The Ultimate Gilmore Girls Episode Guide: Relive the Iconic Chemistry Between Rory and Jess

Summary

The best Rory and Jess episodes in Gilmore Girls show their deep connection and shared interests, regardless of their romantic status.

The revival hints at Jess still harboring feelings for Rory, implying that their relationship remains unresolved. Despite the challenges they've faced, Rory and Jess share a unique connection that is consistently apparent throughout the series, and their undeniable chemistry only adds to this bond.

Rory (Alexis Bledel) and Jess (Milo Ventimiglia) are known for their controversial relationship in Gilmore Girls. However, the most compelling episodes featuring Rory and Jess are not solely focused on their romance. Some fans are enamored by Jess's intelligence and rebellious nature, while others believe he was detrimental to Rory. Even in the Year in the Life revival, Jess's reappearance sparks speculation among fans about his lingering feelings for Rory, and rightfully so.

Although there are no official plans, there are hints that a potential sequel to Gilmore Girls: A Year in the Life may be in the works. If it does happen, there could be further development between Rory and Jess, as their reunion in the revival was limited but hinted at Jess's enduring affection for his former high school sweetheart. Ultimately, Rory and Jess shared a significant connection during their formative years, and their importance to each other remains unchanged. The strongest episodes featuring Jess and Rory in Gilmore Girls aptly reflect this.

The Bracebridge Dinner (Season 2, Episode 10)

In "The Bracebridge Dinner," Rory and Jess cross paths yet again, providing a glimpse into what awaits them. This particular meeting also sheds light on the future of Rory's relationship with Dean. Lorelai's well-planned dinner event at the inn is thwarted by a snowstorm, prompting her to invite the townspeople to partake instead. As the dinner concludes with a sleigh ride, Rory finds herself sharing a carriage with Jess.

Although carriage rides are often associated with romance, this encounter is not centered on that. The sequence rather reveals Jess's persistent efforts to make Rory question her connection with Dean. It marks the beginning of Rory's doubts about their compatibility, even if she is not yet prepared to accept it herself, though the audience can foresee the impending outcome.

A Tisket, A Tasket (Season 2, Episode 13)

"A Tisket, A Tasket," is often cited by fans as one of the standout episodes featuring Jess and Rory in Gilmore Girls. This particular episode showcases the rivalry between Jess and Dean, and delves into the unique traditions of Stars Hollow. One such tradition is the picnic basket auction, which takes center stage in this episode. Despite the customary practice of Rory's suitor winning the auction, Jess decides to outbid Dean for her basket.

Jess' actions further fuel the animosity between him and Dean. While Dean already harbored suspicions about Jess prior to this episode, his dislike for Jess intensifies significantly. Openly displaying hostility towards Jess, Dean inadvertently encourages Jess' growing interest in Rory. Additionally, the episode provides an opportunity for Rory and Jess to spend some quality time together and discover their shared interests. Though Rory initially appears resistant to Jess' advances, it becomes evident that she is captivated by him and appreciates their mutual passion for art and literature.

There's The Rub (Season 2, Episode 16)

"There's The Rub" is another episode in season 2 of Gilmore Girls that strengthens the connection between Jess and Rory while leaving Dean feeling left out. In this episode, Jess demonstrates his literary prowess as Rory chooses to spend alone time, only to have both Jess and Paris unexpectedly join her. Initially wanting solitude, Rory didn't invite them but they assumed she would feel lonely with her mother away.

For Jess fans, this episode highlights his ability to intellectually bond with Rory and Paris, an area where Dean falls short. Paris even acknowledges and appreciates Jess' intellect, going so far as to cover for him when she senses tension between Jess and Dean. Paris' approval suggests that Jess won't be a temporary fling for Rory, as she typically finds other people tiresome.

Teach Me Tonight (Season 2, Episode 19)

Despite Jess being intelligent, he struggles with his schoolwork due to boredom and a lack of motivation. However, Luke believes he can benefit from tutoring, which is where Rory comes in. Their tutoring sessions act as an opportunity for them to spend more time together, deepen their connection, and make Rory realize her true feelings for him.

