While fans debate other aspects of Rory and Lorelai's storylines on Gilmore Girls, many talk about which love interest Rory should have chosen. Rory fell for sweet Dean, book lover Jess, and rich Yale student Logan, and these relationships are each important for different reasons.
When catching up with Rory in the Netflix revival A Year In The Life, she was having an affair with an engaged Logan while dating Paul, who she didn't have feelings for. It was disappointing to see that she hadn't settled down yet or found someone who could bring her real happiness. Fans have strong thoughts about Rory's romantic life and a case can be made for each of her serious partners on Gilmore Girls.
Dean: He Showed Rory How To Have A Relationship
Dean and Rory began talking after meeting at Stars Hollow High. Their romance spans seasons 1 to 3 and while Rory was apprehensive, they began having a healthy relationship soon after their first meeting. Dean showed Rory how to have a relationship and commit to someone. She hadn't dated before Dean and since he had aspirations of getting married and having a family someday, he had no problem letting Rory know that he wanted to be with her. If it wasn't for Dean, it's possible that Rory would have made it to college without having dated anyone, as she might have felt too out of the loop and nervous about it.
Dean: He Brought Rory Out Of Her Shell
Before meeting Dean, Rory was happy with her comfortable Stars Hollow life. She helped her best friend Lane hide her love of music from Mrs. Kim, she and Lorelai had movie nights, and she had her eye on the prize of an Ivy League education. But when she met Dean, she liked him so much that she knew she had to move past her fears of starting a relationship. Dean was a great partner for Rory because he brought her out of her shell and taught her to be less shy and have higher self-esteem. Rory made many decisions that were a big deal for her, from going to Chilton's school dance to volunteering to agreeing to be part of The Puffs. Dean showed Rory that while there was nothing wrong with being on the quiet side, she could go for what she wanted.
Dean: He Showed Rory That A Partner Should Get Along With Lorelai
When Lorelai invited Dean over for a movie night in season 1, they had a tough chat about how the town adored Rory and Dean should be careful. Besides this awkward moment, Dean and Lorelai got along fairly well throughout his relationship with Rory, and Dean knew that he had to accept that Rory would always be super close with her mom.
It was not only convenient that Dean liked Lorelai, but this action proved to Rory that no matter who she was dating, they had to love, respect, and appreciate the positive influence that Lorelai had on her life. This was significant, as Lorelai was nervous about Jess and Logan and their rebellious personalities and lack of responsibility. When Rory dated someone who Lorelai didn't like, it definitely complicated things.
Jess: He's The Love Interest Who Truly Understands Rory
While he had an attitude and didn't understand the charm of Stars Hollow, Rory was excited to meet Jess, and many conversations about books and life revealed they had some things in common. Many fans favor Jess over Rory's other partners and when compared to Dean and Logan, Jess seems to be the love interest who really and truly understands Rory. When she left Yale, he told her she was acting like another person, and when she was lost in the revival, he suggested writing a book. Jess saw Rory as a passionate, dedicated, ambitious writer and he knew that at her core, she needed to fight for success and productivity. Dean complained about Rory's studying and Logan wasn't very responsible, so Jess won here.
Jess: He Made Rory Think And Question Her Life
Stars Hollow was nervous about newcomer Jess but Rory was a fan of his from the beginning. Jess made Rory think hard and question the way that she had always lived her life. Since he lived in California, she began wondering what it would be like to live somewhere else, and when she met him in New York City, she got to see what it was like to live in a big, fun, exciting city. Rory spent a lot of time trying to make Dean happy, and she experienced a lot of drama with Logan. But being with Jess gave her the chance to consider what kind of person she wanted to be and what kind of life she wanted to have.
Jess: They Kept Up A Healthy Friendship After Breaking Up
While it wasn't ideal that Jess left Rory and never told her that he was moving away or that they had to break up, he made many changes after that. Jess came back into Rory's life periodically, telling her about his published novel and giving her the crucial advice to go back to Yale and finish her successful academic journey. Jess was a solid love interest for Rory as even after splitting up, they maintained a friendship that was healthy and positive for both of them. Even in the revival, they still got along well without any negative feelings, grudges, or bad memories. This definitely opens up the door for a rekindled romance if A Year In The Life gets a season 2 and many fans would love that.
Logan: He Helped Rory Grow Up
Many college relationships are casual and neither party wants anything more, but Logan and Rory's strong connection surprised them both. Rory didn't believe Logan wanted a real partner but pretty early on, he said that he wanted to define the relationship.
Logan was a great love interest for Rory as he helped her grow up and figure out her identity as an adult. Instead of being a perfect teen from Stars Hollow who got high grades and could choose between Dean and Jess, she realized that an adult relationship brought expectations, dreams, tension, and other complications.
Logan: His Family Taught Rory Some Crucial Lessons
Logan also taught Rory some lessons through his family. Rory learned from Logan's dad Mitchum that not everyone thought she was made for the tough world of journalism, and she also realized that dating someone with a wealthy, privileged, and judgemental family could cause problems. Logan's negative relationship with his dad affected Rory, too, as he was terrified to stand up to him and make his own decisions in life. Even if these were sad lessons to learn, they were necessary for Rory, and she was a better person for them.
Logan: The Relationship Survived Long Distance
Rory made mistakes while dating Logan but she never minded when he moved to Logan for a period of time. While Rory and Logan broke up when she said that she couldn't marry him, long-distance was never a problem for this Gilmore Girls couple. They seemed to do well when they were really far away, as they focused on what was going on in their lives but never stopped loving each other. If Rory is ever in a long-distance relationship in the future, she can take what she learned from Logan, mainly that respect, love, and communication are crucial here.