The Ultimate Guide to Rory and Jess (Gilmore Girls)

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Gilmore Girls Rory and Jess The Ultimate Guide on a hot pink background.

Note: This post contains spoilers for the plot of Gilmore Girls and Gilmore Girls: A Year in the Life.

Hello, Gilmore Girls lovers! Today I’m coming at you with a cumulative guide to Rory and Jess’ relationship throughout the entirety of the show, plus the revival. Rory’s relationship with Stars Hollow bad boy turned successful book publisher certainly had some ups and downs throughout the seasons. Check out this guide and the Rory and Jess episode guides for each season to figure out what part of Gilmore Girls you want to watch next, or just to revisit Rory and Jess as a couple. 

Rory and Jess Season 2
The Start of It All

The first time we see Jess is at the beginning of season 2 when he arrives to stay with Luke. Jess gets into all kinds of mischief during his early Stars Hollow days including gnome stealing, fighting, and creating a mock crime scene outside the town’s grocery store. However, he also very quickly develops a soft spot for the town’s golden girl, Rory Gilmore. 

Watch this season if you want to see the very beginning of Rory and Jess’ friendship, the start of a Jess-Rory-Dean love triangle, and some of Jess’ Stars Hollow shenanigans. 

Click here or on the image below to check out the best Rory and Jess episodes from season 2. 

Rory and Jess Season 3
Will They or Won't They?

By the end of season 2, it’s very clear that Rory and Jess have feelings for each other, but they are not together as Rory is still with Dean. Will Rory and Jess ever figure things out and give a relationship a try? Season 3 includes all kinds of ups and downs for the non-couple/couple, so buckle up. Watch this season if you want to see even more Jess-Rory-Dean drama, some very sweet Rory and Jess moments, and the rockier parts of their relationship too.

Click here or on the image below to check out the best Rory and Jess episodes from season 3. 

Rory and Jess Season 4
Back in Stars Hollow

Jess comes back to town a couple times throughout this season, which catches Rory off guard. Watch this season if you want to see Jess open up about his feelings for Rory, run away, and then come back again with hopes of getting Rory to go away with him. 

Click here or on the image below to check out the best Rory and Jess episodes from season 4.

Rory and Jess Season 6
An Author and a Yale Dropout Walk Into a Bar

Jess doesn’t show up again until season 6 of the show, when he tracks down Rory at her grandparents’ house to tell her about the book he’s written. This season contains the famous “Why did you drop out of Yale?” speech, a pretty important moment for Rory’s character. Watch this season if you want to see how well Jess still knows Rory and how Jess has matured over the time he’s been absent from the series. 

Rory and Jess A Year In The Life
Some Things Do Stay the Same

Jess is not present at all during season 7 of Gilmore Girls,  so let’s skip ahead to Gilmore Girls: A Year in the Life. Jess shows up in two episodes of the revival- “Summer” and “Fall”. He appears to have grown into a much more steady, mature character, as he helps out Luke with some of his own personal problems. Watch these episodes if you want to see a very grown up Jess, a slightly lost Rory, and how he helps her figure out her path forward in her career and life. 

Click here or on the image below to check out the best Rory and Jess episodes from season 6 of Gilmore Girls, plus their best episodes from Gilmore Girls: A Year in the Life.

What do you think of Rory and Jess' relationship?

Do you ship them? What did you think of where things were left in the revival? Could Jess and Rory ever end up together? Do you prefer Rory with another guy? Let me know down below. 

Gilmore Girls

gift guide

Coffee Mugs

As Lorelai Gilmore once said, “I can’t stop drinking the coffee. I stop drinking the coffee, I stop doing the standing and the walking and the words putting into sentence doing.”

Last update on 2024-11-19 at 12:13 / Affiliate links / Images from Amazon Product Advertising API / Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply to the purchase of this product.

Stars Hollow Blanket

From Luke’s Diner to Doose’s Market to Lorelai’s house, all of your favorite Stars Hollow spots can be found on this blanket.

Last update on 2024-11-19 at 12:13 / Affiliate links / Images from Amazon Product Advertising API / Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply to the purchase of this product.

It's a Lifestyle T-Shirt

Featuring our favorite mother-daughter duo, of course. 

Last update on 2024-11-19 at 12:13 / Affiliate links / Images from Amazon Product Advertising API / Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply to the purchase of this product.

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Camy

Welcome to Happy To Be Here Blog! Here you’ll find lots of recipes, gift guides, lifestyle content, glimpses into my life in the Northwoods, and so much more.

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