Gilmore Girls: A Look at Rory Gilmore's Boyfriends and Why None of Them Are Right For Her

Katherine Schaffstall
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From left: Frank Ockenfels/the WB; Justin Lubin/The WB; Frank Ockenfels/the WB

Ever since it was announced that Netflix is bringing back Gilmore Girls for a four-episode miniseries, fans have been wondering where the revival will find the beloved characters. The miniseries, Gilmore Girls: A Year in the Life, will find the characters close to a decade after the original show ended.

Rory (Alexis Bledel) was single at the end of Season 7, but that hasn't stopped fans from debating which former boyfriend she should end up with. Throughout the show's seven season run, Rory had three serious boyfriends: Dean Forester (Jared Padalecki), Jess Mariano (Milo Ventimiglia) and Logan Huntzberger (Matt Czuchry). While each leading man has great qualities, they all lack important characteristics to be good matches for Rory Gilmore. Here is an explanation of the good and bad qualities for each of Rory's ex-boyfriends.

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Frank Ockenfels/The WB

Dean Forester

The Good Stuff

Dean, played by Supernatural’s Padalecki, was Rory’s first boyfriend. He was introduced in the pilot episode and slowly made his way into Rory’s heart. From attending school dances to having movie nights with her mother Lorelai, Rory and Dean seemed perfect for each other. He even built Rory a car as a way to proclaim his love for her. Eventually Jess came to town and caused some major tension in the relationship, but for the first season and a half Rory and Dean had the perfect high school relationship.

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Patrick Ecclesine/The WB

Dean Forester

Why He's Wrong For Her

With all of the good qualities Dean had, he was definitely a flawed boyfriend. He was easily upset when Rory didn’t have enough time to spend with him and he became slightly possessive of Rory when Jess moved to Stars Hollow.

While he wasn’t the perfect boyfriend, he was an even worse husband to Lindsay Lister (Arielle Kebbel). After he and Rory broke up, he moved on with Lindsay. He proposed to her while they were still teenagers and then got married, even though he wasn’t completely over Rory. He eventually cheated on Lindsay with Rory. Any boy that can make someone as sensible as Rory act so irrationally is not the right partner for her.

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Scott Humbert/The WB

Jess Mariano

The Good Stuff

Jess, played by This Is Us star Ventimiglia, was the mysterious boyfriend with a sensitive side. Not only was he good looking, he was also well read. Dean used to watch Rory read, but Jess would actually have in depth conversations with her about their favorite novels.

There was an undeniable chemistry between Jess and Rory and he never gave up when it came to pursuing her. Even when Rory and Jess weren’t together, he always seemed to find his way back into her life and give her advice that was applicable to whatever situation she was going through. Out of all of Rory’s boyfriends, Jess was the one that really understood her the most.

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Justin Lubin/The WB

Jess Mariano

Why He's Wrong For Her

Even though Rory and Jess seemed like they were perfect for each other, there were definitely some red flags when it came to their relationship. One of the major issues is that Lorelai (Lauren Graham), Rory’s mother, never really warmed up to Jess. This is a major problem because the most important person in Rory’s life is her mother.

Jess definitely had an attitude and sometimes had a difficult time hiding it. He wanted to travel the world and lacks the stability that Rory needs in a partner. In the real world their relationship would never work out because they both have very different plans for their futures.

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Patrick Ecclesine/The WB

Logan Huntzberger

The Good Stuff

Logan, played by The Good Wife's Czurchy, was Rory’s boyfriend for the final seasons of the show. He was first introduced in Season 5 and remained a main character until the end of the original series.

He's the heir of a successful newspaper magnate and knew that he did not need to work due to his large trust fund. Logan was able to push Rory out of her comfort zone and encouraged her to try new things, like when they jumped off seven-story scaffolding (attached to a harness, of course) at the Life and Death Brigade event in Season 5. There is no denying that Logan was good to Rory and that he saw a future with her. He even proposed to her after accepting a job on the west coast at the end of the final season.

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Frank Ockenfels/The WB

Logan Huntzberger

Why He's Wrong For Her

While Logan was definitely a good boyfriend to Rory, everything else about him came off as pretentious. He believed that he was better than many of his peers because of the successful family into which he was born.

Logan’s parents didn’t like Rory because she wanted to work rather than be a stay-at-home mom, which is a lot to ask of someone that has been focusing on her career since high school. Rory transferred high schools to get the best education possible and studied journalism at Yale. She also worked on both her high school and college newspapers. She didn’t put in all that hard work just to stay at home with the kids; she wanted to become an award-winning reporter. Also, after Logan proposed to her and she declined, he immediately broke up with her. While Logan was able to push Rory out of her comfort zone, he also kept her from reaching her full potential.

Netflix

While it’s fun to debate who is Rory’s one true love, it’s important to note that Rory can do better than Dean, Logan and Jess. Rory doesn’t need a man to make her happy and it’s unlikely Rory will end up in a relationship with any of her ex-boyfriends. After all, Rory’s most important relationship will always be with her mother.

We’ll have to wait and see who Rory ends up with, or if she stays single, when Gilmore Girls: A Year in the Life premieres exclusively on Netflix on Nov. 25.

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