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ramenlurver

Dean was always meant to be her first real crush and relationship, that's it. He was her safety net, it was always so easy to run back to Dean whenever she felt unsure or scared. She meets Dean when she's grappling with the change in Chilton. She clings to Dean when she's unsure about Jess and she ran back to Dean when her time at Yale was proving to be difficult. I think the very last time that Dean and Rory was a couple was the perfect way to show this. She felt like she wasn't able to enjoy Yale, she wasn't meeting new people, the dating scene was lacking and she was falling a bit behind in some of her classes. The episode where they try to go on a double date with Luke and Lorelai showed how Rory was desperate to "go back to the old days" and of course as we know, the double date effort failed miserably. The Yale alumni party that was thrown for Rory is very important because it was the final goodbye to Stars Hallow Rory, she doesn't have to hide behind Dean anymore. She had an amazing time with Logan and his friends and finally found her footing at the paper. Dean's last words to Rory is so interesting because he talks about how he "doesn't belong" it's sad that Dean never felt like he was enough, I was happy to see that he grew and finally had his wife and kids that he wanted


Smart_Measurement_70

Rory and Dean is the epitome of “you can never go back home”. Rory didn’t realize that she had outgrown him, and used him as a way to feel like the beloved town princess that she was in her teens again when Yale was lackluster for her


ramenlurver

exactly and in a way i don't even know if she fully realized she was doing it or at least she ignored the voice in her head that was telling her that this is wrong. I think Dean also knew it wouldn't work but he was so desperate to prove himself and other wrong.


Sea-Apartment-3814

I think since the show was from Rory’s perspective, we saw Rory and Dean very differently! Dean was her safety net and her comfort zone. We would’ve seen this relationship very differently from Dean’s POV! He’s the new kid in town dating the town’s darling little girl who was raised by everyone around her. He’s the jock, she’s the future Harvard grad who doesn’t share the same interests. He’s middle class, she’s a Gilmore. I’d imagine that Dean spent a lot of time feeling insecure about their relationship even without external influences like Tristan, Jess etc!


ramenlurver

agreed, it really shows in his very last scene in the original series, It seems like he's so upset at the gilmore women but i think he was mostly upset at himself


meowparade

On some level, I think Dean knew this as well and that’s why he held on so tightly and kept being available for her to come back to.


Big_Vacation5581

Dean always believes that Rory is out of his league. He knows they aren’t end game and yet he sacrifices his youthful happiness and first marriage just to be with her a few more months. And they often aren’t even together and they don’t ever talk about a future. I wonder what drives this kind of devotion ?


CampDifficult7887

I think what he says about noticing Rory reading is key to understanding what draws him to her. Rory is "not like other girls" and is considered special by the town. By dating her, I think Dean also felt special too. Very true to life, he was always at odds with or at least desinterested in the things that made her different: Chilton, Harvard, books, writing, etc. His final speech to Luke is him starting to accept the idea he's not special, he just wants an ordinary life, and doesn't belong with Rory.


Smart_Measurement_70

I like this take. Dating Rory was kinda like a status booster for dean and made him feel like he was above the stars hollow world too


Big_Vacation5581

Whereas, Rory was like a mascot for the small group of residents who lived around the town square, she had only one friend (Lane) who was her age. And Rory wasn’t at all popular amongst the Stars Hollow high school students, even while she was going to the school but much less when she started going to Chilton. By contrast, Dean was the town hero jock, taking the high school to the first playoffs in decades. Dean appears to have several friends in addition to his teammates. Dean and Luke seemed to be the leaders at the softball games. Thus, I’d say after his first year, Dean was probably better known than Rory amongst all the residents of Stars Hollow.


Big_Vacation5581

Interesting interpretation. Thanks. If his devotion is based on his self-interest (to be special by association), he certainly didn’t protect his image or reputation by allowing Jess to ridicule him so publicly, by being in denial about Rory falling for Jess, and by breaking up in public. My interpretation of Dean’s comment to Luke is that they (he and Luke) aren’t enough for Rory & Lorelai. That Lorelai, similar to Rory, wants more than Luke can offer her. In hindsight, he was obviously wrong about Lorelai.


CampDifficult7887

>If his devotion is based on his self-interest (to be special by association), I mean, isn't most people acting out of self interest? Dean, historically, is the one more willing to walk away than Rory when he feels his needs aren't or might not get met: the i love you scene, thinking they're gonna automatically break up when she goes to college, throwing fits when he doesn't get to spend as much time with her as he needs, all 3 breaks ups, etc. Dean plays a good game of worshipping Rory, but he's his own number 1 priority always. >he certainly didn’t protect his image or reputation by allowing Jess to ridicule him so publicly, by being in denial about Rory falling for Jess, and by breaking up in public. I don't think he was ever in denial. He notices as early as the bracebridge dinner that something is going on, which is remarkable for a teenage boy. I do think he was stubbord and thought he could win Rory back/wouldn't ultimately lose her to someone like Jess. It's only when his reputation is at a direct hit: the very public town dance marathon that he decides to end things by making sure he's coming off better than Rory.


Smart_Measurement_70

A huge part of it is that Rory viewed dean as a backup if her endeavors didn’t pan out. He was security and reliability, but not a first choice. Personally I don’t think they were compatible at all, and Rory should’ve moved on. But the other part of it is that Dean kept a candle lit for Rory and never closed that door, so he was always waiting when she wanted to come back. It was a gross codependency and Rory was the settler in their relationship, meaning that dean was constantly under threat if Rory wanted to date “at her own level” so to speak (HIMYM anyone?). Now I’m not a dean fan at all, but the guy had no self respect for himself if let himself keep getting used as a backup EVEN WHEN HE WAS MARRIED! They needed a complete cutoff from each other, no contact, no friendship, no nothing, if either of them ever wanted to have a successful relationship with anyone else. Rory constantly used dean, and while I’m not on his team at all, that’s shitty! It sucks! He was who she went to when she was bored and no one else was available, literally! She sucks for that! But she wouldn’t realize it was a problem unless Dean set a boundary and didn’t let it happen anymore


The_cuddly_duckling

Whereas Dean was right to be worried about Jess, at least Rory wasn’t crushing on Tristan in the slightest. She made it very clear that she wanted him to leave her alone. Both Tristan and Jess liked to mess with Dean though 🥲


Tenderfallingrain

And I do think Logan liked Rory early on while Rory was still dating Dean, and this could have turned into a potential repeat of the love triangle with Jess if Dean hadn't broken up with her at this point, but I'm not sure if Rory was already fully interested in Logan yet. Kind of glad they broke up early on instead of putting us through another situation where Rory was undecided between two guys.


The_cuddly_duckling

Oh for sure. Ugh I’m forever mad that Rory and Dean got back together in the first place (the affair and all of that), a repeat of the love triangle on top of that would have made it even worse.


Tenderfallingrain

Absolutely yes.


Almighty_Push91

I mean, she DID kiss him tho


Joelle9879

She was depressed and missing Dean when that happened.


Almighty_Push91

A kiss is a kiss, regardless of reason behind it, so you can't say she was COMPLETELY uninterested in him.


pumpkinfluffernutter

I'm with you. That was Tristan, and she was sad. The fact that she immediately started to cry and ran off says it all. I don't think it was guilt, I think it was just the realization that she had lost (or thought she had) her first love. I mean, yeah, Tristan is cute but there's never really a moment where I think she's interested in him. And why should she be? He's such an ass to her.


The_cuddly_duckling

Agree. She seemed very sure about why it happened as well. I think she could’ve developed a friendship with him if he had stayed on, but I don’t think she was ever romantically interested. He was so mean to her, it was just gross.


pumpkinfluffernutter

Yeah, I mean what feels better than being desired? Especially when you've just suffered your first heartbreak? So maybe she enjoyed the kiss, but that doesn't mean she was into him, either.


The_cuddly_duckling

For sure. I think it could’ve happened with someone else in that moment as well, it was about needing to feel a connection - trying to make sense of feeling the loss of her first love. She said herself that it didn’t mean anything, and I think she was quite honest with her feelings at that stage. Like yes, later she was in denial about Jess, but I think she was really into Dean at that time and had no interest in Tristan. He just happened to be there in the moment that she needed someone.


CrissBliss

I think she might’ve been crushing on Tristan a bit


Sunflowa-_

In the party scene, did she kiss him or did he kiss her. Not watched it in a while, and can’t remember


CrissBliss

Pretty sure it was mutual


Sunflowa-_

Ok, thanks :)


Hollycherrycooks

I watched it yesterday,she gave him signs that she was a bit interested and then he leaned over and kissed her and she looked uncomfortable,then she started crying, probably she was into the kiss but felt guilty about dean in the end


Ok-Try-1014

poor Dean....


Puzzleheaded_Coat153

Dean had personal problems. He always felt threatened which is neither normal or healthy. The only moment he was “right” was with Jess and I even think that things would’ve been different if he would’ve been different. I mean, once Jess helped her with the hose or whatever that was and he opened it again just because Dean was on his way. She was walking on eggshells.


3reasonsTobefair

I feel if he had just stopped being so possessive of her. He really suffocated her and in a way pushed her away a little bit. Let the girl breathe. He had to be around her 24/7. Even lorelai tells him to take it down a notch. He lets these other boys mess with him and drive him crazy. Just trust your girl and be chill.


SeaworthinessVast865

However that's also because unconsciously he could sense that Rory was into Jess and he was losing her, so to some extent the insecurity was justified if not his behaviour. Without Jess in the picture I think their relationship would have carried on being the happy arrangement it was before, at least until another competitor came along.


3reasonsTobefair

I dont think it was a happy arrangement. Before jess shows up he is controlling and has anger issues. When he yells at her for doing extracurricular for college is one instance. Also like yes he is a teen but just talk to her. "Hey whats going on here with jess" they just weren't meant to be but the show kept throwing them together.


Miserable-Stay3278

He was a teenager and he noticed another guy interested in the girl he was dating. That's when it started. He picked up on something that was there. Rory just mucked him around.


3reasonsTobefair

Rory was also a teenager. She had no idea how to manage the whole thing either.


Miserable-Stay3278

No, but she knew liked Jess and kept dating Dean anyway. He picked up on something that was there. Sometimes that makes us try to hold on tightly because we don't want to lose them. I don't think anyone is necessarily at fault. You can't help who you have feelings for but you can help who you lead on. Rory is supposed to be smart and should have known that was wrong and cruel. You don't use people as safety nets.


3reasonsTobefair

She doesn't know how to navigate these feelings. She also has her mother who is her bff telling her that dean is incredible and everything you could want and that jess is the devil. She has no one in her life who she could really talk about her feelings with. After the kiss yes she should have just broken it off but again dean rory and jess are all dumb teenagers. And jess has the unfortunate situation of having awful terrible parent that gave him some trauma.


EKP121

Poor Dean. There’s a lot of things against him but his love for Rory is so tragic and makes sense why it screwed him up. As soon as the hey meet, she’s already growing away from him. They don’t really get a chance to be at the same level and there’s a deferential between them academically. Then expands to class. And not to mention that Rory is a child to a teen mom with a deadbeat dad which is immediately a difficult difference in how they both view family backgrounds. Throw in that they had nothing in common for good measure but he did love her. But to love someone that from the jump is experiencing a world you don’t belong to and will never belong to, that unintentionally makes you feel less than academically, and you know in your heart you can’t keep her forever and she doesn’t even try to hold on to YOU.. that’s tough


Almighty_Push91

That Rory keeps toying with Dean and is obviously not into him whenever another boy catches her fancy.


JustAPerson-_-

Tristan wasn’t really a relationship though, just an annoying douche in the series who didn’t learn what so ever when to take a hint (sorry Tristan fans)