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I'm glad they address she blew it there. Dean was, indeed, her best boyfriend, it's admitted by Rory herself now. It's one of those things in life you wish you could've changed, but you know you wouldn't be where you are now if that hadn't happened then. Doesn't change the fact you still wish you had that thing or person you lost in your life now. It's a mature conflict that I'm glad was dealt with properly, although I did not love her initial dismissal(that didn't match her altered reaction to seeing him at all).
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Well, yes and no.
Dean was the first year of their relationship really a perfect boyfriend. And she might regret losing such a sweet relationship.
But if she stayed with him, she might have regretted that she wasn't living more exciting life. She would have asked herself: what if...
They were just so young. There is no win situation here.