‘Gilmore Girls’: Did Rory Love Jess?

In Gilmore Girls, Rory and Jess make up one of the most popular ships despite the fact their relationship in the TV show was relatively short-lived. Affectionately known as Literati in the Gilmore Girls fandom, some fans feel that Jess and Rory are each other’s true loves. However, other fans think that while Jess still loved Rory after they broke up, Rory moved on.

Milo Ventimiglia Alexis Bledel
Milo Ventimiglia and Alexis Bledel | Kevin Winter/Getty Images

What happened between Jess and Rory on ‘Gilmore Girls’

Rory and Jess first met in Season 2 when Jess came to stay with his uncle, Luke. The two immediately connect over their love of literature and music, and Rory develops a crush on Jess. She kisses him at the end of the season, but she stays in a relationship with her boyfriend Dean.

The love triangle between Jess, Rory, and Dean continues into Season 3 until Dean breaks up with Rory because of her obvious feelings for Jess. They date for multiple episodes, but before the season ends Jess leaves Stars Hollow and Rory without saying goodbye because he failed out of school.

When he calls Rory from California where he is visiting his estranged father, he is unable to say anything. However, Rory tearfully tells him that she is moving on and will not wait for him.

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“I’m going to Europe tomorrow and I’m going to Yale and I’m moving on. And I’m not going to pine. I hope you didn’t think I was going to pine, okay?” She says. “I think… I think I may have loved you, but I just need to let it go.”

In Season 4, Jess briefly returns and professes his love for Rory, but she turns him down. He appears again in Season 6 of Gilmore Girls and still clearly has feelings for Rory, but Rory is in love with her boyfriend Logan. During Gilmore Girls: A Year in the Life, Rory and Jess are friends who see each other every few years, but it is hinted that Jess still has unresolved feelings for Rory.

Jess always inspired Rory

While Jess and Rory’s romantic relationship did not last long, Jess was a monumental person in Rory’s life. In Season 6, Jess visits Rory and reveals that she inspired him to write his own novel. Fans interpret their encounter as part of what encouraged Rory to go back to Yale.

Later in Gilmore Girls: A Year in the Life, Jess encourages Rory to write a book about her relationship with her mom. His advice works, and by the end of the miniseries Rory has written a portion of the book.

Despite the rocky nature of their teenage relationship, it is clear the two have a stable friendship after their romantic relationship ends.

“Well … Rory changed Jess’s life for the better. She encouraged him to pursue his dreams, she believed in him. Luke was also there for Jess, but Rory also contributed a lot. Jess really was lost at the time. And in the end Jess and Rory had healthy relationhip. They were friends, she even listened to his advice,” one Reddit user wrote.

While Rory never says “I love you” to Jess in the series, it is clear to see that Jess still had a huge impact on her.

Most fans don’t think Rory loved Jess the way Jess loved her

When Rory tells Jess “I think I may have loved you,” this could be interpreted as Rory not knowing her true feelings or her knowing she loves him but choosing not to say it because Jess left her.

“I honestly don’t think Rory or Jess loved each other. I think they loved the idea of each other, the person they wanted/hoped the other would be… He even left, worked on himself and came back presenting this ‘new’, ‘matured’ version of himself to her and still she rejected him,” a Reddit user wrote.


Another fan thinks that while Rory moved on from her romantic feelings for Jess, she loves him in the way someone wants what is best for their friend.

“I think they love one another – certainly romantically (Eros) at the start and now as distant friends (Philia)… I sensed that type of love in season six when they are both clearly happy to see one another again! At that point, Rory loves Logan romantically. But, she still lights up seeing Jess and makes plans to catch up with him,” the fan wrote on Reddit.