Why Didn't Rory Break Up with Dean?


In ‘They Shoot Gilmores, Don’t They?‘, Dean comes to say hi to Rory while she’s at the dance marathon. Jess & Shane are there watching, and Jess makes sure Dean sees that. Jess stays for 8 hours watching Rory – or pissing off Dean – until Dean has enough. He doesn’t want to be Rory’s “pawn” against Jess, which I think is what he feels like.


When Rory later tries to complain to Dean about Jess being there and bugging her – particularly the making out – Dean has obviously had enough. When Jess & Rory fight about him being there, right in front of Dean, Dean simply says “I’m not her boyfriend anymore.” He knows Rory doesn’t want to be with him, though she says she does, and that she really wants to be with Jess. He’s giving her the freedom for that.

Later, when Jess comes to see if Rory is ok, Rory admits everything is true – about how she feels about him. Jess agrees. So, what I want to know is, why did Rory string Dean along like that? If she knew she had feelings for Jess, was it fair to Dean to treat him like that? Should she have broken up with him, even if Jess was not interested in her in return?

What stopped Rory from breaking up with Dean?


Watch this episode of Gilmore Girls on TheWB.com here.

Image: TheWB.com


4 thoughts on “Why Didn't Rory Break Up with Dean?

  • October 31, 2009 at 1:58 pm

    Because this is television (!), Rory probably didn’t break up with Dean so we could have this scene – but in her character, she was designed to be a sweet kid who had a hard time hurting people (she put up with a lot), and like many people who have a hard time admitting they’re in love with someone else when they’re committed to someone who’s kind and does all the right things, she has little to fault Dean for other than loving her too much and can’t bring herself to hurt him.

    Other interesting things about it, from what I see in it, some could say:

    1. If you fit this into the overall pattern of her behavior towards boys, she has a bigger problem, which is denial and an inability to acknowledge her emotions. I think it’s exactly why – sadly – she will convince herself it’s okay to sleep with Dean when he’s married and overlook the consequences, just as she skipped Lorelai’s graduation to run off to New York for Jess, let Logan lead her astray, and so on.

    2. What is well written about it is how it shows the importance of what we get from our parents. She had just seen Lorelai break Max’s heart by agreeing to marry him when she didn’t love him and knows how wrong that was. She knows Lorelai lost Christopher in part because she put him off until it was too late. And yet, because Lorelai is so beautiful, funny and charming and wants to be like her, like her mother she moves on far too quickly and doesn’t even trust Lorelai after Lorelai TOLD her to stop jerking Dean around – after all that happened in Season 2 – and insists she’s with Dean. Lorelai specifically tells her “if you want Jess, there he is, let Dean be with someone who wants him.” And Rory gets ANGRY! Just like she’ll get angry when Lorelai tells her she should not have sex with a married man and knows it’s wrong. It’s sad, and more than a little disturbing.

    3. For all the challenges and problems the writers had, the foreshadowing of what happened with Luke and Lorelai is pretty strong, as Dean will eventually tell Luke what will happen to him, that Lorelai will hurt him by being to drawn someone with a history of trouble – possibly because she loves him as well – because being a good, faithful person is not enough.
    Very realistic, and why the show was a “classical” comedy – one to hold characters to ridicule, not just for laughs.

  • October 31, 2009 at 4:10 pm

    Boy Marie, you do not leave much else to be said.

    I will say that maybe she felt secure with what she had in hand
    and not to gamble on what she really wants.

    I know that I have felt the same with she is not right for me but she is here.

  • November 2, 2009 at 4:19 am

    Up to this point in the series Rory was always the “good girl”, intelligent, hardworking, loyal to friends, cooperative with acquaintances, and mostly sweet and even tempered. She was proud of this self-image she had worked so hard to obtain [as was Lorelai] but of course to this point she had never really been tested in any meaningful way [beyond her own self-imposed scholastic standards] and had no real clue how to handle confrontational emotional situations [all she ever saw from Lorelai was just run away and avoid/deny the problem]. So up till now she always took the safe path until she ran accross Jess, got double-crossed by her own desires, and had to learn these lessons in problem solving the hard way.

    Sadly this was a pattern repeated more often than we would have liked or even expected from someone so smart and decent as Rory. As much as she hated hurting someone else, I think the self-loathing she felt towards herself for this type of behavior was even more devestating to her and at times was really hard to watch.

  • November 2, 2009 at 12:55 pm

    I’m pretty much going to go with the consensus. Rory didn’t want to leave Dean because he was always there for her and it would be wrong to hurt him like that. She would probably feel guilty doing so because like her mother said, “he’s sweet, kind, and patient and he doesn’t deserve to be treated like that” On the other hand, what i want to know is what did she expect to do with the growing feelings she was clearly having for Jess?

    The only thing i can come up with is Rory probably thought she could make it work between them but doesn’t understand that she had subconsciously broken them up already. She was merely with Dean in the physical sense than the emotional one. This is a pattern of self-destruction that she does continue as smart as the character was supposed to be she did a lot of dumb things under pressure and for the sake of the opposite sex. That was one of the bigger if not biggest flaw of the character of Rory, she put herself in a lot of compromising positions for the sake of a guy.


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