One of the reasons I love Gilmore Girls is because of the love interests, and one of Rory's most significant boyfriends is Logan. Played by Matt Czuchry, Logan Huntzberger is introduced in season 5 as though he's the opposite of Rory's past boyfriends; I couldn't help falling in love with him. It doesn't take long for the two to connect and for Rory to start embracing the side of her life that Logan represents. Though I hated it when she was estranged from Lorelai, this wasn't Logan's fault, as he couldn't be blamed for Rory's questionable choices.
Of course, Logan is far from Rory's only love interest, as Dean and Jess also play prominent roles in the series. However, one almost-boyfriend from the show's earliest seasons draws a surprising number of parallels to Logan. I was always intrigued by Chad Micheal Murray's played Tristan Dugray, and though he was written off, it's hard not to see how he and Rory could've followed a similar path to her and Logan. After Gilmore Girls many years later, I started to examine the different paths the series might have taken and how this would've altered the main characters' arcs.
Why I Think Logan's Story Was Originally Intended For Chad Michael Murray's Tristan
Tristan Dugray fits the same archetype as Logan earlier in Rory's story
Gilmore Girls takes place from season 5 onwards, but when adding up the facts, I noticed how similar he is to Tristan. A prominent parallel is that Logan and Tristan are from the upper-class side of Rory's upbringing, which belongs to her grandparents. Rory meets Tristan at Chilton and Logan at Yale, two elite schools that her grandparents fund, populated by the children of powerful and privileged parents. Though Lorelai doesn't get much of a chance to get to know Tristan, I know she would've disapproved of him, as she initially did Logan.
Additionally, Tristan and Logan feel trapped by their strict upbringings and family expectations, which is a large part of why I think Rory softens to Logan and sees the deeper parts of him. For both Tristan and Logan, the response to this pressure is to act out, and it's proven many times over that Rory has her head turned by rebellious men. It's never been confirmed by Amy Sherman-Palladino, the writer and creator of the series, that Tristan was supposed to have a similar story arc or that he would've gone on to be a primary love interest for Rory.
Sherman-Palladino decided to push Tristan's potential plotlines to a later season when he left.
However, based on the clues from the series, I think Tristan would've been Rory's first bad boy. Unfortunately, Murray decided to leave Gilmore Girls early despite plans for a longer arc for Tristan because other roles became available (via best teen romance TV shows. Other elements that seem to be recycled from Tristan's plot line to Logan's, like the nicknames for Rory, Mary/Ace, make me think that Sherman-Palladino decided to push Tristan's potential plotlines to a later season when he left.
How Tristan Replacing Logan Would've Been Different For Gilmore Girls
This could've changed Rory's entire character arc
One of the ways that Tristan differed the most strongly from Logan was that he was a lot less mature and more combative with Rory. Since he's younger and hasn't found any freedom from his parents, he doesn't know how to handle his attraction to Rory, so he makes fun of her and makes Chilton even more difficult for her. This makes it hard for us to root for Tristan initially, and I would've been hesitant to see him fully redeemed if he and Rory had started dating and she started embracing his elite world.
Tristan and Logan are like Christopher, Rory's father and Lorelai's first love, who she continuously returns to throughout the series. Had Rory and Tristan ever been together, this would've pushed up the timeline of Rory embracing her grandparents' lives and influence, which she does a little throughout the early seasons but is most prominent during seasons 5 and 6. However, this wouldn't have aligned with Rory's character arc, as she doesn't become disillusioned with the idea of herself and her inevitable success until college, which Logan helps her navigate. Rory acting out in high school would've changed Gilmore Girls forever.

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While Jess also fulfills this bad boy archetype, he never pretends as if he doesn't care for Rory, and though he ends up hurting her, it's because he has a lot more maturing to do and was damaged by his upbringing. Since Tristan is like Logan and Jess, his relationship with Rory might have altered her timeline with Jess, which I would've been very disappointed about. Tristan might have pushed Rory to break away from Lorelai earlier, which could've set her up for more long-term success in adulthood, but I doubt Rory was ready to attempt this in high school.
I'm Glad Logan's Story Happened Instead Of More Tristan
He was the better match for Rory in the end
Though before the final episode and wasn't always the perfect partner for Rory, he was the ideal person to help her realize what she wanted out of life. Their dynamic worked because Logan had time to grow out of his childish rebellion and immaturity, as he realized he wanted to grow up and be a person for Rory to rely on. Additionally, Logan was a new part of Rory's life, and the drama of their relationship doesn't stem from petty jealousy. Tristan drove a wedge between Rory and Paris, something the later seasons didn't need.
Rory's arc in the second half of Gilmore Girls is one of the most polarizing parts of the series, but it makes sense that she would have a delayed period of rebellion because of her close relationship with Lorelai. Having her estrangement from Lorelai, accompanied by the growth of her connection with Logan, made sense. Rory needed to test her limits and discover what kind of person she wanted to be by exploring the privilege that Lorelai tried to keep her separate from. I was sad that they spent so long apart, but it was in the show's best interest.

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Logan has a lot more time on the series to have a nuanced character arc with significant development, but even if Tristan had stayed, it wouldn't have been the same. Tristan coming back in the later years wouldn't have pushed her forward into a new part of life but instead pulled her back to her teenage years. It's clear to me that one of the reasons Rory and Dean break up in Gilmore Girls season 5 is because she's grown out of the things that made her comfortable in high school and is looking for someone who will challenge her.

Gilmore Girls
- Release Date
- 2000 - 2007-00-00
- Network
- The WB
- Writers
- Amy Sherman-Palladino
In the fictional town of Star's Hollow, single mother Lorelai Gilmore raises her high-achieving teenage daughter Rory. Mother and daughter rely on each other throughout their own life changes, romantic entanglements, and friendships.
- Seasons
- 7
- Streaming Service(s)
- Netflix
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