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She blew it early on when Jess came along but when they got back together and had the affair that was incredibly frustrating to watch and it ruined Dean for me. I was quite glad Logan came along to lure her away from him at that point. But the first year of their relationship was golden.
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As for me, I honestly couldn't care less about the affair, it was the writers making him marry at the age of 18 that ruined it. Not the ship, but the narrative. They had already dumbed Dean down through the previous season, but to make him get married like that was just absurd.
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But if she stayed with him, she might have regretted that she wasn't living more exciting life.
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I agree that they were too young to be together forever, but they could've easily fallen apart and back again if the writers hadn't gotten him married. As for the excitement, Dean's still Dean. He's the bus hopper, car building street fighter that'll make your heart accelerate. So, yes, they shoudn't have sticked together back then as one of those "from 15 to forever" couples, but they could and should have eventually reunited. The writers blew it.
Touldengal I agree, it definitely seemed to mean something. I wouldn't risk it off. I doubt they'd make them get back together, but the story's logic doesn't write it off. It does present it to us as something Rory wished she could have but has lost for good, though.
I wouldn't say regret is a strong word, she did sound regretful back when he got married.
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IMO he was truly over her.
I don't see why would Dean still want to be with her.
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I feel like Dean will always love her somehow, but that he knows better now. As much as he might feel for her, she's messed with him big time.
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But there was still someone who cared for her, although she didn't know it (Jess).
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Dean and Logan definitely still cared for her too. Jess's case, I see as Rory's with Dean in the sense that Rory's done with Jess the way Dean is done with Rory. Rory blew it with Dean, Jess blew it with Rory.