The romance was a highlight of Gilmore Girls, but the show surprisingly ruined my favorite relationship—and it happened very quickly. Luke and Lorelai’s connection was central to the series, and by season four, many viewers believed they were destined to end up together.
Unlike Lorelai, Rory dated several guys during the show, and it was always uncertain who she would ultimately end up with. The ending of A Year in the Life even suggested she didn’t need a partner at all. However, for most of the series, there was one character I really hoped she’d be with. That changed suddenly in season six when I realized they weren’t a good match after all.
I Was Team Jess For Years, But This Gilmore Girls Season 6 Scene Totally Soured Me On Them
Rory Gilmore had a few potential love interests – Dean, Jess, and Logan – but I always hoped she would end up with Jess. From the moment he appeared in season two of Gilmore Girls, he seemed like the best match for Alexis Bledel’s character. While he wasn’t perfect, he truly cared for Rory and showed real growth throughout the series.
Rory and Jess seemed to connect on a deeper level compared to her other relationships. While Dean envisioned a conventional future that didn’t align with Rory’s ambitions, and his infidelity in season four showed he wasn’t ready for a serious commitment, Logan, though a better match than Dean, was held back by his pride and hesitation at first.
Jess definitely had potential, and he was the most charming of Rory’s love interests, which made his occasional returns to the show intriguing. I really wanted him and Rory to end up together for six seasons, and I was particularly optimistic when he encouraged her to return to Yale. But a single scene in season six completely changed my opinion about them being a couple.
In season 6, the episode “The Real Paul Anka” showed how Rory hadn’t matured at the same rate as Jess. Her behavior at his book signing, especially their kiss, made it clear she still had a lot of growing up to do. The episode also suggested that Rory’s relationship with Logan was holding her back from becoming a truly supportive partner.
Rory & Jess’ Season 6 Reunion Proved That Jess Was Better Off Without Rory
In season 6 of Gilmore Girls, Rory kissing Jess while dating Logan showed that they were likely better off apart, and weren’t as well-suited as they once thought. Their relationship actually began similarly – Rory kissed Jess while she was still with Dean. But they were both young teenagers then, and that could have been overlooked if things had played out differently.
Although Jess always remained faithful to his on-screen partners, even ending things with Shane before pursuing Rory, Rory repeatedly made questionable choices in her relationships. She often involved her boyfriends in messy situations and even cheated on or with them. For example, in season six, Rory kissed Jess simply to hurt Logan, which was a selfish and unkind act.
Jess was right to feel he deserved someone who was on the same page, and it became clear by season 6 that he had grown up more than Rory. This difference in maturity made me question whether I was still on ‘Team Jess.’ Later, the revival series, A Year in the Life, really highlighted how much Rory and Jess had changed and grown apart, reinforcing what season 6 had already started to show.
A Year In The Life Drove Home What Gilmore Girls Season 6 Woke Me Up To
Honestly, “The Real Paul Anka” already made me doubt Rory and Jess as a couple, but A Year in the Life completely killed any lingering hope. Throughout the original series, I always felt like Rory and Jess were a little off-sync, but I held onto the idea they could eventually meet in the middle. That revival, though? It just proved they were never meant to be.
The Netflix revival highlighted that Rory hadn’t really grown up. She was still having an affair – this time with Logan, who was already engaged – which showed she hadn’t learned to have healthy relationships. Plus, when Rory reconnected with Jess, it was clear they had very different lives and priorities.
Jess had built a solid career and was actively pursuing his goals, but Rory still felt lost and unsure of her direction. It was a bit surprising to realize she hadn’t really changed much since the end of Gilmore Girls. Jess, on the other hand, always seemed to be evolving and growing with each appearance, showing a stronger commitment to personal development than Rory.
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2025-10-21 05:49