Chad Michael Murray’s Tristan Dugray failed to romance Rory Gilmore. The character’s bad boy antics led to his abrupt exit from the show.
During season 1, Rory left Stars Hollow High School to attend the prestigious Chilton Preparatory School to increase her chances of getting into Harvard. The transition wasn’t an easy one, and Rory wasn’t embraced by the elite private school’s privileged and unwelcoming student body led by Paris Gellar (Liza Weil). Rory also found herself fighting off the handsome but arrogant Tristan’s advances, whose behavior became more provocative when she failed to return his affections. Over time, the pair grew closer as Rory learned that underneath Tristan’s swagger lurked a decent guy plagued with insecurities and fear of rejection.
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During season 2, episode 9, “Run Away Little Boy,” a school project forced Tristan and Rory to play the title roles in a scene from Romeo and Juliet. Tristan’s lack of interest in academics and his increasingly rebellious behavior infuriated both Paris and Rory. Further complicating matters was Tristan’s threats to tell Rory’s first love, Dean Forester, about a kiss he and Rory shared in the wake of Rory and Dean’s season 1 breakup. After Tristan failed to show up for their performance, Rory learned he was leaving Chilton: his punishment for getting caught breaking into a classmate’s parent’s safe. Tristan told Rory his father was sending him to military school in North Carolina. There was chemistry between Tristan and Rory, and he embodied qualities she was attracted to in future love interests. Matt Czuchry’s Logan Huntzberger was also flirtatious and arrogant, and in the days before he met Rory expelled from many private schools. During season 3, Rory would ditch Dean (Jared Padalecki) in favor of another bad boy, Jess Mariano (Milo Ventimiglia).
Chad Michael Murray’s breakout role was playing Lucas Scott on One Tree Hill. The show ran for nine seasons (2003-2012) and aired first on The WB, and later on The CW (He exited the series after season 6.) He also appeared in the remake of Freaky Friday (2003) with Lindsay Lohan. His other films, A Cinderella Story (2004) and House of Wax (2005) cemented his status as both a big and small screen heartthrob for much of the decade. Murray continued to work steadily following One Tree Hill, although his popularity waned. He enjoyed a career resurgence playing cult leader Edgar Evernever on Riverdale in 2019.
While Tristan was mentioned during Gilmore Girls: A Year in the Life (fans will recall the Tristan sighting sent Paris into a tailspin), Chad Michael Murray did not reprise the role. “I heard [it was happening], and I wasn’t available at the time. I’m pretty positive I was having a baby – my first child,” the actor told ET in 2017. The blink-or-you’ll-miss-it Tristan moment required a recast, so Tristan was played by Anton Narinskiy (Jane the Virgin). There are no definitive plans for another Gilmore Girls revival, but if fans get their way, Murray will have another chance to revisit the halls of Chilton.
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