While many fans of Gilmore Girls think that Rory should end up with Logan Huntzberger and were thrilled to see them together in the Netflix revival, others are bigger fans of Jess Mariano and Dean Forester. These two characters, played by Milo Ventimiglia and Jared Padalecki, are her high school boyfriends and although she dates them fairly close them together, they couldn't possibly be more different. It's no wonder that some fans are on Team Jess and others think that Dean and Rory should have lived happily ever after.
Rory learns something important from each relationship and it's fun to compare which of her love interests was a better match for this beloved character.
Jess: They Had More In Common Intellectually
Rory Gilmore is an intelligent "girl next door" and when she was with Jess, it made a lot of sense. Before they started seeing each other, they used to always talk about books, and that wasn't something that Rory could do with Dean as he was always amazed that she was such a big reader.
Jess and Rory had more in common intellectually than she did with Dean. It was good for Rory to date someone who was on her level as they were able to have more interesting and intelligent conversations.
Dean: He Was A More Caring Boyfriend Who Hung Out With Lorelai
While Dean messed up a few times, he was ultimately a more caring boyfriend than Jess was. He had a good upbringing and he's a kind, friendly person.
Dean may be a simple guy but that's exactly why he was such a good match for Rory. He was happy to watch a movie with Rory with take-out on date night, and he felt fortunate to be in her company. He always made sure that Rory was happy and he would never dream of standing her up or hurting her feelings. He also had no problem hanging out with Rory and her mom, and that was always sweet.
Jess: He Challenged Rory
On the other hand, Jess was better for Rory than Dean because he challenged her. He showed her a world outside of Stars Hollow since he came from a less than steady family background and he hadn't lived there all that long.
Jess also saw through Rory's perfect/good girl exterior and knew that she was capable of a lot more than just being shy and hanging out in the background.
Dean: He Was More Stable
Anyone on Team Dean will agree that he was a more stable love interest for Rory.
Sure, Dean wasn't interested in going to college, but that didn't mean that he wanted to sit around and eat candy all day. He worked at Doose's Market and he got a job in construction after high school. While Jess would rather work than go to high school, he wasn't the picture of steadiness as he skipped school often. No one really knew what they would get with Jess, whereas Dean was always calm.
Jess: He Didn't Want A Traditional Domestic Life
Rory and Lorelai have much in common, including not being domestically inclined. Neither one wants to cook or clean, and they would rather order take-out any day.
Jess didn't want a traditional life where he got a nine-to-five job and raised a family in a nice house. He wanted something more interesting, and it's clear that Rory did as well, since she turned down Logan's proposal in the series finale and traveled for her journalism job instead. Rory and Jess would have had a better shot at making things work long-term because Dean always wanted to get married and have kids pretty young.
Dean: He Did Romantic Things For Rory
From building Rory a car on their anniversary to making her a bracelet, Dean was always doing nice and romantic things for Rory. She really appreciated it, and it was nice for Rory to be doted on a bit since she had always kept to herself and never dated before Dean.
Jess would never be able to do those things, as when he was in high school, he was a bitter rebel who scoffed at everything and anything. As he got older, he might have been a more romantic partner for Rory, but definitely not at that stage in his life.
Jess: He Didn't Get So Jealous
Of all of Rory's love interests, Dean definitely became a green-eyed monster when someone liked Rory. He got really upset around Jess and also Rory's rich classmate Tristan (Chad Michael Murray).
Of course, Jess didn't love Dean and didn't want him around Rory once he and Rory started dating, but he was a bit less territorial. This was a better situation for Rory, as Dean always got too worked up.
Dean: Rory Was Herself With Him
While it was cool that Jess pushed Rory out of her comfort zone, it wasn't cool that he sometimes influenced her to act in silly and upsetting ways. One example is when Rory didn't go to her mom's business school graduation ceremony because she went off to New York to visit Jess. This was major problem and proves that Lorelai and Rory's relationship isn't flawless.
When Rory dated Dean, she was totally herself. She wasn't embarrassed that she was a good student who carried more than one book around with her all the time, and she didn't act in an immature way.
Jess: They Always Kept In Touch And Respected Each Other
Even though Jess messed up when he ran away from his relationship with Rory and Stars Hollow, Rory seemed to forgive him because she sees him a few times over the years.
The two always kept in touch and they had a huge amount of respect for each other. When Rory bumped into Dean in the Netflix revival, things were definitely awkward, but Rory and Jess could always banter like they had just seen each other. This proves that their connection was a bit stronger.
Dean: He Didn't Bail On Rory When Things Got Tough
Rory liked Dean from the moment she met him and while it was awful when he broke up with her in season one, he was legitimately hurt. It might not have been the right thing to do, but he had his reasons.
Jess, on the other hand, bailed on Rory when things got complicated. He left Stars Hollow and didn't even end their romance properly. This was horrible and showed his immaturity and is one reason why Dean was a much better match for Rory.