Rory’s boyfriends – Dean, Jess, and Logan – each had a part to play in Rory’s development inGilmore Girls, but there was always one who understood her better than the rest. ThoughGilmore Girls’main goal was to chronicleRory and Lorelai’s developmentas mother and daughter, women, and friends, their respective romances played a major part in their narrative arcs. Rory was never one for a short relationship. Each boyfriend impacted her life deeply, both positively and negatively, even when she was still just a teenager.
Though she certainly relied on her boyfriends emotionally, at heart, Rory was independent, just like her mother. From a young age, she knew what she wanted, and she worked hard to achieve her goals, especially her academic dream of getting into an Ivy League school. Academia and her journalistic ambitions were a core part of her character, andhow each of her boyfriends handled those desires (and her academic pitfalls) tells us a lot about who they are as people, and just how well they knew Rory.
Dean’s Tantrum About Harvard Proves His Insecurities
Their Relationship Was Destined To Fail
It can be hard to objectively analyzeDean and Rory’s first attempt at a relationship; not only were they both romantically inexperienced, but they were also just teenagers. When you’re 16 or 17, every choice, every mistake, every outburst, and every emotion feels definitive. It was hard for both of them to express themselves at times, and that’s understandable. That being said, when Rory spirals about her lack of extracurriculars as she prepares to apply to college, it is abundantly clear that she was dealing with anxiety, and Dean failed to see it.
Rather than recognizing what she was going through, Dean blew up at her instead, telling her,“I couldn’t care less about Harvard,“focusing on the fact that she was canceling their plans. That’s not to say it was wrong or ridiculous for him to feel upset that he hadn’t been able to hang out with Rory in a while. But that was the moment thatDean started feeling increasingly entitled to Rory’s time, spurred on by jealousy and insecurity.
We know that Dean understood Rory’s desire to get to Harvard. There are other times when he’s supportive. But as soon as Harvard became a real possibility for Rory, he couldn’t truly cope. Schooling was everything to Rory, and he just couldn’t see that his desire to keep her close would soon drive a wedge between them. Sooner or later, he would have started resenting her for pursuing her dreams, and that’s not a situation either of them deserved to be in.
Jess Always Knew How Important Education Was To Rory & Supported Her
He Supported Her Dreams Unconditionally
Jess made a lot of mistakes while he was with Rory. He refused to communicate with her, and he left town without even telling her. Jess, much like Dean, didn’t know how to deal with his emotions. Rather than lashing out, however, the way Dean sometimes did, he buried them deep and refused to tell Rory what he was feeling.
When Rory dropped out of Yale indefinitely, he was one of the few people in her life (along with Lorelai) who refused to support her charade.
Despite Jess’s flaws, he had the most in common with Rory by far. He didn’t care about school, but he was genuinely gifted; he loved to read and analyze and write, and he understood and supported her drive to succeed academically. Even when they weren’t as close, he asked her if she was"still going to do the Harvard thing,“and when Rory dropped out of Yale indefinitely, he was one of the few people in her life (along with Lorelai) who refused to support her charade.
Yes, Rory had a setback, but she was better than that.Jess called her out point-blank. More than Dean, more than Logan later, he knew how important her education was to her. When Rory dropped out of Yale, Jess had gotten his act together. Honestly? By that point, they would have been perfect for each other, but Rory was already with Logan (and Jess saw right through him, too).
Logan Was Only Too Happy To Let Rory Be A Kept Woman
Being With Logan Was Distracting And Fun
Logan had a lot of great qualities, but when it came to supporting Rory, he didn’t know what she needed. When she dropped out of school, it barely fazed him. And why would it? He would never truly understand how hard she’d worked to get to Yale. He was set for life, andhe was happy to bring Rory along for the ride, indulging in her self-destructive tendencies. She was lost, and she needed someone to set her on the right path, and that was never going to be Logan.
We know he loved her, and he did help her come out of her shell, but in one of the most important areas of Rory’s life, he was sorely lacking. This comes up again in theGilmore Girlsrevival,Gilmore Girls: A Year in the Life. Logan never actively held her back, but he never set her straight, either. Being with him was easy and fun, and that’s hard to say no to. Each of Rory’s boyfriends inGilmore Girlsadded something to her life, but the person who understood her best was undoubtedly Jess Mariano.
