Does Rory ever date Tristan?

In the TV show Gilmore Girls, Rory Gilmore and Tristan Dugray have a complicated relationship. Tristan clearly has feelings for Rory, but she does not reciprocate. While they go on a few dates and have some romantic moments, Rory and Tristan never officially become a couple.

Tristan’s Interest in Rory

From the moment Tristan meets Rory at Chilton Preparatory School, he takes an interest in her. As the typical “bad boy” character, Tristan enjoys teasing Rory and trying to get her attention. He comes up with the nickname “Mary” for her, referring to her as innocent and wholesome. Tristan asks Rory out repeatedly, though she declines his advances.

Tristan continues to pine after Rory throughout their time together at Chilton. He seems intrigued by the fact that she is immune to his charms and not interested in dating him. Tristan makes excuses to talk to Rory and tries to ingratiate himself by getting her notes when she’s sick. It’s clear that underneath his cocky exterior, Tristan genuinely has feelings for Rory.

Rory’s Hesitance About Tristan

Though Tristan is popular and considered a catch, Rory is reluctant to get involved with him. As a focused student who cares more about academics than dating, she finds Tristan arrogant and irritating. His nickname for her, “Mary,” also bothers Rory.

Additionally, when Rory develops a crush on Dean, she becomes even less interested in Tristan’s advances. Rory sees Dean as the kind, mature boyfriend she would prefer over someone like Tristan. Even after she and Dean break up, Rory continues to dismiss Tristan as an option.

The PJ Harvey Concert

Tristan finally convinces Rory to hang out with him when he gets tickets to see PJ Harvey in concert. Rory’s best friend Lane is obsessed with PJ Harvey, so she agrees to go with Tristan. This could be seen as their first date, even though Rory makes it clear she’s just going for the concert, not for Tristan.

Things get awkward when Tristan tries to put his arm around Rory and kiss her. She rejects his advances, saying she only came for the music. Though it’s not an official date in Rory’s mind, Tristan views it as a chance to romance her.

Romeo and Juliet

Tristan and Rory share their most significant interactions when they get cast as Romeo and Juliet in a Chilton production. During rehearsals, they have to act out romantic scenes which forces intimacy between them. Off stage, they continue to argue as Rory gets increasingly annoyed with Tristan’s arrogance.

However, they finally share a real kiss during a dress rehearsal. After they kiss in character, Tristan tries to get Rory to replicate it off stage. Though she refuses at first, Rory eventually kisses Tristan briefly. She immediately regrets it and lies that it was just for practice, leaving Tristan disappointed again.

Tristan Gets Sent Away

Shortly after the play, Tristan gets caught pulling a dangerous prank and gets sent to military school in North Carolina. This explains actor Chad Michael Murray’s departure from the show after season one. Tristan getting pulled out of Chilton marks the end of any potential romance with Rory.

Rory seems relieved that she no longer has to deal with Tristan’s crush on her with him gone. Meanwhile, Tristan is clearly sad that his chances with Rory are over just as they had a moment together after months of him pursuing her.

No Official Relationship

Though Tristan continued to harbor feelings for Rory until his departure, they never actually dated. The closest they came was going to a concert together and kissing during a play rehearsal. Rory did not see real potential with Tristan.

Some fans wished Tristan had stayed on the show longer so he and Rory could have reconciled their differences. However, Rory did not reciprocate Tristan’s feelings strongly enough to ever become a real couple. Their relationship remained an unrequited love story on Tristan’s part.

Rory’s Other Relationships

While Tristan pined for Rory during season one, she pursued relationships with other characters like Dean and Jess. After Tristan left Chilton, any chance for them to date was gone for good.

Dean was Rory’s first boyfriend at Stars Hollow High School. They had a sweet, innocent romance until Dean became too clingy and jealous. Jess, Luke’s nephew, was Rory’s bad boy replacement for Tristan. Though Jess was not a great boyfriend, Rory fell for his brooding, intellectual personality.

Later at Yale, Rory dated Logan Huntzberger who was from an elite family like Tristan. Logan could also be arrogant and entitled but loved Rory deeply. He was likely her most significant college relationship.

Brief Reunion on the Show

Tristan does briefly return during season two of Gilmore Girls. He visits North Carolina near where Rory is on a school trip and they run into each other. Tristan seems hopeful they might rekindle something, but Rory explains she is still with Dean.

The encounter shows Tristan still has feelings for Rory after all this time. However, with Rory still rejecting him, it cements that they will never end up together. This short scene provides closure to their relationship.

Revival Shows Rory is Single

In the 2016 Gilmore Girls revival on Netflix, a 32-year-old Rory is single and struggling in her journalism career. Though Tristan is not brought up, it shows Rory has still not settled down with a lifelong partner.

Rory had major relationships with Logan, Dean, and Jess but none worked out. This could leave the door open for revisiting her dynamic with Tristan, but the characters never reconnect on screen.

Tristan and Rory Have Chemistry

Though Rory and Tristan never date officially, they have undeniable chemistry on the show. In flashback scenes, we see Tristan had a crush on Rory since they met as Romeo and Juliet. Many fans wished the characters reconciled and got together.

However, Rory’s hesitation about Tristan’s personality prevented them from transitioning their sparks into a real relationship. Their dynamic highlights how even mutual attraction is not always enough to make two people compatible.

Better as a Short-Lived Crush

Tristan’s unrequited feelings for Rory are a classic TV trope of the bad boy falling for the good girl. Their storyline is satisfying in small doses but would not necessarily work long-term.

Having Tristan get sent off to military school after one season preserves the appeal of his crush on Rory. Their sparks flying during brief interactions is more interesting than if they had actually become a couple on the show.

Rory dating someone like Dean instead reinforces that she preferred a nice, stable boyfriend to Tristan’s cockiness. Not every on-screen connection needs to turn into a relationship for audiences to enjoy it.

Other Possible Endings

Gilmore Girls fans have imagined different storylines where Tristan stays at Chilton longer and he and Rory get together. If the show wanted them to become an actual couple, it could have gone a few ways:

  • Tristan matures after pining after Rory and they start dating
  • Rory sees a caring side of Tristan and falls for him after they work on a project together
  • Tristan gets jealous when Rory dates Dean and tries harder to win her over
  • Rory develops feelings for Tristan after he defends her from a bully at Chilton

However, the writers intentionally scripted Rory as resistant to Tristan’s charms to showcase her character. Having her date arrogant guys like Tristan or Jess went against Rory’s persona on the show.


Gilmore Girls never provided romantic closure between Rory Gilmore and Tristan Dugray. Their brief interactions fueled speculation among fans but a real relationship was never in the cards based on Rory’s established character.

Tristan’s unrequited crush and Rory’s reluctance to date him despite their chemistry made for an interesting dynamic. But Rory choosing nice guys like Dean reinforced her personality versus falling for Tristan’s bad boy vibes.

Their separate story arcs and lack of contact after Tristan left Chilton cemented that theirs was an unfinished high school fling. Rory and Tristan connecting again as adults could have been an intriguing revival storyline. Yet the TV show consistently emphasized Rory’s lack of interest prevented it from going anywhere.

Ultimately, Rory and Tristan never progressed past romantic tension and a few almost-dates. While Tristan clearly cared for Rory, she did not feel strongly enough to pursue an actual relationship. Their sputtering dynamic served its narrative purpose without needing to become a fully-realized romance.

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