Note: This post contains spoilers for the plot of Gilmore Girls, so read at your own risk!
Jess Mariano came to Stars Hollow during the second season of Gilmore Girls and quickly fell for Rory Gilmore. If you want to start at the beginning of Jess and Rory’s story, you might want to check out their best episodes from season 2.
By the end of season 2, Jess and Rory have kissed and clearly have feelings for each other but are not yet an official couple. That’s where we’re picking up at the beginning of season 3, which is filled with many ups and downs for the non-couple/couple. Read on for a list of the most important Rory and Jess episodes in season 3 of Gilmore Girls.
The Best Rory and Jess Episodes of Season 3:
"Those Lazy-Hazy-Crazy Days"
(Season 3, Episode 1)
Rory is back in Stars Hollow after spending the summer in Washington, D.C. As Lorelai and Rory walk around the end of summer festival in town, Rory notices Jess and a new girl making out. She becomes visibly upset, prompting some questions from Lorelai (which are warranted, as Rory is still dating Dean).
Rory admits to her that she and Jess kissed at Sookie’s wedding, and Lorelai’s general reaction is that Rory needs to make up her mind. Who does she want- Jess or Dean? Valid question, Lorelai. It’s at this time that Dean shows up, and Rory hugs him while looking over his shoulder at Jess and she-who-shall-not-be-named. I’m not a big Dean fan, but poor Dean.
"Eight O'Clock at the Oasis"
(Season 3, Episode 5)
Lorelai and Rory are helping their new neighbor out by watering his lawn and checking his house plants while he’s away. It’s Rory’s turn to water the lawn, but she has trouble getting the sprinkler system to turn off. She pages Dean to help her but he’s not answering.
Who comes to her rescue? Of course it’s Jess. They have a short and sweet conversation about Rory’s college plans before Rory hears from Dean that he’s on his way. In a showing of selflessness, especially given the fact that he has made his feelings about Rory more than clear, Jess turns the sprinklers back on so Dean can save the day for her.
"They Shoot Gilmores, Don't They?"
(Season 3, Episode 7)
This is probably the most pivotal episode in the Dean-Rory-Jess triangle (and one of my personal favorites). All the drama goes down at the Stars Hollow 24-hour dance marathon, where Rory and Lorelai are dancing together in an attempt to defeat Kirk and win the highly esteemed dance-a-thon trophy.
Lorelai has to take a break to fix her shoe, and Dean steps in to dance with a very sleepy Rory. As tired as she is, she can’t stop focusing and commenting on the fact that Jess is sitting in the stands watching them dance. This prompts Dean, who has finally had enough of Rory’s obvious interest in Jess, to break up with her loudly on the dance floor in front of everyone. Rory runs off crying, and it’s safe to say that she and her mom don’t beat Kirk this time.
"Let the Games Begin"
(Season 3, Episode 8)
This is the first episode that Rory and Jess are together as an official couple, and it starts off a touch awkward. They exchange too many hi’s at Luke’s before getting some alone time. This episode is full of sweet moments as Rory and Jess figure out how to actually be together as an official couple, not just pretend to not be in love with each other while they date other people.
"That'll Do Pig"
(Season 3, Episode 10)
It’s Winter Carnival time in Stars Hollow, and Rory is really looking forward to attending the festival. Jess, however, is unwilling to go with her until he finds out that Dean and his little sister are planning on going and Rory is going to tag along with them. Jess changes his tune then, and accompanies Rory…. and Dean. Thought we were done with this love triangle? Not quite yet.
"Swan Song"
(Season 3, Episode 14)
Rory wants Jess to come to Friday night dinner to meet her grandma, and he begrudgingly agrees. However, when he walks in the door of the Gilmore residence he has a black eye that he refuses to explain to Rory and a sour attitude. Did I mention he’s also late? It’s safe to say he didn’t make the best first impression, although we learn that the black eye was the result of Jess getting beaked in the face by a swan (not from a punch in the face by Dean).
"Face-Off"
(Season 3, Episode 15)
Frustrated by Jess’s lack of planning and communication, Rory decides to stop waiting around for him and instead attends a hockey game with Lane. It’s there that they run into Dean and *plot twist* his new girlfriend, Lindsay.
Perhaps spurred on by seeing her ex with someone new, Rory calls Jess and leaves an angry voicemail. When she leaves the rink, she sees Jess leaning against his car waiting for her with concert tickets for the two of them. It seems all is forgiven and she asks him to not listen to his voicemail when he gets home.
"Happy Birthday, Baby"
(Season 3, Episode 18)
It’s Lorelai’s birthday, and Rory is planning a surprise party for her. This episode shows Rory and Jess happy and very much in love, having worked out their issues from “Face-Off”. Rory is making college plans, and Jess is being 100% supportive. He’s planning when they can see each other, which should be often since Yale is only 22.8 miles away from Stars Hollow (he looked it up). This is a bittersweet moment for any fans of the couple because we know these plans won’t come to fruition, but it shows that both Rory and Jess wanted a future together.
"Keg! Max!"
(Season 3, Episode 19)
If you can’t tell by now, Rory and Jess have a lot of highs and lows- and this episode is one of their lowest lows. They attend a house party to support Lane’s band, but the night goes sideways fairly quickly. Jess has learned that he’s failing school and instead of talking to Rory about it, he begins to treat her more and more poorly throughout the night. These are by far his worst moments as a character, and Rory becomes increasingly upset by his rudeness and anger toward her. Dean notices her crying and an actual fistfight ensues between him and Jess.
The party is ruined and the police show up. Jess walks away from the party without saying a word to Rory, who is holding Lane’s hair as she vomits in a bush. There’s an ominous feeling that this is the beginning of the end for them.
"Say Goodnight, Gracie"
(Season 3, Episode 20)
Maybe this is the lowest low of Rory and Jess’s story. Jess leaves Stars Hollow in this episode to go to California to stay with his father. He doesn’t even say goodbye to Rory, which is now a recurring issue (he didn’t say goodbye before leaving for New York in season 2 either). It seems that part of Rory knew they were done since she didn’t seem all that surprised that he left.
"Those Are Strings, Pinocchio"
(Season 3, Episode 22)
This episode focuses on Rory’s graduation from high school. Throughout the episode, she receives multiple phone calls from someone who says nothing on the other end of the line. While she’s at her graduation, she receives another one. Knowing it’s Jess on the other end, she tells him that she might have loved him but she needs to move on. Understandable, given their tumultuous relationship over the past season, but still heartbreaking for fans of the couple. Jess, in typical Jess fashion at this point, says nothing.
And that's how Rory and Jess end season 3...
Jess is in California, and Rory is in Stars Hollow. They are no longer together, which may be best for both of them right now. Jess, clearly, needs to figure himself out. Maybe Rory does too, especially as she’s entering a new phase of her life – the Yale years.
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