Why Does Rory Apologize to Dean?

In ‘Let the Games Begin‘, as soon as Rory & Jess finally share their first kiss (or two), Rory realizes she has to go. After Jess sighs in saying, “Whatever else happens between us, at least we know that part works”, Rory says “I have to go”, despite obviously enjoying the time herself.

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After this moment, we see Rory climbing up to see Dean in his bedroom. She wants him to know she’s sorry for treating him badly and says he was “the most amazing boyfriend in the world” and that he made her very happy. She won’t talk with him about Jess, but hopes that some day he won’t hate her.

Does Rory go to Dean because she sees her relationship with Jess moving quickly? Or did the kiss make Rory realize how badly things had ended with Dean? What prompted the apology – then and there?

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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.

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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?

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Why Does Dean Forgive Rory?

In ‘Help Wanted‘, Rory has to break it to Dean about the car accident – which involves saying that a) she was with Jess, b) Jess was driving her car, c) the car is totaled. She tells him with a letter. Though he kicks a few things while reading the letter, he doesn’t ask any questions of Rory….

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We know that Dean loves Rory and is perhaps desperate to keep her. With Jess bolting town after the accident, is Dean hoping everything will go back to normal between him and Rory? Does he think Rory still cares for him, and that having Jess out of the picture will erase her feelings for him?

Should Dean have confronted Rory about her feelings?

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Does Lorelai Try to Keep Rory from Jess?

In ‘Back in the Saddle Again‘, Dean is starting to understand that Rory is pulling away from him, even if she doesn’t yet understand that herself.

When Dean comes to the diner, Rory is annoyed. When Dean calls repeatedly – leaving 10 messages on the machine and 4 with Lorelai – Rory admits to feeling overwhelmed. She says she calls him, spends her free time with him, but it’s just “not normal” anymore. Which, of course, it’s not. Dean is very insecure about Jess. Lorelai encourages Rory to “ride it out”, perhaps because she likes Dean more than Jess. Later, when Lorelai comes home to find Dean washing Rory’s car, she suggests Dean give Rory some space – that he’s perhaps holding too tight.

However, while Dean takes Rory’s advice and backs off, and Rory has a chance to miss him a little, she still doesn’t want to call him. She thinks of going off to Luke’s instead (ahem, Jess!). Lorelai doesn’t seem happy, but keeps quiet. When Lorelai drives home alone, she sees Dean waiting:

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This is when he says, so sadly, “She likes Jess, doesn’t she?”, as if Dean has realized that nothing he can do now will make a difference if Rory’s heart has changed. Lorelai just stays quiet. I think she, too, is sad.

Did Lorelai try to coach both Rory & Dean about their relationship because she thought they were good together? Or was it simply because Lorelai didn’t want Rory with Jess?

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Why is Rory in Denial?

In ‘Lost and Found‘, Rory freaks out when she realizes that she lost the bracelet that Dean gave to her. To me, this episode deals with Rory being in denial – about her feelings for both Jess and for Dean and what that means for her.

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Rory is extremely anxious that Jess and Lorelai get along – our first clue. Next, when she confronts Jess about being nice to Lorelai, she stumbles saying “if you care about me at all,” which Jess notices and tries to pry into. He definitely knows how to get Rory to face her own feelings! He also made her stumble over herself earlier when mentioning that her hair looked different.

Meanwhile, Dean notices that Rory isn’t making the bracelet he made for her. Rory lies about having it, but later ransacks the house looking for the bracelet. She has no idea when she last wore it (which was the Bid a Basket picnic). Jess realizes this is the bracelet Rory had dropped then, which he’d kept (cute). He later tries to return it, which Lorelai notices, and retorts to Lorelai that Rory’s most “precious” possession went completely unnoticed for more than 2 weeks. Another clue that Rory had not been in tune, perhaps, with her own feelings.

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What other clues are there that Rory’s feelings have changed?

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Is A Car Too Much?

In ‘Richard in Stars Hollow‘, Dean gives Rory the car he’s been building for her, but Richard doesn’t approve of the gift, being worried that it’s safe. Dean is up-front with Richard about how much he loves Rory, and that’s clear here. But I wonder… is it just too much? Seriously, a car?! That is a HUGE gift and a huge commitment of time, and money, I’m sure.

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Now, the “intensity” of this gift could just be one more of the aspects of Dean’s evolving “clinginess“, his need to be everything to Rory. Or is he trying to over-compensate in some way?

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Is Dean Immature or Insecure?

In ‘Hammers and VeilsDean suddenly seems to become immature. And I say suddenly, because prior to this I always got the impression that Dean was kind of the independent tough guy. Sure, he gushes over Rory, but he has a life too.

However, in this episode, Dean is not happy that Rory is spending so much of her summer doing school-related activities. Rory calls him immature for pouting, since Harvard is her dream.

Do you think Dean is being immature? And is it really immaturity? I think perhaps part of it is the fact that Rory is heading for this *big* life – that Dean glimpsed what it meant to be a Gilmore in the previous episode, and he’s already starting to feel like he doesn’t fit in.

Is Dean’s immaturity here actually insecurity?

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