t much on Dean in the series. Who is he? He became jealous and possessive when Jess came into the picture and quickly hated him. He didn’t even want to try to tolerate him for Rory’s sake. Jess wasn’t the only guy he didn’t like, there was also Tristan before him. After Rory, Dean jumped into a loveless marriage straight out of high school, while he still had feelings for her. He then went on to pursue Rory and sleep with her, while still married.
In his defense: Sure, he got a little jealous when Jess came into the picture, but who wouldn’t when seeing their significant other falling for someone else? Many disapprove of Dean because of his poor judgement while being married, but he was young, dumb, and in love. We all make mistakes, and that was Dean’s. His mistake doesn’t make him a bad person.
Team Jess
Jess is Luke’s nephew who is forced in a small town he doesn’t like. Jess is introduced to Rory in season two’s episode “Nick & Nora/Sid & Nancy” when Luke and him are invited to dinner at Lorelei’s. Jess looked uninterested by the dinner, and wandered into Rory’s room.
Pros: Jess is the brooding, bad boy type that makes girls swoon. He’s intellectual and shares Rory’s love of books. He shows her another side of life that she wouldn’t have seen otherwise. When Rory sees Jess again later in the series, he proved to have matured in many ways. The Jess who ran off to California isn’t the same Jess who puts Rory in her place when she dropped out of Yale and let Logan be a drunk jerk in the episode “Let Me Hear Your Balalaikas Ringing Out.” In all, Jess shows a lot of potential.
Cons: He doesn’t try. Jess comes off as uncaring. He’s the bad boy type after all. Jess messing with Dean is a low move. He purposefully put him down and got between Dean and Rory. When Rory asked him to try to get along with her mother, he was never interested. Jess also doesn’t say what he feels, which leaves Rory in the dark. He ran off to California without telling her about it, without even saying goodbye. To top it off, he comes back a year after leaving, declares his love for Rory and then walks away. Later in season four, he arrives at Rory’s dorm to tell her he wants to be with her, but “not here” where her home and school is, where she wants to stay.
In his defense: Like Dean, Jess was a dumb teenager. He was angry at his situation, and he was in a place he didn’t want to be. Having a bad past with authority figures, he was on guard with everyone and constantly had a wall up. He did grow up though and showed a lot of improvement throughout the series.
Team Logan
Rory has the pleasure of meeting Logan during her time at Yale in the episode “Written in the Stars” in season five. Logan comes off as a snob and Rory dislikes him right away. Especially since the next day he runs into her again, flirts with her, and doesn’t remember their meeting nor her name.
Pros: He’s a good balance between Dean and Jess; he’s caring like Dean, but has a more adventurous side like Jess. He’s the “live in the moment” type of guy. He doesn’t give up on his relationship with Rory, and when they’re in trouble he fights for them. He tries to get on Lorelei’s good side because he knows that’s important to Rory. When Rory dropped out of Yale and stopped talking to her mother, he encouraged her to reach out to Lorelei. He supported Rory when she felt unsure, and he understood when she was upset about her parents’ marriage. Logan was both loving and caring.
Cons: He had a rocky start by coming off as the stereotypical spoiled rich boy, but he grew up a lot during the last two seasons. Rory was Logan’s first serious girlfriend, and it took him a while to adjust to his new life of no longer being a bachelor. He slept with his sister’s bridesmaids while thinking Rory and him are on a break. Though he promised to plan his future around Rory’s plans, he ended up giving her an ultimatum when she refused his proposal. It was all, or nothing. That was unfair and selfish of him to force Rory into that decision after promising her something else.
In his defense: In Ross Geller’s words: THEY WERE ON A BREAK.
In the end, does Rory have to choose among her exes? Rory is an independent woman who values her family, maintains a beautiful friendship with her mother and is passionate about her career goals. She is capable of going far on her own. Rory was never really single, after Dean there was Jess, and then back to Dean and soon after there was Logan. Who knows what happened after refusing Logan’s proposal, maybe it was her chance to discover herself.
So the question remains, who will Rory choose? All three brought something she needed in her life at that moment, but all three had their own flaws. Will Rory pick one of her ex-boyfriends? Or will she go for team Rory?