Why Do Rory and Jess Break up in ‘Gilmore Girls’?

#TeamJess fans were left heartbroken when Rory and Jess broke up. Learn why they called it quits.

Sarah Kester - Author

Jun. 20 2024, Published 3:00 a.m. ET

If you’re a true fan of Gilmore Girls, there’s a good chance that you’ve rewatched the beloved series oh, about a million times. It’s so easy to get lost in the wonderful, chaotic, and homey world of mother and daughter duo Lorelai and Rory.

The cozy town of Stars Hollow, the strict-yet-well-intentioned Richard and Emily, and all the side characters add only to the charm.

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But on each rewatch, more questions may crop up. How did Lorelai and Rory eat so much and stay so trim? Why do they order a ton of food at Luke’s Diner and then waste it all? And why did Rory and Jess break up?

That last one is a sore spot for fans of #TeamJess. Here, we finally get to the bottom of this short-lived yet passionate love story.

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Why did Rory and Jess break up? First, a little background on their relationship.

Fans first meet Jess, the quintessential misunderstood bad boy, in Season 2. After getting into trouble at school, he comes to Stars Hollow to live with Luke, his uncle. He also has a rocky relationship with his mother, Liz.

When Jess arrives, Rory is in a safe and comfortable relationship with Dean, her longtime boyfriend. Even though the people of Stars Hollow resent Jess for the trouble he causes (including her mother), Rory sees the best in Jess.

She sees that he’s sweet and sensitive. He’s also a bookworm like she is, which allows them to connect on a deeper level than she can with Dean. In other words, all this spells trouble for her relationship.

After Rory hid her feelings about Jess for so long, Dean broke up with Rory at the dance marathon. This leaves Rory finally single and able to pursue Jess.

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So what happened in Jess and Rory's tumultuous relationship?

Their relationship is bliss at first. After liking each other from afar for so long, they have a lot of pent-up passion. Sadly, things start to unravel. It starts with Rory feeling self-conscious that the town prefers her to Dean. Even her mom criticizes their lack of passion when they kiss.

Then, Jess struggles to keep a girl like Rory happy. When upset, he acts avoidant and leaves her waiting for him to call.

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During that time, they were both headed in different directions. Rory was off to college soon while Jess was skipping school and unable to graduate. Once Luke finds out that Jess had been skipping classes, Luke kicks him out and Jess takes off to California without telling Rory. This leaves their relationship with no official split or closure.

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Rory is understandably heartbroken. But with college on the horizon, she has to compartmentalize her feelings and move on. Jess doesn’t get exactly a welcome homecoming when he returns to Stars Hollow. Rory doesn’t want anything to do with him. They don’t get back on good terms until Jess has cleaned up his life. By then, it’s too late, as Rory is dating Logan.

When the Gilmore Girls: A Year in the Life special premiered on Netflix, the parallels between Rory and Lorelai’s life are evident. Both had relationships with wealthy, upper-class men — Logan for Rory; Jason for Lorelai. Meanwhile, both Luke and Jess pined after these women. Luke eventually got the girl. Maybe there’s still hope for Jess?

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