Rory was with Dean- Tristan is many things, but separating people is not one of them. Yes, he had tried to get with Rory before. Yes, they kissed.

Yet the show writers did not need Rory to date Tristan for her arc. Dean was Rory’s “good” boyfriend while Jess was her “bad” boyfriend. Tristan is “bad” like Jess but more like “Logan”, except Logan had a more fleshed out character.

Kissed once, Tristin had feelings for Rory and she was a little interested later on, but never acted on it. Tristin & Rory is a relationship on Gilmore Girls, portrayed by Chad Michael Murray and Alexis Bledel .

Rory’s short-lived fling with the gorgeous Chilton bad boy was a blip on the radar compared to her other relationships, but it’s one that certainly had effects on her chemistry with Dean. Tristan and Rory shared some pretty flirtatious moments, and of course there was their kiss.

How do Tristan and Rory meet?

Tristan and Rory meet when Rory starts Chilton, and he instantly starts teasing and toying with her, which Rory finds at first bewildering and, as time passes, offensive and annoying. Rory is convinced that Tristan teases her because he is flirtatious by nature and keeps it up because she’s not interested, but it turns out that Tristan actually has feelings for Rory. Oblivious to this, Rory strikes up a friendship with Tristan, who wants more but is unsuccessful due to Rory’s feelings for Dean. Though Rory sometimes seems like she could be interested, their connection is also complicated by Paris feelings for Tristan. Before Tristan gets in trouble and is sent to military school, he and Rory end on good terms.

On Rory’s first day at Chilton, Tristan walks in and is immediately attracted to Rory. He makes a move on her in his typical douche fashion, assuming she’s a doe-eyed girl, who will find him interesting, but is surprised to soon learn that she doesn’t find his ways enchanting. This only makes Tristan pursue an obnoxious behaviour toward Rory, both teasing and being mean to her, while also continuing flirtation. Emily ignorantly invites Rory’s classmates to her 16th birthday party, embarrassing her because they were not her friends. Tristan arrives at the party and teases her about kissing him. Rory doesn’t think his behaviour means that Tristan truly likes her, rather that he’s trying to prove that he can get any girl he sets his sights on, but his altercation with Dean at the Chilton dance is the first time she considers otherwise .

Following Rory’s break-up with Dean, she attends a party at Madeline’s just in time to witness Summer dumping Tristan, and the two share common ground, Tristan being vulnerable and kind to Rory for the first time. He kisses her and she kisses back, but is heartbroken over Dean and leaves Tristan sitting at the piano.. Rory initiates a conversation about their ensuing awkwardness and insists that the two should be friends, which Tristan hesitantly accepts.

Tristin arrives at the party and teases her about kissing him. Rory doesn’t think his behaviour means that Tristin truly likes her, rather that he’s trying to prove that he can get any girl he sets his sights on, but his altercation with Dean at the Chilton dance is the first time she considers otherwise .

Why was Tristan interested in Rory?

4 Tristan: He Understood And Loved Rory’s Ambition. Tristan was interested in Rory because he liked how smart she is. It also seems like he enjoyed her self-confidence and the way she never let him down easily.

Rory was right to stay with Dean because he understood her life in her small town, and he liked how wholesome and charming it was.

While Tristan seemed like a jerk at first, since he insulted Rory by calling her “Mary” and teased her at every opportunity, Rory got to know him and realized that he might not be so terrible. It’s true that Rory and Tristan never officially dated, and she continued her romance with Dean, but what if Rory had made a different decision? When thinking about Rory’s love life, it’s interesting to compare Tristan and Dean.

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Rory did love Dean, and she was able to tell him a little while later, but Tristan was able to let Rory know that he had feelings for her, and he didn’t have any conditions attached. This felt much healthier.

While Dean did tell Rory that he loved her, he did so on their three-month anniversary, and there was a string attached: Rory had to say it back right at that moment. Since she wasn’t ready and felt overwhelmed, he ended the relationship.

3 Dean: He Was More Optimistic And Less Jaded Than Tristan. Tristan had known Paris and his other rich classmates since childhood as they had been all running in the same social circles, and he was jaded and cynical about his life and his future.

Rory had never been in a relationship before , and while she was full of nerves and butterflies, Dean made her feel safe. They took things slow, enjoying their time together, watching movies, and talking about books. Since Rory was figuring out what a relationship even meant, Dean was the best person for her at this time.

Why did Rory stay friends with Dean?

For some reason, Rory thought it would be a great idea to hide the fact that she was still hanging out with Dean from Jess, because obviously sitting on a bed of lies is a great way to maintain a relationship. That she didn’t come clean to Jess about this friendship is confusing to say the least, and by keeping it a secret, she only made Jess suspect there was something more going on.

Constantly pretending that she’s not like her privileged Yale pals, Rory assumes a lifestyle with Logan that is exactly like the one her mother tried to steer her away from. The fact that she dates Logan, and takes so long to realize she’s in this world, is just bizarre.

Many people who have revisited Gilmore Girls as adults have criticized Rory for her complete lack of self-awareness as a privileged, white woman. People who may have been fans of the show as young teens now often view Rory as a bratty, spoiled girl who doesn’t realize how good she’s got it, and this has led many people to lash out against both her and Lorelai.

While it might be understandable that Rory got upset with Logan for sleeping with other people while they were on a break, it’s her double standard behavior that’s really the confusing part of this whole plotline. While she may have thought they were just taking some time apart from each other, and Logan was under the impression they had broken up for good, the fact of the matter is, Rory is getting upset with her ex for seeing other people.

She then gets so distracted and caught up in Logan’s world of parties and privilege that she completely neglects her education and the pursuit of her writing dreams. For someone who was made out to be so focused at the start, it’s very confusing that she’s so willing to drop everything for the men that come swanning into her life.

Rory commits a whole heap of relationship crimes, including cheating on several of her partners as well as having double standards and being flaky, but it’s the way she reacts to the news about Logan’s fiancee moving in with him that really makes you want to question everything.

Some of the first impressions we’re given of Rory at the start of the show are that she’s smart, hard-working, and she aspires to be a journalist. Why is it that at the slightest sign of romance or boy-trouble, Rory is ready to throw in the towel on her dreams?

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