This is particularly evident in the episode "Teach Me Tonight" when they take a drive together. Instead of returning to study, Rory wants to continue driving. Although the episode ends on a negative note with a car accident that leads Lorelai to want Jess completely out of her daughter's life, their undeniable chemistry in the episode only strengthens the notion that they are meant to play a role in each other's lives.

Lorelai's Graduation Day (Season 2, Episode 21)

Rory and Jess have some of the best episodes, however, they also have some of the worst ones when it comes to Rory and Lorelai. This particular episode falls into the latter category as Rory skips her mother's graduation to spend time with Jess in NYC. It's always difficult to witness any conflicts or letdowns between Rory and her mother because their relationship is incredibly significant in Gilmore Girls.

Despite the disappointing daughter moment in this episode, it showcases a truly romantic day for Jess and Rory. The two of them wander around Manhattan, flirting and enjoying each other's company. While it may not be filled with grand gestures, this episode exemplifies what their relationship could be like.

I Can't Get Started (Season 2, Episode 22)

This is a pivotal moment for fans of Rory and Jess. It confirms that Jess cannot hide his feelings for Rory, making it difficult for her to simply dismiss him in favor of Dean. Finally, after much anticipation, the two of them share a long-awaited kiss.

However, the timing of the kiss is far from romantic. It occurs at Sookie's wedding, where Rory is in attendance with Dean. Initially meant as a farewell, the kiss ends up foreshadowing future events. When Jess expresses a desire to return to Stars Hollow, and this passionate moment takes place, it becomes evident to all that Rory and Dean's relationship is nearing its end.

Eight O Clock At The Oasis (Season 3, Episode 5)

Dean and Rory are still in a relationship in season 3, but it's becoming increasingly apparent that their connection is fading. It is evident that Rory and Jess will become the next couple in Stars Hollow. The period between their kiss at Sookie's wedding and their actual relationship is filled with moments of strong chemistry, and this particular moment stands out.

Rory is caught dealing with a broken sprinkler, and Jess happens to come by to fix it. Standing together, both drenched from the sprinkler, Rory informs Jess that Dean is on his way to help her. Despite Jess's clear feelings for Rory, he displays remarkable consideration for their relationship. He turns the sprinkler back on and walks away, leaving Rory watching him. Even though Jess openly expresses his feelings for Rory to the entire town, he never seeks to create difficulties for her with Dean. When she repeatedly chooses Dean, he chooses to walk away and avoid a confrontation. Paradoxically, this action reinforces his deep care for her.

Let The Games Begin (Season 3, Episode 8)

Since their first kiss at Sookie's wedding, Rory and Jess have finally become a couple in "Let The Games Begin." This episode beautifully showcases the potential sweetness of their relationship.

Alongside navigating Luke and Lorelai's reactions to their newfound romance, this episode is filled with heartwarming moments, despite occasional awkwardness that comes with teenage love. Nonetheless, this stage of their relationship is filled with excitement and novelty, making it a perfect episode to revisit the feelings of new love. When reflecting on the best Rory and Jess episodes, conflict doesn't have to be the only defining factor.

Face Off (Season 3, Episode 15)

This episode is not a favorite for many fans of Jess and Rory because Jess does not treat Rory well for most of the episode. However, the episode is important and has a satisfying ending. The focus is on Rory's struggle to communicate with Jess and make plans with him. Rory likes to plan, while Jess is more spontaneous, and this frustrates her.

Rory's anger towards Jess's casual attitude leaves her alone at home. In addition, Rory is not happy when she sees Dean with his new girlfriend, which further strains her relationship with Jess. However, Jess eventually shows Rory how much he cares, and they have a sweet moment at the end of the episode. "Face Off" demonstrates that even when Rory and Jess have conflicts, they can find a way to compromise and make each other happy.

Happy Birthday Baby (Season 3, Episode 18)

By this point in the series, Rory and Jess have resolved their issues and are happily and deeply in love. Despite their complicated relationship and extended periods of being apart, this episode exemplifies their strong bond. They possess a mature perspective that recognizes the importance of time apart, unlike most teenage couples on television who fear it may lead to a breakup.

