Jess Mariano rolled into town during the second season of Gilmore Girls and changed Rory Gilmore’s world forever. If you are a Rory and Jess shipper, then here are all the important episodes to watch (or rewatch!) from season 2 of the series.
Note: This post contains spoilers for the plot of Gilmore Girls, so read at your own risk!
The Best Rory and Jess Episodes of Season 2:
"Nick and Nora/Sid and Nancy"
(Season 2, Episode 5)
Let’s start at the beginning, shall we? In this episode, Jess first steps foot off a bus and into Stars Hollow. He was sent to live with his uncle, Luke, because his mother felt that she couldn’t control him anymore. He comes into town with a chip on his shoulder, monosyllabic grunts as answers to questions, and a lot of band t-shirts.
Lorelai hosts Luke and Jess for dinner that night, which is where Rory and Jess meet for the first time. Jess immediately tries to get Rory to ditch the dinner party, to which she tells him that there is nowhere to go in Stars Hollow at that time of night. This interaction seems to establish the good girl-bad body dynamic that persists throughout the early parts of their relationship.
Jess also seems to take an interest in Rory’s reading habit, although he claims that he doesn’t read much. Contrary to this, he steals one of Rory’s books and then gives it back to her with notes in the margins.
"The Ins & Outs of Inns"
(Season 2, Episode 8)
This is the episode in which Jess meets his arch nemesis, who also happens to be Rory’s boyfriend (total coincidence, of course). Dean and Jess get off to a rough start when Dean tries to break up a fight between Jess and another guy at school.
Jess is also wreaking havoc in Stars Hollow. Turns out all you have to do to be labeled the town’s “bad boy” is steal some garden gnomes and create an obviously fake crime scene outside Doose’s Market. The town blames Luke for Jess’ behavior, which Taylor makes clear at a public town meeting.
Rory is frustrated with Jess because of his treatment of Luke and the position he has put him in with the town, and she lets Jess have it. Although Jess rarely listens to anyone, he seems to pay attention to what Rory says as he later helps Luke fix his toaster and seems to quit causing so much trouble.
My favorite moment of the episode is one of the funniest in the entire series- when Luke pushes Jess into the lake. To be honest, Jess deserved it!
"The Bracebridge Dinner"
(Season 2, Episode 10)
A formal dinner is held at the Independence Inn, and Lorelai invites all our Stars Hollow favorites to attend. Rory ends up taking a horse-drawn sleigh ride with Jess, while Dean goes off with his little sister.
At the end of the night, we see Dean looking across the room at Rory, but she’s not looking back at him. Instead, her eyes are locked on Jess. This subtle moment felt like the true start of the love triangle between the three of them.
"A-Tisket, A-Tasket"
(Season 2, Episode 13)
The Stars Hollow Bid On A Basket event is at the center of this episode. Rory puts together a basket full of admittedly disgusting food, expecting Dean to bid on and win her basket. What she doesn’t see coming is a bidding war between Jess and Dean.
Jess wins Rory’s basket and, to Dean’s chagrin, Rory agrees to go on a picnic date with him. Her defense? It’s tradition to go with the person who won the basket. However, it’s becoming more and more obvious that she’s interested in Jess.
"Lost and Found"
(Season 2, Episode 15)
Dean notices that Rory is no longer wearing the bracelet he made her for her birthday, and she makes up some story about how it was giving her a rash so she took it off. She frantically looks for the bracelet at Lorelai’s house, where Jess happens to be cleaning the house’s gutters (after Rory practically begged Lorelai to hire him).
Rory’s bracelet magically reappears in her room, right after Lorelai catches Jess leaving it. Coincidence? I think not. Lorelai confronts Jess, and he admits to being the one who had the bracelet. However, he says it took Rory two weeks to even notice it was gone, implying that she may not be as in love with Dean as she says she is.
"There's the Rub"
(Season 2, Episode 16)
Lorelai is on a spa getaway with Emily (nothing can go wrong there!). Since she’s away, Dean wants to come over but Rory tells him that she wants to spend a night alone doing laundry and ordering her favorite takeout. Her plans go awry after Paris shows up to force Rory to study with her. Jess then shows up unexpectedly with food from Luke’s, and he quickly makes himself at home to eat with Rory and Paris.
As Rory is ushering Jess out the front door, Dean shows up. Not a great look when Rory said she wanted to be alone! Paris tries to cover for Rory, saying that she was the one who wanted Jess to stay because she has a crush on him. This is one of the first moments of true friendship between the two girls.
"Teach Me Tonight"
(Season 2, Episode 19)
Jess is struggling in school, seemingly from a lack of effort not intelligence. Luke gets Rory to tutor him at the diner one night, and they end up taking a drive later on to get ice cream. Unfortunately, the study night ends poorly- with a car accident and Rory in the hospital with a broken arm.
"Lorelai's Graduation Day"
(Season 2, Episode 21)
In one of her worst moments, Rory is a no-show at Lorelai’s graduation from community college. How could she miss this? Why would she do that to her mom? Because she went to visit Jess in New York City- that’s why. It’s clear at this point that Rory has developed real feelings for Jess, but she doesn’t want to accept it yet.
"I Can't Get Started"
(Season 2, Episode 22)
In the season finale, Jess returns to Stars Hollow and goes to find Rory at Sookie and Jackson’s wedding. They kiss, and it’s clear at this point that neither of them can deny their feelings for each other. There’s a slight problem though- Rory attended the wedding with Dean as her date.
That's all for Rory and Jess in Season 2...
Do you ship them? What was your favorite Rory and Jess moment from season 2? Let me know down below.
Check out more of Rory and Jess’ story:
