There’s always been a big debate about Rory (Alexis Bledel) and her boyfriends on “Gilmore Girls,” dividing fans into Team Dean and Team Jess. Yet I firmly believe neither of them were good for her. There’s a third group, with which I’m firmly aligned, that holds the unpopular — but I’d argue correct — opinion that Logan (Matt Czuchry) was actually Rory’s best boyfriend. I’ve broken down the reasons why Logan and Rory were actually good together — and why Dean and Rory and Jess and Rory just weren’t.
Dean Was Controlling of Rory
The first of Rory’s “Gilmore Girls” love interests is Dean (Jared Padalecki). Before there were genuine issues in their relationships, there were problematic signs that went ignored. Dean got wrapped up in everything Gilmore, letting his world revolve entirely around Rory. He put her on a pedestal and didn’t hold back from letting her know anytime she didn’t live up to his standards.
Dean didn’t have any big aspirational dreams, much to Rory’s dismay. She constantly pushed him to want more for himself, as a good partner should. Since Dean essentially worshipped the ground she walked on, he never even thought of pushing her. If anything, he hindered her progress. I know I’m not the only one who remembers Season 1, Episode 14, when Dean and Rory fought because he said he liked a ‘50s housewife type. In response, Rory took on the role for an evening to prove how ridiculous it was, but Dean seemed to like the display.
Also, can we talk about Dean’s Jekyll and Hyde personality? The longer the two dated, the more controlling he became. Of course, any oversteps were always followed by heaps of apologizing and love bombing. When Rory told him about the car accident she was in with Jess (Milo Ventimiglia), things really came to a head. Dean became angry, violently yelling at her and kicking things. He was only placated when he learned Jess had left town for good. It was as if a switch was flipped, and he was suddenly calm again. The eventual end of the Dean era was a step forward.
Rory and Jess Were a Mess
No one was ready for Jess when he moved to Stars Hollow. He was quickly dubbed the “bad boy” with a reputation for being reckless. On top of that, Jess was a complete player, with a different girl on his arm every episode, all the while making moves on Rory. She became helplessly torn between her loyalties to her boyfriend Dean and her growing crush on Jess until Dean finally removed himself from the situation. But once Jess had Rory all to himself, it was as if he had a case of buyer’s remorse.
Jess consistently downplayed his intelligence, much to Rory’s irritation. It was an uphill battle to get him to care about anything, much less act like he cared. This applied not only to his academics but also to his relationship with Rory. Time and time again, he let her down, making her feel less than. More than once, Rory was left waiting for Jess to call, at home on a Friday night just hoping for the phone to ring.
Their breakup wasn’t even a real breakup. Jess suddenly left town, and that was it — the relationship was over. At least Rory learned she deserved to be treated better than that.
Logan and Rory’s Worlds Don’t Revolve Around Each Other
Rory and Logan got off to a rocky start, but honestly, they worked together. Why? For starters, Logan didn’t put Rory up on a pedestal. His world didn’t revolve around her. While they went to events together, they also maintained their individual identities by having girls’ and boys’ nights with their separate friend groups. Plus, Logan didn’t just glom onto Rory’s world like Dean did. They seemed to merge their worlds together.
Logan Sparks Rory’s Character Growth
In both of Rory’s previous relationships, she was the partner who always pushed the other to better themselves. With Dean, she pushed him to attend community college, and with Jess, she pushed him to care about his life. Yet, in both of those relationships, she got nothing in return. For the first time, with Logan, Rory had a boyfriend who wanted to see her succeed, pushing her to be a better version of herself. He believed in her writing career and encouraged her to focus on school and not let herself down.
A great example of Logan’s support is when Rory decided to take a year off from Yale. It was a decidedly bad move on her part, but hey — we all make mistakes. He thought she just needed time to figure out what she wanted to do, and he supported that. When Logan found out later that she took the year off due to his father sowing seeds of doubt in her mind about her talents, he was the first to push her back to school. He realized she was taking a break for the wrong reasons and attempted to persuade her to see the importance of her education.
Logan wasn’t just supportive of Rory’s professional ambitions; he also pushed her in her personal life. During her time away from school, Rory and her mom, Lorelai (Lauren Graham), weren’t speaking, which was the biggest rift fans saw between the mother-daughter duo. Throughout this disagreement, Logan pushed for Rory and her mom to make up — certainly a kind thing for him to do, particularly since Lorelai didn’t approve of him.
Logan and Rory Stand Up for Each Other
Throughout their relationship, Rory combats her mother’s impression of Logan as an entitled rich boy. It takes a while, but Lorelai finally comes around. Yet, it’s Mitchum Huntzberger (Gregg Henry), Logan's dad, telling Logan that Rory isn’t good enough for him that’s forever etched into my mind. Logan immediately tells his father off and comes to Rory’s defense. Thankfully, someone in the Huntzberger family has some sense.
Logan and Rory Actually Talk Out Their Problems
In her previous relationships, Rory’s arguments with her boyfriends consisted of shouting matches and angrily storming off. Considering that Logan didn’t have much experience in having a real relationship before dating Rory, it’s surprising he was the one teaching her how to have good communication with a partner. Every time they disagreed, he always wanted to have a calm conversation about it, and by the end of things, they had a solid path for moving their relationship forward.
Logan and Rory Have a Foundation of Respect
Logan was utterly head over heels for Rory. He insisted he wasn’t a “relationship guy,” but when Rory said she wasn’t OK with being friends with benefits anymore, he leapt into commitment. Not only that, but he also got his feet underneath him pretty quickly with his newfound title of “boyfriend.”
Logan showed Rory he respected her opinions and needs at every turn. When she needed space, he gave her space. When she needed him to be there, like when her grandfather was in the hospital, he came to her aid even though it meant taking a helicopter and disappointing his father. When she took him to Stars Hollow to show him around, he was interested and happy to be there purely because it meant so much to her.
Another moment that stood out was when Logan asked Lorelai for permission to seek Rory’s hand in marriage. With Rory’s dad out of the picture, Logan could’ve easily skipped this step. However, Logan knew how much Lorelai’s approval meant to Rory, so he did the hard thing and asked for her mother’s blessing. Logan proved over and over again how committed he was to Rory and her happiness. It’s just a shame she didn’t say yes.