In this particular episode, Rory is making plans for university and Jess wholeheartedly supports her. He actively considers ways to stay connected, plans visits, and demonstrates unwavering confidence in their ability to maintain their relationship even after she attends Yale. It's unfortunate that this scenario never played out in the show because it is evident that they were willing to put in the effort to make it work.

Nag Hammadi is Where They Found the Gnostic Gospels (Season 4, Episode 13)

This episode marks a bittersweet moment for Jess and Rory as they officially end their relationship. Despite this, it stands out as one of the most powerful episodes in Gilmore Girls for the couple. It holds a pivotal moment that has been building up since Jess first arrived in Stars Hollow.

In this episode, after a significant amount of time spent with Rory, followed by a period of separation and a dramatic departure from Stars Hollow, Jess finally confesses his love for her. Although he drives off immediately after, following a day of trying to avoid each other, this declaration is still a transformative moment. Jess has always been transparent about his feelings and attraction towards Rory, but admitting his love is a major milestone for him, as his actions have always spoken louder than his words.

Last Week Fights, This Week Tights (Season 4, Episode 21)

Despite not rekindling their romance in the original series, this particular moment presented the potential for Rory and Jess to reconcile, leading some to argue that they should have. This episode not only stands out as one of the finest Rory and Jess moments, but also showcases remarkable character growth for Jess.

After being absent for a considerable period, Jess returns for his mother's wedding and demonstrates his maturity. Additionally, this episode provides a significant opportunity for Jess and Luke to reconcile, as Jess acknowledges and expresses gratitude for everything Luke has done for him. Moreover, it could have been an ideal moment for Jess and Rory, as Jess visits Rory at Yale and invites her to return to New York with him. However, since she declines his offer, it remains uncertain whether they could have made it work.

Let Me Hear Your Balalaikas Ringing Out (Season 6, Episode 8)

Not all of the best episodes featuring Jess and Rory in Gilmore Girls are necessarily romantic. This particular episode may not be the most romantic, but it showcases the growth in their relationship and gives hope to fans of their potential reunion. Jess proves here that he is actually good for Rory.

At this point, Rory has left Yale and is living with her grandparents, not speaking to her mother. Jess's unexpected return and the news of his success, including writing a book, make Rory question her own choices. Jess plays a pivotal role when he confronts her about her current situation, prompting Rory to return home and pursue what truly matters to her. Jess is beloved in Gilmore Girls for his ability to provide perspective and help Rory make important decisions.

The Real Paul Anka (Season 6, Episode 18)

Rory and Jess fans who truly believe in their relationship are eagerly anticipating a second revival, hoping for another chance for the two of them. However, in the original series, this particular moment serves as their last significant encounter, and it's quite impactful. Taking place in "The Real Paul Anka" episode, Rory is still harboring anger towards Logan for being unfaithful while they were on a break. Meanwhile, as Logan joins the Life and Death Brigade for an outing, Rory attends an event at Jess's publishing house.

As expected, there is still a strong chemistry between Rory and Jess. During their interaction, Jess asks if everything between them is "fixed," to which Rory responds positively. In a beautiful moment, he kisses her. Nonetheless, despite the emotional connection they share, the beauty of the moment is overshadowed by the fact that Rory is betraying Logan by cheating on him. Overwhelmed with guilt, she confesses everything to Jess. This particular episode serves as a snapshot, revealing the constant confusion and conflict within Rory's heart throughout the series and its sequel, as she consistently gravitates towards her major love interests.

A Year In The Life: Summer

In the revival series, Rory and Jess appear to have moved on from each other - Rory is dating someone else, while also having an affair with Logan in London. However, when Jess returns to town during the summer, there is still undeniable chemistry between them. Despite limited screen time, the "Summer" episode of A Year In The Life showcases their potential as an adult couple and remains one of the best Jess and Rory episodes.

Their connection remains strong, with Jess now showing maturity and continuing to inspire Rory. He plants the idea of writing a book in her mind, highlighting their compatibility. Although Jess claims to be completely over Rory when speaking to Luke at the end of the revival, his lingering gaze suggests otherwise. This subtle hint leaves open the possibility of future Gilmore Girls episodes featuring Jess and Rory.