Gilmore Girls: 20 Best Episodes to Rewatch If You Miss Rory & Jess

Although Rory (Alexis Bledel) and Jess (Milo Ventimiglia) have one of the most contentious relationships on Gilmore Girls, fans of the duo will discover that their relationship isn’t the focus of the best episodes of Rory and Jess. While some admirers adore Jess’s wit and macho demeanor, others believe he is too good for Rory. He continues to stir up controversy all the way up to the Year in The Life reunion, when he emerges and, understandably, leaves fans wondering if he still has feelings for Rory.

There are various indications that a Gilmore Girls sequel is in the works, but there is no official plan to produce a second season of Gilmore Girls: A Year in the Life. If it does happen, there could be more story to come between Rory and Jess, as they were only given a few scenes in the revival, and those scenes suggest that Jess still has some feelings for his high school sweetheart. Rory and Jess were incredibly important to each other during their formative years, and they always will be.

Summary

• Rory and Jess’s relationship is controversial, but Jess’s intelligence and bad-boy ways intrigue Rory.
• A second season of Gilmore Girls: A Year In The Life may be in the works, hinting at more Rory and Jess storylines.
• Jess and Rory share important moments throughout the series, showing their connection and potential as a couple.

“Nick & Nora/Sid & Nancy”

Season 2, Episode 5

Fans of Rory and Jess should only watch this episode because it features Jess’s first appearance on Gilmore Girls. He doesn’t yet play a significant role in the plot, and the audience doesn’t know much about him other than the impression of a bad kid that he gives off during his initial encounters with Rory and Luke. Notwithstanding this, Rory and Jess click right away.

Although the two of them don’t meet quite as sweetly as Rory and Dean did in the show’s pilot, Jess’s presence in the program indicates that going forward, the literary allusions will surpass the general pop culture allusions. It’s also clear that Jess and Rory are attracted to one another right away. Jess is surly to everyone he meets in Stars Hollow except for Rory. Rory is ready to banter with him without knowing his backstory.

This is the episode that makes the audience wonder if Rory might be better suited to someone other than Dean.

The Ins and Outs of Inns

Season 2, Episode 8

…confirms that they will remain the show’s love triangle for the foreseeable future.

This episode, which airs just three episodes after Jess’s unpleasant entrance, aims to solidify Jess’s reputation as a troublemaker even more than the first one. It actually just serves to highlight his clownish nature. As an example, he draws the outline of a purported body in chalk in front of Doose’s. While Jess never acknowledges that he was the one who did it, Rory finds it amusing. With the exception of Rory, this episode makes clear that Jess is still rude and snarky to everyone in the community, even Luke.

To her credit, Rory confronts Jess about how he is treating Luke. Even though she seems to understand that he’s mad at the world, she points out how badly he’s treating the one person trying to help him, and it does get through to Jess. He even fixes Luke’s toaster, though, like the chalk outline, he won’t admit that he’s the one to fix it.

This is also the first episode in which Jess and Dean meet. Jess doesn’t even know that Rory has a boyfriend up to this point, and that reveal helps to solidify that they are the love triangle of the show for the foreseeable future.

The Bracebridge Dinner

Season 2, Episode 10

While Rory and Jess have met before, “The Bracebridge Dinner” is the first instance that suggests what awaits both of them as well as Rory and Dean (Jared Padalecki). In this episode, a snowfall cancels Lorelai’s (Lauren Graham) large-scale supper that was scheduled for an event at the inn. Since everything has already been planned, she ends up inviting the town’s residents to the celebration instead, and when the supper concludes with a sleigh ride, Rory ends up riding in Jess’s carriage.

Although romantic moments are frequently associated with carriage rides, romance isn’t the main focus of the experience. In the scene, Jess presses Rory to consider her relationship with Dean in depth. It’s when Rory first begins to doubt that she and Dean aren’t meant to be, even if she’s not ready to admit it to herself, and even if the audience can see it coming.

A Tisket, A Tasket

Season 2, Episode 13

“A Tisket, A Tasket,” one of the Gilmore Girls episodes starring Jess and Rory, is a staple in fan discussions. It makes Jess and Dean’s rivalry more transparent. This episode centers on one of the many hilarious and endearing customs of Stars Hollow: the picnic basket auction. Even though custom would have it that Rory’s boyfriend wins the basket, Jess chooses to outbid Dean in this instance.

