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I took it as more of a "she's over not being able to be with him, but she still wishes she could be somehow".
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Exactly how I saw it. She basically flat out told him she wished they had met when she was more mature because then it might've worked out. It reminded me of her telling Lane "I think I really blew it there, I didn't appreciate it".
To me Dean will always be the best boyfriend Rory has ever had.
I'm glad that he got a very happy ending. He deserved nothing less.