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During Gilmore Girls’ seven-season run, Rory Gilmore had three serious relationships. She dated Dean Forrester during seasons 1 and 2 and part of season 3. In season 3, she hooked up with Jess Mariano, Luke Danes’ nephew, and in season 5, she settled into a relationship with Logan Huntzberger. Rory also had an often forgotten almost flirtation with Tristan Dugray, her Chilton classmate, during the show’s earliest seasons. Tristan shipped off to boarding school, never to be heard from again, ensuring a romance would never actually blossom. Was that the original plan, though? According to Chad Michael Murray, the actor who portrayed Tristan, it was not. 

Chad Michael Murray left Gilmore Girls’ in season 2 

Tristan Dugray first appeared in episode 2 of Gilmore Girls. Initially, he was one of Rory’s antagonists, picking on her mercilessly. While Rory was never a huge fan of Tristan, it quickly became clear that Tristan was interested in Rory. He continued to pick on her, but he occasionally did show his softer side. Amy Sherman-Palladino had just begun to develop the character when Tristan was suddenly sent to boarding school after yet another problematic prank. In his final appearance, it was pretty obvious that Rory was starting to warm up to him, too. 

Chad Michael Murray visits Hallmark Channel's "Home & Family" at Universal Studios Hollywood. Murray portrayed Tristan Dugray in 'Gilmore GIrls' before landing his breakout role
Chad Michael Murray | Paul Archuleta/Getty Images

While Tristan left Hartford, Connecticut, to attend boarding school when his behavior got out of control, that reportedly wasn’t the plan. Tristan was supposed to be a pretty significant character during Rory’s high school career. The actor behind the role wasn’t interested in returning, though. 

Murray sat down to discuss his time on the show with Scott Patterson during an episode of I Am All In. During the chat, Murray revealed that he was offered the chance to sign onto Gilmore Girls long-term but turned down the proposal so that he could explore who he was as an actor. The decision was a solid one for Murray. The big risk quickly led to his breakout role on One Tree Hill

Sending Tristan Dugray to boarding school might have changed the course of the show 

While Amy Sherman-Palladino has never spelled out exactly how Murray’s departure from the show changed her plans, we think the actor’s decision to take another role changed a lot. After Tristan left Chilton, Jess Mariano’s role in Rory’s life expanded. Tristan and Jess shared a lot of personality traits. They both had a baseless desire to mess with Dean Forrester, too. 

Milo Ventimiglia and Chad Michael Murray attend the season 2 screening of 'Chosen' on December 3, 2013
Milo Ventimiglia and Chad Michael Murray | Barry King/FilmMagic

While it’s never been completely confirmed, it’s safe to assume Jess became what Tristan was always meant to be. Based on Murray’s statements about the network’s offer, we can surmise that he was supposed to be pretty important to Rory, although we doubt he was ever meant to be her endgame love. Perhaps, Tristan was supposed to be Rory’s version of Christopher Hayden. At the very least, we think they probably would have dated if Murray had stuck around long enough. 

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If you think about it, Logan was likely what Tristan would have grown into. Logan was a problematic high school student who was kicked out of multiple prep programs. He landed at Yale but took time off and didn’t take things seriously. Deep down, though, he was a good guy who was deeply conflicted about his desires and his family’s expectations. We could see Tristan being just like that if the character had had the chance to mature on-screen.