Jess’s behavior fuels Dean and Jess’s animosity. Even though Dean had misgivings about Jess earlier in the series, after this he simply cannot bear her. When Dean shows Jess his true colors, it just makes Jess more interested in Rory. The episode also creates space for Rory and Jess to spend some time together, and realize just how much they have in common. While Rory is outwardly resistant to Jess’ attention, it’s clear that she is fascinated by him and appreciates how much of the same interests in art and literature they have.

Lost And Found

Season 2, Episode 15

“A Tisket, A Tasket,” one of the Gilmore Girls episodes starring Jess and Rory, is a staple in fan discussions. It makes Jess and Dean’s rivalry more transparent. This episode centers on one of the many hilarious and endearing customs of Stars Hollow: the picnic basket auction. Even though custom would have it that Rory’s boyfriend wins the basket, Jess chooses to outbid Dean in this instance.

Jess’s behavior fuels Dean and Jess’s animosity. Even though Dean had misgivings about Jess earlier in the series, after this he simply cannot bear her. When Dean shows Jess his true colors, it just makes Jess more interested in Rory.

There’s The Rub

Season 2, Episode 16

It’s a great one for Jess fans, as it shows that he can connect with Rory and Paris on an intellectual level – something that Dean fails to do. Paris even appreciates Jess’ mind in the episode. She covers for his presence when she realizes there’s tension between Jess and Dean. Paris’ approval of Jess is a big sign that he won’t be a passing fling for Rory as Paris notoriously finds other people tiring.

“There’s The Rub” is another episode from season 2 that lets Jess and Rory get to know each other better but Dean ultimately feels as though he’s looking in. In this episode, Jess demonstrates his literary prowess when Rory tells Dean she wants to spend some time by herself, only for him to discover her with Jess and Paris (Liza Weil). She didn’t invite Paris or Jess over; they just turned up to spend time with her since they assumed she would be lonely without her mother. Originally, she had wanted to spend that time alone.

Teach Me Tonight

Season 2, Episode 19

Jess fails academically despite his intelligence (due to boredom and lack of motivation). However, Luke (Scott Patterson) believes he needs tuition, which is where Rory steps in. The “tutoring” session they had in “Teach Me Tonight” actually allows them to spend more time together, strengthens their bond, and makes Rory realize how much she values him.

This is particularly evident in “Teach Me Tonight,” when they go for a drive and Rory expresses a desire to continue driving instead of returning to his studies.

The episode might not end in a great moment as Jess and Rory end up in a car accident that sees Lorelai wanting him out of her daughter’s life completely, but their chemistry in the episode only furthers the idea that they’re meant to be in one another’s life in some capacity.

Lorelai’s Graduation Day

Season 2, Episode 21

“Lorelai’s Graduation Day” is a prime example, as Rory skips her mother’s graduation because she’s hanging out with Jess in New York City. Some of the best episodes featuring Rory and Jess are also some of the worst featuring Lorelai. Since Rory and her mother are the most significant relationship in Gilmore Girls and are incredibly close throughout the series, it is difficult to watch whenever they fight or let each other down.

Even though there is a horrible-daughter incident in this episode, Jess and Rory have a very beautiful day. The two flirt all day as they go around Manhattan. It’s not an episode full of big moments for them, but it is an episode that demonstrates what a relationship between them would look like as Jess shows her his life outside of Stars Hollow.

I Can’t Get Started

Season 2, Episode 22

For fans of Rory and Jess, “I Can’t Get Started” is one of the most important episodes. In this episode, it becomes evident that Jess will not be pretending to be without feelings for Rory and that she will not be able to ignore him in favor of Dean. Following much anticipation, Jess asks Luke if he can move back in with him when she returns to Stars Hollow, and eventually the two have a kiss.

Naturally, it’s not quite as romantic as it should be because Rory and Dean are attending Sookie’s (Melissa McCarthy) wedding, and Rory isn’t ready to let go of Dean. The kiss is meant to be a goodbye of sorts, but it ends up being a promise of what’s to come. When Jess asks to come back to Gilmore Girls’ Stars Hollow, and then this happens, everyone knows that Rory and Dean are on their last legs.